Ergonovine

{{Short description|Lysergamide}} {{Use dmy dates|date=April 2025}} {{cs1 config|name-list-style=vanc|display-authors=6}}

: {{distinguish||text=Ergometrine (another ergot alkaloid, used in childbirth and delivery)}} {{Infobox drug | Watchedfields = changed | verifiedrevid = 443732517 | image = Ergonovine-skeletal.svg | image_class = skin-invert-image | width = 200px | image2 = Ergonovine 3D.png | image_class2 = bg-transparent | width2 = 200px

| tradename = Ergotrate, Ergotrate Maleate<ref name="MortonHall1999" /><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA397|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=397–}}</ref> | Drugs.com = {{drugs.com|monograph|ergonovine-maleate}} | pregnancy_category = | routes_of_administration = oral, intramuscular, intravenous | class = Serotonin receptor agonists; Uterotonic | ATC_prefix = G02 | ATC_suffix = AB03

| legal_AU = | legal_BR = D1 | legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}</ref> | legal_CA = Schedule VI | legal_UK = | legal_US = Rx only | legal_status =

| IUPHAR_ligand = 148 | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 60-79-7 | PubChem = 443884 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01253 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 391970 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = WH41D8433D | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D07905 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 4822 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 119443 | synonyms = Ergometrine;<ref name=ergonovine>{{Cite book |vauthors= Wasson RG, Hofmann A, Ruck CA, Webster P |url=https://books.google.com/books?id=7JC7EAAAQBAJ&pg=PA38 |title=The Road to Eleusis: Unveiling the Secret of the Mysteries |publisher=North Atlantic Books |publication-date=2008-11-25 |orig-date=1978 |isbn=978-1-55643-752-6 |location=Berkeley, California |page=38 }}</ref><ref name=incb>{{cite report |title=International Narcotics Control Board Red List, 17ᵗʰ edition, January 2020 |publisher=International Narcotics Control Board |location=Vienna International Centre, Vienna, Austria |url=https://www.incb.org/documents/PRECURSORS/RED_LIST/2020/Red_List_2020_E.pdf |access-date=2024-11-17}} ''ergometrine'' is on p. 11, the other three are on p. 13.</ref> Ergobasin;<ref name=ergonovine/> Ergotocine;<ref name=ergonovine/> Ergostetrine;<ref name=ergonovine/> Lysergic acid propanolamide;<ref name=incb /> Lysergic acid hydroxymethylethylamide;<ref name=incb /> ᴅ-Lysergic acid-1,2-propanolamide;<ref name=incb/> ᴅ-Lysergic acid 1-(hydroxymethyl)ethylamide;<ref name=incb/> ᴅ(+)-Lysergic acid-β-hydroxyisopropylamide<ref name=incb/>

| IUPAC_name = (6a''R'',9''R'')-''N''-((''S'')-1-Hydroxypropan- 2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-''fg'']quinoline-9-carboxamide | C = 19 | H = 23 | N = 3 | O = 2 | SMILES = [H][C@@]12Cc3c[nH]c4cccc(C1=C[C@@H](C(=O)N[C@@H](C)CO)CN2C)c34 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = WVVSZNPYNCNODU-XTQGRXLLSA-N }}  '''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.<ref name=AHFS2015>{{cite web|title=Ergonovine Maleate|url=https://www.drugs.com/monograph/ergonovine-maleate.html|publisher=The American Society of Health-System Pharmacists|access-date=1 December 2015|url-status=live|archive-url=https://web.archive.org/web/20151225224708/http://www.drugs.com/monograph/ergonovine-maleate.html|archive-date=2015-12-25}}</ref><ref name="MortonHall1999">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=mqaOMOtk61IC&pg=PA113|date=31 October 1999|publisher=Springer Science & Business Media|isbn=978-0-7514-0499-9|pages=113–}}</ref> It can be used either by mouth, by injection into a muscle, or injection into a vein.<ref name=AHFS2015/>

