UV,
         r y , \  United States
SEPA
               Environmental Protection
               Agency
                                                    FINAL DRAFT
                                                    ECAO-CIN-GQ91
                                                    October, 1990
        Research and
        Development
        HEALTH AND ENVIRONMENTAL EFFECTS DOCUMENT
        FOR TRENITROPHENYLMETHYLNITRAMINE
        Prepared for
        OFFICE OF SOLID WASTE AND
        EMERGENCY RESPONSE
       Prepared by
       Environmental  Criteria and  Assessment  Office
       Office of Health and  Environmental Assessment
       U.S. Environmental Protection  Agency
       Cincinnati, OH  45268
                    HEADQUARTERS LIBRARY
                    ENVIRONMENTAL PROTECTION AGENCY
                    WASHINGTON, D.C. 20460


                     DRAFT: DO NOT CITE OR QUOTE
55                           NOTICE

oo    This document Is a preliminary draft.  It has not been formally released
^by the U.S. Environmental Protection Agency and should not at this stage be
^construed to represent Agency  policy.   It 1s being circulated for comments
=£on Its technical accuracy and policy Implications.

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                                  DISCLAIMER

    This  report  1s  an external  draft  for review purposes only  and does not
constitute  Agency policy.   Mention of  trade  names  or  commercial  products
does not constitute endorsement or recommendation for use.
                                      11

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                                    PREFACE
    Health and  Environmental  Effects  Documents (HEEOs) are  prepared  for  the
Office of  Solid  Waste  and Emergency Response  (OSWER).  This  document series
Is 1nt;nded to  support  listings  under  the  Resource  Conservation and Recovery
Act  (RCRA)  as  well as  to provide health-related limits and  goals  for  emer-
gency  and  remedial actions  under the Comprehensive  Environmental  Response,
Compen;at1on  and  Liability  Act  (CE8CLA).   Both  published  literature  and
Information obtained  for  Agency  Program Office  files are evaluated  as  they
pertali to potential human health,  aquatic  life  and environmental  effects of
hazard)us  waste  constituents.   The  literature searched for  1n  this document
and  tfe  dates  searched  are  Included 1n  "Appendix: Literature  Searched."
Literature search  material  Is current up  to 8 months previous  to  the  final
draft  date listed  on  the front  cover.   Final  draft document  dates  (front
cover) reflect the date the document 1s sent to the  Program Officer (OSHER).

    Several quantitative  estimates  are  presented  provided  sufficient  data
are available.   For systemic  toxicants,  these  Include Reference doses (RfDs)
for  cironlc  and  subchronlc  exposures  for  both  the  Inhalation  and  oral
exposures.  The subchronlc  or   partial  lifetime RfD  1s  an  estimate of  an
exposure  level   that  would not  be expected  to  cause  adverse effects  when
exposure occurs  during a  limited time  Interval  I.e.,  for an  Interval  that
does  not  constitute a  significant portion  of the  llfespan.  This  type  of
exposure estimate  has  not been  extensively used,  or rigorously defined  as
previous risk assessment  efforts  have  focused  primarily on  lifetime exposure
scenarios.   Animal data  used  for  subchronlc estimates  generally  reflect
exposure durations  of  30-90  days.   The  general  methodology  for  estimating
subchronlc RfDs  1s  the  same as  traditionally  employed for  chronic  estimates,
except that subchronlc data are utilized  when available.

    In the case  of suspected carcinogens,  a carcinogenic potency  factor,  or
q-j*  (U.S.  EPA,  1980),  Is  provided.   These  potency  estimates are  derived
for both  oral  and  Inhalation  exposures  where  possible.   In  addition,  unit
risk estimates  for  air  and drinking water are presented  based on  Inhalation
and oral data, respectively.  An  RfD may also  be  derived  for the noncarclno-
genlc health effects of compounds that are also carcinogenic.

    Reportable quantities  (RQs)  based  on both chronic toxlclty and carclno-
genlclty are derived.  The RQ 1s  used  to determine  the  quantity of a  hazard-
ous substance  for  which  notification  Is  required In the event of  a  release
as  specified  under  the  Comprehensive  Environmental Response,  Compensation
and L  abH-Uy  Act   (CERCLA).  These  two  RQs  (chronic toxlclty and cardno-
genldty)  represent two of  six  scores  developed  (the remaining four  reflect
IgnltabUHy,  reactivity,  aquatic toxlclty,  and  acute mammalian  toxlclty).
Chemical-specific RQs reflect the lowest of  these six primary criteria.   The
methocology for  chronic  toxldty and  cancer  based  RQs  are  defined  1n  U.S.
EPA, 1984 and 1986a, respectively.
                                      111

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                               EXECUTIVE SUMMARY
    Trlnltrophenylmethylnltramlne  Is  a buff-colored  solid  at room  tempera-
ture  (Small  and  Rosenblatt,  1974}.   It  Is  slightly soluble  In  water and
soluble In common nonpolar organic  solvents  (Small and Rosenblatt, 1974; Sax
and Lewis, 1987;  Hlndholz  et  al., 1983).   The U.S. EPA TSCA  production  file
lists  two  U.S.  companies  as  processors of  trlnltrophenylmethylnltramlne  1n
1977,  one  of  which  was  located  1n Jollet,  IL (TSCAPP; 1989).  According  to
Small  and  Rosenblatt  (1974),  production of  trlnltrophenylmethylnltramlne for
military purposes  was  limited  to  the  Jollet Army  Ammunition Plant,  which
ceased production July  31,  1973.   Trlnltrophenylmethylnltramlne was  produced
In  a   batch  synthesis  In  which  N,N-d1methyl  aniline In  sulfurlc  add was
treated  with  nitric  acid,  followed  by  a   mult 1 step  purification  process
(Small and Rosenblatt, 1974).
    Trlnltrophenylmethylnltramlne has been used as a  booster  charge  In  muni-
tions  to  detonate  less  sensitive  explosives  (Small  and Rosenblatt,  1974).
This compound 1s also used as a  pH Indicator, as  1t  Is colorless  at  pH  <10.8
and turns dull red at pH >13.0 (Sax and Lewis, 1987;  Wlndholz  et al., 1983).
    Few experimental  data  on  the  environmental  fate  of trlnltrophenylmethyl-
nltramlne  were  located   In  the  available  literature.  If  released to water,
direct photolysis of  trlnltrophenylmethylnltramlne 1s  expected to be signif-
icant.  Under ambient lighting  In the  laboratory,  1t  underwent -95X removal
after  20  days  In  distilled  water  (Kayser  et  al.,  1984).   Hydrolysis  of
trlnltrophenylmethylnltramlne  In  water  in the environmentally significant  pH
range  of  5-9  1s expected  to  be  slow.   Hydrolysis  1s more  rapid  under  basic
conditions (Belkln et al.. 1985; Kayser et al., 1984).
l»
                                      tv

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    Tr InUrophenylmethylnltramlne Is  not  expected  to adsorb significantly to
sedlmeit or suspended organic  matter,  nor  Is  H  expected to bloaccumulate In
fish  and  aquatic  organisms.   No  experimental   data  were located  1n  the
ava1la>1e  literature  on  the  atmospheric  fate of  trlnltrophenylmethylnltra-
mlne.   In  general,  polynltrated compounds associated with  the  production of
mun1t1>ns  undergo  direct  photolysis  In the  atmosphere  If  they  undergo  this
reactljn  In  water  (Ryon  et  a!., 1984).   Therefore,  tr1n1trophenylmethyln1-
tramlnj may undergo direct photochemical degradation In  the atmosphere.
    Th;  limited  water solubility of  this compound,  75 mg/l at  20°C  (Small
and   Rosenblatt,   1974),   suggests   that   rainwater   washout   may  not   be
significant.   Dry  deposition  of  partlculate  compound  Is  expected.    If
released  to  the  soil,  a  calculated K    suggests  that  1t may  be moderately
mobile  In  soil.    In  one experimental  study,  however,  no  trlnltrophenyl-
methylnltramlne was  found In  the leachate  from  a  soil  cqlumn  to which  this
compound  had  been  applied  (Kayser  and  Burllnson,  1988).  Thus,  trlnltro-
phenylnethylnltramlne may not  leach   from  soil  and  enter  groundwater.   In
genera  , polynltrated compounds associated with  munitions  production are  not
expected to volatilize from soil to  the atmosphere  (Ryon et al., 1984).
    Feu quantitative  data  on  human  exposure  to tMnltrophenylmethylnltramlne
were   located   In  the  available  literature.    Occupational   exposure   to
trlnltiophenylmethylnltramlne  Is  believed to  have occurred as  a result  of
dermal contact and  Inhalation  for those working  In or around the areas where
trlnlti ophenylmethylnltramlne  was  produced and  packaged  (Hardy  and Maloof,
1950).
    Pei tlnent data  regarding  the environmental  toxUUy of  trlnltrophenyl-
methyli Hramlne   were  not located   in  the  available   literature  cited  In
Append'x A.

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    Studies  to  determine the  pharmacoklnetlc  properties of  trlnltrophenyl-
methylnltramlne  have   only   been  performed  with  rabbits   (Zambrano  and
Mandovano,  1956).    Tr1n1trophenylmethyln1tram1ne  1s  absorbed  through  the
digestive  tract,  although   data  were  Insufficient  to  estimate  rate  and
extent.  It may, however, be poorly absorbed because the  metabolite  plcramlc
add  does  not appear  In  the  urine of  rabbits until  after  several days of
treatment.  Metabolism  of tr1n1tropheny1methyln1tram1ne 1n rabbits  Involved
the  transformation  of  the  material   to  picric  acid   which  was,  In turn,
transformed to  plcramlc acid.   Plcramlc add  was  also present 1n  the urine
of  rabbits   In  the   sulfoconjugated  form.    The   only  excretion  route
Investigated was the urine,  and  plcramlc add and sulfoconjugates were the
only metabolites detected (Zambrano and Mandovano,  1956}.
    Trlnltrophenylmethylnltramlne was  not  carcinogenic when administered to
female Sprague-Dawley  rats  by  gavage  In  10 doses of  40 mg/rat  (114 mg/kg)
over  a 30-day  period (GMswold et  al.,  1968).  However, the brevity of the
observation period (9 months),  the  small  sample sizes, and lack  of  multiple
doses precludes  any conclusions about  potential cardnogenldty.
    Trlnltrophenylmethylnltramlne was  found to be  genotoxlc  In  Salmonella
typhlmurlum. Saccharomyces cerevlslae  and Neurospora  crassa  In  the  absence
of  S-9   activation   (Uhong   et   al.,   1980a;  McGregor   et  al.,  1980).
Dose-related Increases  were  reported  In  these  studies   (Whong et  al.. 1980a;
McGregor  et al., 1980).
    Pertinent data  regarding teratogenlc  and  other  reproductive  effects of
trlnltrophenylmethylnltramlne  were  not located  1n the available  literature
cited In  Appendix A.
    Toxldty  data  Indicate  that  exposure  to  trlnltrophenylmethylnHramlne
results 1n  toxic effects  In  rabbits (Danlele,  1964; Fatl  and  Danlele, 1965;
                                      v1

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Guarlnn and Zambrano, 1957), dogs  (Hells  et  al.,  1920)  and rats (Parmeglannl
et al.  1956), and  the  liver,  kidney,  spleen and  blood  are the most affected
organs,   In  rats,  a single  oral  dose of 1000  mg/kg  did not  produce  toxlc-
Hy, wlereas the same dose repeated  10  times was  lethal  (Parmeglannl  et  al.,
1956).  However,  the route  of  administration was not stated.   Subcutaneous
administration of  a single  dose  of  5000 mg/kg Induced  death  1n dogs In  18
hours  (Wells et al., 1920).
    Data  regarding  subchronlc  exposure  to tr1n1trophenylmethyln1tram1ne are
limited to  studies  In rabbits  (Danlele,  1964;  Fat1  and Danlele, 1965).   In
this  sfecles,  administration of 125 mg/kg/day  (only  dose  tested)  by  gavage
for 6-?  months produced  alterations  In coagulation  parameters,  as well  as
moderats  to  severe hlstologlcal  effects  In   the  liver,  kidneys and  spleen.
Data  were not  available regarding  the chronic  effects of  trlnltrophenyl-
methylnltramlne.
    The  toxlclty  of  trlnltrophenylmethylnUramlne   following  occupational
exposure  was   evaluated  by  several   Investigators  (Andersen  et  al., 1942;
Bergman, 1952; Brabham, 1943; Crlpps, 1917;  Eddy,  1943;  Fischer  and Hurdock.
1946;   Gah,  1984;  Hardy and  Maloof,  1950;  Hilton  and Swanston,  1941;  Murray
et al., 1944;  Parmegg1an1,  1983;  Probst et  al.,  1944; Ruxton,  1917;  Silver,
1938;  Snlth, 1916; Troup, 1946; Nitkowski et al.,  1942;  Zambrano  and  Pedone,
1955);  however,  the  routes  of  exposure,  exposure  durations  and  exposure
levels  were  not  reported   In  these  case   studies.   Consistently  reported
effects Include dermal  reactions, dermal sensltlzatlon, respiratory  Irrita-
tion,  dyspnea, abdominal  effects, menstrual  problems, weight loss,  liver and
spleen effects, headaches. Irritability and  general malaise.
    Based  on  the  weight  of  evidence,  trlnltrophenylmethylnUramlne  was
assigned to U.S. EPA Group D:  not classifiable  as to  human carclnogenlclty.
                                      vll

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A cancer-based  RQ  was not derived.  A  provisional  RfD of 0.01 mg/kg/day was
derived by applying an uncertainty factor of  10  for  subchronlc oral  exposure
to  trlnUrophenylmethylnltramlne  based  on   the  LOAEL  of  125  mg/kg/day  1n
rabbits  In  the  study by Fatl  and  Danlele  (1965).   The RfD  value  Is  well
below  the  line  for adverse effects  In  a dose/duration-response plot of the
oral  toxldty  data.   An  RQ  of 1000 was  derived based  on  liver and kidney
effects In rabbits  In a subchronlc duration  study (Fatl  and  Danlele,  1965).

