Compound: galanthamine
SMILES: O1c2c(OC)ccc3c2[C@]4([C@@H]1C[C@@H](O)C=C4)CCN(C3)C
InChIKey: ASUTZQLVASHGKV-JDFRZJQESA-N
Synonyms: galanthamine, Galantamine, 357-70-0, (-)-Galanthamine, Lycoremine, Galantamina, (-)-Galantamine, Reminyl, Galanthaminum, Galantaminum, NSC-100058, 0D3Q044KCA, (1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol, DTXSID2045606, CHEBI:42944, (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, Reminyl XL, (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol, Galzemic xl, Lotprosin xl, Consion xl, Gatalin xl, Gazylan xl, Luventa xl, Zeebral xl, Acumor xl, Elmino xl, Galsya xl, (1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo(8.6.1.01,12.06,17)heptadeca-6(17),7,9,15-tetraen-14-ol, RefChem:56716, DTXCID0025606, N06DA04, 6H-Benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Lycoremin, Jilkon, (+/-)-Galantamine, Bodamine, (+/-)-Galanthamine, Reminyl (TN), Galantamine, (+/-)-, MFCD00867189, 23173-12-8, Galanthamine, (+/-)-, CHEMBL659, 1T835Z585R, (4aS,6R,8aS)-3-Methoxy-11-methyl-5,6,9,10,11,12-hexahydro-4aH-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol, Galantaminum [INN-Latin], GNT, Galantamina [INN-Spanish], NSC 100058, (1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6,8,10(17),15-tetraen-14-ol, 6H-Benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aR,6S,8aR)-rel-, 6H-Benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aS,6R,8aS)-, BRN 0093736, HSDB 7361, Galantamine (USAN/INN), UNII-0D3Q044KCA, Galantamine [USAN:INN:BAN], SR-05000001783, s3866, 1qti, Galanthamine, 12, (1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6(17),7,9,15-tetraen-14-ol, 6H-Benzofuro[3a,3,2-ef][2]benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aS,6R,8aS)-, Spectrum_001271, 1dx6, Galanthamine (Standard), Galanthamine Impurity 3, GALANTAMINE [MI], Prestwick0_000588, Prestwick1_000588, Prestwick2_000588, Prestwick3_000588, Spectrum3_001738, Spectrum4_000839, Spectrum5_001673, GALANTAMINE [INN], GALANTAMINE [HSDB], GALANTAMINE [USAN], Probes1_000055, Probes2_000395, GALANTAMINE [VANDF], SCHEMBL2577, BSPBio_000436, BSPBio_003416, GALANTAMINE [WHO-DD], KBioGR_001417, KBioSS_001751, 4-27-00-02184 (Beilstein Handbook Reference), BIDD:GT0517, DivK1c_000590, SPBio_002655, BPBio1_000480, GTPL6693, orb1302305, SCHEMBL4696585, SCHEMBL7166507, SCHEMBL29379520, UNII-1T835Z585R, ASUTZQLVASHGKV-JDFRZJQESA-, BDBM10404, KBio1_000590, KBio2_001751, KBio2_004319, KBio2_006887, KBio3_002636, ASUTZQLVASHGKV-JDFRZJQESA-N, NINDS_000590, GLXC-03030, HMS2089H03, HMS3885C10, Pharmakon1600-01501202, MSK10278, EBC-26461, HY-76299R, NSC759861, AKOS015965330, CCG-212961, CS-1217, DB00674, FH15703, NSC-759861, SDCCGMLS-0066737.P001, IDI1_000590, SMP1_000131, NCGC00017256-05, NCGC00017256-11, NCGC00017256-17, NCGC00024731-02, (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofurol[3a,3,2,-ef][2]benzazepin-6-ol, AC-20240, AC-34328, AS-56354, HY-76299, SBI-0051689.P002, NS00003061, A11538, C08526, D04292, EN300-708805, AB00053614-09, AB00053614_10, AC-542/20973006, Q412690, Galanthamine ( Jilkon, Lycoremine, Nivalin and oth, SR-05000001783-4, BRD-K49481516-001-01-5, BRD-K49481516-004-03-5, BRD-K49481516-004-04-3, BRD-K49481516-004-09-2, BRD-K49481516-004-18-3, (4aS,6R,8aS)-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol, 1008759-59-8, 6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-, (4A.ALPHA.,6.BETA.,8AR*)-, 6H-Benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aalpha,6beta,8ar*)-, 6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-, (4AS,6R,8AS), InChI=1/C17H21NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m0/s1
Theoretical properties:
molecular_formula: C17H21NO3
molecular_weight: 287.35 g/mol
exact_mass: 287.15214353 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 21
topological_polar_surface_area: 41.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from benzene
color: Crystals from benzene
melting_point: 126-127 °C
solubility: Crystals from water; decomposition 256-257 °C. Sparingly sol in cold; more sol in hot water. Very sparingly sol in alcohol, acetone. /Hydrochloride/
Descriptions:
{"pubchem": "Galanthamine is a benzazepine alkaloid isolated from certain species of daffodils. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor, a cholinergic drug, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an antidote to curare poisoning and a plant metabolite. It is an organic heterotetracyclic compound, a benzazepine alkaloid, a benzazepine alkaloid fundamental parent and a tertiary amino compound. It is a conjugate base of a galanthamine(1+).", "chebi": "A benzazepine alkaloid isolated from certain species of daffodils.", "chembl": "GALANTAMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Galantamine is a type of acetylcholinesterase inhibitor. It is an alkaloid extracted from the bulbs and flowers of Galanthus nivalis (common snowdrop), Galanthus caucasicus (Caucasian snowdrop), Galanthus woronowii (Voronov's snowdrop), and other members of the family Amaryllidaceae, such as Narcissus (daffodil), Leucojum aestivum (snowflake), and Lycoris including Lycoris radiata (red spider lily). It can also be produced synthetically.\nGalantamine is used clinically for treating early-stage Alzheimer's disease and memory impairments, although it has had limited success with the more advanced condition of dementia.\nWhile the exact mechanism of galantamine in treating Alzheimer's disease is unknown, it is hypothesized to exert its therapeutic effects by enhancing cholinergic function. Galantamine inhibits the activity of acetylcholinesterase, an enzyme that catalyzes the breakdown of the neurotransmitter acetylcholine. This action elevates and prolongs synaptic acetylcholine concentrations, increasing the availability of acetylcholine to its receptors. The cholinergic system is involved in a variety of functions relevant to Alzheimer's symptomology, such as memory processing, reasoning, and thinking. Galantamine may cause serious adverse effects, such as stomach bleeding, liver injury or chest pain.\nGalantamine was isolated for the first time from bulbs of Galanthus nivalis (common snowdrop) in the Soviet Union in the 1940s. The active ingredient was extracted, identified, and studied, in particular in relation to acetylcholinesterase (AChE)-inhibiting properties. The first industrial process was developed in 1959. However, it was not until the 1990s when full-scale synthesis was upscaled and optimized."}