Compound: methysergide
SMILES: O=C(N[C@H](CO)CC)[C@@H]1C=C2c3c4c(n(C)cc4C[C@H]2N(C1)C)ccc3
InChIKey: KPJZHOPZRAFDTN-ZRGWGRIASA-N
Synonyms: methysergide, Methysergid, 361-37-5, Desernil, Deseril, 1-Methylmethylergonovine, Methysergidum, Metisergide, Metisergido, metisergida, Methyllysergic acid butanolamide, XZA9HY6Z98, N-(alpha-(Hydroxymethyl)propyl)-1-methyl-dextro-lysergamide, DTXSID2023307, 1-Methyl-D-lysergic acid butanolamide, DTXCID703307, N-(1-(Hydroxymethyl)propyl)-1-methyl-dextro-(+)-lysergamide, Ergoline-8-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, (8beta)-, Ergoline-8beta-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, (+)-N-(1-(Hydroxymethyl)propyl)-1-methyl-D-lysergamide, 1-Methyl-dextro-lysergic acid (+)-1-hydroxy-2-butylamide, Dimethylergometrin, 9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8-carboxamide, (+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8beta-carboxamide, Methylmethylergonovine, (4R,7R)-N-((2S)-1-hydroxybutan-2-yl)-6,11-dimethyl-6,11-diazatetracyclo(7.6.1.0^(2,7).0^(12,16))hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide, (4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide, (6aR,9R)-N-((1S)-1-(hydroxymethyl)propyl)-4,7-dimethyl-6,6a,8,9-tetrahydroindolo(4,3-fg)quinoline-9-carboxamide, (6aR,9R)-N-[(1S)-1-(hydroxymethyl)propyl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide, Maleate, Methysergide, Dimaleate, Methysergide, RefChem:818760, Ergoline-8-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, (8beta(S))-, UML491, N02CA04, (4R,7R)-N-(1-hydroxybutan-2-yl)-6,11-dimethyl-6,11-diazatetracyclo(7.6.1.02,7.012,16)hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide, 206-644-0, CHEBI:584020, Sansert, Deseryl, UML-491, Desernyl, Metisergide [DCIT], Methysergidum [INN-Latin], Metisergido [INN-Spanish], UML 491, CHEMBL1065, (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide, Desril, NCGC00024027-05, Methysergide [USAN:INN:BAN], MLS000069364, (8alpha)-N-[(2S)-1-hydroxybutan-2-yl]-1,6-dimethyl-9,10-didehydroergoline-8-carboxamide, (8beta)-9,10-Didehydro-N-[(1S)-1-(hydroxymethyl)propyl]-1,6-dimethylergoline-8-carboxamide, Lysergamide, N-(1-(hydroxymethyl)propyl)-1-methyl-, D-, CAS-361-37-5, HSDB 3237, SMR000058483, EINECS 206-644-0, Methysergide (USAN/INN), UNII-XZA9HY6Z98, BRN 0765985, Desernil Sandoz, Methylergometrine EP impurity G, (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide;(Z)-but-2-enedioic acid, METHYSERGIDE [MI], METHYSERGIDE [INN], Biomol-NT_000155, METHYSERGIDE [HSDB], METHYSERGIDE [USAN], METHYSERGIDE [VANDF], Lopac0_000863, SCHEMBL41843, GTPL134, METHYSERGIDE [MART.], METHYSERGIDE [WHO-DD], BPBio1_000486, BDBM30708, CHEBI:92629, cid_5281073, KPJZHOPZRAFDTN-ZRGWGRIASA-N, HMS2090P04, Tox21_110895, BDBM50031942, Tox21_110895_1, CCG-204945, FM31590, SDCCGSBI-0050838.P003, (8beta)-N-[(1S)-1-(hydroxymethyl)propyl]-1,6-dimethyl-9,10-didehydroergoline-8-carboxamide, Ergoline-8-beta-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, NCGC00024027-04, NCGC00024027-06, NCGC00024027-07, NCGC00024027-08, NCGC00024027-09, NCGC00024027-13, SBI-0050838.P002, NS00001621, C07199, D02357, AB00513725-14, AB00513725_15, Q424442, ERGOMETRINE MALEATE IMPURITY G [EP IMPURITY], BRD-K35941380-001-01-7, BRD-K35941380-050-17-0, BRD-K35941380-050-27-9, Methylergometrine Maleate EP Impurity