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Substance Name: Aminopterin
RN: 54-62-6
UNII: JYB41CTM2Q
InChIKey: TVZGACDUOSZQKY-LBPRGKRZSA-N

Note

  • A folic acid derivative used as a rodenticide that has been shown to be teratogenic.

Molecular Formula

  • C19-H20-N8-O5

Molecular Weight

  • 440.418
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Folic Acid Antagonists
  • Human Data
  • Mutation Data
  • Reproductive Effect
  • Rodenticide
  • Tumor Data

Superlist Classification Code

  • Threshold Planning Quantity (TPQ) = 500/10000 lb
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Names and Synonyms

Name of Substance

  • Aminopterin

MeSH Heading

  • Aminopterin

Synonyms

  • 4'-Amino-folsaeure
  • 4'-Desoxy-4'-aminofolsaeure
  • 4-26-00-03831 (Beilstein Handbook Reference)
  • 4-Amino pteroylglutamic acid
  • 4-Amino-4-deoxypteroylglutamate
  • 4-Amino-4-desoxy-pteroylglutaminsaeure
  • 4-Amino-PGA
  • 4-Aminofolic acid
  • 4-Aminopteroylglutamic acid
  • A-Ninopterin
  • AI3-26079
  • Aminopteridine
  • Aminopterin
  • Aminopterine
  • Aminopterinum
  • APGA
  • BRN 0069045
  • CCRIS 5856
  • EINECS 200-209-9
  • ENT-26079
  • Folic acid, 4-amino-
  • Glutamic acid, N-(p-(((2,4-diamino-6-pteridinyl)methyl)amino)benzoyl)-, L-
  • HSDB 6374
  • Kyselina 4-aminolistova
  • Kyselina 4-aminolistova [Czech]
  • Kyselina 4-aminopteroylglutamova
  • Kyselina 4-aminopteroylglutamova [Czech]
  • Kyselina N-(p-((2,4-diamino-6-pteridinyl)methyl)benzoyl)-L(+)-glutamova
  • Kyselina N-(p-((2,4-diamino-6-pteridinyl)methyl)benzoyl)-L(+)-glutamova [Czech]
  • Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)amino)benzoyl)-L(+)-glutamova
  • Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)amino)benzoyl)-L(+)-glutamova [Czech]
  • L-Glutamic acid, N-(4-(((2,4-diamino-6-pteridinyl)methyl)amino)benzoyl)-
  • N-(1-((2,4-Diamino-6-pteridinylmethyl)amino)benzoyl)glutaminsaeure
  • N-(4-(((2,4-Diamino-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid
  • N-(4-(((2,4-Diamino-6-pteridyl)-methyl)amino)benzoyl)-L-glutamic acid
  • NSC 739
  • Pteramina
  • Pteramina [Czech]
  • UNII-JYB41CTM2Q

Systematic Names

  • Aminopterin
  • Glutamic acid, N-(p-(((2,4-diamino-6-pteridinyl)methyl)amino)benzoyl)-, L-
  • L-Glutamic acid, N-(4-(((2,4-diamino-6-pteridinyl)methyl)amino)benzoyl)-
  • N-(4-(((2,4-Diamino-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid

Superlist Name

  • Aminopterin

Registry Numbers

CAS Registry Number

  • 54-62-6

FDA UNII

  • JYB41CTM2Q

Other Registry Numbers

  • 120382-78-7
  • 64801-55-4

Related Registry Number

  • 31823-54-8 (hydrochloride salt)

System Generated Number

  • 0000054626

Structure Descriptors

InChI

1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)/t12-/m0/s1

InChIKey

TVZGACDUOSZQKY-LBPRGKRZSA-N

Smiles

c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCc2cnc3c(n2)c(nc(n3)N)N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1900ug/kg (1.9mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Journal of Pharmacology and Experimental Therapeutics. Vol. 95, Pg. 303, 1949.
mouse LD50 oral 3mg/kg (3mg/kg)   Cesko-Slovenska Farmacie. Vol. 28, Pg. 159, 1979.
mouse LDLo unreported 500ug/kg (0.5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 142, 1967.
rat LD50 intraperitoneal 3mg/kg (3mg/kg)   Cancer Vol. 9, Pg. 955, 1956.
rat LDLo oral 2500ug/kg (2.5mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Journal of Pharmacology and Experimental Therapeutics. Vol. 95, Pg. 303, 1949.
women TDLo oral 120ug/kg (0.12mg/kg) GASTROINTESTINAL: OTHER CHANGES

BEHAVIORAL: ANOREXIA (HUMAN

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
American Journal of Obstetrics and Gynecology. Vol. 63, Pg. 1298, 1952.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -1.820 (none)   EST
Atmospheric OH Rate Constant 2.21E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.