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an alkaloid derived from ergot (trade name Ergotrate Maleate) that is less toxic than ergot; induces muscular contraction of the uterus and is administered after childbirth or abortion (同)Ergotrate Maleate
march in protest; take part in a demonstration; "Thousands demonstrated against globalization during the meeting of the most powerful economic nations in Seattle" (同)march

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/04/24 16:30:51」(JST)

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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 muscles) 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, 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, e.g. diarrhea, 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.
^ 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).

UpToDate Contents

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1. 分娩第3期のマネージメントのための薬物療法 pharmacologic management of the third stage of labor
2. 異型狭心症 variant angina
3. 経腟分娩後の出血管理 management of postpartum hemorrhage at vaginal delivery
4. 労作性頭痛 exertional headache
5. 一次性咳嗽性頭痛 primary cough headache

English Journal

Sequential spasm provocation tests might overcome a limitation of the standard spasm provocation tests.

Sueda S1, Miyoshi T, Sasaki Y, Sakaue T, Habara H, Kohno H.
Coronary artery disease.Coron Artery Dis.2015 Sep;26(6):490-4. doi: 10.1097/MCA.0000000000000267.
OBJECTIVE: We examined the clinical usefulness of sequential spasm provocation tests as follows: first, acetylcholine (ACh) test, second, ergonovine (ER) test, and finally, the ACh test following the ER test.PATIENTS AND METHODS: We performed the ACh and ER tests in 461 patients (294 men, 64.4±11.3
PMID 25974266

Comparison of electrospray ionization and atmospheric pressure photoionization liquid chromatography mass spectrometry methods for analysis of ergot alkaloids from endophyte-infected sleepygrass (Achnatherum robustum).

Jarmusch AK1, Musso AM1, Shymanovich T2, Jarmusch SA1, Weavil MJ1, Lovin ME1, Ehrmann BM1, Saari S2, Nichols DE3, Faeth SH2, Cech NB4.
Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2015 Aug 22;117:11-17. doi: 10.1016/j.jpba.2015.08.031. [Epub ahead of print]
Ergot alkaloids are mycotoxins with an array of biological effects. With this study, we investigated for the first time the application of atmospheric pressure photoionization (APPI) as an ionization method for LC-MS analysis of ergot alkaloids, and compared its performance to that of the more estab
PMID 26340558

Overview of the Acetylcholine Spasm Provocation Test.

Sueda S1, Kohno H1, Ochi T2, Uraoka T3.
Clinical cardiology.Clin Cardiol.2015 Jul;38(7):430-8. doi: 10.1002/clc.22403. Epub 2015 Jul 14.
The acetylcholine (ACh) spasm provocation test proposed by Yasue, Okumura et al more than a quarter-century ago has become a popular method for induction of coronary spasm. This test is safe and has a low rate of complications. However, it may be limited in its ability to document attacks in daily l
PMID 26175183

Japanese Journal

Low Glomerular Filtration Rate Is Associated With High Prevalence of Vasospastic Angina

KOGA Seiji,IKEDA Satoshi,NAKATA Tomoo,YASUNAGA Tomohiko,TAKENO Masayoshi,KOIDE Yuji,MAEMURA Koji
Circulation journal : official journal of the Japanese Circulation Society 75(7), 1691-1695, 2011-06-25
… Methods and Results: We evaluated 139 patients with chest pain at rest who had no significant organic stenosis on coronary angiograms and who underwent coronary spasm provocation tests using acetylcholine or ergonovine. …
NAID 10029126777

Ischemia-Induced Prominent J Waves in a Patient with Brugada Syndrome

Yagihara Nobue,Sato Akinori,Furushima Hiroshi,Chinushi Masaomi,Hirono Takashi,Aizawa Yoshifusa
Internal Medicine 49(18), 1979-1982, 2010
… During cardiac catheterization, baseline coronary angiography was normal, but intracoronary ergonovine maleate induced spasms of the right and left coronary arteries concomitant with chest pain and ST elevation on ECG. …
NAID 130000336887

「demonstrate」

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 O=C(N[C@@H](C)CO)[C@@H]3/C=C2/c4cccc1c4c(cn1)C[C@H]2N(C3)C;
	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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論証/証明/立証する。(事物などが)～の証拠となる
(機械など)の実地説明/演習説明をする。(商品を)実物宣伝する。(実例で)明らかにする、(模型・実験などで)(具体的に)説明する。
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ergonovine, acetylcholine, other vasoconstrictor medications, and hyperventilation have been used to provoke and demonstrate focal coronary stenosis to establish the diagnosis.(HIM.1531)