Ergometrine

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.

Mechanism of action
While it acts at alpha-adrenergic, dopaminergic and serotonin receptors (the 5-HT2 receptor), it exerts on the uterus and other smooth muscle a powerful stimulant effect not clearly associated with a 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. It is used to diagnose Variant (Prinzmetal's) angina.

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. 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.

Chemistry
Ergometrine, 1-hydroxymethylethylamide lysergic acid, is synthesized by esterification of D-lysergic acid using 2-aminopropanol in dimethylformamide and direct treatment of the reaction mixture with phosgene.
 * A. Stoll, A. Hofmann, Helv. Chim. Acta, 26, 956 (1943).
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