Common side effects include high blood pressure, vomiting, seizures, headache, and low blood pressure.<ref name=AHFS2015/> Other serious side effects include ergotism.<ref name=AHFS2015/>

Ergonovine was discovered in 1932.<ref name=Rav2011>{{cite book| vauthors = Ravina E |title=The evolution of drug discovery: from traditional medicines to modern drugs|date=2011|publisher=Wiley-VCH|location=Weinheim|isbn=978-3-527-32669-3|page=245|edition= 1st |url=https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA245|url-status=live|archive-url=https://web.archive.org/web/20151226162800/https://books.google.ca/books?id=iDNy0XxGqT8C&pg=PA245|archive-date=2015-12-26}}</ref> It is on the World Health Organization's List of Essential Medicines.<ref name="WHO21st">{{cite book | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> Ergonovine is controlled in some countries because it can be used to make the psychedelic drug lysergic acid diethylamide (LSD).<ref>{{cite book| vauthors = King LA |title=Forensic chemistry of substance misuse: a guide to drug control|date=2009|publisher=Royal Society of Chemistry|location=Cambridge, UK|isbn=978-0-85404-178-7|page=190|url=https://books.google.com/books?id=x9Z1QZ5NIEIC&pg=PA190|url-status=live|archive-url=https://web.archive.org/web/20151226165636/https://books.google.ca/books?id=x9Z1QZ5NIEIC&pg=PA190|archive-date=2015-12-26}}</ref> It is also known to produce psychedelic effects itself at high doses.<ref name="eleusis" /><ref name="BigwoodOttThompson1979" />

==Medical uses== 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.{{Citation needed|date=April 2026}} It is usually combined with oxytocin (Syntocinon) as syntometrine. It begins working within 15{{nbsp}}minutes when taken by mouth and is faster in onset when used by injection.<ref name=AHFS2015/> Its duration is between 45 and 180{{nbsp}}minutes.<ref name=AHFS2015/>

It can induce spasm of the coronary arteries.<ref name="pmid16162623">{{cite journal | vauthors = Romagnoli E, Niccoli G, Crea F | title = Images in cardiology: A coronary organic stenosis distal to severe, ergonovine induced spasm: decision making | journal = Heart | volume = 91 | issue = 10 | page = 1310 | date = October 2005 | pmid = 16162623 | pmc = 1769140 | doi = 10.1136/hrt.2004.058560 }}</ref> It is used to diagnose variant (Prinzmetal's) angina.<ref name="pmid10987346">{{cite journal | vauthors = Sunagawa O, Shinzato Y, Touma T, Tomori M, Fukiyama K | title = Differences between coronary hyperresponsiveness to ergonovine and vasospastic angina | journal = Japanese Heart Journal | volume = 41 | issue = 3 | pages = 257–268 | date = May 2000 | pmid = 10987346 | doi = 10.1536/jhj.41.257 | doi-access = free }}</ref>

==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.<ref>{{cite web | url = http://www.drugsupdate.com/generic/view/138 | title = Ergometrine drug information | work = DrugsUpdate.com | archive-url = https://web.archive.org/web/20120425092448/http://www.drugsupdate.com/generic/view/138 | archive-date=2012-04-25 }}</ref> An overdose produces a characteristic poisoning, ergotism or "St. Anthony's fire": prolonged vasospasm resulting in gangrene and amputations; hallucinations and dementia; unsafe abortions.