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                              TABLE OF CONTENTS
1.  IIITRODUCTION	    1

    1 1.   STRUCTURE AND CAS NUMBER	    1
    1 2.   PHYSICAL AND CHEMICAL PROPERTIES 	    1
    1 3.   PRODUCTION DATA	    2
    1 4.   USE DATA	    2
    1 5.   SUMMARY	    2

2.  EIIVIRONMENTAL FATE AND TRANSPORT	    4

    2 1.   AIR	    4

           2.1.1.   Reaction with Hydroxyl Radicals 	    4
           2.1.2.   Reaction with Ozone 	    4
           2.1.3.   Photolysis	    4
           2.1.4.   Physical Removal Processes	    5

    2 2.   WATER	    5

           2.2.1.   Hydrolysis	    5
           2.2.2.   Oxidation 	    6
           2.2.3.   Photolysis	    6
           2.2.4.   Mlcroblal Degradation 	    6
           2.2.5.   B1oconcentrat1on	    7
           2.2.6.   Adsorption	    7
           2.2.7.   Volatilization	    7

    2.3.   SOIL	    7

           2.3.1.   Mlcroblal Degradation 	    7
           2.3.2.   Adsorption	    8
           2.3.3.   Volatilization	    8

    2.4.   SUMMARY	    8

3.  E>POSURE	   10

    3.1.   WATER	   10
    3,2. - FOOD	   10
    3.3.   INHALATION	   10
    3.4.   DERMAL	   11
    3.5.   OTHER	   11
    3.6.   SUMMARY	   11
                                     1x

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                          TABLE  OF  CONTENTS  (cont.)

                                                                       Page

4.  ENVIRONMENTAL TOXICOLOGY	    12

    4.1.   AQUATIC TOXICOLOGY 	    12

           4.1.1.   Acute Toxic Effects on Fauna	    12
           4.1.2.   Chronic Effects on Fauna	    12
           4.1.3.   Effects on Flora	    12
           4.1.4.   Effects on Bacteria 	    12

    4.2.   TERRESTRIAL TOXICOLOGY 	    12

           4.2.1.   Effects on Fauna	    12
           4.2.2.   Effects on Flora	    13

    4.3.   FIELD STUDIES	    13
    4.4.   AQUATIC RISK ASSESSMENT	    13
    4.5.   SUMMARY	    13

5.  PHARMACOKINETCS	    14

    5.1.   ABSORPTION	    14
    5.2.   DISTRIBUTION	    14
    5.3.   METABOLISM	    14
    5.4.   EXCRETION	    15
    5.5.   SUMMARY	    17

6.  EFFECTS	    18      W

    6.1.   SYSTEMIC TOXICITY	    18

           6.1.1.   Inhalation Exposure 	    18
           6.1.2.   Oral Exposure	    18
           6.1.3.   Other Relevant Information	    19

    6.2.   CARCINOGENICITY	    23

           6.2.1.   Inhalation	    23
           6.2.2.   Oral	    23
         -  6.2.3.   Other Relevant Information	    24

    6.3.   MUTAGENICITY	    24
    6.4.   DEVELOPMENTAL TOXICITY 	    24
    6.5.   OTHER REPRODUCTIVE  EFFECTS 	    24
    6.6.   SUMMARY	    27

7..  EXISTING GUIDELINES AND STANDARDS	    29

    7.1.   HUMAN	    29
    7.2.   AQUATIC	    29

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                           TABLE OF CONTENTS (cont.)

                                                                        Page

 8.  IIISK ASSESSMENT	   30

     iU.   CARCINOGENICITY	   30

            8.1.1.   Inhalation	   30
            8.1.2.   Oral	   30
            8.1.3.   Other Routes	   30
            8.1.4.   Weight of Evidence	   30
            8.1.5.   Quantitative Risk Estimates 	   31

     11.2.   SYSTEMIC TOXICITY	   31

            8.2.1.   Inhalation Exposure 	   31
            8.2.2.   Oral Exposure	   31

 9.  IMPORTABLE QUANTITIES	   33

     •1.1.   BASED ON SYSTEMIC TOXICITY	   33
     'K2.   BASED ON CARCINOGENICITY	   33

10.  INFERENCES	   37

APPENDIX A: LITERATURE  SEARCHED	   46
APPENDIX B: SUMMARY TABLE FOR TRINITROPHENYLMETHYLNITRAMINE	   49
APPENDIX C: DOSE/DURATION RESPONSE GRAPH(S) FOR EXPOSURE TO
            TRINITROPHENYLMETHYLNITRAMINE	   50
                                      xl

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                                LIST OF TABLES
JCK_                              Title                                Page
 6-1      Mutagenlclty Testing  of Tr1n1trophenylmethyln1tram1ne ....   25
 9-1      Oral  {gavage)  Toxlclty  Summary of Trlnltrophenylmethyl-
         nltramlne  Using  the Rabbit	   34
 9-2      Composite  Scores  for  TMnltrophenylmethylnltramlne to
         Rabbits  by Gavage	   35
 9-3      Tr1n1trophenylmethyln1tram1ne: Minimum Effective Dose (MED)
         and Reportable Quantity 	   36
                                     xll

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                             LIST OF ABBREVIATIONS
BCF
CAS
CS
KQC
LOAEL
MED
NOAEL
NOEL
PEL
ppb
ppm
RfD
RQ
RVd
RVe
SC
TS
TWA
w/w
B1oconcentrat1on factor
Chemical Abstract Service
Composite score
Soil sorptlon coefficient
Lowest-observed-adverse-effect-level
Minimum effective dose
No-observed-adverse-effect-level
No-observed-effect-level
Permissible exposure level
Parts per billion
Parts per million
Reference dose
Reportable quantity
Dose-rating scale
Effect-rating scale
Sulfoconjugatlon
Total urinary sulfates
Time-weighted average
Weight per weight

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                               1.  INTRODUCTION
1.1.   STRUCTURE AND CAS NUMBER
    Tr m1trophenylmethyln1tram1ne  Is  known by  the  commercial names  tetryl,
tetraltte and  nHramlne (Chemllne. 1989;  Sax and  Lewis,  1987),  and by  the
synonyns    N-methyl-N,2,4,6-tetran1troan1l1ne,    N-p1cry1-N-methyln1tram1ne,
tr1n1trophenylmethy1n1tram1ne,   among   others   {Chemllne,   1989).     The
structure,  CAS  Registry number, empirical  formula  and molecular weight  are
given below.
                              0,N
                                    NO;
CAS number:  479-45-8
Empirical formula:  C,H,N,Q0
                     / D D 0
Holecjlar weight:  287.IS
1.2.   PHYSICAL AND CHEMICAL PROPERTIES
    Trin1trophenylmethy1n1tram1ne  Is  a buff-colored  solid  at room  tempera-
ture  (Small  and Rosenblatt,  1974).   It 1s  sparingly soluble 1n water,  and
soluble 1n acetone, 95% ethanol, ether, glacial acetic acid  and  benzene  (Sax
and lewis,  1987;  Small and Rosenblatt, 1974;  Ulndholz et al..  1983).   Trl-
nltrcphenylmethylnltramlne explodes when heated to 180-190'C  (Sax and  Lewis,
1987;  Wlndholz  et al.,  1983).   The limited data  available  on  the  physical
and chemical properties of tr1n1trophenylmethy1n1tram1ne  are  given below:
Melt mg point:
Boll ing point:
Wale- solubility
  at 20"C:
130°C
explodes before boiling
75 mg/l
Small and Rosenblatt,  1974
Sax and Lewis, 1987
Small and Rosenblatt,  1974;
Seldell, 1941
02441
              -1-
                   09/13/89

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 Density  (bulk):
 Conversion factors
  at 25'C:
1.73 g/ml
1  mg/m3 = 0.0852 ppm;
1  ppm = 11.74 mg/m3
Small and Rosenblatt,  1974
1.3.   PRODUCTION DATA
    Data  from  the  U.S.  EPA  TSCA  production  file  (TSCAPP,  1989) list  two
chemical companies as  processors  of tr1n1trophenylmethyln1tram1ne: Hercules,
Inc.,  In  Wilmington, DE,  and  Unlroyal, Inc.,  1n Jollet, IL.   According  to
Small and  Rosenblatt  (1974),  production of trlnltrophenylmethylnltramlne for
military purposes  was   confined  to  the  Jollet  Army  Ammunition  Plant,  which
ceased production of this compound as of July 31, 1973.
    Trlnltrophenylmethylnltramlne was  synthesized In a batch  process  by the
nitration  of  N,N-d1methylan1l1ne  1n  concentrated  sulfurlc   acid to  which
nitric acid  was  added.   Several  purification steps  resulted directly  In the
desired product (Small  and Rosenblatt, 1974).
1.4.   USE DATA
    Trlnltrophenylmethylnltramlne  has  been  used as  a  booster  explosive,
which 1s the explosive  that Initiates the  detonation of  the  bursting charge
In certain armaments (Small  and  Rosenblatt, 1974).  It 1s also  used  as a  pH
Indicator,  as  It Is colorless  at  pH 13.0
(Sax and Lewis, 1987; Wlndholz et al.. 1983)
1.5.   SUMMARY
    Trlnltrophenylmethylnltramlne Is  a  buff-colored  solid  at room  tempera-
ture  (Small  and Rosenblatt,  1974).   It 1s  sparingly  soluble In  water,  and
soluble 1n common nonpolar organic  solvents  (Small and  Rosenblatt, 1974; Sax
and Lewis, 1987; Wlndholz et  al., 1983).   The  U.S.  EPA TSCA  production file
lists two  U.S. companies  as  processors of  trlnltrophenylmethylnltramlne  1n
1977, one  of  which  was  located In  Jollet, IL  (TSCAPP, 1989).   According
0244d
              -2-
                   11/02/89

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to  SmpH  13.0  (Sax  and Lewis, 1987; Wlndholz  et
al., 1)83).
0244d                               -3-                              11/02/89

