Ergometrine

Last updated
Ergometrine
Ergonovine-skeletal.svg
Clinical data
Trade names Ergometrine Maleate, Ergonovine Maleate, Ergotrate, Ergotrate Maleate, Ergostat, Syntometrine, others [1] [2]
Other namesErgonovine; d-Lysergic acid β-propanolamide
AHFS/Drugs.com Monograph
Pregnancy
category
  • X
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolism Liver (partly CYP3A4)
Elimination half-life 2-phase (10 min; 2 hrs)
Excretion Biliary
Identifiers
  • (6aR,9R)-N-((S)-1-Hydroxypropan- 2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.441 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H23N3O2
Molar mass 325.412 g·mol−1
3D model (JSmol)
  • [H][C@@]12Cc3c[nH]c4cccc(C1=C[C@@H](C(=O)N[C@@H](C)CO)CN2C)c34
  • 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 Yes check.svgY
  • Key:WVVSZNPYNCNODU-XTQGRXLLSA-N Yes check.svgY
   (verify)

Ergometrine, also known as ergonovine and sold under the brand names Ergotrate, Ergostat, and Syntometrine among others, is a medication used to cause contractions of the uterus to treat heavy vaginal bleeding after childbirth. [4] [1] It can be used either by mouth, by injection into a muscle, or injection into a vein. [4] It begins working within 15 minutes when taken by mouth and is faster in onset when used by injection. [4] Effects last between 45 and 180 minutes. [4]

Contents

Common side effect include high blood pressure, vomiting, seizures, headache, and low blood pressure. [4] Other serious side effects include ergotism. [4] It was originally made from the rye ergot fungus but can also be made from lysergic acid. [5] [6] Ergometrine is regulated because it can be used to make lysergic acid diethylamide (LSD). [7]

Ergometrine was discovered in 1932. [5] It is on the World Health Organization's List of Essential Medicines. [8] [9]

Medical uses

Ergometrine 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. [10] It is used to diagnose variant (Prinzmetal's) angina. [11]

Side effects

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. [12] 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. [13] The drug is contraindicated in pregnancy, vascular disease, and psychosis.

Pharmacology

Pharmacodynamics

While ergometrine acts at α-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.[ citation needed ]

Ergometrine produces psychedelic effects at high doses (e.g., 2–10 mg; normal therapeutic doses are 0.2 to 0.4 mg). [14] This can be attributed to activation of 5-HT2A receptors. [15] Ergometrine is an agonist of the serotonin 5-HT2B receptor and has been associated with cardiac valvulopathy. [16]

History

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. [17]

Ergometrine was first isolated and obtained by the chemists C Moir, H W Dudley and Gerald Rogers[ citation needed ] in 1935. [18] [19] Caroline De Costa has argued that the adoption of ergometrine for preventative use and for treating bleeding contributed to the decline in the maternal mortality rate in much of the West during the early 20th century. [17]

Society and culture

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. [20] 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.

Related Research Articles

<span class="mw-page-title-main">Ergoline</span> Chemical compound

Ergoline is a chemical compound whose structural skeleton is contained in a variety of alkaloids, referred to as ergoline derivatives or ergoline alkaloids. Ergoline alkaloids, one being ergine, were initially characterized in ergot. Some of these are implicated in the condition ergotism, which can take a convulsive form or a gangrenous form. Even so, many ergoline alkaloids have been found to be clinically useful. Annual world production of ergot alkaloids has been estimated at 5,000–8,000 kg of all ergopeptines and 10,000–15,000 kg of lysergic acid, used primarily in the manufacture of semi-synthetic derivatives.

<span class="mw-page-title-main">Ergotamine</span> Chemical compound in the ergot family of alkaloids

Ergotamine, sold under the brand names Cafergot and Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It possesses structural similarity to several neurotransmitters, and has biological activity as a vasoconstrictor.

<span class="mw-page-title-main">Pergolide</span> Chemical compound

Pergolide, sold under the brand name Permax and Prascend (veterinary) among others, is an ergoline-based dopamine receptor agonist used in some countries for the treatment of Parkinson's disease. Parkinson's disease is associated with reduced dopamine activity in the substantia nigra of the brain. Pergolide acts on many of the same receptors as dopamine to increase receptor activity.

<span class="mw-page-title-main">Cisapride</span> Chemical compound

Cisapride is a gastroprokinetic agent, a drug that increases motility in the upper gastrointestinal tract. It acts directly as a serotonin 5-HT4 receptor agonist and indirectly as a parasympathomimetic. Stimulation of the serotonin receptors increases acetylcholine release in the enteric nervous system. It has been sold under the trade names Prepulsid (Janssen-Ortho) and Propulsid (in the United States). It was discovered by Janssen Pharmaceuticals in 1980. In many countries, it has been either withdrawn from the market or had its indications limited due to incidence of serious cardiac side-effects. Propulsid was linked to children's deaths.

