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Substance Name: Monocrotaline
RN: 315-22-0
UNII: 73077K8HYV
InChIKey: QVCMHGGNRFRMAD-XFGHUUIASA-N

Note

  • A pyrrolizidine alkaloid and a toxic plant constituent that poisons livestock and humans through the ingestion of contaminated grains and other foods. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature. Significant attenuation of the cardiopulmonary changes are noted after oral magnesium treatment.

Molecular Formula

  • C16-H23-N-O6

Molecular Weight

  • 325.3587
 

Classification Codes

Classification Codes

  • Drug / Therapeutic Agent
  • Mutation Data
  • Natural Product
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 2B
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Names and Synonyms

Name of Substance

  • Monocrotaline

MeSH Heading

  • Monocrotaline

Synonyms

  • (13-alpha,14-alpha)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione
  • (2,3,4-gh)pyrrolizine-2,6(3H)-dione, (4,5,8,10,12,13,13a,13b)-octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-(1,6)dioxacycloundecino-
  • 12-beta,13-beta-Dihydroxy-12-alpha,13-alpha,14-alpha-trimethylcrotal-1-enine
  • 14,19-Dihydro-12,13-dihydroxy(13-alpha,14-alpha)-20-norcrotalanan-11,15-dione
  • 14,19-Dihydro-12,13-dihydroxy-20-norcrotolanan-11,15-dione
  • 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13alpha,14alpha)-
  • 4-27-00-06660 (Beilstein Handbook Reference)
  • A 6080
  • BRN 0048732
  • CCRIS 416
  • Crotaline
  • HSDB 3513
  • Monocrotalin
  • Monocrotaline
  • NCI-C56462
  • NSC 28693
  • Retronecine cyclic 2,3-dihydroxy-2,3,4-trimethylglutarate
  • UNII-73077K8HYV

Systematic Names

  • 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13-alpha,14-alpha)- (9CI)
  • 2H-(1,6)Dioxacycloundecino(2,3,4-gh)pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-, (3R,4R,5R,13aR,13bR)-
  • Monocrotaline

Superlist Names

  • 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13-alpha,14-alpha)-
  • Monocrotaline

Registry Numbers

CAS Registry Number

  • 315-22-0

FDA UNII

  • 73077K8HYV

System Generated Number

  • 0000315220

Structure Descriptors

InChI

1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1

InChIKey

QVCMHGGNRFRMAD-XFGHUUIASA-N

Smiles

C[C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LDLo unreported 60mg/kg (60mg/kg)   Pharmacological Reviews. Vol. 22, Pg. 429, 1970.
mouse LD50 intraperitoneal 259mg/kg (259mg/kg)   Toxicology and Applied Pharmacology. Vol. 59, Pg. 424, 1981.
mouse LD50 intravenous 261mg/kg (261mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 75, Pg. 78, 1942.
rat LD50 intravenous 92mg/kg (92mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 83, Pg. 265, 1945.
rat LD50 oral 66mg/kg (66mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" Toxicology and Applied Pharmacology. Vol. 18, Pg. 387, 1971.
rat LD50 subcutaneous 60mg/kg (60mg/kg)   Toxicology and Applied Pharmacology. Vol. 23, Pg. 470, 1972.
rat LD50 unreported 60mg/kg (60mg/kg)   Cancer Research. Vol. 28, Pg. 2237, 1968.
rat LDLo intraperitoneal 130mg/kg (130mg/kg) LIVER: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Chemico-Biological Interactions. Vol. 12, Pg. 299, 1976.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 197 dec deg C   EXP
log P (octanol-water) -1.180 (none)   EST
Atmospheric OH Rate Constant 1.24E-10 cm3/molecule-sec 25 EST

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