TOXICOLOGICAL PROFILE FOR
4-AMINO-2,6-DINITROTOLUENE
Criteria and Standards Division
Office of Drinking Water
U.S. Environmental Protection Agency
Washington, DC 20460
August 1989
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August 1989
TOXICOLOGICAL PROFILE
FOR
4-AMINO-2.6-DINITROTOLUENE
Criteria and Standards Division
Office of Drinking Water
U.S. Environmental Protection Agency
Washington, DC 20460
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4-AMINO-2,6-DINITROTOLUENE
A. GENERAL
1. CAS Number: 19406-51-0
2. RTECS Number: XU6080000
3. General Name/Svnonvms: 4-ADT
4-Methyl-3,5-dinitroaniline
4-Methyl-3,5-dintirobenzenamine
3,5-Dinitro-p-toluidine
4. Molecular Formula: C7H7N,04
5. Molecular Weight: 197
6. Structure; CH3
°2N A NO,
101
NH2
B. PHYSICAL AND CHEMICAL PROPERTIES
1. State: Yellow needles Buckingham and Donaghy (1982)
2. Vapor Pressure: No information was found.
3. Melting Point: 171°C Buckingham and Donaghy (1982)
4. Boiling Point: No information was found.
5. Specific Gravity: No information was found.
6. Solubility: No information was found.
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7. Loo Kr.: 1.06 Liuetal. (1983)
8. UV Absorption: No information was found.
C. PHYSICAL/CHEMICAL EQUILIBRIUM FACTORS:
1. Bioconcentration Factors (BCR: Liu et al. (1983) reported a steady-
state BCF of 3.76 for 4-ADT; the value was based on an estimated log
Kow.
2. Kwa: No information was found.
3. K,,,.: No information was found.
D. ENVIRONMENTAL FATE
1. Photolysis: Liu et al. (1983) demonstrated that 4-ADT (at a
concentration of 1.8 mg/L of synthetic condensate wastewater) was
readily and completely degraded by light. The wastewater sample was
photoirradiated until a 44-mg/L concentration of 2,4-dinitrotoluene
dropped to 10 mg/L (± 10%).
2. Leaching; No information was found.
3. Route of Water Contamination: No information was found.
4. Hvdrolvsis: No information was found.
5. Plant Uptake: No information was found.
6. Microbial Deoradation; No information was found.
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7. Persistence in Soil/Water; No information was found.
8. Byproducts: No information was found.
9. Vaporization: No information was found.
E. ACUTE TOXICITY IN MAMMALS
Animal/strain/sex Route
LDSO (mg/kg)
Reference
Mouse/CD-1/M
Rat/CD/M
F
Oral 1342 ± 107
(1141-1611 mg/kg)'
Oral 1495 ± 90
(1318-1713 mg/kg)
Oral 1360 ± 53
(1260-1465 mg/kg)
Oral 959 ± 76
(787-1154 mg/kg)
Ellis et al. (1980)
Ellis et al. (1980)
"95% confidence limits.
F. SKIN AND EYE IRRITATION AND SENSITIZATION IN MAMMALS
In a primary dermal and eye irritation study, 4-ADT (dose not specified)
was nonirritating to the skin and eyes of rabbits (sex, strain, and number not
reported) (Ellis et al., 1980).
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In a sensitization study, no skin sensitization was observed in guinea
pigs (sex, strain, and number not specified) exposed to 4-ADT (dose not
specified) (Ellis et al., 1980).
G. SUBCHRONIC TOXICITY IN MAMMALS
No information was found.
H. REPRODUCTIVE EFFECTS AND TERATOGENICITY IN MAMMALS
No information was found.
I. MUTAGENICITY/GENOTOXICITY
Data are presented in tabular form on page 5.
J. CHRONIC/CARCINOGENICITY STUDIES IN MAMMALS
No information was found.
K. PHARMACOKINETICS IN MAMMALS
A single oral dose of uC-ring-labeled 4-ADT was readily absorbed and
eliminated by CD albino rats (sex and number not given) (Ellis et al., 1980).
The exact dosage was not specified, but the authors noted that animals were
given approximately one-tenth of the LDSO (i.e., 136 and 95.9/kg for males and
females, respectively). Within 24 hours postdosing, about 40% of the
administered radioactivity was recovered from the urine; 41% was found in the
gastrointestinal tract and feces combined. The carcass contained about 2%.
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Biliary excretion of 14C-ring-labeled 4-ADT by another group of rats was about
1 to 2% and 13% of the radioactive dose at 4 and 24 hours after administration
of the test material, respectively (Ellis et al., 1980). The data from the
biliary excretion study suggest that total absorption of 4-ADT is probably
greater than the value reported in the first (i.e., oral dosing) study
described above.
The biochemical effects of 4-ADT were examined by two groups of
investigators. In one study, concentrations of 10"12 to 1(T8 M 4-ADT had no
effect on the synthesis of protein (globin) in cell-free extracts of
reticulocytes from New Zealand white rabbits (Fournier and Parsons, 1980). In
the second study, the activities of two heme synthesis regulatory enzymes,
delta-aminolevulinic acid (the initial enzyme in heme production) and
ferrochelatase (the final enzyme), remained unchanged in the presence of up to
10"3 M 4-ADT. The test system included liver microsomes from male Walter Reed
rats (Johnson et al. 1985).
L. HUMAN HEALTH EFFECTS
No information was found.
M. EXISTING STANDARDS/CRITERIA
No information was found.
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I. MUTAGENICITY/GENOTOXICITY
Test
Strain
Activation
Dose/concentration
Toxic effects
Reference
Ames mutagenicity
assay
Salmonella
typhimurium
TA1535. TA1537.
TA1538, TA98.
TA100. TA100 NR3
S9
10 to 5000 jig/plate
I
O\
I
Positive both
with and without
activation in
TA98 and TA100.
Negative both
with and without
activation in
TA1537 and
TA100 NR3. In
strain TA1535.
positive with
activation but
negative without
activation.
In strain TA1538,
positive without
activation but
negative with
activation.
Spanggord et
(1982)
al.
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N. REFERENCES
Buckingham J, Donaghy SM. 1982. Dictionary of organic products. 5th ed.
Vol. 4. New York: Chapman and Hall. p. 3827.
Ellis HV III, Hong C-B, Lee C-C. 1980. Mammalian toxicity of munitions
compounds. Contract No. DAMD-17-74-C-4073. Environmental Protection Research
Division. Available from: NTIS, Springfield, VA; ADA080146.
Fournier MJ, Parsons PP. 1980. The effects of specific environmental
pollutants on the biosynthetic functions of mammalian cells in vitro. A
search for structure/activity relationships. Contract Nos. DAMD-17-77-C-7044
and DAMD17-77-7045. Frederick, MD: U.S. Army Medical Research and
Development Command. Available from: DTIC, Cameron Station, Alexandria, VA;
ADA149184.
Johnson DJ, Williams HL, Slater S, Haut MJ, Alsfatt LB. 1985. The in vitro
effects of selected environmental toxicants on two heme synthesis enzymes. J.
Environ. Pathol. Toxicol. Oncol. 6:211-218.
Liu DHW, Bailey HC, Pearson JG. 1983. Toxicity of a complex munitions
wastewater to aquatic organisms. ASTM Spec. Tech. Publ. 802:135-150.
Spanggord RJ, Mortelmans KE, Griffin AF, Simmon VF. 1982. Mutagenicity in
Salmonella tvphimurium and structure-activity relationships of wastewater
components emanating from the manufacture of trinitrotoluene. Environ.
Mutagen. 4:163-179.
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