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                     2.  ENVIRONMENTAL FATE AND TRANSPORT
 2.1.   AIR
 2.1.1.   Reaction  with  Hydroxyl  Radicals.   Using  the  method  of  Atkinson
 (1985),  a  rate constant for the gas  phase  reaction  of trlnltrophenylmethyl-
 nltramlne with photochemical1y produced hydroxyl  radicals  In  the atmosphere
 can  be estimated  to be  1.44xlO~12  cmVmolecule-sec.   If  an average  atmo-
 spheric  hydroxyl  radical   concentration  1s  taken  to  be  5xl05  molecules/
 cm3,  then  the half-life for  the  vapor phase destruction  of  tr1n1trophenyl-
 methylnltramlne  In  the  atmosphere would  be -11  days.   In  general,  poly-
 nitrated compounds  associated  with the production of  munitions  are expected
 to  exist both  In  the  vapor  phase and  In  participate  form  In  the  ambient
 atmosphere  {Elsenrelch  et al., 1981;  Ryon  et  al.,  1984;  Spanggord  et  al.,
 1980).   If  this  1s  so  for  tr1n1trophenylmethyln1tram1ne,  then  the  actual
 rate  of  gas phase destruction by  photochemically  produced  hydroxyl radicals
will be considerably slower.  However, direct measures do not  exist.
 2.1.2.   Reaction  with  Ozone.   Destruction  of  atmospheric  trlnltrophenyl-
methylnltramlne by the gas  phase  reaction  with  ozone Is not expected to be a
 significant process  because this  compound  does  not contain  unsaturated bonds
 that  are likely  to  undergo  this  reaction.  Experimental  evidence was  not
 located In the literature.
 2.1.3.   Photolysis.  Pertinent data  regarding  the  gas  phase photolysis  of
 tr1n1trophenylmethy1n1tram1ne  In   the  atmosphere  were  not  located  In  the
available   literature   cited   In   Appendix   A.    In  general,   polynltrated
compounds  associated  with  the   production  of  munitions  are  believed  to
undergo direct photolytlc  degradation  In  the atmosphere  If they  can  undergo
this process  In water  (Ryon et al.,  1984).   Trlnltrophenylmethylnltramlne Is
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known  to  undergo direct photolysis  In water  (Section  2.2.3.);  thus,  photo-
lytlc  degradation  1n  the atmosphere may occur.   The  fact that this compound
turns  yellow  on  exposure  to  light  (Small  and  Rosenblatt,  1974)  also
1nd1ca:es Its photosensK1v1ty.
2.1.4.   Physical  Removal  Processes.  Pertinent  data  regarding  the  removal
of  trlnltrophenylmethylnltramlne from the  atmosphere by  physical  processes
were  rot   located  In  the  available literature  cited   In  Appendix A.   The
!1m1te<  water  solubility  of  trlnltrophenylmethylnltramlne  suggests  that
rainwater  washout  may  occur,  but  It  1s not  expected  to  be a  significant
process.   In  general,  polynltrated  compounds  associated with the production
of mun'tlons  are  believed  to exist  In both  the  vapor  phase and  the partlcu-
late  form  In  the ambient  atmosphere (Elsenrelch et al., 1981;  Ryon  et  al.,
1984;  Jpanggord  et  al.,  1980).   If  this   Is  so  for   trlnltrophenylmethyl-
nltramlne, then dry deposlton of the partlculate form may occur.
2.2.   MTER
2.2.1.   Hydrolysis.    Trlnltrophenylmethylnltramlne  at   a  concentration  of
10  ppb In distilled  water underwent  little hydrolysis  over  33 days at  pH
<4.0.  At  pH  6.0,  18%  was  lost  after  33 days.   Under  basic  conditions, 59%
and >90'4 were lost after 33 days  at pH 7.9  and pH 10.3, respectively (Belkln
et  al.,  1985).   Dark  hydrolysis  of  15 mg/i  tr1n1trophenylmethyln1tram1ne
In a bo-ax buffer  (pK=8.9)  proceeded at  a  rate equal  to 98.7% degradation In
90  days.  'Methylnltramlne  was  Identified as  the major  hydrolysis  product.
Other  products   were  detected  but  could  not  be  Identified.   In  related
experiments,    trlnltrophenylmethylnltramlne    hydrolysis  was   studied   at
elevatec  temperatures  as  a  function  of   pH   to  obtain  the  activation
parameters for  this   reaction.   Based on  the limited  experimental data,  a
half-life of 302 days at pH 6.8 (20°C)  was estimated (Kayser et al., 1984).


