Ergometrine

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Ergometrine
Ergonovine-skeletal.svgErgometrine3.png
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.commonograph
Pregnancy cat.
  • X
Legal status
  • List I precursor (US)
RoutesOral
Pharmacokinetic data
Metabolismhepatic
Excretionrenal
Identifiers
CAS number60-79-7 YesY
ATC codeG02AB03
PubChemCID 443884
DrugBankDB01253
ChemSpider391970 YesY
UNIIWH41D8433D YesY
KEGGD07905 YesY
ChEBICHEBI:4822 YesY
ChEMBLCHEMBL119443 YesY
SynonymsErgonovine, lysergic acid beta- propanolamide
Chemical data
FormulaC19H23N3O2 
Mol. mass325.41 g/mol
 YesY (what is this?)  (verify)
 
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Ergometrine
Ergonovine-skeletal.svgErgometrine3.png
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.commonograph
Pregnancy cat.
  • X
Legal status
  • List I precursor (US)
RoutesOral
Pharmacokinetic data
Metabolismhepatic
Excretionrenal
Identifiers
CAS number60-79-7 YesY
ATC codeG02AB03
PubChemCID 443884
DrugBankDB01253
ChemSpider391970 YesY
UNIIWH41D8433D YesY
KEGGD07905 YesY
ChEBICHEBI:4822 YesY
ChEMBLCHEMBL119443 YesY
SynonymsErgonovine, lysergic acid beta- propanolamide
Chemical data
FormulaC19H23N3O2 
Mol. mass325.41 g/mol
 YesY (what is this?)  (verify)

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.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medications needed in a basic health system.[1]

Medical use[edit]

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.[2] It is used to diagnose variant (Prinzmetal's) angina.[3]

Side effects[edit]

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.[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 such as diarrhea, nausea, and vomiting, are common.[5] The drug is contraindicated in pregnancy, vascular disease, and psychosis.

Mechanism of action[edit]

While it acts at alpha-adrenergic, dopaminergic, and serotonin receptors (the 5-HT2 receptor), it exerts on the uterus (and other smooth muscles) a powerful stimulant effect not clearly associated with a specific receptor type.

Legal status[edit]

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.[6] 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.

Chemistry[edit]

Ergometrine can be synthesized by esterification of D-lysergic acid using 2-aminopropanol in dimethylformamide and direct treatment of the reaction mixture with phosgene.[7]

Ergonovine synthesis.png

References[edit]

  1. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  2. ^ 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. 
  3. ^ 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. 
  4. ^ Ergometrine drug information
  5. ^ McDonald S, Abbott JM, Higgins SP (2004). "Prophylactic ergometrine-oxytocin versus oxytocin for the third stage of labour". Cochrane Database Syst Rev 1: CD000201. PMID 14973949. 
  6. ^ List Of Precursors And Chemicals Frequently Used In The Illicit Manufacture Of Narcotic Drugs And Psychotropic Substances Under International Control.
  7. ^ A. Stoll, A. Hofmann, Helv. Chim. Acta, 26, 956 (1943).