(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

• ChemBase ID: 534
• Molecular Formular: C19H27NO
• Molecular Mass: 285.42378
• Monoisotopic Mass: 285.20926449
• SMILES: [C@@]12(c3cc(ccc3C[C@H]([C@@H]1C)N(CC2)CC=C(C)C)O)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
• Brand Name: Fortalgesic; Fortalin; Fortral; Liticon; Pentagin; Soseton; Sosigon; Talwan
• Synonyms: L-pentazocine; Pentazocaine; Pentazocin; Pentazocine

Database IDs

• CAS Number: 359-83-1
• PubChem SID: 160963997; 46506363
• PubChem CID: 441278

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 4.44
• LOG S: -3.37
• Solubility (Water): 1.22e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.7

DETAILS

DrugBank - DB00652

• Drug Groups: approved
• Description: The first mixed agonist-antagonist analgesic to be marketed. It is an agonist at the kappa and sigma opioid receptors and has a weak antagonist action at the mu receptor. (From AMA Drug Evaluations Annual, 1991, p97)
• Indication: For the relief of moderate to severe pain.
• Pharmacology: Pentazocine is a potent analgesic which when administered orally in a 50 mg dose appears equivalent in analgesic effect to 60 mg (1 grain) of codeine. Onset of significant analgesia usually occurs between 15 and 30 minutes after oral administration, and duration of action is usually three hours or longer. Onset and duration of action and the degree of pain relief are related both to dose and the severity of pretreatment pain. Pentazocine weakly antagonizes the analgesic effects of morphine and meperidine; in addition, it produces incomplete reversal of cardiovascular, respiratory, and behavioral depression induced by morphine and meperidine. Pentazocine has about 1/50 the antagonistic activity of nalorphine. It also has sedative activity.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Well absorbed from the gastro-intestinal tract.
• Half Life: 2 to 3 hours
• External Links: Wikipedia; RxList; Drugs.com