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     Tr1n1trophenylmethyln1tram1ne  at a  concentration  of -15  mg/i underwent
 88% removal  by hydrolysis  In 101  days \n seawater |pH=8.1) stored In actinic
 glassware  at  room temperature.   Picric  add  was  Identified  as  the  major
 product  of  the  reaction  (Hoffsommer   and  Rosen,  1972a).   Hydrolysis  of
 tr1n1trophenylmethy1n1tram1ne  at  the environmentally  significant  pH  range
 (5-9} will probably occur, but  Is not expected to be rapid.
 2.2.2.   Oxidation.   Pertinent  data regarding  the oxidation  of  trlnltro-
 phenylmethyln1tram1ne  In  water were  not  located  In  the available literature
 cited In Appendix A.
 2.2.3.   Photolysis.   A solution  containing  12  mg/i  trlnltrophenylmethyl-
 nltramlne  In  distilled  water  at   pH   5.95  was  subjected  to  laboratory
 photolysis using  ambient  light at  room  temperature.   Photolysis under  these
 conditions was  found  to be  at least one order of magnitude  faster than the
 hydrolysis of  a control  sample run  concurrently.   Direct photolytlc degrada-
 tion  In  this experiment occurred at a  rate equal to  95.4X  loss of starting
material after  20  days.   This corresponds  to  a  photolytlc  half-life of -4.5
 days.   In  bright  sunlight,  the  half-life  Is expected to be  shorter.   The
major  detectable  photodegradatlon  product  was  N-methylplcramlde;  methyl-
 nltramlne, plcrate  1on, nitrate  and nitrite  were  also observed  (Kayser  et
 a"1.,  1984).   Photolytlc degradation  In  clear surface  waters,  therefore.  Is
 expected to be a dominant removal pathway.
 2 2.4.   Mlcroblal  Degradation.   Pertinent  data  regarding  the  mlcroblal
degradation  of  tr1n1trophenylmethyln1tram1ne  In  water  were  not  located  In
 the  available  literature  cited   In Appendix A.   Also,  no  compound  was
 Identified that could  serve as a  model   {based on structure)  to predict the
potential  for  mlcroblal blodegradatlon  of  trinltrophenylmethylnltramlne  1n
water.
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2.2.5.   B1oconcentrat1on.    Using  the   linear   regression   equation   log
BCF=2.791-0.564  log S  (Bysshe,  1982),  where  S  1s  the water  solubility  In
ppm,  a  BCF  of 54 can be  obtained  for  trinltrophenylmethylnltramlne based  on
Us  witter  solubility  of 75  mg/a  at  20°C  (Small  and  Rosenblatt,  1974).
This  value  suggests  that  blaccumulatlon  In fish  and aquatic organisms 1s not
expected  to be  significant.   In general,  polynHrated compounds  associated
with  the  production of  munitions  are  not  expected  to  bloaccumulate  In
aquatic organisms (Ryon et al., 1984).
2.2.6.   Adsorption.  For trinltrophenylmethylnltramlne,  a  K   of  406 can
be  calculated  (see  Section  2.3.2.).   This  suggests  that  adsorption  to
sediment and  suspended  organic matter  may occur,  but  that  It Is not expected
to  be significant.    In general,  polynHrated  compounds associated  with  the
production  of  munitions are not expected to adsorb  to sediment  In environ-
mental waters (Ryon et al., 1984).
2.2.7.   Volatilization.   Pertinent data  regarding  the  volatilization  of
trlnlt-ophenylmethylnltramlne  from  the  soil surface  to the  atmosphere  were
not  located In  the  available  literature  cited  In Appendix  A.   In general,
howeve-, polynltrated compounds  associated with  the  production of munitions
are  not  expected to volatilize  significantly  from soil (Ryon  et  al.,  1984;
Spangg>rd et al., 1980).
2.3.   SOIL
2.3.1.   M4crob1al   Degradation.    Pertinent    data   regarding   mlcroblal
degradation of trinltrophenylmethylnltramlne In soil  were not located In  the
ava1la)le literature  cited  In  Appendix A.  Also,  no  adequate model compound
can  be  used  to  predict  the  potential  for  the  blodegradatlon of  trinltro-
phenylmethylnltramlne In soil.
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2.3.2.   Adsorption.   The KQC  Is  useful  1n  Interpreting  the mobility  of  a
chemical  through soil.   The  linear  regression equation log  K   = -0.55 log
S*3.64,  where S  Is  the water  solubility  In mg/i,  can be used  to estimate
this  value when  experimental  data are unavailable  (Lyman,  1982).   Using  a
water  solubility of  75 mg/fc  at   20°C  (Small  and  Rosenblatt,  1974), a K
of  406  can  be  obtained  for  trinltrophenylmethylnltramlne,   which suggests
moderate  mobility In  soil (Swann  et  a!.,  1983).   However,   In  a lyslmeter
column study  using different  types of  soil  (clay, silt loam and sandy loam),
no  trinltrophenylmethylnltramlne  was  found  In  water samples  taken from the
bottom  of  the  column  over  a  period   of  6  months.   Picric  acid,  a  known
hydrolysis product, was  detected  In  the leachate, along with  other unidenti-
fied  polar compounds.   After  termination of  the study,  no  trinltrophenyl-
methylnltramlne  was  adsorbed  to  the soil  1n any of  the columns  (Kayser and
Burllnson,  1988).  These  data suggest  that  although  trinltrophenylmethyl-
nltramlne  may  not leach  through  soil  and enter  groundwater.  Its  hydrolysis
products may.   The authors  stated that  hydrolysis  of trinltrophenylmethyl-
nltramlne  In  soil  may  be   particularly  rapid  because  of  macromolecular
Interactions between this  compound and the soil (Kayser and Burllnson, 1988).
2.3.3.   Volatilization.   Pertinent data  regarding the  volatilization  of
trinltrophenylmethylnltramlne  from soil to  the  atmosphere were  not located
In the available  literature cited 1n Appendix  A.   In general, however, poly-
nitrated compounds associated  with munitions production are  not  expected to
volatilize from water (Ryon et al., 1984;  Spanggord et a!., 1980).
2.4.   SUMMARY
    Little experimental  data  on   the  environmental  fate  of  trinltrophenyl-
methylnltramlne  were  located  In   the  available  literature.    If  released to
water, direct  photolysis of  trinltrophenylmethylnltramlne 1s  expected to be
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significant.   Under ambient  lighting 1n  the laboratory.  It  underwent ~95X
removal after  20 days  In distilled water  (Kayser  et al., 1984).  Hydrolysis
of  trliltrophenylmethylnltramlne  In  water  at the environmentally significant
pH  range  of 5-9  Is expected  to  be  slow.   Hydrolysis  has been  found  to be
more r.ipld under basic conditions (Belkln et al., 1985; Kayser et al., 1984).
    Trinltrophenylmethylnltramlne Is  not  expected  to adsorb significantly to
sediment or  suspended  organic  matter,  nor  Is It expected to bloaccumulate In
fish  
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                                 3.  EXPOSURE
3.1.   WATER
    Tr1n1trophenylmethyln1tram1ne  was  detected  1n  the wash  water from. Its
production at  the Jollet Array Ammunition Plant.  At  the  height  of trinltro-
phenylmethylnltramlne  production,  the wastewater effluent  concentration  was
estimated  at  400  mg/i,  which  corresponds   to a  dally  discharge  of  36
pounds/day  from each  production  line  (12  lines were  1n operation  at  this
plant).  Since  It  has  been reported  that  trinltrophenylmethylnltramlne 1s no
longer produced  at this  site,  contamination of nearby environmental waters
could  then emanate from ground deposits and waste  ditches.   A 1974 calcula-
tion  based  on the  average precipitation In  that  geographic  area concluded
that  trinltrophenylmethylnltramlne  estimated to be  1n soil,  waste ditches,
etc.,  of  the  Jollet  Army  Ammunition  plant would  be removed completely  In
surface runoff within  7  years  (Small  and  Rosenblatt,  1974).  Trlnltrophenyl-
methylnltramlne  was  not  found  1n the  water  or sediment  200 miles  off  the
coast of Florida and 45  miles  west of San Francisco,  where ships loaded with
antiquated  munitions  were   scuttled   at   sea   (Hoffsommer  et   al.,  1972;
Hoffsomer and Rosen, 1972b).
3.2.   FOOD
    Pertinent data  regarding exposure  to  trinltrophenylmethylnltramlne  from
food were not located In the available literature cited In Appendix A.
3.3.   INHALATION
    Pertinent  data  regarding  the   monitoring of   atmospheric  levels   of
trlnltrophenylmethylnltramlne  were  not located  In  the available  literature
cited  In  Appendix A.   However,  workers  In  munitions plants  when trinltro-
phenylmethylnltramlne was  manufactured are  believed to have  been  exposed to
this compound by Inhalation (Hardy and Mai oof, 1950).
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3.4.   DERMAL
    Quantitative  data  regarding  dermal   exposure  to  trlnHrophenylmethyl-
nHranrne  were  not  located In the available  literature  cited  In Appendix A.
Howevei, workers  In munitions plants  when trlnltrophenylmethylnHramlne  was
manufactured are believed  to  have  been dermally  exposed  to this compound, as
evidenced  by skin and hair discoloration (Hardy and Haloof, 1950).
3.5.   OTHER
    Pertinent  data  regarding  other   routes  of  human  exposure  to  trlnltro-
phenyln,ethyln1tram1ne were  not  located 1n the available  literature  cited In
Appendix A.
3.6.   SUMMARY
    Little  quantitative  data  on  human   exposure  to  trlnltrophenylmethyl-
nltramlne  were  located 1n  the  available  literature.  Occupational  exposure
to  trliltrophenylmethylnltramlne  when  It was  manufactured  Is believed  to
have occurred as a  result  of  dermal  contact  and  Inhalation for those working
In or  around  the areas where trlnltrophenylmethylnltramlne was  produced  and
packaged (Hardy and Maloof, 1950).
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                         4.  ENVIRONMENTAL TOXICOLOGY
4.1.   AQUATIC TOXICOLOGY
4.1.1.   Acute  Toxic  Effects  on  Fauna.   Pertinent  data   regarding   the
effects  of  acute  exposure of aquatic  fauna  to  trlnUrophenylmethylnltramlne
were not located 1n the available literature cited In Appendix  A.
4.1.2.   Chronic Effects on Fauna.
    4.1.2.1.   TOXICITY — Pertinent data  regarding  the  effects  of  chronic
exposure of  aquatic  fauna to trlnltrophenylmethylnltramlne were  not  located
In the available literature cited 1n Appendix A.
    4.1.2.2.   BIOACCUMULATION/BIOCONCENTRATION  - Pertinent  data  regarding
the   b1oaccumulat1on/b1oconcentrat1on   potential   of   trlnUrophenylmethyl-
nltramlne  1n aquatic  fauna  were  not   located  In  the  available  literature
cited In Appendix A.
4.1.3.   Effects on Flora.
    4.1.3.1.   TOXICITY — Pertinent data  regarding  the  toxic  effects  of
exposure of  aquatic  flora to trlnltrophenylmethylnUramlne were  not  located
In the available literature cited In Appendix A.
    4.1.3.2.   BIOCONCENTRATION — Pertinent data regarding  the  bloconcen-
tratlon potential of  trlnltrophenylmethylnUramlne  1n aquatic  flora were  not
located 1n the available literature cited In Appendix A.
4.1.4.   Effects  on   Bacteria.   Pertinent  data  regarding the  effects  of
exposure  of  aquatic   bacterial   to  trlnltrophenylmethylnltramlne  were  not
located In the available literature cited 1n Appendix A.
4.2.   TERRESTRIAL TOXICOLOGY
4.2.1.   Effects  on   Fauna.   Pertinent   data   regarding  the   effects  of
exposure  of  terrestrial   fauna   to  trlnltrophenylmethylnltramlne  were  not
located 1n the available literature dted In Appendix A.
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4.2.2.   Effects  on  Flora.   Pertinent   data   regarding   the  effects  of
exposure  of  terrestrial   flora   to  trlnltrophenylmethylnHramlne  were not
located In the available literature cited  In  Appendix  A.
4.3.   FIELD STUDIES
    Pe-tlnent data  regarding  the  effects  of  trlnltrophenylmethylnHramlne on
flora and  fauna In  the  field were not located  In the available  literature
cited in Appendix A.
4.4.   AQUATIC RISK ASSESSMENT
    No  data were  available  regarding  the effects  of exposure  of aquatic
fauna ind  flora  to  trlnUrophenylmethylnltramlne,  preventing the development
of freihwater and saltwater criteria  by the method  of  U.S.  EPA/OWRS  (1986).
4.5.   SUMMARY
    Pertinent data  regarding the  environmental  toxldty  of tMnltrophenyl-
methylrHramlne  were  not   located  In  the  available  literature  cited  In
Appendix A.
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                             5.  PHARHACOKINETICS
 5.1.   ABSORPTION
    Pertinent data  regarding  the rate and extent of absorption  of  trlnltro-
 phenylmethylnltramlne were  not located In the available  literature  dted  In
 Appendix  A.   Nevertheless,  Indirect  evidence  for  absorption Is  provided  by
 the Induction of adverse  effects  1n  several  organs  and tissues  In humans and
 experimental  animals  after  exposure  to  trinltrophenylmethylnltramlne  by
 various routes  (Chapter 6).   Zambrano and  Mandovano (1956)  administered tri-
 nltrophenylmethylnltramlne by  gavage to rabbits (Section 5.3.)  and  reported
 that  trinltrophenylmethylnltramlne  may have  been   poorly  absorbed  from the
 digestive tract because the metabolite  plcramlc  acid was  not detected In the
 urine until  after  several days of treatment, with  a cumulative  dose of >100
 centigrams   (1 g)   trlnltrophenylmethylnHramlne.   The   Investigators   also
 noted, however, that other routes of excretion  were not  Investigated In this
 study.    Hawley   (1981)  reported   that  trinltrophenylmethylnltramlne  Is
absorbed through the skin (species not specified).
 5.2!.   DISTRIBUTION
    Pertinent  data  regarding   the   distribution   of   trlnltrophenylmethyl-
 nUramlne were not  located  In the available literature cited  1n Appendix  A.
Adverse  effects  observed primarily  1n  the  liver,  kidneys and  spleen  of
animals exposed to  trinltrophenylmethylnltramlne Indicate possible distribu-
 tion  of  the chemical  (or  a  metabolite)  Into those  organs  and  tissues
 (Chapter 6).
5.3.   METABOLISM
    Zambrano  and  Handovano  (1956)   administered dally  gavage  doses of  10
centigrams  (100 mg)  of  tHnUrophenylmethylnltramlne mixed  with  dextrose  to
a group  of  seven rabbits (sex  and   strain not  reported)  for >30  days.   The
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levels  of  picric   add,  plcramlc  add  and  sulfoconjugated  products were
measured  In  the  urine  both  before the  treatments and  at  "regular  Intervals"
during  treatment.   Two  untreated  rabbits (controls)  were  monitored for  30
days.  Since the reported mean  body weight of the  rabbits was  -2.8 kg,  dally
doses of  36  mg/kg  of  trlnltrophenylmethylnltramlne can be estimated.   Picric
add  rfas  not  detected  In  the  urine  of  any   treated  or  control  rabbit.
Plcranlc  add,  however,  appeared  In  the  urine  of all  treated animals at a
level >0.05  mg/i,   but  only after  Ingestlon  of  a  cumulative  dose of >100
centigrams  trlnltrophenylmethylnltramlne   (1 g);  none  was   detected  before
treatment  or  1n  the  controls.   SC products (not  specified)  Increased with
relation  to  TS,  with the SC/TS ratios  ranging  from 3.7-8X  before  treatment
and  7 09-28.1% after  30 days of  treatment.  The two control  rabbits  showed
no  Increase  In this ratio.   The Investigators  reported that the presence  of
plcrarrlc  acid  In  the  urine of treated rabbits reflected  the oxidation  of
trlnltrophenylmethylnltramlne to picric add  and the  subsequent transforma-
tion  3f  picric  acid  to  plcramlc  add   (Figure  5-1).   According  to the
authors,  picric  acid was not   detected  1n  the  urine  of  any  treated  animal
because  It was present  at  a level too  low  for  detection  (<0.33 mg/i) or  It
was  ompletely   converted  to  plcramlc  add  In  the  body.   The   Increased
presence  of  sulfoconjugatlon   products  In  the   urine,  as  compared  with
pretreatment values,  suggested  that  plcramlc add  was also  present In the
conjugated'form (Zambrano and Nandovano, 19S6).
5.4.   EXCRETION
    Zanbrano and  Handovano  (1956) analyzed  the  presence   of  picric add,
plcramlc  acid and   sulfoconjugated products  1n  the urine of rabbits admin-
istered   dally doses of  trlnltrophenylmethylnltramlne  by gavage (see  Section
5.3.).  The Identification of plcramlc  add and sulfoconjugatlon products  Is


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                                FIGURE 5-1
                 Metabolism of TMnUrophenylmethylnUramlne
                    Source:  Zambrano and Handovano, 1956
                                                                            
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qua "M at We  evidence  for  urinary excretion, but quantitative data  regarding
rate «,nd extent were not available.   No other  excretion  routes were  examined.
5.5.   SUMMARY
    Smdles  to determine  the  pharmacoklnetlc  properties of  trlnltrophenyl-
methy'nHramlne have  been  performed only  In rabbits  (Zambrano and Mandovano,
1956).   Tr1n1trophenylmethyln1tram1ne  Is  absorbed   through  the   digestive
tract;  however,  data  were  not  sufficient to  estimate  the  rate and extent.
It  maf,  however,  be  poorly absorbed  because  the metabolite  plcramlc  acid
does  not  appear  In   the   urine  of  rabbits   until  after  several   days  of
treatment.   Metabolism  of  tMnltrophenylmethylnltramlne In  rabbits  Involved
the   ransformatlon   of  the   material   to  picric   acid,  which  was  then
transformed  to  plcramlc  acid.   Plcramlc add  was also  present  In the urine
of  mbblts,   1n   the  sulfoconjugated  form.    The   only  excretion  route
Investigated was  the  urine, and plcramlc  add and  sulfoconjugates  were the
only netabolUes detected (Zambrano  and Mandovano, 1956).
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                                  6.   EFFECTS
6.1.   SYSTEMIC TOXICITY
6.1.1.   Inhalation  Exposure.   Pertinent  data regarding Inhalation  exposure
to  trlnltrophenylmethylnltramlne  were not  located  In the available  litera-
ture cited In Appendix A.
6.1.2.   Oral Exposure.
    6.1.2.1.   SUBCHRONIC -- Oanlele   (1964)    examined   the   effects    of
trlnltrophenylmethylnltramlne  on  blood coagulation  factors  In  rabbits.   In
this  study,   12  rabbits  (sex  and  strain  not  reported)  were  administered
trlnltrophenylmethylnltramlne  (purity  not  reported)  by gavage  In doses  of
125  mg/kg/day for  6 months.   Three  untreated  rabbits  served  as  controls.
Indices  of coagulation  mechanisms  were  not  significantly  altered after  3
months  of   treatment.    After  6  months  of  treatment  significant  changes.
Indicative of low coagulability, were observed.
    Fatl  and  Danlele  (1965)  examined  the   hlstopathologlcal   changes   In
selected organs  of  12 male  rabbits  (strain not reported) after  exposure  to
trlnltrophenylmethylnltramlne  (purity  not  reported)  doses  of 125  mg/kg/day
by gavage  for 6 (three  rabbits)  or  9 months  (nine  rabbits).  Gross  altera-
tions  In the  liver  were limited  to  an Increase In consistency  of  the organ
In 2/9 rabbits  treated  for  9 months.  After 6 months  of treatment,  hUto-
pathologlcal  examination of  the  liver  revealed  hepatocyte  swelling.    In
addition,  rabbits  treated for  9 months  had  circumscribed  necrosis of  the
liver.   There  was   also  evidence  of  vascular congestion  and  hyperplaslc
Kuppfer  cells.   Treatment with  tHnltrophenylmethylnUramlne did  not cause
gross  alterations  In  the  kidneys.   Microscopic alterations  In  the  kidneys
were limited  to  rabbits treated  for  9 months and Included mild congestion,
tubular  distress  (turbid  swelling  and  vacuolar  degeneration)  and  swollen
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cells  with  opaque  and  granular  or  vacuo11 zed  protoplasm.   Macroscopic
examliatlon  of  the spleen at  6 months revealed  signs  of congestion, slight
thickening  of  the  capsula,  and  atrophy  of  the  lymphatic  follicles  with a
moderate  degree  of hemoslderosls.  Macro- and microscopic  evaluation of the
heart,  lungs and  Intestinal  mucosa revealed no  alterations  attributable to
trlnllrophenylmethylnltramlne.
    Ztmbrano and  Mandovano  (1956) administered tr1n1trophenylmethyln1tram1ne
(presimably  by  gavage)  mixed with dextrose  to a  group  of seven rabbits (sex
and  s :ra1n  not  reported) 1n  doses  of 10 centigrams  (100 mg)/rabb1t/day for
>30  days.   Two  untreated  rabbits  were  used  as  controls,  but  1t  was  not
statec  If  they  received dextrose alone.  From data  provided by the Investi-
gators,  an average  body weight  of 2.8  kg  was  calculated for  the  exposed
rabbits;  therefore,  the  dose  of trlnltrophenylmethylnltramlne  received  by
each rabbit  can be estimated  as 36  mg/kg/day.   The only reported detrimental
effect was  weight  loss  after 2-3 months.  No  other  endpolnts were examined.
Statistical  analysis  was not  performed,  and  the exact  length  of  treatment
was not reported.
    6.1.2.2.   CHRONIC — Pertinent data  regarding chronic oral  exposure  to
trlnltrophenylmethylnltramlne  were  not located  In the  available literature
cited In Appendix A.
6.1.3.   Other  Relevant  Information.   Parmegglanl  et   al.   (1956)  examined
the effects  of  dally  oral administration  of  trlnltrophenylmethylnltramlne to
rats (sex,  strain and number  of rats  not  reported) In doses between 0.05 and
2.0 g/kg  bw; It Is not  clear  If dosing was by gavage  or dietary.   Although
not  c  early stated,  H  appears  that  hlstologkal  examination  of  selected
organs  was  performed.   A  single dose of   1  g/kg resulted  1n  no  effects;
however,  1  g/kg  administered  for  3  days   resulted  1n  degenerative  kidney

