Compound: metergoline
SMILES: O=C(OCc1ccccc1)NC[C@H]2CN([C@@H]3Cc4cn(c5c4c([C@H]3C2)ccc5)C)C
InChIKey: WZHJKEUHNJHDLS-QTGUNEKASA-N
Synonyms: metergoline, 17692-51-2, Liserdol, Metergolin, Methergoline, Metergolina, Metergolinum, FI 6337, FI-6337, (+)-N-(Carboxy)-1-methyl-9,10-dihydrolysergamine benzyl ester, 1-Methyl-N-carbobenzyloxydihydro-D-lysergamin, DTXSID5042584, 1-Methyl-8-beta-carbobenzyloxyaminomethyl-10-alpha-ergoline, 1,6-Dimethyl-8-beta-carbobenzyloxaminomethyl-10-alpha-ergoline, D-8-beta-((Carbobenzoxyamino)methyl)-1,6-dimethyl-10-alpha-ergoline, (((8-beta)-1,6-Dimethylergolin-8-yl)methyl)carbamic acid phenylmethyl ester, NSC-755878, 1501393LY5, DTXCID3022584, CHEBI:64216, Carbamic acid, (((8beta)-1,6-dimethylergolin-8-yl)methyl)-, phenylmethyl ester, benzyl {[(8alpha)-1,6-dimethylergolin-8-yl]methyl}carbamate, benzyl N-[[(6aR,9S,10aR)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-yl]methyl]carbamate, benzyl (((8alpha)-1,6-dimethylergolin-8-yl)methyl)carbamate, benzyl N-(((6aR,9S,10aR)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo(4,3-fg)quinoline-9-yl)methyl)carbamate, RefChem:156826, G02CB05, 241-686-3, MLS000069437, MCE, SMR000059050, CHEMBL19215, Metergoline (INN), NCGC00017257-09, METERGOLINE [INN], benzyl N-[[(6aR,9S,10aR)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinolin-9-yl]methyl]carbamate, Metergolina [DCIT], Metergolinum [Latin], Metergolina [Spanish], Metergoline [INN:BAN], Substance 355/255, D-8-beta-((Carboxyamino)methyl)-1,6-dimethylergoline benzyl ester, (((8-beta)-1,6-Dimethylergolin-8-yl)methyl)carbamic acid benzyl ester, Metergolinum [INN-Latin], benzyl (((6aR,9S,10aR)-4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl)methyl)carbamate, SR-01000000003, AHR 3009, EINECS 241-686-3, Methergoline;, MFCD00153829, D-N-Carbobenzoxydihydro-1-methyllysergamine I, Al-Migren;, UNII-1501393LY5, Benzyl 1,6-dimethylergolin-8beta-ylmethylcarbamat, Prestwick_657, CAS-17692-51-2, D-N-Carboxydihydro-1-methyllysergamine I benzyl ester, METERGOLINE [MI], Opera_ID_1642, Prestwick0_000364, Prestwick1_000364, Prestwick2_000364, Prestwick3_000364, Carbamic acid, ((1,6-dimethylergolin-8-beta-yl)methyl)-, benzyl ester, D-8-beta-((Carboxyamino)methyl)-1,6-dimethylergoline I benzyl ester, N-Cbz-[(8beta)-1,6-Dimethylergolin-8-yl]methylamine, Biomol-NT_000134, UPCMLD-DP151, METERGOLINE [MART.], Lopac0_000726, BSPBio_000487, GTPL133, METERGOLINE [WHO-DD], cid_28693, MLS001148102, MLS002207142, SCHEMBL117882, REGID_for_CID_28693, SPBio_002408, BPBio1_000287, BPBio1_000537, orb1303313, SCHEMBL29392365, UPCMLD-DP151:001, BDBM30704, HMS1569I09, HMS2096I09, HMS2234H19, HMS3262A14, HMS3411I04, HMS3675I04, HMS3713I09, Lysergamine, N-carboxy-9,10-dihydro-1-methyl-, benzyl ester, HY-B1033, Tox21_110808, Tox21_500726, EBC-26963, HB1623, STL525769, [(8beta)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl ester, AKOS015889165, Carbamic acid, (((8-beta)-1,6-dimethylergolin-8-yl)methyl)-, benzyl ester, Tox21_110808_1, AT31965, CCG-204811, CS-4551, DB13520, FM12444, KS-1369, LP00726, NSC 755878, SDCCGSBI-0050704.P002, Carbamic acid, (((8-beta)-1,6-dimethylergolin-8-yl)methyl)-, phenylmethyl ester, NCGC00017257-05, NCGC00017257-06, NCGC00017257-07, NCGC00017257-08, NCGC00017257-10, NCGC00017257-11, NCGC00017257-14, NCGC00017257-19, NCGC00022834-04, NCGC00022834-05, NCGC00022834-06, NCGC00022834-07, NCGC00022834-08, NCGC00261411-01, DA-75438, ST056348, EU-0100726, D07218, M 3668, EN300-18386599, SR-01000075561, Q6823517, SR-01000000003-2, SR-01000000003-4, SR-01000000003-5, SR-01000000003-6, SR-01000075561-1, BRD-K56699285-001-03-7, BRD-K56699285-001-18-5, BRD-K56699285-001-23-5, 8b-Carbobenzyloxyaminomethyl-1,6-dimethyl-10a-ergoline, Benzyl [(1,6-dimethylergolin-8beta-yl)methyl]carbamate, benzyl {[(8beta)-1,6-dimethylergolin-8-yl]methyl}carbamate, [(8b)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl ester, [[(8beta)-1,6-Dimethylergolin-8-yl]-methyl]carbamic acid phenylmethyl ester, (phenylmethyl) N-[[(6aR,9S,10aR)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-yl]methyl]carbamate, benzyl N-{[(2R,4S,7R)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl}carbamate, N-[[(6aR,9S,10aR)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-yl]methyl]carbamic acid (phenylmethyl) ester, N-[[(6aR,9S,10aR)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-yl]methyl]carbamic acid benzyl ester
Theoretical properties:
molecular_formula: C25H29N3O2
molecular_weight: 403.5 g/mol
exact_mass: 403.22597718 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 5
heavy_atom_count: 30
topological_polar_surface_area: 46.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Metergoline is an ergoline alkaloid that is the N-benzyloxycarbonyl derivative of lysergamine. A 5-HT2 antagonist. Also 5-HT1 antagonist and 5-HT1D ligand. Has moderate affinity for 5-HT6 and high affinity for 5-HT7. It has a role as a geroprotector, a serotonergic antagonist and a dopamine agonist. It is a carbamate ester and an ergoline alkaloid.
chebi: An ergoline alkaloid that is the <em>N</em>-benzyloxycarbonyl derivative of lysergamine. A 5-HT<small><sub>2</sub></small> antagonist. Also 5-HT<small><sub>1</sub></small> antagonist and 5-HT<small><sub>1D</sub></small> ligand. Has moderate affinity for 5-HT<small><sub>6</sub></small> and high affinity for 5-HT<small><sub>7</sub></small>.
chembl: METERGOLINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Metergoline (INNTooltip INN, BANTooltip British Approved Name), also known as methergoline and sold under the brand names Contralac (veterinary) and Liserdol (clinical), is a monoaminergic medication of the ergoline group which is used as a prolactin inhibitor in the treatment of hyperprolactinemia (high prolactin levels) and to suppress lactation.