Ergometrine

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
Clinical data
AHFS/Drugs.com	monograph
Pregnancy cat.	X
Legal status	List I precursor (US)
Routes	Oral
Pharmacokinetic data
Metabolism	hepatic
Excretion	renal
Identifiers
CAS number	60-79-7
ATC code	G02AB03
PubChem	CID 443884
DrugBank	DB01253
ChemSpider	391970
UNII	WH41D8433D
KEGG	D07905
ChEBI	CHEBI:4822
ChEMBL	CHEMBL119443
Synonyms	Ergonovine, lysergic acid beta- propanolamide
Chemical data
Formula	C19H23N3O2
Mol. mass	325.41 g/mol
SMILES	eMolecules & PubChem
	InChI InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1 ; Key:WVVSZNPYNCNODU-XTQGRXLLSA-N ;
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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 lysergic acid diethylamide (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.¹ It is used to diagnose Variant (Prinzmetal's) angina.²

Recreational use

According to the book TiHKAL by Alexander Shulgin, ergometrine 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, ergometrine is also covered by the Misuse of Drugs Act 1971, effectively rendering it illegal in the United Kingdom.

Side effects

Possible side effects include nausea, vomiting, abdominal pain, diarrhea, headache, dizziness, tinnitus, chest pain, palpitation, bradycardia, transient hypertension and other cardiac arrhythmias, dyspnoea, rashes, and shock.⁴ 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.⁵

References

^ Romagnoli E, Niccoli G, Crea F (October 2005). "Images in cardiology: A coronary organic stenosis distal to severe, ergonovine induced spasm: decision making". Heart 91 (10): 1310. doi:10.1136/hrt.2004.058560. PMC 1769140. PMID 16162623. http://heart.bmj.com/cgi/pmidlookup?view=long&pmid=16162623.
^ Sunagawa O, Shinzato Y, Touma T, Tomori M, Fukiyama K (May 2000). "Differences between coronary hyperresponsiveness to ergonovine and vasospastic angina". Jpn Heart J 41 (3): 257–68. doi:10.1536/jhj.41.257. PMID 10987346.
^ List Of Precursors And Chemicals Frequently Used In The Illicit Manufacture Of Narcotic Drugs And Psychotropic Substances Under International Control.
^ Ergometrine drug information
^ A. Stoll, A. Hofmann, Helv. Chim. Acta, 26, 956 (1943).
- A. Stoll, A. Hofmann, U.S. Patent 2,090,430 (1937).
- A. Stoll, A. Hofmann, U.S. Patent 2,447,214 (1948).
- R.P. Pioch, U.S. Patent 2,736,728 (1956).
- W.L. Garbrecht, U.S. Patent 2,774,763 (1956).
- A. Hofmann, A. Brack, U.S. Patent 2,809,920 (1957).
- B. Patelli, L. Bernardi, U.S. Patent 3,141,887 (1964).

[pmid16162623-0] Romagnoli E, Niccoli G, Crea F (October 2005). "Images in cardiology: A coronary organic stenosis distal to severe, ergonovine induced spasm: decision making". Heart 91 (10): 1310. doi:10.1136/hrt.2004.058560. PMC 1769140. PMID 16162623. http://heart.bmj.com/cgi/pmidlookup?view=long&pmid=16162623.

[pmid10987346-1] Sunagawa O, Shinzato Y, Touma T, Tomori M, Fukiyama K (May 2000). "Differences between coronary hyperresponsiveness to ergonovine and vasospastic angina". Jpn Heart J 41 (3): 257–68. doi:10.1536/jhj.41.257. PMID 10987346.

[2] List Of Precursors And Chemicals Frequently Used In The Illicit Manufacture Of Narcotic Drugs And Psychotropic Substances Under International Control.

[3] Ergometrine drug information

[4] A. Stoll, A. Hofmann, Helv. Chim. Acta, 26, 956 (1943).

A. Stoll, A. Hofmann, U.S. Patent 2,090,430 (1937).

A. Stoll, A. Hofmann, U.S. Patent 2,447,214 (1948).

R.P. Pioch, U.S. Patent 2,736,728 (1956).

W.L. Garbrecht, U.S. Patent 2,774,763 (1956).

A. Hofmann, A. Brack, U.S. Patent 2,809,920 (1957).

B. Patelli, L. Bernardi, U.S. Patent 3,141,887 (1964).

[6] A. Stoll, A. Hofmann, U.S. Patent 2,090,430 (1937).

[7] A. Stoll, A. Hofmann, U.S. Patent 2,447,214 (1948).

[8] R.P. Pioch, U.S. Patent 2,736,728 (1956).

[9] W.L. Garbrecht, U.S. Patent 2,774,763 (1956).

[10] A. Hofmann, A. Brack, U.S. Patent 2,809,920 (1957).

[11] B. Patelli, L. Bernardi, U.S. Patent 3,141,887 (1964).

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