Gastrointestinal disturbances such as diarrhea, nausea, and vomiting, are common.<ref>{{cite journal | vauthors = McDonald S, Abbott JM, Higgins SP | title = Prophylactic ergometrine-oxytocin versus oxytocin for the third stage of labour | journal = The Cochrane Database of Systematic Reviews | volume = 2004 | issue = 1 | article-number = CD000201 | date = 2004 | pmid = 14973949 | pmc = 6491201 | doi = 10.1002/14651858.CD000201.pub2 }}</ref> The drug is contraindicated in pregnancy, vascular disease, and psychosis. It passes on in breastmilk and can cause side effects (ergotism) in nursing infants. Ergonovine is used postpartum after the delivery of the placenta, and after ruling out the possibility of twins<ref>{{Cite web |title=Ergonovine Maleate Injection USP - PRESCRIBING INFORMATION - IV/IM use |url=https://pdf.hres.ca/dpd_pm/00061054.PDF |website=Drug and Health Product Register (CA)}}</ref> probably to stop bleeding. It is in (Australia) AU Pregnancy category C,<ref>https://www.drugs.com/pregnancy/ergonovine.html</ref> like ergotamine/caffeine.<ref>https://www.drugs.com/pregnancy/caffeine-ergotamine.html</ref> Use during pregnancy can cause harm to the fetus.

==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

==Pharmacology== ===Pharmacodynamics=== Ergonovine stimulates the uterus and other smooth muscles. It targets α-adrenergic, dopaminergic, and serotonin receptors (the 5-HT2 receptor). Its uterotonic effect has not been identified with a specific receptor type.{{cn|date=August 2020}} The drug has been found to bind to and activate the rat and human serotonin 5-HT2A receptor with similar affinity as lysergic acid diethylamide (LSD).<ref name="HagenPiercePeroutka1994">{{cite journal | vauthors = Hagen JD, Pierce PA, Peroutka SJ | title = Differential binding of ergot compounds to human versus rat 5-HT2 cortical receptors | journal = Biol Signals | volume = 3 | issue = 5 | pages = 223–229 | date = 1994 | pmid = 7704103 | doi = 10.1159/000109549 | url = }}</ref><ref name="WackerWangMcCorvy2017">{{cite journal | vauthors = Wacker D, Wang S, McCorvy JD, Betz RM, Venkatakrishnan AJ, Levit A, Lansu K, Schools ZL, Che T, Nichols DE, Shoichet BK, Dror RO, Roth BL | title = Crystal Structure of an LSD-Bound Human Serotonin Receptor | journal = Cell | volume = 168 | issue = 3 | pages = 377–389.e12 | date = January 2017 | pmid = 28129538 | pmc = 5289311 | doi = 10.1016/j.cell.2016.12.033 | url = }}</ref> Ergonovine is an agonist of the serotonin 5-HT2B receptor and has been associated with cardiac valvulopathy.<ref name="pmid24361689">{{cite journal | vauthors = Cavero I, Guillon JM | title = Safety Pharmacology assessment of drugs with biased 5-HT(2B) receptor agonism mediating cardiac valvulopathy | journal = Journal of Pharmacological and Toxicological Methods | volume = 69 | issue = 2 | pages = 150–161 | date = 2014 | pmid = 24361689 | doi = 10.1016/j.vascn.2013.12.004 }}</ref><ref name="WackerWangMcCorvy2017" /> A computer-predicted binding profile of ergonovine at an array of serotonin, dopamine, and other receptors has been published.<ref name="PaulkeKremerWunder2013">{{cite journal | vauthors = Paulke A, Kremer C, Wunder C, Achenbach J, Djahanschiri B, Elias A, Schwed JS, Hübner H, Gmeiner P, Proschak E, Toennes SW, Stark H | title = Argyreia nervosa (Burm. f.): receptor profiling of lysergic acid amide and other potential psychedelic LSD-like compounds by computational and binding assay approaches | journal = J Ethnopharmacol | volume = 148 | issue = 2 | pages = 492–497 | date = July 2013 | pmid = 23665164 | doi = 10.1016/j.jep.2013.04.044 | url = }}</ref> It was predicted to bind to most of the serotonin receptors with moderately high affinity, albeit lower than LSD.<ref name="PaulkeKremerWunder2013" /> Ergometrine produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.<ref name="BalsaraBapatNandal1986">{{cite journal | vauthors = Balsara JJ, Bapat TR, Nandal NV, Gada VP, Chandorkar AG | title = Head-twitch response induced by ergometrine in mice: behavioural evidence for direct stimulation of central 5-hydroxytryptamine receptors by ergometrine | journal = Psychopharmacology (Berl) | volume = 88 | issue = 3 | pages = 275–278 | date = 1986 | pmid = 2938207 | doi = 10.1007/BF00180824 | url = }}</ref><ref name="BalsaraJadhavGaonkar2005">{{cite journal | vauthors = Balsara JJ, Jadhav SA, Gaonkar RK, Gaikwad RV, Jadhav JH | title = Effects of the antidepressant trazodone, a 5-HT 2A/2C receptor antagonist, on dopamine-dependent behaviors in rats | journal = Psychopharmacology (Berl) | volume = 179 | issue = 3 | pages = 597–605 | date = May 2005 | pmid = 15614572 | doi = 10.1007/s00213-004-2095-0 | url = }}</ref><ref name="CornePickering1967">{{cite journal | vauthors = Corne SJ, Pickering RW | title = A possible correlation between drug-induced hallucinations in man and a behavioural response in mice | journal = Psychopharmacologia | volume = 11 | issue = 1 | pages = 65–78 | date = 1967 | pmid = 5302272 | doi = 10.1007/BF00401509 | url = }}</ref> However, it was 222-fold less potent than LSD in producing this effect.<ref name="CornePickering1967" />

