Compound: CYPRENORPHINE
SMILES: O1c2c(O)ccc3c2[C@@]45[C@@H]1[C@@]6(OC)C=C[C@]4([C@H](N(CC7CC7)CC5)C3)C[C@@H]6C(O)(C)C
InChIKey: VSKIOMHXEUHYSI-KNLIIKEYSA-N
Synonyms: CYPRENORPHINE, Ciprenorfina, 4406-22-8, Cyprenorphinum, 1P6HEG5ZHS, DTXSID80905125, RefChem:130151, DTXCID701334231, (1R,2R,6S,14R,15R,19R)-3-(cyclopropylmethyl)-19-(2-hydroxypropan-2-yl)-15-methoxy-13-oxa-3-azahexacyclo(13.2.2.12,?.01,?.0?,1?.0?,12)icosa-7,9,11,16-tetraen-11-ol, 6,7,8,14-N-(Cyclopropylmethyl)tetrahydro-7alpha-(1-hydroxy-1-methylethyl)-6,14-endo-ethenonororipavine, N-cyclopropylmethyl-6,14-endoetheno-7 alpha-(1-hydroxy-1-methylethyl)-6,7,8,14-tetrahydronororipavine, (1R,2S,6R,14R,15R,19R)-5-(cyclopropylmethyl)-19-(2-hydroxypropan-2-yl)-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11,16-tetraen-11-ol, UNII-1P6HEG5ZHS, Cyprenorphine [INN:BAN], Ciprenorfina [INN-Spanish], Cyprenorphinum [INN-Latin], RX 285M, UM 531, CYPRENORPHINE [MI], CYPRENORPHINE [INN], SCHEMBL157320, DEA No. 9054, CHEMBL2110789, 6,7,8,14-N-(Cyclopropylmethyl)tetrahydro-7.alpha.-(1-hydroxy-1-methylethyl)-6,14-endo-ethenonororipavine, DB01480, 2-(N-Cyclopropylmethyl-4,5-epoxy-6-methoxy-6,14-endo-morphinan-7alpha-yl)-2-propanol, 6,14-endo-Ethenotetrahydrooripavine, 21-cyclopropyl-7alpha-(1-hydroxy-1-methylethyl)-, NS00068010, Q5200299, (7R)-17-(Cyclopropylmethyl)-7-(2-hydroxypropan-2-yl)-6-methoxy-5alpha-4,5-epoxy-6,14-ethenomorphinan-3-ol, 6,14-Ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-4,5-epoxy-3-hydroxy-6-methoxy-alpha,alpha-dimethyl-, (5alpha,7alpha)-, Cyprenorphine; 6,14-Ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-4,5-epoxy-3-hydroxy-6-methoxy-a,a-dimethyl-, (5a,7a)- (9CI, ACI); (5a,7a)-17-(Cyclopropylmethyl)-4,5-epoxy-3-hydroxy-6-methoxy-a,a-dimethyl-6,14-ethenomorphinan-7-methanol (ACI); 6,14-endo-Ethenotetr, N-Cyclopropylmethyl-6,14-endoetheno-7alpha-(1-hydroxy-1-methylethyl)-6,7,8,14-tetrahydronororipavine
Theoretical properties:
molecular_formula: C26H33NO4
molecular_weight: 423.5 g/mol
exact_mass: 423.24095853 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 4
heavy_atom_count: 31
topological_polar_surface_area: 62.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: CYPRENORPHINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Cyprenorphine (M285), N-cyclo-propylmethyl-6,14-endoetheno-7α-(1-hydroxy-1-methylethyl)-6,7,8,14-tetrahydronororipavine, is an opioid drug. It is related to more well-known opioids such as buprenorphine, which is used as an analgesic and for the treatment of opioid addiction, and diprenorphine, which is used as an antidote to reverse the effects of other opioids. It is roughly 35 times as strong as nalorphine.
Cyprenorphine is a powerful antagonist of opioid receptors and a highly potent specific antagonist. It blocks the binding of morphine and etorphine to these receptors.
Cyprenorphine has mixed agonist–antagonist effects at opioid receptors, like those of buprenorphine. However the effects of cyprenorphine are somewhat different, as it produces pronounced dysphoric and hallucinogenic effects which limit its potential use as an analgesic.
Cyprenorphine also has been shown to suppress the intake of sweet solution but doesn't suppress the increase in food consumption that is produced by the alpha-2-adrenoceptor antagonist idazoxan. Idazoxan may lead to the release of endogenous opioid peptides and increase food intake, this effect is attenuated by (-)-naloxone but not by the mu/delta-antagonist cyprenorphine.