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

• ChemBase ID: 165157
• 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+/m1/s1
• InChIKey: YQYVFVRQLZMJKJ-ALTJMEPPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9R)-10-(cyclopropylmethyl)-1,13-dimethyl-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-4-ol
• IUPAC Traditional name: (1S,9R)-10-(cyclopropylmethyl)-1,13-dimethyl-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-4-ol
• Synonyms: (2S,6S,11S)-3-(Cyclopropylmethyl)-1,2,3,4,5,6-hexahydro-6,11-dimethyl-2,6-methano-3-benzazocin-8-ol; (+)-Cyclazocine; (+)-cis-Cyclazocine; (+)-α-Cyclazocine; MCV 4511; NIH 10449; d-Cyclazocine; (+)-Cyclazocine

Database IDs

• CAS Number: 7313-87-3
• PubChem SID: 162259290
• PubChem CID: 46783573

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: 32.232426 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C987735

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

REFERENCES

• Remmers, A., et al.: J. Pharmacol. Exper. Ther., 288, 827 (1999)
• Wentland, M., et al.: Bioorg. Med. Chem. Lett., 11, 623 (1999)