==Chemistry== ===Synthesis=== Ergonovine was originally made from the rye ergot fungus but can also be made from lysergic acid.<ref name=Rav2011/><ref>{{cite book| vauthors = Sneader W |title=Drug Discovery: a History |date=2005 |publisher=Wiley |location=Chichester|isbn=978-0-471-89979-2|page=349|edition=Rev. and updated|url=https://books.google.com/books?id=Cb6BOkj9fK4C&pg=PA349|url-status=live|archive-url=https://web.archive.org/web/20151226180447/https://books.google.ca/books?id=Cb6BOkj9fK4C&pg=PA349|archive-date=2015-12-26}}</ref>

===Analogues=== A simplified analogue of ergonovine that was also investigated as an oxytocic is tochergamine.

==Natural occurrence== According to Albert Hofmann and other researchers, although ergonovine is naturally occurring in morning glory seeds and is known to produce psychedelic effects at higher doses,<ref name="BigwoodOttThompson1979">{{cite journal | vauthors = Bigwood J, Ott J, Thompson C, Neely P | title = Entheogenic effects of ergonovine | journal = J Psychedelic Drugs | volume = 11 | issue = 1–2 | pages = 147–149 | date = 1979 | pmid = 522166 | doi = 10.1080/02791072.1979.10472099 | url = https://bibliography.maps.org/resources/download/12845 | quote = In 1977 and 1978 Hofmann reported that ergonovine maleate was entheogenic,1 a surprising finding in view of its widespread use in obstetrics (Wasson, Hofmann & Ruck 1978; Hofmann 1977). This report was based on a self-experiment conducted by Hofmann on 1 April 1976, with 2.0 mg of ergonovine maleate taken orally. Hofmann reported that this dose manifested a "slightly hallucinogenic activity" lasting more than five hours.2 [...] Our experiments corroborate Hofmann's report that ergonovine possesses entheogenic properties. We found the active dose to lie between 5.0 and 10.0 mg, peroral. It is interesting to note that Hofmann experienced distinct entheogenic effects at 2.0 mg, while Wasson and Ruck did not. Similarly, J.B. experienced distinct entheogenic effects at 3.0 mg, whereas J.O. and P.N. did not. This underscores the importance of metabolic individuality in the uptake and metabolism of mind-altering drugs. With respect to entheogenic effects 10 mg of ergonovine maleate is roughly equivalent to 50 μg is, ergonovine possesses about that LSD-tartrate, 1/200th the entheogenic potency of LSD. | archive-date = 28 March 2025 | access-date = 30 March 2025 | archive-url = https://web.archive.org/web/20250328185507/https://bibliography.maps.org/resources/download/12845 | url-status = bot: unknown }}</ref><ref name="Hofmann1978">{{cite book | vauthors = Hofmann A | chapter = [Chapter Two:] A Challenging Question and My Answer | pages = 35–44 | editor = Robert Forte | title = The Road to Eleusis: Unveiling the Secret of the Mysteries | chapter-url = https://the-eye.eu/tasra/pages/DavidsWelt/media/16305.pdf#page=37 | publisher = North Atlantic Books | location = Berkeley, California | date = 2008 | edition = Thirtieth Anniversary | orig-date = 1978 | isbn = 978-1-55643-752-6 | url = https://books.google.com/books?id=9o8lAQAAIAAJ}}</ref> it is present in too small of amounts to contribute to their psychoactive or hallucinogenic effects.