<span class="mw-page-title-main">Psilocin</span> Chemical compound

Psilocin is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. Acting on the 5-HT2A receptors, psilocin modulates the production and reuptake of serotonin. The mind-altering effects of psilocin are highly variable and subjective and resemble those of LSD and DMT.

<span class="mw-page-title-main">Cabergoline</span> Chemical compound

Cabergoline, sold under the brand name Dostinex among others, is a dopaminergic medication used in the treatment of high prolactin levels, prolactinomas, Parkinson's disease, and for other indications. It is taken by mouth.

<span class="mw-page-title-main">Dihydroergotamine</span> An ergot alkaloid used to treat migraines

Dihydroergotamine (DHE), sold under the brand names D.H.E. 45 and Migranal among others, is an ergot alkaloid used to treat migraines. It is a derivative of ergotamine. It is administered as a nasal spray or injection and has an efficacy similar to that of sumatriptan. Nausea is a common side effect.

<span class="mw-page-title-main">Lysergic acid hydroxyethylamide</span> Chemical compound

D-Lysergic acid α-hydroxyethylamide, also known as D-lysergic acid methyl carbinolamide, is a is a Lysergamide and alkaloid of the Ergoline family, it is present in higher concentrations in the parasitic fungi species "Claviceps", mainly the Claviceps Paspali, also in Claviceps Purpurea. This fungi grows in various species in the Convolvulaceae family like the Ipomoea violacea, the Rivea corymbosa (Ololiuhqui), and the Argyreia nervosa. Heavenly Blue Morning Glory and Hawaiian Baby Woodrose especially contain high amounts of LSH, with content varying between species and by how fresh are the seeds. LSH is a psychoactive Ergoline and has effects similar to LSD due to similarity in the structure and is the main psychoactive compound found in Claviceps Paspali and in (fresh) Heavenly Blue Morning Glory Seeds. LSH is unstable and breaks down into LSA quickly, so old seeds often only contains LSA and iso-LSA. When the seeds are fresh, they contain significantly higher amounts of LSH.

<span class="mw-page-title-main">Methylergometrine</span> Chemical compound

Methylergometrine, also known as methylergonovine and sold under the brand name Methergine, is a medication of the ergoline and lysergamide groups which is used as an oxytocic in obstetrics and in the treatment of migraine. It reportedly produces psychedelic effects similar to those of lysergic acid diethylamide (LSD) at high doses.

<span class="mw-page-title-main">Methysergide</span> Chemical compound

Methysergide, sold under the brand names Deseril and Sansert, is a monoaminergic medication of the ergoline and lysergamide groups which is used in the prophylaxis and treatment of migraine and cluster headaches. It has been withdrawn from the market in the United States and Canada due to adverse effects. It is taken by mouth.

<span class="mw-page-title-main">Lisuride</span> Chemical compound

Lisuride, sold under the brand name Dopergin among others, is a monoaminergic medication of the ergoline class which is used in the treatment of Parkinson's disease, migraine, and high prolactin levels. It is taken by mouth.

<span class="mw-page-title-main">Indole alkaloid</span> Class of alkaloids

Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.

<span class="mw-page-title-main">Pipamperone</span> Antipsychotic drug

Pipamperone, also known as carpiperone and floropipamide or fluoropipamide, and as floropipamide hydrochloride (JAN), is a typical antipsychotic of the butyrophenone family used in the treatment of schizophrenia and as a sleep aid for depression. It is or has been marketed under brand names including Dipiperon, Dipiperal, Piperonil, Piperonyl, and Propitan. Pipamperone was discovered at Janssen Pharmaceutica in 1961, and entered clinical trials in the United States in 1963.

Oxytocin/ergometrine (trade name Syntometrine) is an obstetric combination drug. The components are synthetically produced oxytocin, a human hormone produced in the hypothalamus, and ergometrine, an alpha-adrenergic, dopaminergic and serotonin (5-HT2) receptor agonist.

A uterotonic, also known as an oxytocic or ecbolic, is a type of medication used to induce contraction or greater tonicity of the uterus. Uterotonics are used both to induce labor and to reduce postpartum hemorrhage.

<span class="mw-page-title-main">25I-NBF</span> Chemical compound

25I-NBF is a derivative of the phenethylamine hallucinogen 2C-I, which acts as a highly potent partial agonist for the human 5-HT2A receptor, with bias towards the β-arrestin 2 coupled signalling pathway. It has been studied in its 11C radiolabelled form as a potential ligand for mapping the distribution of 5-HT2A receptors in the brain, using positron emission tomography (PET).

<span class="mw-page-title-main">25D-NBOMe</span> Chemical compound

25D-NBOMe is a derivative of the phenethylamine derived hallucinogen 2C-D. It acts in a similar manner to related compounds such as 25I-NBOMe, which is a potent agonist at the 5HT2A receptor. 25D-NBOMe has been sold as a street drug since 2010 and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe. It was banned as a Temporary Class Drug in the UK on 10 June 2013 after concerns about its recreational use.

