Aminopterin

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Names

[ CAS No. ]:
54-62-6

[ Name ]:
Aminopterin

[Synonym ]:
4-Aminopteroyl-L-glutamic acid
L-Glutamic acid, N-(4-(((2,4-diamino-6-pteridinyl)methyl)amino)benzoyl)-
L-Glutamic acid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-
apga
4-AMINO-PGA
N-(4-{[(2,4-Diamino-6-pteridinyl)methyl]amino}benzoyl)-L-glutamic acid
4-Aminofolic acid
MFCD00036692
N-(4-{[(2,4-Diaminopteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid
AGPA
EINECS 200-209-9
UNII-JYB41CTM2Q
Aminoperin
4-aminopteroylglutamic acid
aminopteridin
Aminopterin
L-N-[p-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-Glutamic acid
N-[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid
Minopterin
pteramina

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Melting Point ]:
228-235 °C (dec.)

[ Molecular Formula ]:
C19H20N8O5

[ Molecular Weight ]:
440.413

[ Exact Mass ]:
440.155670

[ PSA ]:
219.33000

[ LogP ]:
-1.21

[ Index of Refraction ]:
1.762

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MA1050000
CHEMICAL NAME :
Glutamic acid, N-(p-(((2,4-diamino-6-pteridinyl)methyl)amino)benzoyl )-, L-
CAS REGISTRY NUMBER :
54-62-6
BEILSTEIN REFERENCE NO. :
0069045
LAST UPDATED :
199701
DATA ITEMS CITED :
56
MOLECULAR FORMULA :
C19-H20-N8-O5
MOLECULAR WEIGHT :
440.47
WISWESSER LINE NOTATION :
T66 BN DN GN JNJ CZ EZ H1MR DVMYVQ2VQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
120 ug/kg
TOXIC EFFECTS :
Behavioral - anorexia (human) Gastrointestinal - other changes Skin and Appendages - hair
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2500 ug/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3 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 :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3 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 :
1900 ug/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 ug/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 :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1 mg/kg/10D-I
TOXIC EFFECTS :
Gastrointestinal - alteration in gastric secretion Gastrointestinal - hypermotility, diarrhea Blood - changes in bone marrow (not otherwise specified)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
246 ug/kg/5D-I
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Blood - changes in other cell count (unspecified) Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
24300 ug/kg/9D-I
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Blood - changes in bone marrow (not otherwise specified) Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
22200 ug/kg/20D-I
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Blood - changes in bone marrow (not otherwise specified) Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1200 ug/kg/17W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Blood - leukemia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
240 ug/kg
SEX/DURATION :
female 55-66 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - eye/ear 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 :
580 ug/kg
SEX/DURATION :
female 6-8 week(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 :
2880 ug/kg
SEX/DURATION :
female 56-67 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - Apgar score (human only)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
165 ug/kg
SEX/DURATION :
female 40-44 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
188 ug/kg
SEX/DURATION :
female 54-55 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
151 ug/kg
SEX/DURATION :
female 35-36 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
240 ug/kg
SEX/DURATION :
female 1-30 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
240 ug/kg
SEX/DURATION :
female 53-55 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
15 ug/kg
SEX/DURATION :
female 1-3 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
150 ug/kg
SEX/DURATION :
female 9-11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
112 ug/kg
SEX/DURATION :
female 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
75 ug/kg
SEX/DURATION :
female 10 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 :
200 ug/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
150 ug/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - homeostasis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
150 ug/kg
SEX/DURATION :
female 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
280 ug/kg
SEX/DURATION :
male 28 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 :
Parenteral
DOSE :
75 ug/kg
SEX/DURATION :
female 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
75 ug/kg
SEX/DURATION :
female 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - body wall
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
50 ug/kg
SEX/DURATION :
female 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
200 ug/kg
SEX/DURATION :
female 10 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 :
3 mg/kg
SEX/DURATION :
female 1 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
2 mg/kg
SEX/DURATION :
female 14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
20 mg/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - live birth index (measured after birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
20 mg/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - physical
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2500 ug/kg
SEX/DURATION :
female 18-27 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
500 ug/kg
SEX/DURATION :
female 18-27 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
500 ug/kg
SEX/DURATION :
female 16-25 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
300 ug/kg
SEX/DURATION :
female 20-22 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 :
Intravenous
DOSE :
15 mg/kg
SEX/DURATION :
female 15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1100 ug/kg
SEX/DURATION :
female 12-33 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
Micronucleus test