<ref name="Hofmann1968">{{cite book | author = Albert Hofmann | chapter = Psychotomimetic Agents | pages = 169–235 | veditors = Burger A | title = Drugs Affecting the Central Nervous System | volume = 2 | date = 1968 | publisher = M. Dekker | location = New York | oclc = 245452885 | ol = OL13539506M | chapter-url = https://archive.org/details/drugsaffectingce0000edit/page/169/mode/1up | url = https://books.google.com/books?id=o_GMwgEACAAJ | quote = Psychotomimetic effects are unknown for ergometrine, which is used to a large extent in obstetrics as a uterotonic and hemostatic agent. In small dosages, which are administered for this purpose, the alkaloid apparently has no action on the psychic functions. Its occurrence in the alkaloid mixture of ololiuqui can thus have no significant effects on its mental action.}}</ref><ref name="BrimblecombePinder1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | pages = 98–144 | title = Hallucinogenic Agents | date = 1975 | publisher = Wright-Scientechnica | location = Bristol | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1 | quote = d-Lysergic acid amide (ergine) is the major constituent of the seeds of both Rivea corymbosa and Ipomoea violacea, together with smaller amounts of d-isolysergic acid amide (isoergine), chanoclavine, elymoclavine, and the N-(1-hydroxyethyl)amides of lysergic and isolysergic acids. [...] Lysergol is found in Rivea but not in Ipomoea, while ergometrine (ergonovine) is present in the latter but not the former (Hofmann and Tscherter, 1960; Hofmann, 1961b, 1964; Hofmann and Cerletti, 1961; Greger, 1963). [...] [...] It is clear that the pharmacologically active constituents of ololiuqui are the isomeric lysergic acid amides. [...] [...] Certainly elymoclavine, lysergol, chanoclavine, and ergometrine produce no psychic changes in man (Isbell and Gorodetzky, 1966; Hofmann, 1968), though the first two do produce central excitation in animals (Yui and Takeo, 1958). [...] Five-hundred seeds of certain ornamental Ipomoea varieties contain as much as 1 mg. of ergometrine, which is usually considered to be an effective oxytocic in doses as low as 0·2-0·5 mg.}}</ref><ref name="ChenDeWitBos2020">{{cite report | vauthors = Chen W, De Wit-Bos L | title=Risk assessment of Argyreia nervosa | date=2020 | doi=10.21945/rivm-2019-0210 | url = https://www.rivm.nl/bibliotheek/rapporten/2019-0210.pdf | quote = Some of the ergot alkaloids assessed by EFSA, ergometrine and ergometrinine, do occur in A. nervosa, however in lesser amounts than the main active alkaloids LSA and iso-LSA. [...] Iso-LSA and LSA were most prominent with relative amounts of 31% and 23% of total alkaloids, respectively. Other ergot alkaloids present included, amongst others, lysergic acid-α-hydroxy ethyl amide (5.8% of total alkaloids) and ergometrine (8.2% of total alkaloids) (Chao & Der Marderosian, 1973).}}</ref><ref name="Shulgin1976">{{cite book | veditors=Gordon M | title=Psychopharmacological Agents: Use, Misuse and Abuse | series=Medicinal Chemistry: A Series of Monographs | volume=4 | vauthors = Shulgin AT | chapter=Psychotomimetic Agents | date=1976 | isbn=978-0-12-290559-9 | doi=10.1016/b978-0-12-290559-9.50011-9 | pages=59–146 | publisher=Academic Press | chapter-url=https://bitnest.netfirms.com/external/10.1016/B978-0-12-290559-9.50011-9 | quote=Ergometrine has, of course, been extensively used in clinical work as an oxytocic following the latter stages of labor at dosages frequently in excess of a milligram, and although nausea can be encountered as an undesirable side reaction, there appears to be no adverse effects of a psychopharmacological nature. [...] It appears that the agents that are responsible for the human activity of these plants are ergine and isoergine, and possibly the corresponding α-hydroxyethylamides of lysergic acid which could serve as metabolic precursors.}}</ref>