0244d                               -19-                             11/02/89

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 effects  but no  effects  In liver  or  spleen,  and the  same  dose administered
 for  10-14  days  resulted  In  mortality  and  lesions  of  the   renal  tubular
 epithelium.   A  dose of  2  g/kg  resulted  In prollferatlve  changes  1n  the
 liver,  tubular  epithelial  swelling   In  the  kidney  and  hemoslderosls  and
 atrophlc  changes  1n the  spleen.   A  dose  of 0.25  g/kg  of  tMnltrophenyl-
 methylnltramlne  for  15 days resulted in degenerative changes 1n the kidney.
    Guarlno and  Zamblano  (1957)  treated rabbits (sex,  strain  and  number  not
 reported)  orally with trlnltrophenylmethylnltramlne doses of  0.250 g/kg  bw;
 dosing schedule,  vehicle,  and  duration of treatment were  not  reported.   The
 liver  appeared  to be  the most  affected  organ,  with turbid swelling of  the
 epithelium, necrotlc foci  and  lobule  enlargement  evident.  The  kidneys  and
 the spleen  were  also affected with turbid swelling  and degenerative  changes
 In the convoluted tubules,  and congestion,  hemoslderln pigments, hyperplasla
 and macrophaglc cells In the spleen.
    Hells  et   al.  (1920)   evaluated  the  toxlclty   of  trlnltrophenylmethyl-
 nltramlne  In  dogs and rabbits  (total  number  of animals,  sex  and  strain  not
 reported).   Five  dally  doses  of  0.1  g/kg  trlnltrophenylmethylnltramlne
 administered  subcutaneously In  olive  oil  to a  dog  resulted  In  mortality
 after  15  days.   A single  subcutaneous  dose  of 2.5 g/kg, however, was  not
 lethal, whereas  5 g/kg  resulted  In death  within  18  hours.   Rabbits  admin-
 istered 1 g/kg of  trlnUrophenylmethylnltramlne  1n milk by gavage died  after
 1-3  doses;   however,   the  same   amount  administered  subcutaneously   was
 generally not fatal  until 6-10 doses had been administered.   Gross necropsy
 revealed  mild  nephritis   In  the   dogs.   Microscopic  examination  revealed
 Inflammation at  the  Injection  site In  both dogs  and  rabbits  exposed subcuta-
 neously.   The  kidneys  of  the  animals  showed  evidence  of  toxic degeneration
with swollen eplthella and  areas of necrosis  In  the  convoluted tubules.   Fat
 granules  were detected In  the  epithelium  of  the  Loop of Henle In dogs  only.
0244d
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Similarly,  liver  effects  (necrosis, fatty  degeneration  and fat In  the  bile
duct  epithelium)  were  detected only In dogs.  Edema was  also  evident  In the
lungs  and bronchi of several rabbits (exposure route not reported}.
    Oc:upat1onal  exposure  data  from  munitions  factories consistently  Indi-
cated  that  trlnltrophenylmethylnltramlne  caused contact  dermatitis  (persons
with  clly  skin Incurred the  greatest  reactions),  yellowing of the  hair  and
skin,  swelling of the  face and  hands, asthma-like coughing,  pharyngeal  and
nasal   Irritation,   nosebleeds,  nausea,   cramps   and   vomiting,   malaise,
menstrjal problems,  weight loss, liver atrophy  and spleen  effects,  Irrita-
bility,  headaches,  abdominal  swelling  and  dyspnea   In  workers   handling
tr1n1t-ophenylmethyln1tram1ne  pellets  or  packing  the powder  (Andersen  et
al.,  1942;  Bergman,  1952;  Brabham,  1943;  CMpps,  1917; Eddy,  1943;  Fischer
and Hurdock,  1946;  Goh, 1984; Hardy  and  Maloof,  1950; Hilton  and  Swanston,
1941;  Murray  et al., 1944; Parmegg1an1,  1983;  Probst  et al.,  1944;  Ruxton,
1917;  Silver,  1938; Smith,   1916;   Troup,  1946;   WUkowsk!  et  al.,  1942;
Zambrano  and  Redone,   1955).   The  specific  routes   of  exposure,   exposure
durations and levels were  not  clearly  reported.   WUkowskl  et  al.  (1942)
noted    that    trlnltrophenylmethylnHramlne-lnduced    dermatitis    normally
appeared between  the second  and third week  of  exposure.  Nitkowski et  al.
(1942) also noted that  -23X of 5000 workers  exposed to trlnltrophenylmethyl-
nltram'ne developed  toxic  reactions,  and   75X  of  these affected workers  had
deflnlle "trlnHrophenylmethylnltramlne dermatitis."
    Parmegg1an1 (1983)  described the  manifestations of acute  and  prolonged
occupational  exposure  to  trlnltrophenylmethylnUramlne as  follows.   Initial
exposure to the compound results  1n the discoloration  of  skin  and hair,  and
pharyngeal   and nasal Irritation.   "Severe"  exposure may cause conjunctlvae
0244d                               -21-                             09/13/89

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effects  and edema.  High  dust  concentrations  may result  In  headaches,  nose-
bleeds,  respiratory problems,  diarrhea  and  menstrual  disorders  In  workers
exposed  for only 3-4 days.   Dermatitis,  however, develops  during  the  first
2-3  weeks  and may  spread  and  worsen following  further  exposure,  especially
In workers  with  poor  hygiene or  fair skin.   "Severe  and prolonged" exposure
may  result  1n digestive  disorders,  weight loss, hepatitis,  central  nervous
system Irritation,  leukocytosls and anemia.
    Goh  (1984)  reported  a case  of  dermal sens1t1zat1on  to tMnltrophenyl-
methylnltramlne  1n  an  employee  at  an ammunition  factory.   The  Individual
                                                                t
developed yellow  discoloration  of the hands,  swelling  of the  lips,  fingers
and  hands,  and  a   rash  on the neck  following contact  with trlnltrophenyl-
methylnltramlne, TNT and  cyclotrlmethylene tr1n1tram1ne  (RDX).   A  patch test
with  trlnltrophenylmethylnltramlne as a  0.01, 0.05, 0.1  or  0.5X w/w  mixture
In petroleum  for 48 or  96 hours yielded  positive reactions at concentrations
>0.01X for  96 hours and  >0.05X for  48  hours.  The test  compound  mixed with
olive  oil  or acetone  did not  result  1n  a  positive  reaction.  The  patient
also  had a positive reaction  to TNT  (5% w/w  In petroleum) but  a negative
reaction  to  RDX (1%  w/w  In  petroleum).   Goh  (1984)   suggested that  the
patient  exhibited  signs   of  trlnltrophenylmethylnltramlne  rather  than  TNT
allergy,  and that  the  positive reaction to  TNT was  a  result  of  cross-
sensitivity because of  the similar chemical structure.
    Sens1t1zat1on  to  trlnltrophenylmethylnltramlne  was  also  reported  In
laboratory  animals.  Four  female  and  four  male  guinea pigs  (strain  not
reported) were exposed  to the test compound  as  a "smoke" created  by  blowing
compressed  air  through  a 10X  solution of  the  compound In acetone  (Gell,
1944).   The  Investigator  estimated  that  the  chambers   contained  trlnltro-
phenylmethylnltramlne  at  a  concentration   of   0.4  mg/t  as   measured  by
0244d
-22-
11/02/89

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colorlitetMc analysis,  with a maximum  particle  size of  2-3  pm.   The guinea
pigs vere  exposed for  six  30-m1nute  treatments  over 14  days;  the treatment
frequeides were  not reported.  The Investigator estimated  that  each guinea
pig  "absorbed" a  cumulative dose  of  7-10 mg of tr1n1trophenylmethyln1tram1ne
based  on an average ventilation  rate  of  6-8  I/hour  for  the 250 g  guinea
pigs.   The  actual  dose  cannot   be  determined  because  the  exposure  was
appareitly  "whole  body" and oral. Inhalation  or  dermal absorption may  have
occurred.   Further  details  regarding the  protocol  were not  provided.   Gell
(1944) concluded  that  the path of sensltlzatlon 1s  through  the  lungs  rather
than  Ihe skin, because a  skin  reaction was elicited  1n only 1/8  animals,
wherea; anaphylactlc sensitivity was  observed In  6/8.
6.2.   CARCINOGENICITY
6.2.1.   Inhalation.   Pertinent  data  regarding  the  Inhalation   cardnogen-
Iclty  of  trlnltrophenylmethylnltramlne  were not  located  In the  available
11tera:ure cited In Appendix A.
6.2.2.   Oral.    GMswold   et  al.   (1968)  evaluated  the   carclnogenldty
(primarily  mammary  gland  cancer)  of  tr1n1trophenylmethyln1tram1ne  In  rats.
In  this  study,  20  female  Sprague-Dawley  rats  received 10  equal doses  of
trlnlti ophenylmethylnltramlne  (purity not  reported)  dissolved 1n  sesame oil
by  gavage  at  the maximum  tolerated level  of  40  mg/rat;  the   total  dose,
admlnV tered over  a  30-day period,  was  400 mg/rat.   Assuming  a  reference
body w>1gh4 of 0.35  kg for rats  (U.S.  EPA,  1980),  the  dose of 40 mg/rat  of
trlnlti ophenylmethylnltramlne  Is  equivalent  to  114  mg/kg  body  weight.   A
group  jf  140 rats  received the  vehicle  alone,  and  40  wet-e given a  single
dose  cf   18 mg  of  7,l2-d1methylbenz[a]anthracene   and  served  as  positive
centre's.  One treated  rat  died  before  45 days and  was  not  necropsled.   Two
treatec  rats  that died  after  45 days were  necropsled  after death.  The  17