G; Methysergide, (8beta)-N-[(2S)-1-Hydroxybutan-2-yl]-1,6-dimethyl-9,10-didehydroergoline-8-carboxamide, N-[(2S)-1-Hydroxybutan-2-yl]-1,6-dimethyl-9,10-didehydroergoline-8beta-carboxamide, (6aR,9R)-4,6a,7-Trimethyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (1-hydroxymethyl-propyl)-amide, (6aR,9R)-4,7-Dimethyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid ((S)-1-hydroxymethyl-propyl)-amide, (6aR,9R)-4,7-dimethyl-N-[(1S)-1-methylolpropyl]-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide;maleate, (6aR,9R)-4,7-dimethyl-N-[(1S)-1-methylolpropyl]-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide;maleic acid, (6aR,9R)-4,7-dimethyl-N-[(2S)-1-oxidanylbutan-2-yl]-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide;(Z)-but-2-enedioic acid, (6aR,9R)-4-Methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (1-hydroxymethyl-propyl)-amide, (6aR,9R)-5,7-Dimethyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid diethylamide, (6aR,9R)-N-((S)-1-hydroxybutan-2-yl)-4,7-dimethyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide, (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide;(Z)-2-butenedioic acid, (methylsergide)4,7-Dimethyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (1-hydroxymethyl-propyl)-amide, 4,7-Dimethyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (1-hydroxymethyl-propyl)-amide, H8J
Theoretical properties:
molecular_formula: C21H27N3O2
molecular_weight: 353.5 g/mol
exact_mass: 353.21032711 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 4
heavy_atom_count: 26
topological_polar_surface_area: 57.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals
color: Crystals
solubility: MP IS UNCHARACTERISTIC SHOWING DECOMP ABOVE APPROX 165 °C; ODORLESS OR HAS NOT MORE THAN SLIGHT ODOR; WHITE TO YELLOWISH WHITE OR REDDISH WHITE CRYSTALLINE POWDER; 1 G SOL IN 200 ML WATER, 165 ML ALCOHOL, 3400 ML CHLOROFORM; PRACTICALLY INSOL IN ETHER /MALEATE/
Descriptions:
pubchem: (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide is an ergoline alkaloid.
chembl: METHYSERGIDE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Methysergide, sold under the brand names Deseril and Sansert, is a monoaminergic medication which is used in the prevention and treatment of migraine and cluster headaches. It has been withdrawn from the market in the United States and Canada due to safety concerns. The drug has also been found to produce psychedelic effects at high doses. It is taken orally.
The drug is a prodrug of methylergometrine (methylergonovine), which circulates at levels about 10 times higher than those of methysergide. Whereas methysergide is a mixed agonist of some serotonin receptors (e.g., the serotonin 5-HT1 receptors) and antagonist of other serotonin receptors (e.g., the serotonin 5-HT2 receptors), methylergonovine is a non-selective agonist of most of the serotonin receptors, including of both the serotonin 5-HT1 and 5-HT2 receptor subgroups. Methysergide and methylergometrine are ergolines and lysergamides and are related to the ergot alkaloids.
Methysergide was first described in the literature by 1958. It is no longer recommended as a first-line therapy for migraines or cluster headaches. This is due to toxicity, such as cardiac valvulopathy, which was first reported with long-term use in the late 1960s. Ergot-based medications like methysergide fell out of favor for treatment of migraine with the introduction of the triptans in the 1980s.