Propisergide

Propisergide (INNTooltip International Nonproprietary Name; developmental code name PML-946), 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.^{[2][3][4][5][6]} It is the 1-methyl derivative of ergometrine (ergonovine) and is a close analogue of methylergonovine and methysergide (UML-491).^[7][5][8] Extensive metabolism of other 1-methylated lysergamides to their secondary amine derivatives, for instance methysergide (1-methylmethylergometrine) conversion into methylergometrine, has been observed.^[9][10] Propisergide has 259% of the antiserotonergic activity of LSD.^[7][1] Its average clinical dose range for preventative treatment of migraine is 1 to 3 mg orally.^[1] Propisergide was first described in the literature by 1958^[7][11] and then further around 1980 and after.^[6][12][13]

Propisergide

Clinical data
Other names	PML-946; PML946; Ergalgin; N-Methylergobasine; N-Methylergonovine; N-Methylergometrine; 1-Methylergonovine
Routes of administration	Oral[1]
Drug class	Serotonin receptor modulator; Antimigraine agent
ATC code	None
Identifiers
IUPAC name (6aR,9R)-N-[(2S)-1-hydroxypropan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number	5793-04-4
PubChem CID	20055549
ChemSpider	16737112
UNII	1Q1AWW2JET
ChEMBL	ChEMBL3989790
CompTox Dashboard (EPA)	DTXSID701018134
Chemical and physical data
Formula	C20H25N3O2
Molar mass	339.439 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2CC3=CN(C4=CC=CC(=C34)C2=C1)C)C
InChI InChI=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 Key:XUKAVPATXGYVKJ-WPKBUWHJSA-N

See also

• Substituted lysergamide
• Methysergide (UML-491)