0244d                               -23-                             11/02/89

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 surviving  rats  were  sacrificed  9 months  later.   Among the 19  treated  rats
 examined,  one case  of  mammary gland hyperplasla  and  one of adenoma  of  the
 stomach   were  observed.    Three  mammary  carcinomas  were   found   In   127
 necropsled  negative  controls  (vehicle alone).   The  statistical  significance
 of the lesions was not reported.
 6.2.3.   Other  Relevant  Information.   Other  pertinent  data  regarding  the
 cardnogenlclty  of  trlnltrophenylmethylnltramlne  were  not  located   In  the
 available literature cited 1n Appendix A.
 6.3.   MUTAGENICITY
    Data  regarding  the  mutagenldty of  trlnltrophenylmethylnltramlne  are
 presented  In  Table  6-1.   Trlnltrophenylmethylnltramlne  caused  dose-related
 Increases  In  reverse  mutations  In  Salmonella  typhlmurlum  (Kawal  et  al.,
 1987;  McGregor  et  al.,  1980;  Whong et  al., 1980a)  and  Neurospora  crassa
 (Whong  et  al.,  1980a).   The  presence  of the  S-9  activation  system often
 resulted  In  no  mutations  or   a  reduced  mutagenlc activity  In  Salmonella
 (McGregor et  al.,  1980; Whong  et  al., 1980a).  Trlnltrophenylmethylnltramlne
also  produced mltotlc  recombination  In  tests  with  yeast  (Whong  et  al.,
 1980a; McGregor  et al.,  1980).   Mltotlc  recombination was not  found  1n  the
 presence of the S-9 activation system (McGregor et al., 1980).
6.4.   DEVELOPMENTAL TOXICITY
    Pertinent  data  regarding   the   teratogenlclty  of  trlnltrophenylmethyl-
 nltramlne -were not located 1n the available literature cited In Appendix A.
 6.!>.   OTHER REPRODUCTIVE  EFFECTS
    Pertinent  data  regarding  the  reproductive   effects  of  trlnltrophenyl-
methylnltramlne  were  not  located   1n   the   available  literature  cited  1n
Appendix A.
0244d
-24-
10/23/90

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6.6.   SUHMARY
    TMnltrophenylmethylnltramlne was  not  carcinogenic  when administered to
femal* Sprague-Dawley  rats  by gavage  1n  10 doses of  40  mg/rat (1H mg/kg)
over  ,i  30-day period (Grlswold  et  al.,  1968).   The  brevity of the observa-
tion  ;ier1od  (9 months),  the  small  sample sizes and  lack  of multiple doses
precludes any conclusions about potential  cardnogenldty.
    Trinltrophenylmethylnltramlne   was   found   to  be   genotoxlc   In   S.
typhlnuMum. S. cerevlslae and N. crassa (Whong et al., 1980a;  Kawal et al.,
1987; McGregor et  al.,  1980).   Genotoxldty  was reduced or not found In the
preserce of S-9 activation.
    Pertinent  data  regarding  teratogenlc  and other  reproductive  effects of
tr1n1trophenylmethylnHram1ne  were not  located In  the available  literature.
    ToxicHy  data   Indicate  that  exposure  to  tr1n1trophenylmethyln1tram1ne
results  In  toxic effects  1n  rabbits (Danlele,  1964;  Fat1  and Danlele, 1965;
Guarlno and Zambrano, 1957), dogs (Wells et al., 1920) and  rats (Parmeglannl
et al.,  1956), and  the  liver,  kidney,  spleen and blood are  the  most affected
organs.  In rats, a  single oral  dose of 1000 mg/kg did not  produce toxldty;
however,  the  same  dose  repeated  10 times was  lethal  (administration route
not specified) (Parmeglannl  et al,, 1956).  Subcutaneous administration of a
single dose  of 5000 mg/kg Induced death In dogs  In  18  hours (Hells  et al.,
1920).
    Data regarding  subchronk  exposure to tMnltrophenylmethylnUramlne are
limited  to  studies using rabbits  (Danlele,  1964; Fat1 and Danlele,  1965).
In  this  species,  administration  of  125  mg/kg/day  (only  dose  tested)  by
gavage for  6-9  months  produced  alterations  In coagulation  parameters,  as
well  
-------
    Tlje   toxlclty  of  tr1n1trophenylmethylnKram1ne  following  occupational
exposure  was  evaluated  by  several  Investigators  (Andersen  et  a!.,  1942;
Bergman,  1952;  Brabham,  1943;  Crlpps,  1917;  Eddy,  1943;  Fischer  and  Murdock,
1946;  Goh,  1984; Hardy  and  Maloof,  1950;  Hilton and Swanston,  1941;  Hurray
et  al.,  1944;  Parmegglanl,  1983; Probst et  al.,  1944;  Ruxton,  1917;  Silver,
1938;  Smith, 1916; Troup, 1946;  Nitkowski  et al..  1942;  Zambrano and Pedone,
1955);  however,  the  routes,  durations  and  levels  of  exposure  were  not
reported  In  these  case studies.    Consistently   reported  effects  Include
dermal  reactions,  dermal   sens1t1zat1on,  respiratory  Irritation,  dyspnea,
abdominal  effects,  menstrual   problems,  weight   loss,   liver   and  spleen
effects, headaches, Irritability and general  malaise.
0244d
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                     7.   EXISTING GUIDELINES AND STANDARDS
7.1.   HUMAN
    ACilH  (1988)  reports  an  adopted TWA for trlnltrophenyliriethylnltramlne of
1.5  nu/m3.   This  recommendation  Is  based largely  on  the  dermal  effects
described  by  Probst  et al.  (1944)  and Bergman  (1952)  In  reviews  of  occupa-
tional  exposure reports  (ACGIH,  1986).  OSHA  (1989)  established  a PEL  for
tMnlti ophenylmethylnltramlne of 0.1 mg/m3 TWA.
7.2.   AQUATIC
    Gu dellnes  and  standards  to  protect   aquatic  life  from  exposure  to
trlnltrophenylmethylnHranilne were  not  located  In the  available  literature
cited  'n Appendix A.
0244d                               -29-                             09/13/89

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                              8.   RISK  ASSESSMENT
8.1.   CARCINOGENICITY
8.1.1.   Inhalation.   Pertinent  data  regarding the  Inhalation carcinogen-
IcHy  of  trlnltrophenylmethylnltramlne  were not  "located  1n  the  available
literature cited In Appendix A.
8.1.2.   Oral.   The  oral   carclnogenlclty  of  trlnltrophenylmethylnltramlne
was  evaluated In  female  Sprague-Oawley rats administered  the substance  by
gavage In  sesame oil  In 10  doses  of  40 mg/rat over  30 days  (Grlswold et  a!.,
1968).   Assuming  a  reference  body weight  of  0.35  kg for  rats  (U.S.  EPA,
1980), the dose  of 40 mg/rat  Is equivalent  to  114 mg/kg/day.   The  rats  were
necropsled 9  months  after   treatment  started.   One  case  of  mammary  gland
hyperplasla and one  of adenoma of  the  stomach were  observed In a  total  of  19
rats examined.  In  a total  of 127 rats  necropsled  that received  the vehicle
alone, three  mammary carcinomas  were  reported.  Administration of  trlnHro-
phenylmethylnltramlne was  not carcinogenic  to  rats  under  the  conditions  of
the  study.   The study was,  however,  of  Inadequate  duration to show either
the presence or absence of carcinogenic activity.
8.1.3.   Other  Routes.    Pertinent  data  regarding  the  carclnogenlclty  of
trlnltrophenylmethylnUramlne administered  by other  routes were not located
In the available literature cited In Appendix A.
8.1.4.   Height of  Evidence.   No  data  were available  regarding the carclno-
genlclty of trlnltrophenylmethylnltramlne  In  humans.   The animal  carclnogen-
lclty data are  limited  to negative results  In  female  rats  (Grlswold et  al.,
1968), but this  study was of  Inadequate duration for  evaluating  carclnogen-
lclty.  Trlnltrophenylmethylnltramlne  was  mutagenlc when  tested In  bacterial
systems but has not  been  tested  In  mammalian systems.   Trlnltrophenylmethyl-
nltramlne  can be  placed  1n  U.S.  EPA  Group  D,  not  classifiable as  to  human
carclnogenlclty {U.S. EPA, 1986b).
0244d
-30-
10/23/90

-------
8.1.5.   Quantitative  Risk  Estimates.  The  lack  of positive  data  precludes
estimation  of carcinogenic  potencies for  trlnltrophenylmethylnltramlne for
either Inhalation or oral exposure.
8.2.   SYSTEMIC TOXICITY
8.2.1.   Inhalation  Exposure.   Pertinent  data  regarding  Inhalation exposure
to   tr1n1trophenylmethyln1tram1ne  were   not   located   In   the  available
I1tera:ure cited In Appendix A.
8.2.2.   Oral Exposure.
    8.;!.2.1.   LESS  THAN LIFETIME  (SUBCHRONIC) - Three subchronlc  studies
have  bsen  performed with  trlnltrophenylmethylnltramlne  In  rabbits.   In the
study  )y  Zambrano  and Handovano  (1956),  rabbits exhibited  weight  loss (not
quant It led) when  treated with an  estimated  dose of  36  mg/kg/day (only dose
level  tested) by  gavage for  an  unspecified  period  of  time  >30  days.   No
other (ffects were reported.
    Darlele  (1964)  administered  a  dose  of  125  mg/kg/day   (only dose  level
tested] to  rabbits by  gavage for  6  months.   Only blood  coagulation param-
eters  i*ere  examined.   Significant  alterations,  Indicative of  an  Increased
clotting  time,  were  observed after 6  months  of  treatment  (Rec.  #2  1n
Appendix C).
    Fat1 and  Danlele  (1965)  reported  that rabbits  administered  doses  of 125
mg/kg/day  (only  dose  level  tested)  by gavage  for 9 months,  had hepatocyte
swelling,  hyperplasla and necrosis  of the liver (Rec.  #1  1n Appendix C).  In
addltloi,  In  three of the  rabbits  treated for 9 months mild  kidney conges-
tion  with  swelling of the  convoluted tubules  and  vacuolar  degeneration was
observej.    Moderate  hemoslderosls  was present In the  spleen.  No  effects
were observed In heart, lungs and Intestinal  mucosa.
0244d                               -31-                             09/13/89

-------
     The  study by  Zambrano  and Mandovano  (1956)  Is  not suitable  for  use 1n
 risk assessment  because  adequate  endpolnts of  toxlclty were not examined and
 treatment  duration was not  clearly stated.  The  study conducted  by Fat1 and
 Darlele  (1965)  Is the most  complete  of the three  studies  summarized.  From
 this  study,  a LOAEL of  125 mg/kg/day  (Rec.  #2  1n Appendix  C) can be defined
 for  hepatic, renal and  spleen effects.   Applying  an uncertainty  factor of
 1000  (10  to  reflect  the  use  of a LOAEL Instead of NOAEL, 10 for Interspedes
 extrapolation and  10  to  protect  the more  sensitive Individuals) to the LOAEL
 of   125  mg/kg/day  results   In a  provisional   subchronlc   oral  RfD  of  0.1
 mg/kg/day.
     Confidence  In the data  base  In  low,  largely  because  only  one  species
 (rabbits)  has been studied  In subchronlc experiments,  data  on reproductive
 toxlclty  are lacking, and  chronic data were  not available.   Confidence In
 the  key  study Is  low, because only one dose level was  tested and endpolnts
 other  than histology  of  selected organs  were  not examined.   Confidence 1n
 the  RfD   Is  low,  because,  In  the study  by Fatl  and Danlele  (1965).  body
weight was not  examined,  and there  1s an  Indication that effects  of  body
weight  may  occur  with   doses  below   the  LOAEL  chosen as   basis  for  the
 provisional RfO (Zambrano and Mandovano, 1956).
    8.2.2.2.   CHRONIC — Pertinent data  regarding the  toxlclty  of  chronic
 oral  exposure  to  trinltrophenylmethylnltramlne  were  not   located  In  the
available  literature cited In  Appendix  A.   In  the absence  of chronic data, a
provisional  RfD   for  chronic  oral  exposure can  be  derived  by  applying an
additional uncertainty factor  of  10 to the  subchronlc oral  RfD to expand to
chronic exposure.   This  calculation  results In  a  chronic  oral  RfD  of  0.01
mg/kg/day.   Confidence In  the data base  and key study  Is  low, as discussed
above.
0244d
-32-
11/02/89