<span class="mw-page-title-main">25G-NBOMe</span> Chemical compound

25G-NBOMe (NBOMe-2C-G) is a derivative of the phenethylamine hallucinogen 2C-G, which acts as a highly potent agonist for the human 5-HT2A receptor.

<span class="mw-page-title-main">25H-NBOMe</span> Chemical compound

25H-NBOMe (NBOMe-2C-H) is a derivative of the phenethylamine hallucinogen 2C-H, which acts as a highly potent full agonist for the human 5-HT2A receptor.

<span class="mw-page-title-main">25-NB</span> Family of serotonergic psychedelics

The 25-NB (25x-NBx) series, sometimes alternatively referred to as the NBOMe compounds, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C family. They act as selective agonists of the serotonin 5-HT2A receptor. The 25-NB family is unique relative to other classes of psychedelics in that they are, generally speaking, extremely potent and relatively selective for the 5-HT2A receptor. Use of NBOMe series drugs has caused many deaths and hospitalisations since the drugs popularisation in the 2010s. This is primarily due to their high potency, unpredictable pharmacokinetics, and sellers passing off the compounds in the series as LSD.

References

  1. 1 2 Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 113–. ISBN   978-0-7514-0499-9.
  2. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 397–. ISBN   978-3-88763-075-1.
  3. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  4. 1 2 3 4 5 6 "Ergonovine Maleate". The American Society of Health-System Pharmacists. Archived from the original on 2015-12-25. Retrieved 1 December 2015.
  5. 1 2 Ravina E (2011). The evolution of drug discovery : from traditional medicines to modern drugs (1st ed.). Weinheim: Wiley-VCH. p. 245. ISBN   9783527326693. Archived from the original on 2015-12-26.
  6. ↑ Sneader W (2005). Drug Discovery: a History (Rev. and updated ed.). Chichester: Wiley. p. 349. ISBN   9780471899792. Archived from the original on 2015-12-26.
  7. ↑ King LA (2009). Forensic chemistry of substance misuse : a guide to drug control. Cambridge, UK: Royal Society of Chemistry. p. 190. ISBN   9780854041787. Archived from the original on 2015-12-26.
  8. ↑ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl: 10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  9. ↑ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl: 10665/345533 . WHO/MHP/HPS/EML/2021.02.
  10. ↑ 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.
  11. ↑ Sunagawa O, Shinzato Y, Touma T, Tomori M, Fukiyama K (May 2000). "Differences between coronary hyperresponsiveness to ergonovine and vasospastic angina". Japanese Heart Journal. 41 (3): 257–268. doi: 10.1536/jhj.41.257 . PMID   10987346.
  12. ↑ "Ergometrine drug information". DrugsUpdate.com. Archived from the original on 2012-04-25.
  13. ↑ McDonald S, Abbott JM, Higgins SP (2004). "Prophylactic ergometrine-oxytocin versus oxytocin for the third stage of labour". The Cochrane Database of Systematic Reviews. 2004 (1): CD000201. doi:10.1002/14651858.CD000201.pub2. PMC   6491201 . PMID   14973949.
  14. ↑ Ott J, Neely P (1980). "Entheogenic (hallucinogenic) effects of methylergonovine". Journal of Psychedelic Drugs. 12 (2): 165–166. doi:10.1080/02791072.1980.10471568. PMID   7420432.
  15. ↑ Halberstadt AL, Nichols DE (2020). "Serotonin and serotonin receptors in hallucinogen action". Handbook of the Behavioral Neurobiology of Serotonin. Handbook of Behavioral Neuroscience. Vol. 31. pp. 843–863. doi:10.1016/B978-0-444-64125-0.00043-8. ISBN   9780444641250. ISSN   1569-7339. S2CID   241134396.
  16. ↑ Cavero I, Guillon JM (2014). "Safety Pharmacology assessment of drugs with biased 5-HT(2B) receptor agonism mediating cardiac valvulopathy". Journal of Pharmacological and Toxicological Methods. 69 (2): 150–161. doi:10.1016/j.vascn.2013.12.004. PMID   24361689.
  17. 1 2 De Costa C (May 2002). "St Anthony's fire and living ligatures: a short history of ergometrine". Lancet. 359 (9319): 1768–1770. doi:10.1016/S0140-6736(02)08658-0. PMID   12049883. S2CID   53277037.
  18. ↑ Dudley HW, Moir C (March 1935). "The Substance Responsible for the Traditional Clinical Effect of Ergot". British Medical Journal. 1 (3871): 520–523. doi:10.1136/bmj.1.3871.520. PMC   2459740 . PMID   20778930.
  19. ↑ Hoyer D (November 2020). "Targeting the 5-HT system: Potential side effects". Neuropharmacology. 179: 108233. doi:10.1016/j.neuropharm.2020.108233. PMID   32805212. S2CID   221118172.
  20. ↑ "List of Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances Under International Control" (PDF) (Eleventh ed.). Vienna, Austria: International Narcotics Control Board. January 2007. Archived from the original (PDF) on February 27, 2008.
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