Compound: CYTISINE
SMILES: O=c1n2c(ccc1)[C@H]3CNC[C@@H](C2)C3
InChIKey: ANJTVLIZGCUXLD-DTWKUNHWSA-N
Synonyms: CYTISINE, 485-35-8, Baptitoxine, Sophorine, Cytisinicline, Baptitoxin, Cytiton, Laburnin, Ulexine, Ulexin, Cytitone, Citizin, Cystisine, Cytizin, (1r,5s)-1,2,3,4,5,6-Hexahydro-8h-1,5-Methanopyrido[1,2-A][1,5]diazocin-8-One, 6039 Sopharma, citisiniclina, NSC-407282, 53S5U404NU, (1R,9S)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one, CHEBI:4055, DTXSID00883395, 1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,9S)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one, citizine, cystisin, cytisiniclinum, (1R,9S)-7,11-diazatricyclo(7.3.1.02,7)trideca-2,4-dien-6-one, (1R,9S)-7,11-diazatricyclo(7.3.1.0^(2,7))trideca-2,4-dien-6-one, (1R,5S)-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido(1,2-a)(1,5)diazocin-8-one, TBX-Free, RefChem:54921, DTXCID501022929, 207-616-0, (-)-Cytisine, Tabex, Tsitizin, Cytisin, Tabax, MFCD00136048, (1R,5S)-3,4,5,6-Tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one, Cytisine (-), 1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-, Cytisinicline [USAN], CHEMBL497939, 1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-, Baphitoxine, SMR001233264, HSDB 3560, MLS003171607, EINECS 207-616-0, NSC 407282, BRN 0083882, UNII-53S5U404NU, NSC407282, C5E, Prestwick_140, (?)-Cytisine, Cytisine ((+)-), Tocris-1390, CYTISINE [HSDB], CYTISINE [MI], Cytisinicline (Standard), 115051-74-6, Prestwick3_000624, CYTISINE [MART.], CYTISINICLINE [INN], BSPBio_000588, Cytisine, >=99%, powder, 5-24-02-00535 (Beilstein Handbook Reference), MLS002153916, MLS002222174, SCHEMBL161398, CYTISINICLINE [WHO-DD], BPBio1_000648, GTPL5347, orb1310572, orb3140155, (1R,9R)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one, (1S,9R)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one, HY-N0175R, 1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one (cytisine), Cytisine1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one, HMS2096N10, HMS2235L06, HMS3267D20, HMS3414N03, HMS3678L21, HMS3884L11, HY-N0175, MSK40318, TNP00030, BDBM50143282, EBC-09113, HB2033, PDSP1_000461, s2287, WLN: T C666 A GVN LM&TTJ, AKOS000276818, AKOS015833102, CCG-208621, DB09028, FC09851, (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido[1,2a][1,5]diazocin-8-one, NCGC00016463-01, NCGC00016463-02, NCGC00016463-03, NCGC00016463-04, NCGC00017171-01, NCGC00025138-01, NCGC00025138-02, NCGC00179513-01, AC-34317, AS-19539, CAS-485-35-8, SY057153, CS-0007888, NS00067015, SW219952-1, Cytisine, >=99.0% (HPLC), >=99%, EN300-224852, F049425, Q417343, BRD-K74186897-001-02-5, BRD-K74186897-001-04-1, BRD-K74186897-001-10-8, BRD-K74186897-001-11-6, BRD-K74186897-001-12-4, BRD-K74186897-001-13-2, F9994-5373, Z1203159860, 1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, 1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R)-, (1R,9S)-7,11-diazatricyclo[7.3.1.0,2,7]trideca-2,4-dien-6-one, (1R,9S)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one, 1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R-cis)-, (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one, (1R,5S)-1,2,3,4,5,6-HEXAHYDRO-1,5-METHANO-8H-PYRIDO-(1,2-A)(1,5)DIAZOCIN-8-ONE, (1R,5S)-1,2,3,4,5,6-HEXAHYDRO-8H-1,5-METHANOPYRIDO(1,2-A)(1,5)DIAZOCIN-8-ONE (CYTISINE)
Theoretical properties:
molecular_formula: C11H14N2O
molecular_weight: 190.24 g/mol
exact_mass: 190.110613074 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 14
topological_polar_surface_area: 32.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Orthorhombic prisms from acetone
color: Orthorhombic prisms from acetone
melting_point: 152-153
solubility: Soluble in 13 parts acetone, 1.3 parts methanol, 3.5 parts alcohol, 30 parts benzene, 10 parts ethyl acetone, 2.0 parts chloroform; practically insoluble in petroleum ether
Descriptions:
pubchem: Cytisine is an organic heterotricyclic compound that is the toxic principle in Laburnum seeds and is found in many members of the Fabaceae (legume, pea or bean) family. An acetylcholine agonist, it is widely used throughout Eastern Europe as an aid to giving up smoking. It has a role as a phytotoxin, a nicotinic acetylcholine receptor agonist and a plant metabolite. It is an alkaloid, a lactam, an organic heterotricyclic compound, a bridged compound and a secondary amino compound.
chebi: An organic heterotricyclic compound that is the toxic principle in <em>Laburnum</em> seeds and is found in many members of the <em>Fabaceae</em> (legume, pea or bean) family. An acetylcholine agonist, it is widely used throughout Eastern Europe as an aid to giving up smoking.
chembl: CYTISINICLINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Cytisine, also known as baptitoxine, cytisinicline, or sophorine, is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus of the family Fabaceae. It has been used medically to help with smoking cessation. It has been found effective in several randomized clinical trials, including in the United States and New Zealand, and is being investigated in additional trials in the United States and a non-inferiority trial in Australia in which it is being compared head-to-head with the smoking cessation aid varenicline (sold in the United States as Chantix). It has also been used entheogenically via mescalbeans by some Native American groups, historically in the Rio Grande Valley predating even peyote.
Cytisine is on the World Health Organization's List of Essential Medicines.