Compound: LYSERGAMIDE
SMILES: O=C(N)[C@@H]1C=C2c3c4c([nH]cc4C[C@H]2N(C1)C)ccc3
InChIKey: GENAHGKEFJLNJB-QMTHXVAHSA-N
Synonyms: LYSERGAMIDE, 478-94-4, Lysergic acid amide, D-Lysergic acid amide, CHEBI:4819, 073830XH10, 9,10-didehydro-6-methylergoline-8 beta-carboxamide, (8R)-9,10-didehydro-6-methylergoline-8-carboxamide, (6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide, (6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo(4,3-fg)quinoline-9-carboxamide, RefChem:800201, 207-524-0, Ergine, (+)-Lysergamide, 9,10-Didehydro-6-methylergoline-8beta-carboxamide, (6aR,9R)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide, d-Lyergic acid amide, DTXSID20893673, UNII-073830XH10, EINECS 207-524-0, BRN 0090708, LYSERGAMIDE [MI], 4-25-00-00937 (Beilstein Handbook Reference), Ergine (Lysergic acid amide), SCHEMBL183540, 9,10-Didehydro-6-methyl-ergoline-8-beta-carboxamide, CHEMBL227213, DEA No. 7310, Ergoline-8-beta-carboxamide, 9,10-didehydro-6-methyl-, PDSP2_001113, AKOS030240648, Methylergometrine Maleate EP Impurity C, DB-230603, NS00042929, C09160, 6-Methyl-9,10-didehydroergoline-8beta-carboxamide, ERGOMETRINE MALEATE IMPURITY C [EP IMPURITY], Q2041643, (8beta)-6-methyl-9,10-didehydroergoline-8-carboxamide, (8.BETA.)-9,10-DIDEHYDRO-6-METHYLERGOLINE-8-CARBOXAMIDE, (4R,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0?,?.0??,??]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide
Theoretical properties:
molecular_formula: C16H17N3O
molecular_weight: 267.33 g/mol
exact_mass: 267.137162174 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 20
topological_polar_surface_area: 62.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Lysergamide is an ergoline alkaloid comprising ergoline lacking hydrogens at positions 9 and 10 and also having a methyl group attached to the piperidine nitrogen. It derives from a hydride of an ergoline.
chebi: An ergoline alkaloid comprising ergoline lacking hydrogens at positions 9 and 10 and also having a methyl group attached to the piperidine nitrogen.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Lysergamides, also known as ergoamides or as lysergic acid amides, are amides of lysergic acid (LA). They are ergolines, with some lysergamides being found naturally in ergot as well as other fungi. Lysergamides are notable in containing embedded phenethylamine and tryptamine moieties within their ergoline ring system.
The simplest lysergamides are ergine (lysergic acid amide; LSA) and isoergine (iso-lysergic acid amide; iso-LSA). In terms of pharmacology, the lysergamides include numerous serotonin and dopamine receptor agonists, most notably the psychedelic drug lysergic acid diethylamide (LSD) but also a number of pharmaceutical drugs like ergometrine, methylergometrine, methysergide, and cabergoline. Various analogues of LSD, such as the psychedelics ALD-52 (1A-LSD), ETH-LAD, LSZ, and 1P-LSD and the non-hallucinogenic 2-bromo-LSD (BOL-148), have also been developed. Ergopeptines like ergotamine, dihydroergotamine, and bromocriptine are also lysergamides, but with addition of a small peptide moiety at the amide. Close analogues of lysergamides that are not technically lysergamides themselves include lisuride, terguride, bromerguride, and JRT.
Lysergamides were first discovered and described in the 1930s.
Simplified or partial ergolines and lysergamides, such as NDTDI (8,10-seco-LSD), DEMPDHPCA, and N-DEAOP-NMT, are also known.