(1R,9R,13R)-1,13-dimethyl-10-(3-methylbut-2-en-1-yl)-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-ol

• ChemBase ID: 128862
• Molecular Formular: C19H27NO
• Molecular Mass: 285.42378
• Monoisotopic Mass: 285.20926449
• SMILES: Oc1ccc2c(c1)[C@]1([C@H]([C@H](N(CC1)CC=C(C)C)C2)C)C
• Canonical SMILES: CC(=CCN1CC[C@@]2([C@H]([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+/m0/s1
• InChIKey: VOKSWYLNZZRQPF-GDIGMMSISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R,13R)-1,13-dimethyl-10-(3-methylbut-2-en-1-yl)-10-azatricyclo[7.3.1.0^2,^7]trideca-2,4,6-trien-4-ol
• IUPAC Traditional name: pentazocine
• Synonyms: Pentazocine

Database IDs

• CAS Number: 359-83-1
• PubChem SID: 162223165
• PubChem CID: 441278
• ATC CODE: N02AD01
• CHEMBL: 560
• Chemspider ID: 390041
• DrugBank ID: DB00652
• IUPHAR ligand ID: 1606
• KEGG ID: D00498
• Unique Ingredient Identifier: RP4A60D26L
• Wikipedia Title: Pentazocine

CALCULATED PROPERTIES

• Acid pKa: 7.5909266
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.0965846
• LogD (pH = 7.4): 2.504246
• Log P: 2.9029462
• 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

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral, IV, IM
• Bioavailability: ~20% orally
• Excretion: Renal
• Half Life: 2 to 3 hours
• Metabolism: Hepatic
• Legal Status: Schedule IV (U.S.); III international
• Pregnancy Category: C/D (U.S.)