-------
                           9.   REPORTA8LE  QUANTITIES
9.1.   BASED ON SYSTEMIC TOXICITY
    The  toxlclty  of  tr1n1trophenylmethyln1tram1ne was  discussed  1n  Chapter
6,  and  dose-response  data considered  for  CS derivation  are summarized  1n
Table  9-1.   Since  no  chronic  data  were  available,  subchronlc  data  were
considered.  The  study by Zambrano and  Mandovano  (1956) was not  considered
because the reporting of the protocol  was Incomplete.
    Effects attributed  to  subchronlc  oral exposure to  trlnHrophenylmethyl-
nltranlne   are  liver   necrosis   (RV =6),   kidney   degeneration   (RV  =6),
                                      t?                                6
spleen  pigmentation  (hemoslderosls)  (RV =5)  and  altered  blood  coagulation
parameters  (RVe=2)  (Danlele, 1964; Fat1  and Danlele, 1965).
    C!,s  and  the  corresponding  RQs  are calculated  1n  Table  9-2  for   the
effeds Identified  1n Table 9-1.  From  the  study by Fat1 and Danlele  (1965),
only  the   highest  RV  ,   associated  with  liver  and   kidney   effects,   1s
presetted In Table 9-2.
    Ir  the  derivation  of  the CSs  from  subchronlc studies, an  uncertainty
factor  of   10  was   applied  to expand  from subchronlc  to  chronic  exposure.
From  :he  two  studies  presented  1n  Table  9-2,  the  highest  CS of  10.8, which
corresponds to  an  RQ  of 1000,  1s chosen to represent the hazard  associated
with chronic exposure  to tr1n1trophenylmethyln1tram1ne  (Table 9-3).
9.2.   BASED ON CARCINOGENICITY
    Limited carclnogenlclty data, summarized 1n Section 6.2., consist  of  the
Inadecuate  study  by  Grlswold  et al.   (1968).   Additionally, data  regarding
cardrogenlcHy  1n   humans  were  lacking.    Hence,   trlnltrophenylmethyl-
nltranlne was  classified  In U.S. EPA Group D  (I.e.,  not classifiable as  to
cardrogenlcHy In humans).  No  hazard ranking or cancer-based RQ  1s  derived
for Group D substances.
0244d
-33-
10/23/90

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0244d
               -35-
09/13/89

-------
                                  TABLE 9-3
                         Trlnltrophenylmethylnltramlne
           Minimum Effective  Dose  (MED) and Reportable Quantity (RQ)
Route:
Species/sex;
Dose*:
Duration:
Effect:
RVd:
RVe:
CS:
RQ:
Reference:
oral/gavage
rabbit/male
295.6 mg/day
9 months
liver necrosis; kidney degeneration; spleen congestion
1.8
6
10.8
1000
Fat1 and Danlele, 1965
^Equivalent human dose
02444
             -36-
09/13/89

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ACGIH  (American Conference  of  Governmental  Industrial  Hyglenlsts).   1986.
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ACGIH  (American Conference  of  Governmental  Industrial  Hyglenlsts).   1988.
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Anderssn,  A.H., J.B.  Funder,   F.  Halstrom  and  A.R.  Meyer.   1942.   Unter-
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Atkinson, R.   1985.   Kinetics  and  mechanisms  of  the gas-phase  reactions  of
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Belkln,   F.,  R.W.  Bishop and H.V.  Sheely.  1985.    Analysis of  explosives  In
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Bergmar,  B.B.   1952.   Tetryl  toxlclty:  A  summary  of  10 years  experience.
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Brabhair,  V.U.   1943.   Tetryl  Illness  In munition  plants.   J.  S.  Carolina
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0244d
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Danlele,  E.   1964.   Hemocoagulatlve  modifications  In  chronic  experimental
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0244d
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0244d                               -39-                             10/23/90

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0244d                               -40-                             10/23/90   *"

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0244d                               -41 -                             10/23/90

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Frederick, MD.  p. 120-128, 131, 133, 136, 138-140.   NTIS AD-A145417.

Sax, N.I.  and  R.J.  Lewis.   1987.   Hawley's Condensed  Chemical  Dictionary,
llth ed.  Van Nostrand Relnhold Co.,  New York,  NY.   p. 1141.
Seldell,  A.   1941.   Solubilities  of organic  compounds.   Van Nostrand  Co.,
Inc., New York, NY.  p. 496.
Silver, A.L.L.   1938.   The  treatment  and prevention of  Industrial  diseases
1n filling factories.  J.  Roy. Army Med. Corp.  71: 87-96.

Small, M.J.  and  D.H.  Rosenblatt.  1974.   Munitions  production products  of
potential  'concern as waterborne pollutants  -  phase II.   In.:  Tech.  Rep.  7404.
U.S. Army Medical Bloenglneerlng  Res.  Devel.  Lab.,  Aberdeen,  MD.   101    NTIS
AD-919031.

Smith, E.   1916.   Prevention,  symptoms  and treatment of  tetryl  dermatitis.
Br. Med.  J.  1: 618.
0?44d
-42-
10/23/90

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Spangjord,  R.J.,  T.  Hill,  T.H.  Chou,  W.R.  Habey,  J.H.  Smith  and  S.  Lee.
1980.   Environmental  fate studies  on certain munition  wastewater  constitu-
ents.   U.S. Army  Medical Research and  Development  Command, Fort  Detrlck,
Frederick, ND.  p. 6-8, 10-13, 21-23, 26-27.  LSU-7934.

Swann   R.L., O.A. Laskowskl,  P.J.  McCall,  K.  Vander-Kuy  and H.J. Dlshburger.
1983.   A rapid method  for  the  estimation of  the environmental  parameters
octant1/yater  partition  coefficient,  soil  sorptlon constant,  water  to  air
ratio and water solubility.  Res. Rev.  85: 17-28.

Troup,  H.B.   1946.    Clinical  effects of  tetryl  (CE  powder).   Br.   J.  Ind.
Ned.  3: 20-23.

TSCAPP.   1989.   Computer  printout  of non-confidential production data  from
TSCA liventory.  OPTS, CID, U.S. EPA, Washington, DC.   Online 4/21/89.

U.S.  EPA.   1980.   Guidelines and  Methodology  Used  In  the Preparation  of
Health  Effect  Assessment Chapters  of  the  Consent   Decree Water  Criteria
Documents.  Federal  Register.  45(231): 79347-79357.

U.S. E!>A.   1984.  Methodology and Guidelines  for  Ranking  Chemicals  Based  on
Chronic  ToxUHy  Data.   Prepared by  the  Office  of Health  and  Environmental
Assessment, Environmental Criteria  and Assessment  Office,  Cincinnati, OH  for
the Office of Emergency and Remedial Response, Washington,  DC.
0244d                               -43-                             10/23/90

-------
 U.S.  EPA.  1986a.   Methodology  for  Evaluating  Reportable Quantity  Adjust-
 ments  Pursuant  to  CERCLA  Section  102.   Prepared  by  the  Carcinogen  Assessment
 Group,  Office  of  Health  and Environmental  Assessment  for  the  Office  of
 Emergency and Remedial Response,  Washington, DC.
U.S.  EPA.   1986b.   Guidelines  for   Carcinogen  Risk  Assessment.   Federal
Register.  51(185): 33992-34003.

U.S.  EPA/OHRS  (U.S.  Environmental Protection Agency/Office of Water  Regula-
tions  and  Standards).   1986.   Guidelines  for  Deriving  Numerical  National
Water  Quality  Criteria  for  the  Protection  of Aquatic  Organisms and  Their
Uses.  U.S. EPA. Washington, DC.  p.  22-58,  98.  NTIS PB85-227049/XAB.
Wells, H.G., J. Lwels, W.  Sansum,  W.  HcClure  and  H.  Lussky.   1920.   Toxlclty
of   tetranHromethylandrlne   (tetryl),   tetranitroxylene  (T.N.X.),   tetra-
n1tran1!1ne  (T.N.A.),  dlnltrodlchlorobezene  (Parazol)  and  metamltanlUne.
J. Ind. Hyg.   2:  247-252.
Whong, W.,  N.D.  Speclner  and  G.S. Edwards.   1980a.   Mutagenlc activity  of
tetryl,  a   nUroaromatlc   explosive.   In  three  mlcroblal   test   systems.
Toxlcol.  Lett.  5: 11-17.

Whong, W.,  N.D.  Speclner  and  G.S. Edwards.   1980b.   MutagenUHy of  poly-
nltroaromatlc explosives In mlcroblal test  systems.  Proc. Am.  Assoc.  Cancer
Res.  21: 195.
0?44d
-44-
10/23/90

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hhndhclz, M.,  S.  Budavarl,  R.F.  Blumettl  and  E.S.  Otterbeln.   1983.   The
Merck Index.  Merck  and Co.,  Inc.,  Rahuay,  NJ.   p.  942-943.
         , L.J., C.N. Fischer and D. Murdock.  1942.  Industrial Illness due
to tetryl.  J. Am.  Med.  Assoc.   119:  1406-1409.
Zajnbrano, A.  and S.  Mandovano.   1956.   Urinary  excretion of  picric  add,
plcranlc  add  and   of  sulfoconjugatlon   products   In  experimental  tetryl
poisoning.  Folia. Medlca.   39:  161-171.

Zambraio, A.  and R.  Redone.   1955.   Pathology  In workers employed  In  the
preparation  of   tetryl  1n  Italian  Industry.   Folia.  Med.  (Naples).   38:
433-45 i.
0244d
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10/23/90

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                                  APPENDIX A

                              LITERATURE SEARCHED



    This  HEED   1s  based  on  data  Identified  by  computerized  literature

 searches of  the  following:

              CHEMLINE
              TSCATS
              CASR online (U.S. EPA Chemical Activities Status Report)
              TOXLINE
              TOXLIT
              TOXLIT 65
              RTECS
              OHM TADS
              STORET
              SRC Environmental Fate Data Bases
              SANSS
              AQUIRE
              TSCAPP
              NTIS
              Federal Register
              CAS ONLINE (Chemistry and Aquatic)
              HSOB
              SCISEARCH
  „            Federal Research In Progress


These  searches  were conducted  In April.  1989,  and the  following secondary

sources were reviewed:
    ACGIH  (American  Conference of  Governmental  Industrial  Hyglenlsts).
    1986.   Documentation  of the  Threshold Limit  Values  and Biological
    Exposure Indices, 5th ed.  Cincinnati, OH.

    ACGIH  (American  Conference of  Governmental  Industrial  Hyglenlsts).
    1987.   TLVs:  Threshold  Limit  Values for  Chemical  Substances  1n the
    Work  -Environment  adopted  by   ACGIH   with   Intended  Changes  for
    1987-1988.  Cincinnati,  OH.  114 p.

    Clayton,  G.O. and  F.E.  Clayton,  Ed.   1981.   Patty's  Industrial
    Hygiene  and   Toxicology,  3rd  rev.  ed.,  Vol.  2A.   John Wiley  and
    Sons, NY.  2878 p.

    Clayton.  G.D. and  F.E.  Clayton,  Ed.   1981.   Patty's  Industrial
    Hygiene  and   Toxicology,  3rd  rev.  ed.,  Vol.  2B.   John Wiley  and
    Sons, NY.  p. 2879-3816.
0244d
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10/23/90

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    Clayton,  6.D.  and  F.E.  Clayton,  Ed.   1982.   Patty's  Industrial
    Hygiene  and  Toxicology,  3rd  rev.  ed.,  Vol.  2C.   John Wiley  and
    Sons, NY.  p. 3817-5112.

    Grayson,  M.  and 0.  Eckroth,  Ed.   1978-1984.   K1rk-0thmer  Encyclo-
    psdla of  Chemical  Technology,  3rd  ed.   John  Wiley  and Sons, NY.   23
    VDlumes.

    Hamilton, A.  and H.L.  Hardy.   1974.  Industrial  Toxicology, 3rd  ed.
    pjbllshlng Sciences Group, Inc., Littleton, MA.   575 p.

    URC  (International Agency  for  Research on  Cancer).  IARC  Hono-
    g-aphs  on  the  Evaluation  of  Carcinogenic  Risk   of  Chemicals  to
    Hjmans.   IARC, WHO, Lyons, France.

    Jiber,  H.H.,  W.R.   Mabey,  A.T.  Lieu,  T.W.  Chou  and  H.L.  Johnson.
    1)84.    Data  acquisition   for   environmental   transport  and  fate
    s:reenlng for  compounds of Interest  to  the Office of Solid  Waste.
    E'A  600/6-84-010.    NTIS  P884-243906.   SRI  International,   Menlo
    P.irk, CA.

    N"P  (National  Toxicology  Program).  1987.   Toxicology Research  and
    Testing   Program.    Chemicals   on   Standard   Protocol.   Management
    S .atus.

