Procarbazine

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Names

[ CAS No. ]:
671-16-9

[ Name ]:
Procarbazine

[Synonym ]:
4-[(2-methylhydrazinyl)methyl]-N-(propan-2-yl)benzamide
Natulan
Procarbazine
N-(1-methylethyl)-4-[(2-methylhydrazino)methyl]benzamide
Benzamide, N-(1-methylethyl)-4-((2-methylhydrazino)methyl)-
N-Isopropyl-4-[(2-methylhydrazino)methyl]benzamide
Procarbazina
[4-(2-methyl-hydrazino)-methyl-benzoic acid-isopropylamide]
Procarbazinum
Ibenzmethyzin
EINECS 211-582-2
MFCD00866411
N-Isopropyl-4-((2-methylhydrazinyl)methyl)benzamide
Benzamide, N-(1-methylethyl)-4-[(2-methylhydrazino)methyl]-
Benzamide, N-(1-methylethyl)-4-[(2-methylhydrazinyl)methyl]-
4-[(2-methylhydrazinyl)methyl]-N-propan-2-ylbenzamide
Procarbazin
N-isopropyl-4-[(N'-methylhydrazino)methyl]benzamide

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
384.6±35.0 °C at 760 mmHg

[ Molecular Formula ]:
C12H19N3O

[ Molecular Weight ]:
221.299

[ Flash Point ]:
148.9±26.1 °C

[ Exact Mass ]:
221.152817

[ PSA ]:
53.16000

[ LogP ]:
0.77

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.529

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XS4550000
CHEMICAL NAME :
p-Toluamide, N-isopropyl-alpha-(2-methylhydrazino)-
CAS REGISTRY NUMBER :
671-16-9
LAST UPDATED :
199706
DATA ITEMS CITED :
84
MOLECULAR FORMULA :
C12-H19-N3-O
MOLECULAR WEIGHT :
221.34
WISWESSER LINE NOTATION :
1Y1&MVR D1MM1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
350 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
614 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1250 mg/kg/1Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
125 mg/kg female 22 day(s) after conception
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Reproductive - Tumorigenic effects - transplacental tumorigenesis Brain and Coverings - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1200 mg/kg/4W-I
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
7 gm/kg/7Y-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Blood - leukemia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
540 mg/kg
SEX/DURATION :
female 13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
960 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - gastrointestinal system Reproductive - Specific Developmental Abnormalities - homeostasis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
540 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
60 mg/kg
SEX/DURATION :
female 3 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
50 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
200 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1050 mg/kg
SEX/DURATION :
male 1-5 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - other effects on male Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
600 mg/kg
SEX/DURATION :
male 14 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - other effects on male
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intratesticular
DOSE :
20 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
53 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
10 mg/kg
SEX/DURATION :
female 16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
400 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
200 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material) Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
20 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - delayed effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
100 mg/kg
SEX/DURATION :
male 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
500 mg/kg
SEX/DURATION :
male 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sex chromosome loss and nondisjunction
TYPE OF TEST :
Sex chromosome loss and nondisjunction
TYPE OF TEST :
Dominant lethal test
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Morphological transformation
TYPE OF TEST :
DNA damage
TYPE OF TEST :
DNA damage
TYPE OF TEST :
DNA damage
TYPE OF TEST :
DNA inhibition
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sperm Morphology
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Unscheduled DNA synthesis
TYPE OF TEST :
Mutation test systems - not otherwise specified
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sister chromatid exchange
TYPE OF TEST :
Dominant lethal test
TYPE OF TEST :
Dominant lethal test
TYPE OF TEST :
Dominant lethal test
TYPE OF TEST :
Sperm Morphology
TYPE OF TEST :
Sperm Morphology
TYPE OF TEST :
Sister chromatid exchange
TYPE OF TEST :
Sister chromatid exchange
TYPE OF TEST :
Sister chromatid exchange

MUTATION DATA

TEST SYSTEM :
Rodent - rabbit
DOSE/DURATION :
5 mg/kg
REFERENCE :
ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 46,139,1980 *** REVIEWS *** TOXICOLOGY REVIEW MIMDAL Minnesota Medicine. (Minnesota Medical Assoc., 2221 University Ave., SE, Suite 400, Minneapolis, MN 55414) V.1- 1918- Volume(issue)/page/year: 57,19,1974 TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 TOXICOLOGY REVIEW MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 39,111,1977 TOXICOLOGY REVIEW MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 55,1,1978 TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 2,159,1973 TOXICOLOGY REVIEW BLFSBY Basic Life Sciences. (Plenum Pub. Corp., 223 Spring St., New York, NY 10003) V.1- 1973- Volume(issue)/page/year: 24,129,1983

Safety Information

[ Hazard Codes ]:
Xn

[ HS Code ]:
2928000090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • 4-[(2-methyl-1,2-dicarbobenzoxyhydrazino)-methyl]-benzoic acid isopropylamide
  • methyl p-toluate
  • 1-[(4-Carboxyphenyl)methyl]-2-methyl-1,2-hydrazinedicarboxylic acid bis(phenylmethyl) ester
  • Methyl 4-(bromomethyl)benzoate

DownStream

  • 4-Formyl-N-isopropylbenzamide
  • 4-(N-Methyl-N-nitroso-hydrazonomethyl)-benzoesaeureisopropylamid

Customs

[ HS Code ]: 2928000090

[ Summary ]:
2928000090 other organic derivatives of hydrazine or of hydroxylamine VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

Related Compounds

  • procarbazine
  • Procarbazine HCl
  • Procarbazine hydrobromide
  • 1-[(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-(methylsulfanyl)butanoyl]-3-hydroxypiperidine-3-carboxylic acid
  • 1-[2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-methylbutanoyl]-3-hydroxypyrrolidine-3-carboxylic acid
  • 1-[(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-methylbutanoyl]-3-hydroxypyrrolidine-3-carboxylic acid
  • 1-{2-[2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)ethoxy]acetyl}-3-hydroxypyrrolidine-3-carboxylic acid
  • 1-[3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2,2-difluoropropanoyl]-3-hydroxypyrrolidine-3-carboxylic acid
  • 3-{[2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)acetamido]methyl}pentanoic acid
  • 2-[(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-N-(prop-2-yn-1-yl)propanamido]acetic acid
  • 4-[(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanamido]but-2-enoic acid
  • 2-{4-[3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2,2-dimethylpropanoyl]-1,4-diazepan-1-yl}acetic acid
  • 4-bromo-2-[3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2,2-dimethylpropanamido]benzoic acid