Compound: Bulbocapnine
SMILES: O1c2c3-c4c(O)c(OC)ccc4C[C@H]5c3c(CCN5C)cc2OC1
InChIKey: LODGIKWNLDQZBM-LBPRGKRZSA-N
Synonyms: Bulbocapnine, 298-45-3, (+)-Bulbocapnine, Bulbokaprin, (S)-(+)-Bulbocapnine, O0TGI865QO, DTXSID20183940, EINECS 206-061-1, BULBOCAPNINE [MI], 4-Hydroxy-3-methoxy-5,6-methylenedioxy-aporphin, CHEBI:3211, 5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinolin-12-ol, 6,7,7a,8-tetrahydro-11-methoxy-7-methyl-, (S)-, 6a-alpha-APORPHIN-11-OL, 10-METHOXY-1,2-(METHYLENEDIOXY)-, (7aS)-11-methoxy-7-methyl-6,7,7a,8-tetrahydro-5H-[1,3]benzodioxolo[6,5,4-de]benzo[g]quinolin-12-ol, (7aS)-11-methoxy-7-methyl-6,7,7a,8-tetrahydro-5H-(1,3)benzodioxolo(6,5,4-de)benzo(g)quinolin-12-ol, RefChem:570471, DTXCID60106431, 206-061-1, d-Bulbocapnine, (S)-BULBOCAPNINE, CHEMBL157912, (12S)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14(19),15,17-hexaen-18-ol, UNII-O0TGI865QO, Bulbocapnin, LODGIKWNLDQZBM-LBPRGKRZSA-N, Buibocapnine hydrochloride, SCHEMBL678694, BDBM50016018, NSC785188, PDSP2_000621, AKOS000276822, FB65594, NSC-785188, NS00028785, C09367, Q1003526, (7aS)-11-Methoxy-7-methyl-6,7,7a,8-tetrahydro-2H,5H-[1,3]benzodioxolo[6,5,4-de]benzo[g]quinolin-12-ol, (S)-11-methoxy-7-methyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4'',5'':4,5]benzo[1,2,3-de]quinolin-12-ol, 11-Methoxy-7-methyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4'',5'':4,5]benzo[1,2,3-de]quinolin-12-ol (Bulbocapnine)
Theoretical properties:
molecular_formula: C19H19NO4
molecular_weight: 325.4 g/mol
exact_mass: 325.13140809 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 1
heavy_atom_count: 24
topological_polar_surface_area: 51.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Bulbocapnine is an aporphine alkaloid that has been isolated from Corydalis and exhibits inhibitory activity against enzymes such as tyrosine 3-monooxygenase and diamine oxidase. It has a role as an EC 1.4.3.22 (diamine oxidase) inhibitor, an EC 1.14.16.2 (tyrosine 3-monooxygenase) inhibitor and a plant metabolite. It is an aporphine alkaloid, a member of phenols, an aromatic ether and an oxacycle. It is functionally related to an aporphine. It is a conjugate base of a bulbocapnine(1+).", "chebi": "An aporphine alkaloid that has been isolated from <em>Corydalis</em> and exhibits inhibitory activity against enzymes such as tyrosine 3-monooxygenase and diamine oxidase.", "chembl": "(S)-BULBOCAPNINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Bulbocapnine is an alkaloid found in Corydalis (notably the European species C. cava) and Dicentra, genera of the plant family Fumariaceae which have caused (notably the American species Corydalis caseana) the fatal poisoning of sheep and cattle. It has been shown to act as an acetylcholinesterase inhibitor, and inhibits biosynthesis of dopamine via inhibition of the enzyme tyrosine hydroxylase. Like apomorphine, it is reported to be an inhibitor of amyloid beta protein (A\u03b2) fiber formation, whose presence is a hallmark of Alzheimer's disease (AD).  Bulbocapnine is thus a potential therapeutic under the amyloid hypothesis. According to the Dorlands Medical Dictionary, it \"inhibits the reflex and motor activities of striated muscle. It has been used in the treatment of muscular tremors and vestibular nystagmus\".   \nA psychiatrist at Tulane University named Robert Heath carried out experiments on prisoners at the Louisiana State Penitentiary using bulbocapnine to induce stupor. This work at Tulane inspired, and was continued parallel to, experiments carried out at the behest of the Central Intelligence Agency. The bulbocapnine work Heath conducted for the government was one component of a large investigation into the potential of psychoactive compounds as aids to interrogation."}