Chemicals and Drugs

Monocrotaline

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.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

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.

Chemical Identity

Chemical Information

Molecular Formula
C16H23NO6
Molecular Weight
325.36 g/mol
CAS Registry No.
315-22-0
IUPAC Name
(1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione
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
MeSH Unique ID
D016686
Source
PubChem CID 9415

MeSH Record

Classification

Broader headings

Related Concepts

Knowledge Graph

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MeSH Record

Synonyms

2 entry terms
  • Monocrotaline Hydrochloride (13alpha,14alpha)-Isomer
  • Monocrotaline, (all-xi)-Isomer

MeSH Record

Aspects Covered

26 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

92; was MONOCROTALINE (NM) 1973-91

MeSH Record

Previous Indexing

  • Pyrrolizidine Alkaloids (1971-1973)

MeSH Hierarchy

Tree Numbers

  1. D03w.132w.716w.500w
  2. D03w.633.100.772w.500w

AMA Style

References

  1. National Library of Medicine. Monocrotaline. Medical Subject Headings (MeSH). 2026. Unique ID D016686. http://id.nlm.nih.gov/mesh/2026/D016686
  2. Monocrotaline. In: Wikipedia. https://en.wikipedia.org/wiki/Monocrotaline
  3. Monocrotaline. In: Wikidata. https://www.wikidata.org/wiki/Q27107379
  4. Monocrotaline. In: PubChem Compound. CID 9415. https://pubchem.ncbi.nlm.nih.gov/compound/9415