propisergide

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| image = Propisergide.svg

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| class = Serotonin receptor modulator; Antimigraine agent

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| CAS_number = 5793-04-4

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| PubChem = 20055549

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| ChemSpiderID = 16737112

| UNII = 1Q1AWW2JET

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| ChEMBL = 3989790

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| synonyms = Ergalgin; N-Methylergobasine; N-Methylergonovine; N-Methylergometrine; 1-Methylergonovine

| IUPAC_name = (6aR,9R)-N-[(2S)-1-hydroxypropan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide

| C=20 | H=25 | N=3 | O=2

| SMILES = C[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2CC3=CN(C4=CC=CC(=C34)C2=C1)C)C

| StdInChI = 1S/C20H25N3O2/c1-12(11-24)21-20(25)14-7-16-15-5-4-6-17-19(15)13(9-22(17)2)8-18(16)23(3)10-14/h4-7,9,12,14,18,24H,8,10-11H2,1-3H3,(H,21,25)/t12-,14+,18+/m0/s1

| StdInChIKey = XUKAVPATXGYVKJ-WPKBUWHJSA-N

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Propisergide ({{Abbrlink|INN|International Nonproprietary Name}}), also known as ergalgin or as N-methylergometrine or 1-methylergometrine, is a serotonin receptor modulator and antimigraine agent of the ergoline and lysergamide families which was never marketed.{{cite book | vauthors = Elks J | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer US | year=2014 | isbn=978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ | access-date=13 March 2025}}{{cite book | vauthors = Ganellin CR, Triggle DJ | title=Dictionary of Pharmacological Agents | publisher=Taylor & Francis | year=1996 | isbn=978-0-412-46630-4 | url=https://books.google.com/books?id=Z_mfTTIApVEC | access-date=13 March 2025}}{{cite journal | vauthors = Waldman M, Fraczkiewicz R, Clark RD | title = Tales from the war on error: the art and science of curating QSAR data | journal = Journal of Computer-Aided Molecular Design | volume = 29 | issue = 9 | pages = 897–910 | date = September 2015 | pmid = 26290258 | doi = 10.1007/s10822-015-9865-0 | bibcode = 2015JCAMD..29..897W }}{{cite journal | vauthors = Oelszner W | title = Displacement of specific serotonin and lysergic acid diethylamide binding by Ergalgin, a new antiserotonin drug | journal = Acta Biologica et Medica Germanica | volume = 39 | issue = 8–9 | pages = 897–901 | date = 1980 | pmid = 7282219 | doi = }} It is the 1-methyl derivative of ergometrine (ergonovine) and is a close analogue of methylergonovine and methysergide.{{cite web | title=Propisergide | work = PubChem | publisher = U.S. National Library of Medicine | url=https://pubchem.ncbi.nlm.nih.gov/compound/20055549 | access-date=13 March 2025}} The drug was first described in the literature by 1962{{cite book | author=World Health Organization | title=Cumulative List of Proposed International Non-proprietary Names for Pharmaceutical Preparations. 1962- | publisher=World Health Organization | issue=6 | year=1962 | isbn=978-92-4-056013-0 | url=https://books.google.com/books?id=TKFQAAAAYAAJ | access-date=13 March 2025 | page=}} and then further around 1980 and after.{{cite journal | vauthors = Bartsch R, Nowak R | date = January 1979 | title = Pharmacological Evaluation of a New Ergolin Derivative (Ergalgin) | journal = Die Pharmazie | volume = 34 | issue = 5–6 | pages = 358 | location = Eschborn, Germany | publisher = Govi-Verlag Pharmazeutischer GmbH }}{{cite journal | vauthors = Harhammer R, Morgenstern R, Ott T | date = 1992 | title = Pharmacological Effects of Ergalgin, a Potent Antagonist at Central and Peripheral 5-Ht (2) Receptors. | journal = Biogenic Amines | volume = 8 | issue = 3–4 | pages = 267–275 }}

References