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

• ChemBase ID: 176329
• Molecular Formular: C19H27NO
• Molecular Mass: 285.42378
• Monoisotopic Mass: 285.20926449
• SMILES: N1([C@H]2C([C@](CC1)(c1c(C2)ccc(c1)O)C)C)CC=C(C)C
• Canonical SMILES: CC(=CCN1CC[C@]2(C([C@H]1Cc1c2cc(cc1)O)C)C)C
• InChI: InChI=1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14?,18-,19+/m1/s1
• InChIKey: VOKSWYLNZZRQPF-BRQZFJGMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9R)-1,13-dimethyl-10-(3-methylbut-2-en-1-yl)-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-4-ol
• IUPAC Traditional name: (1S,9R)-1,13-dimethyl-10-(3-methylbut-2-en-1-yl)-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-4-ol
• Synonyms: (2S,6S,11S)-1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-methano-3-benzazocin-8-ol; cis-(+)-(1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-methano-3-benzazocin-8-ol; (+)-Pentazocine; (+)-α-Pentazocine; d-Pentazocine; (+)-cis-Pentazocine

Database IDs

• CAS Number: 7361-76-4
• PubChem SID: 164232239
• PubChem CID: 6328623

CALCULATED PROPERTIES

• Acid pKa: 10.421619
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.8584462
• LogD (pH = 7.4): 1.9896134
• Log P: 3.89362
• Molar Refractivity: 89.7993 cm^3
• Polarizability: 34.580894 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P274290

Mixed opioid agonist-antagonist. Controlled substance. Analgesic (narcotic).

REFERENCES

• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)
• Brogden, et al.: Drugs, 5, 6 (1971)
• Camu, F., et al.: Eur. J. Clin. Pharmacol., 19, 259 (1971)