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
2 mg/kg/5D
REFERENCE :
PNASA6 Proceedings of the National Academy of Sciences of the United States of America. (National Academy of Sciences, Printing & Pub. Office, 2101 Constitution Ave., Washington, DC 20418) V.1- 1915- Volume(issue)/page/year: 72,4425,1975 *** REVIEWS *** TOXICOLOGY REVIEW BCSTB5 Biochemical Society Transactions. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1973- Volume(issue)/page/year: 2,695,1974 TOXICOLOGY REVIEW PLMJAP Pahlavi Medical Journal. (Shiraz, Iran) V.1-9, 1970-78. Volume(issue)/page/year: 6,160,1975 TOXICOLOGY REVIEW JAMAAP JAMA, Journal of the American Medical Association. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1883- Volume(issue)/page/year: 172,1765,1960 TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 TOXICOLOGY REVIEW JOGBAS Journal of Obstetrics and Gynaecology of the British Commonwealth. (London, UK) V.68-81, 1961-74. For publisher information, see BJOGAS. Volume(issue)/page/year: 75,307,1968 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965 TOXICOLOGY REVIEW ADVPA3 Advances in Pharmacology. (New York, NY) V.1-6, 1962-68. For publisher information, see AVPCAQ. Volume(issue)/page/year: 4,263,1966 TOXICOLOGY REVIEW ATXKA8 Archiv fuer Toxikologie. (Berlin, Fed. Rep. Ger.) V.15-31, 1954-74. For publisher information, see ARTODN. Volume(issue)/page/year: 28,135,1971

Safety Information

[ Symbol ]:

GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300-H360

[ Precautionary Statements ]:
P201-P264-P301 + P310-P308 + P313

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+:Verytoxic;

[ Risk Phrases ]:
R61;R28

[ Safety Phrases ]:
S53-S28-S36/37-S45

[ RIDADR ]:
UN 2811 6.1/PG 1

[ WGK Germany ]:
3

[ RTECS ]:
MA1050000

[ Packaging Group ]:
I

[ Hazard Class ]:
6.1(a)

[ HS Code ]:
3822009000

Precursor & DownStream

Precursor

  • 6-(Brommethyl)pteridin-2,4-diamin
  • N-(4-aminobenzoyl)-L-glutamic acid
  • Folic Acid
  • Water
  • 6-(Bromomethyl)-2,4-pteridinediamine hydrobromide
  • Propanal, 2,3-dibromo-
  • 4-(N-[2,4-DIAMINO-6-PTERIDINYLMETHYL]-AMINO)BENZOIC ACID SODIUM SALT
  • 2,4-diamino-6-(hydroxymethyl)pteridine
  • 4-[[2-(2,4-diaminopteridin-6-yl)acetyl]amino]benzoic acid

DownStream

  • Pterin-6-carboxylic acid
  • dimethyl 2-[[4-[(2,4-diaminopteridin-6-yl)methyl-(trideuteriomethyl)amino]benzoyl]amino]pentanedioate
  • 4-(N-[2,4-DIAMINO-6-PTERIDINYLMETHYL]-AMINO)BENZOIC ACID SODIUM SALT
  • 4-[[2-(2,4-diaminopteridin-6-yl)acetyl]amino]benzoic acid
  • Methotrexate-d3

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Related Compounds

  • Aminopterin
  • Nhs-aminopterin
  • Deazaminopterin
  • 2-desaminopterin
  • Aminopterin-Homologes
  • 7-Hydroxy Aminopterin
  • 4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
  • 1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
  • 2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
  • 1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
  • (4-Methyl-tetrahydro-furan-2-yl)-methanol
  • N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
  • 4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
  • tert-Butyl-DL-alanine
  • 4-amino-N-[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-ethylbenzenesulfonamide
  • N-(3,4-dimethoxyphenyl)-2-(3-(4-fluorobenzoyl)-4-oxoquinolin-1(4H)-yl)acetamide