(1S,13R)-1,13-dimethyl-10-[2-(2H5)phenylethyl]-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol

• ChemBase ID: 176446
• Molecular Formular: C22H27NO
• Molecular Mass: 321.45588
• Monoisotopic Mass: 321.20926449
• SMILES: c1(cc2c(cc1)CC1[C@@H]([C@@]2(CCN1CCc1ccccc1)C)C)O
• Canonical SMILES: Oc1ccc2c(c1)[C@@]1(C)CCN(C(C2)[C@@H]1C)CCc1ccccc1
• InChI: InChI=1S/C22H27NO/c1-16-21-14-18-8-9-19(24)15-20(18)22(16,2)11-13-23(21)12-10-17-6-4-3-5-7-17/h3-9,15-16,21,24H,10-14H2,1-2H3/t16-,21?,22-/m0/s1
• InChIKey: ZQHYKVKNPWDQSL-URJRECBDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,13R)-1,13-dimethyl-10-[2-(^2H₅)phenylethyl]-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-4-ol
• IUPAC Traditional name: (1S,13R)-1,13-dimethyl-10-[2-(^2H₅)phenylethyl]-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-4-ol
• Synonyms: 1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(2-phenylethyl)-2,6-methano-3-benzazocin-8-ol-d5; 2'-Hydroxy-5,9-dimethyl-2-phenethyl-6,7-benzomorphan-d5; 1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-phenethyl-2,6-methano-3-benzazocin-8-ol-d5; Phenethylazocine-d5; Phenobenzorphan-d5; Phenazocine-d5

Database IDs

• PubChem SID: 164232356
• PubChem CID: 71751565

CALCULATED PROPERTIES

• Acid pKa: 9.964461
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.4474213
• LogD (pH = 7.4): 1.9716463
• Log P: 4.0765004
• Molar Refractivity: 100.0487 cm^3
• Polarizability: 38.851093 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P295402

Labelled analogue of Phenazocine, an opioid analgesic drug related to Pentazocine (P274300) and has a similar profile of effects. The use of Phenazocine results in analgesia and euphoria and in some cases dysphoria and hallucinations at high doses, most l

REFERENCES

• Hopton, D. et al.: Gut, 12, 51 (1971)
• Eckenhoff, J.E. et al.: Anesthesiology, 20, 355 (1971)
• Clarke, E.G. et al.: Nature, 184, 451 (1971)