(1R,9S)-10-[(1-2H)cyclopropyl(2H2)methyl]-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol

• ChemBase ID: 165160
• Molecular Formular: C18H25NO
• Molecular Mass: 271.3972
• Monoisotopic Mass: 271.19361443
• SMILES: N1([C@@H]2C([C@@](CC1)(c1c(C2)ccc(c1)O)C)C)CC1CC1
• Canonical SMILES: Oc1ccc2c(c1)[C@]1(C)CCN([C@@H](C2)C1C)CC1CC1
• InChI: InChI=1S/C18H25NO/c1-12-17-9-14-5-6-15(20)10-16(14)18(12,2)7-8-19(17)11-13-3-4-13/h5-6,10,12-13,17,20H,3-4,7-9,11H2,1-2H3/t12?,17-,18+/m0/s1
• InChIKey: YQYVFVRQLZMJKJ-OTLVQASYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S)-10-[(1-^2H)cyclopropyl(^2H₂)methyl]-1,13-dimethyl-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-4-ol
• IUPAC Traditional name: (1R,9S)-10-[(1-^2H)cyclopropyl(^2H₂)methyl]-1,13-dimethyl-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-4-ol
• Synonyms: (2R,6R,11R)-3-(Cyclopropylmethyl)-1,2,3,4,5,6-hexahydro-6,11-dimethyl-2,6-methano-3-benzazocin-8-ol-d3; (-)-cis-Cyclazocine-d3; (-)-α-Cyclazocine-d3; MCV 4512-d3; NIH 10450-d3; l-Cyclazocine-d3; (-)-Cyclazocine-d3

Database IDs

• PubChem SID: 162259293
• PubChem CID: 57369100

CALCULATED PROPERTIES

• Acid pKa: 9.936118
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.21794558
• LogD (pH = 7.4): 0.8067302
• Log P: 2.9150462
• Molar Refractivity: 82.6231 cm^3
• Polarizability: 32.23243 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C987742

Cyclazocine is a mu opioid antagonist and kappa opioid agonist; it blocks the dopamine response to nicotine.

REFERENCES

• Carr, L., et al.: Neurochem Res., 14, 511 (1989)
• Imperato, A., et al.: Eur. J. Pharmacol., 132, 337 (1989)
• Debonnel, G., et al.: Life Sci., 58, 721 (1989)
• Glick, S., et al.: Eur. J. Pharmacol., 357, 9 (1989)