    Onellette,  R.P. and  J.A.  King.   1977.   Chemical  Week  Pesticide
    Register.  McGraw-Hill  Book Co., NY.

    Six, I.N.   1984.   Dangerous  Properties  of Industrial  Materials,  6th
    e< .  Van Nostrand Relnhold Co., NY.

    SH  (Stanford Research  Institute).   1987.   Directory  of  Chemical
    Producers.  Menlo Park, CA.

    U.S. EPA.   1986.    Report  on  Status  Report In  the Special  Review
    Program,  Registration  Standards  Program  and  the  Data  Call   1n
    Programs.   Registration Standards  and  the  Data  Call 1n  Programs.
    Office of Pesticide Programs, Washington, DC.

    USITC  (U.S.  International  Trade  Commission).    1986.    Synthetic
    Organic  Chemicals.   U.S.  Production  and  Sales,  1985,  USITC  Publ.
    1892, Washington,  DC.

    Verschueren.  K.   1983.  Handbook  of  Environmental Data on Organic
    Chemicals, 2nd ed.   Van Nostrand Relnhold Co.,  NY.

    Wlndholz, M., Ed.   1983.  The Merck Index,  10th  ed.   Merck  and Co.,
    In:., Rahway, NJ.

    Wo-th1ng, C.R.  and S.B. Walker,  Ed.   1983.  The  Pesticide Manual.
    British Crop Protection Council.  695  p.
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     In  addition, approximately  30 compendia  of  aquatic toxldty  data  were

 reviewed,  Including the following:


     Battelle's  Columbus  Laboratories.   1971.   Water Quality  Criteria
     Data   Book.   Volume  3.  Effects  of  Chemicals  on  Aquatic  Life.
     Selected  Data  from the  Literature  through 1968.  Prepared  for the
     U.S. EPA under Contract No. 68-01-0007.  Washington, DC.

     Johnson,  W.W.  and M.T.  Flnley.   1980.  Handbook of  Acute  Toxldty
     of  Chemicals  to  Fish   and  Aquatic   Invertebrates.   Summaries  of
     Toxlclty  Tests  Conducted  at  Columbia National  Fisheries  Research
     Laboratory.   1965-1978.   U.S.  Dept.  Interior,  Fish and  Wildlife
     Serv.  Res. Publ. 137, Washington, DC.

     McKee,  J.E.  and  M.W.  Wolf.  1963.  Water  Quality Criteria,  2nd ed.
     Prepared  for  the  Resources  Agency  of  California,  State  Water
     Quality Control Board.  Publ. No. 3-A.

     Plmental, D.  1971.   Ecological  Effects  of Pesticides on Non-Target
     Species.  Prepared for the U.S. EPA, Washington, DC.  PB-269605.

     Schneider, B.A.   1979.   Toxicology  Handbook.   Mammalian and Aquatic
     Data.   Book  1: Toxicology  Data.   Office  of Pesticide Programs, U.S.
     EPA, Washington, DC.  EPA 540/9-79-003.  NTIS PB 80-196876.
0244d
-48-
10/23/90

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0244d
-49-
10/23/90

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                                  APPENDIX C
                 DOSE/DURATION RESPONSE GRAPHS FOR EXPOSURE TO
                         TRINITROPHENYLMETHYLNITRAHINE
 C.I.    DISCUSSION
    A   dose/duratlon-response  graph  for  oral  exposure  to  trlnltrophenyl-
 methylnltramlne  generated  by the method of  Crockett  et  al. (1985) using the
 computer  software  by  Durkln and Meylan  (1988)  developed  under  contract to
 ECAO-C1nc1nnat1  Is  presented  In  Figure C-l.   Data  used to  generate  this
 graph  are presented In  Section  C.2.   In the  generation of this figure, all
 responses  are classified as adverse  (FEL, AEL or  LOAEL) or nonadverse  (NOEL
 or NOAEL)  for  plotting.
    For oral  exposure,  the  ordlnate expresses  dose as human equivalent dose.
 The animal  dose  1n mg/kg/day 1s multiplied  by the cube  root  of the ratio of
 the  animalthuman  body  weight  to   adjust  for  species  differences  In  basal
 metabolic   rate  (Mantel   and   Schnelderman,   1975).    The  result  Is   then
 multiplied  by 70 kg,  the  reference human body  weight,  to express the human
 equivalent dose as mg/day for a 70  kg human.
    The boundary for adverse  effects (solid  line)  Is  drawn  by Identifying
 tjie lowest  adverse effect  dose or  concentration at  the  shortest duration of
 exposure at which  an adverse effect  occurred.   From  this point, an Infinite
 line Is extended upward, parallel  to the dose  axis.  The starting point 1s
 then connected to  the  lowest  adverse  effect dose  or  concentration  at the
 next longer duration of exposure that has an  adverse effect  dose or concen-
 tration equal  to or  lower  than the previous  one.   This  process Is continued
 to the  lowest  adverse  effect dose  or  concentration.   From this point, a line
 1s extended to  the  right,  parallel  to  the  duration axis.   The  region of
adverse effects lies above the adverse effects boundary.
0244d
-50-
10/23/90

-------
\
V-
*
If
c
           r—,
           h
                                                            ry
        n
      	N:
                             	F5
                                                                                      I
      JFff
          3.001
                             O Mi                      P.i
                             EQ'JIV DURATION (frastii^ lif-span)
N . NOEL
L » LOAEL
A . AEL
F - PEL
Solid Line
Dashed Line
                   Adeverse  Effects  Boundary
                   »  No Adverse  Effects  Boundary
                                       FIGURE C-l

                   Dose/Duration-Response Graph for Oral  Exposure to
                  TrlnltrophenylmethylnUrantne (Envelope Data Method)
     0244d
                                   -51-
10/23/90

-------
    Using  the  envelope method,  the  boundary  for no adverse  effects  (dashed
 line)  Is drawn  by  Identifying  the highest  no  adverse effects  dose or  concen-
 tration.   From  this  point, a line parallel to  the  duration axis  Is extended
 to  the dose or  concentration axis.  The starting point  Is  then connected to
 the next lower  or  equal no adverse  effect  dose  or  concentration  at a longer
 duration of  exposure.   When this process can no  longer  be  continued, a line
 li  dropped  parallel  to the dose  or  concentration axis  to the duration axis.
 The no adverse effects  region lies below  the  no  adverse  effects  boundary.
 At  either   ends  of  the  graph  between  the adverse effects  and no  adverse
 effects boundaries  are regions  of  ambiguity.   The area (If  any)  resulting
 from  Intersection  of the  adverse effects  and no adverse  effects boundaries
 Is defined as the region of contradiction.
    In  the  censored  data method,  all no  adverse  effect  points located 1n the
 region  of  contradiction are  dropped from  consideration  and   the no  adverse
effect boundary 1s redrawn so  that  H  does  not  Intersect the adverse effects
boundary and no region of  contradiction  1s generated.    This  method  results
 In the most conservative definition of  the no adverse effects  region.
    Figure  C-l  shows  the  dose/duration-effects  graph  generated  by  the
envelope method for  oral  exposure  to  tetryl.   The  graph generated  by the
censored data method Is  not shown because  It 1s Identical  to that  generated
by  the  envelope method because of the absence of a region of contradiction.
The boundary for  no adverse effects Is  defined  by  only  one  data point, N3,
which  corresponds  to a NOEL 1n rats In  the Parmeglannl  et  al. (1956) study.
The remaining points define the region of  adverse  effects  and correspond to
 short  duration  rat  studies (A4, F5,  A6 and A7)  by  Parmeglannl et al. (19S6)
and a short duration rabbit study (F8)  by Wells  et al.  (1920).
                                           o
0244d
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10/23/90

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       DATA USED TO GENERATE DOSE/DURATION-RESPONSE GRAPHS

C.2.1    Oral Exposure.
Chemical Name:
CAS Number:
Document Title:
Tr1n1trophenylmethylnHram1ne
479-45-9
Health and Environmental Effects Document on
Tr1n1trophenylmethyln1tram1ne
Document Number:
Document Date:
Document Type: HEED
RECORE # 1: Species: Rabbits
Sex: Male
Effect: LOAEL
Route: Gavage
Number Exposed:
Number Responses:
Type of Effect:
Site of Effect:
Severity Effect:






9
NR
NECRO
LIVER
6


Dose:
Duration Exposure:
Duration Observation:

9 9
3 NR
DEGEN PIGMN
KIDNY SPLEN
6 5


125.000
9.0 months
9.0 months






Comment:       Only one  dose level was  used.   No  effects  were observed  In
               heart,   lungs  and  Intestinal  mucosa.  Moderate  hemoslderosls
 _             was evident 1n the spleen.

Citation:      Fatl and Danlele, 1965
RECORD # 2:







•
Species: Rabbits
Sex: NR
Effect: LOAEL
Route: Gavage
Number Exposed:
Number Responses:
Type of Effect:
Site of Effect:
Severity Effect:




12
NR
ENZYM
BLOOD
2
Dose: 125.000
Duration Exposure: 6.0 months
Duration Observation: 6.0 months






Commen::       Only one  dose level  was  used.
               Increased clotting time.

Citation:      Danlele,  1964
                               Changes  were  Indicative  of
0244(5
                  -53-
10/23/90

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 RECORD #3:
Comment:


Citation:
Species:
Sex:
Effect:
Route:
Rats
NR
NOEL
Oral (NOS)
Dose:                   1000.000
Duration Exposure:      1.0 days
Duration Observation:   1.0 days
Number Exposed:     NR
Number Responses:   0
Type of Effect:
Site of Effect:
Severity Effect:    6

Doses  tested  ranged from  50-2000  mg/kg/day.
of selected organs was performed.

Parmeglannl et al., 1956
                                    Only histology
RECORD # 4:



Species:
Sex:
Effect:
Route:
Rats
NR
AEL
Oral {NOS}
Dose:
Duration
Duration


Exposure:
Observation:

1000.000
3.0 days
3.0 days

Comment:

Citation:
Number Exposed:     NR
Number Responses:   NR
Type of Effect:     DE6EN
SUe of Effect:     KIDNY
Severity Effect:    6

See previous record.

Parmeglannl et al., 1956
RECORD #5:



Species:
Sex:
Effect:
Route:
Rats
NR
PEL
Oral (NOS)
Dose:
Duration
Duration


Exposure:
Observation:

1000.000
10.0 days
10.0 days

Comment:
Citation:
               Number Exposed:     NR
               Number Responses:   NR
               Type of Effect:     DEATH
               Site of Effect:     BODY
               Severity Effect:    10
See previous record.
were observed.
           Lesions In the renal tubular  epithelium
Parmeglannl et al., 1956
0244d
                     -54-
                                           10/23/90

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RECORC |6:

Commer t :
CHat'on:
RECORl # 7:

Commer t:
CHat'on:
RECORl' #8:
-
Species: Rats
Sex: NR
Effect: AEL
Route: Oral (NO!
Number Exposed:
Number Responses:
Type of Effect:
Site Of Effect:
Severity Effect:
See previous record
Parmeglannl et al. ,
Species: Rats
Sex: NR
Effect: AEL
Route: Oral,(NO!
Number Exposed:
Number Responses:
Type of Effect:
Site of Effect:
Severity Effect:
See previous record
Parmeglannl et al. ,
Species: Rabbits
Sex: NR
Effect: PEL
Route: Gavage
Number Exposed:
Number Responses:
Type of Effect:
Site of Effect:
Severity Effect:
5)
NR
NR
PROLF
LIVER
4

1956
J)
NR
NR
DEGEN
KIONY
6

1956

NR
NR
DEATH
BODY
10
Dose:
Duration Exposure:
Duration Observation:
NR NR
NR NR
HYPRT PIGMN
K1DNY SPLEN
3 4


Dose:
Duration Exposure:
Duration Observation:



Dose:
Duration Exposure:
Duration Observation:

2000.000
1.0 days
1.0 days



250.000
15.0 days
15.0 days



1000.000
3.0 days
3.0 days

Comment:       Tetryl  was  administered  1n  milk.   The   study   1s   poorly
               reported.  Necrosis  of  the  kidney  was observed,  1n  addition
               to edema In the lungs and bronchi.

C1tat on:      Wells et al., 1920
NR = Not reported
0244d
-55-
10/23/90

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                                                  o
'•.V-.3Xv>... UJ 20460

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