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Ergonovine, also known as ergometrine and lysergic acid propanolamide is a medication used to cause contractions of the uterus to treat heavy vaginal bleeding after childbirth.[6][1] It can be used either by mouth, by injection into a muscle, or injection into a vein.[6] It begins working within 15 minutes when taken by mouth and is faster in onset when used by injection.[6] Effects last between 45 and 180 minutes.[6]
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| Trade names | Ergotrate, Ergotrate Maleate, Ergostat, Syntometrine[1][2] |
| Other names | ergometrine[3][4] ergobasin[3] ergotocine[3] ergostetrine[3] ᴅ-lysergic acid-1,2-propanolamide[4] ᴅ-lysergic acid 1-(hydroxymethyl)ethylamide[4] ᴅ(+)-lysergic acid-β-hydroxyisopropylamide[4] |
| AHFS/Drugs.com | Monograph |
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| Routes of administration | oral, injection |
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| Metabolism | Liver (partly CYP3A4) |
| Elimination half-life | 2-phase (10 min; 2 hrs) |
| Excretion | Biliary |
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| ECHA InfoCard | 100.000.441 |
| Chemical and physical data | |
| Formula | C19H23N3O2 |
| Molar mass | 325.412 g·mol−1 |
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Common side effect include high blood pressure, vomiting, seizures, headache, and low blood pressure.[6] Other serious side effects include ergotism.[6] It was originally made from the rye ergot fungus but can also be made from lysergic acid.[7][8] Ergonovine is regulated because it can be used to make lysergic acid diethylamide (LSD).[9]
Ergonovine was discovered in 1932.[7] It is on the World Health Organization's List of Essential Medicines.[10][11]
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Ergonovine 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.[12] It is used to diagnose variant (Prinzmetal's) angina.[13]
Possible side effects include nausea, vomiting, abdominal pain, diarrhea, headache, dizziness, tinnitus, chest pain, palpitation, bradycardia, transient hypertension and other cardiac arrhythmias, dyspnea, rashes, and shock.[14] 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 such as diarrhea, nausea, and vomiting, are common.[15] The drug is contraindicated in pregnancy, vascular disease, and psychosis.
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Pharmacodynamics
Ergonovine stimulates the uterus and other smooth muscles. It tragets α-adrenergic, dopaminergic, and serotonin receptors (the 5-HT2 receptor). Its uterotonic effect has not been identified with a specific receptor type.[citation needed] Ergonovine is an agonist of the serotonin 5-HT2B receptor and has been associated with cardiac valvulopathy.[16]
Psychedelic Effects
Ergonovine induces psychedelic effects at doses of 2–10mg, in contrast to its medical use in doses of 0.2–0.4mg.[17][18][19][20][21] The most common source of ergonovine for drug users is Ipomoea tricolor seeds, as they are the only commonly available natural product that hosts an ergoline-generating fungus.[22] The ergonovine content of I. tricolor seeds varies between one-tenth and one-third of ergine, an ergonovine analog.[23] One person who had the opportunity to try ergonovine to see its psychedelic potential stated that it was mild relative to other psychedelics, but that ergine may synergize with it;[24] indeed the contrast between Hofmann's self-administration of Ipomoea corymbosa extract and synthetic ergine is apparent in his essay on the initial analysis of I. corymbosa and I. tricolor seeds.[25]
The psychoactive property of these simple lysergic acid amides, closely related to LSD, is well established. The question presented itself whether ergonovine, being not only an alkaloidal component of ergot but also of ololiuhqui, possessed hallucinogenic activity. In the light of its chemical structure this did not seem unlikely: it does not differ much from LSD. But one may ask why, if it is hallucinogenic, this astonishing fact has not been announced, in the light of its use over recent decades in obstetrics. Undoubtedly the answer lies in the extremely low dosage of ergonovine used to stop postpartum bleeding, viz 0.1 to 0.25 mg. The effective dose of lysergic acid amide is 1 to 2 mg by oral application. I decided therefore to test in a self-experiment a corresponding dose of ergonovine:
–Albert Hofmann[17]
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The pharmacological properties of ergot were known and had been utilised by midwives for centuries, but were not thoroughly researched and publicized until the early 20th century. However, its abortifacient effects and the danger of ergotism meant that it was only prescribed cautiously, as in the treatment of postpartum haemorrhage.[26]
Ergonovine was first isolated and obtained by the chemists C Moir, H W Dudley and Gerald Rogers[citation needed] in 1935.[27][28] Caroline De Costa has argued that the adoption of ergonovine for preventive use and for treating bleeding contributed to the decline in the maternal mortality rate in much of the West during the early 20th century.[26]
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Legal status
Ergonovine 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.[29] As an N-alkyl derivative of ergine, ergonovine is also covered by the Misuse of Drugs Act 1971, effectively rendering it illegal in the United Kingdom.
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