==History== The pharmacological properties of ergot were known and had been utilized 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.<ref name="decosta">{{cite journal | vauthors = De Costa C | title = St Anthony's fire and living ligatures: a short history of ergometrine | journal = Lancet | volume = 359 | issue = 9319 | pages = 1768–1770 | date = May 2002 | pmid = 12049883 | doi = 10.1016/S0140-6736(02)08658-0 | s2cid = 53277037 }}</ref>

Ergonovine was first isolated and obtained by the chemists C Moir, H W Dudley and Gerald Rogers{{fact|date=July 2021}} in 1935.<ref>{{cite journal | vauthors = Dudley HW, Moir C | title = The Substance Responsible for the Traditional Clinical Effect of Ergot | journal = British Medical Journal | volume = 1 | issue = 3871 | pages = 520–523 | date = March 1935 | pmid = 20778930 | pmc = 2459740 | doi = 10.1136/bmj.1.3871.520 }}</ref><ref name="pmid32805212">{{cite journal | vauthors = Hoyer D | title = Targeting the 5-HT system: Potential side effects | journal = Neuropharmacology | volume = 179 | issue = | article-number = 108233 | date = November 2020 | pmid = 32805212 | doi = 10.1016/j.neuropharm.2020.108233 | s2cid = 221118172 }}</ref> 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.<ref name="decosta" />

