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Ergometrine
Systematic (IUPAC) name
(6aR,9R)- N- ((S)- 1-hydroxypropan- 2-yl)- 7-methyl- 4,6,6a,7,8,9- hexahydroindolo [4,3-fg] quinoline- 9-carboxamide
Identifiers
CAS number 60-79-7
ATC code G02AB03
PubChem 443884
Chemical data
Formula C 19H23N3O2  
Mol. mass 325.41 g/mol
Synonyms Ergonovine, Lysergic acid beta- propanolamide
Pharmacokinetic data
Bioavailability  ?
Metabolism hepatic
Half life  ?
Excretion renal
Therapeutic considerations
Pregnancy cat.  ?
Legal status List I precursor (US)
Routes Oral
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Ergometrine (other names include ergonovine and d-lysergic acid beta-propanolamide), is an ergoline (and lysergamide) derivative, and one of the primary ergot and morning glory alkaloids . It is chemically similar to LSD, ergine, and lysergic acid.

Contents

Mechanism of action

It acts at alpha-adrenergic, dopamine and serotonin (5-HT2) receptors to exert a powerful stimulant effect on the uterus and other smooth muscle not clearly associated with any specific receptor type.

Medical use

It has a medical use in obstetrics to facilitate delivery of the placenta and to prevent bleeding after childbirth by causing smooth muscle tissue in the blood vessel walls to narrow, thereby reducing blood flow. It is usually combined with oxytocin (Syntocinon) as syntometrine.

It can induce spasm of the coronary arteries.[1] This is sometimes used in the differential diagnosis of angina.[2]

Recreational use

According to TIHKAL by Alexander Shulgin, ergonovine has LSD-like action at levels of 2-10 milligrams. Clinical dosages are about ten times lower.

Legal status

Ergometrine is listed as Table I precursors under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances, as possible precursor compound for LSD. [3] As an N-alkyl derivative of lysergamide, ergonovine is also covered by the Misuse of Drugs Act 1971, effectively rendering it illegal in the United Kingdom.

Side effects

An overdose produces a characteristic poisoning, ergotism or "St. Anthony's fire": prolonged vasospasm resulting in gangrene and amputations; hallucinations and dementia; and abortions. Gastrointestinal disturbances, e.g. diarrhoea, nausea and vomiting, are common. The drug is contraindicated in pregnancy, vascular disease and psychosis.

See also

Medicinal mushrooms

References








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