==Society and culture== ===Recreational use=== Ergonovine induces hallucinogenic effects at doses of 2–10{{nbsp}}mg, in contrast to its medical use in doses of 0.2–0.4{{nbsp}}mg.<ref name="eleusis">{{Cite book | vauthors = Wasson RG, Hofmann A, Ruck CA, Webster P |chapter-url=https://books.google.com/books?id=7JC7EAAAQBAJ&pg=PA39 |title=The Road to Eleusis: Unveiling the Secret of the Mysteries |publisher=North Atlantic Books |publication-date=2008-11-25 |orig-date=1978 |isbn=978-1-55643-752-6 |location=Berkeley, California |pages=39–41 |chapter=Chapter 2, A Challenging Question and My Answer (Hofmann)}}</ref><ref name="BigwoodOttThompson1979" /><ref>{{Cite book | vauthors = Ripinsky-Naxon M |title=The Nature of Shamanism: Substance and Function of a Religious Metaphor |publisher=State University of New York Press |year=1993 |isbn=978-1-4384-1741-7 |location=Albany, NY |page=146 |chapter=Chapter 5, The Ritual Drug Complex: Ethnobiology of Heaven and Hell. Psychoactivity and Mechanisms of Hallucinations}}</ref><ref>{{cite web | vauthors = Eisner B | title = Interview with an Alchemist: Bear Owsley Interview | work = Bruce Eisner's Writings | date = January 10, 2004 | url = http://www.bruceeisner.com/writings/2004/01/interview_with__2.html | archive-url = https://web.archive.org/web/20040929080225/http://www.bruceeisner.com/writings/2004/01/interview_with__2.html | access-date = 2024-11-18 | archive-date = 29 September 2004}}</ref><ref>{{cite AV media |title=Hofmann's Potion |year=2002 |publisher=Conceptafilm |author=Connie Littlefield |url=https://m.imdb.com/title/tt0439611/}}</ref> 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.<ref>{{cite book | vauthors = Leistner E, Steiner U | chapter = The Genus Periglandula and Its Symbiotum with Morning Glory Plants (Convolvulaceae) |publication-date=February 3, 2018 | veditors = Anke T, Schüffler A | title = Physiology and Genetics |pages=131–147 |chapter-url= http://link.springer.com/10.1007/978-3-319-71740-1_5 |access-date=2024-11-21 |place=Cham |publisher=Springer International Publishing |language=en |doi=10.1007/978-3-319-71740-1_5 |isbn=978-3-319-71739-5 }}</ref> The ergonovine content of ''I. tricolor'' seeds varies between one-tenth and one-third of ergine, an ergonovine analog.<ref name=nowak>{{cite journal | vauthors = Nowak J, Woźniakiewicz M, Klepacki P, Sowa A, Kościelniak P | title = Identification and determination of ergot alkaloids in Morning Glory cultivars | journal = Analytical and Bioanalytical Chemistry | volume = 408 | issue = 12 | pages = 3093–3102 | date = May 2016 | pmid = 26873205 | pmc = 4830885 | doi = 10.1007/s00216-016-9322-5 | publication-date = February 14, 2016}}</ref> 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;<ref>{{Cite book | vauthors = Ripinsky-Naxon M |title=The Nature of Shamanism: Substance and Function of a Religious Metaphor |publisher=State University of New York Press |year=1993 |isbn=978-1-4384-1741-7 |location=Albany, NY |page=146 |chapter=Chapter 5, The Ritual Drug Complex: Ethnobiology of Heaven and Hell. Psychoactivity and Mechanisms of Hallucinations}}</ref> 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.<ref>{{Cite journal |author=Hofmann A |title=The Active Principles of the Seeds of ''Rivea corymbosa'' and ''Ipomoea violacea'' |journal=Harvard Botanical Museum Leaflets |volume=20 |issue=6 |date=1963 |publisher=Harvard University Herbaria |pages=194-212 (19 pgs.) |doi=10.5962/p.168542 |url=https://archive.org/details/biostor-160836|doi-access=free }}</ref><ref name="eleusis" />

{{quote|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 [...]}}

===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.<ref>{{cite web | publisher = International Narcotics Control Board | location = Vienna, Austria | edition = Eleventh | date = January 2007 | url = http://www.incb.org/pdf/e/list/red.pdf | title = List of Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances Under International Control | archive-url = https://web.archive.org/web/20080227224025/http://www.incb.org/pdf/e/list/red.pdf | archive-date=February 27, 2008 }}</ref> It is also regulated in the United States.<ref name="OrangeBook2026">{{citation | title = Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) | date = January 2026 | publisher = U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division | location = United States | url = https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf}}</ref> As an ''N''-alkyl derivative of ergine, ergonovine is covered by the Misuse of Drugs Act 1971, effectively rendering it illegal in the United Kingdom as well.{{cn|date=April 2025}}

==See also== * Substituted lysergamide

==References== {{Reflist}}

==External links== * [https://isomerdesign.com/pihkal/explore/5313 Ergometrine - Isomer Design] * [https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml LSD-25 (Discusses Ergonovine) - TiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/tk/26 LSD-25 (Discusses Ergonovine) - TiHKAL - Isomer Design] * [https://nervewing.blogspot.com/2020/06/obscure-and-unknown-ergometrine-and.html Hallucinogens You Probably Haven't Heard of: Ergometrine and Methylergometrine - Nervewing - Blogger]

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