(1R,9S)-15-amino-1-methyltricyclo[7.5.1.0^{2,7}]pentadeca-2(7),3,5-trien-4-ol

• ChemBase ID: 1079
• Molecular Formular: C16H23NO
• Molecular Mass: 245.35992
• Monoisotopic Mass: 245.17796436
• SMILES: Oc1cc2[C@@]3(C(N)[C@H](Cc2cc1)CCCCC3)C
• Canonical SMILES: Oc1ccc2c(c1)[C@@]1(C)CCCCC[C@@H](C2)C1N
• InChI: InChI=1S/C16H23NO/c1-16-8-4-2-3-5-12(15(16)17)9-11-6-7-13(18)10-14(11)16/h6-7,10,12,15,18H,2-5,8-9,17H2,1H3/t12-,15?,16+/m0/s1
• InChIKey: VTMVHDZWSFQSQP-ZDKIRESNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S)-15-amino-1-methyltricyclo[7.5.1.0^{2,7}]pentadeca-2(7),3,5-trien-4-ol
• IUPAC Traditional name: dezocine
• Brand Name: Dalgan
• Synonyms: Dezocina [INN-Spanish]; Dezocinum [INN-Latin]; Dezocine

Database IDs

• CAS Number: 53648-55-8
• PubChem SID: 160964542
• PubChem CID: 40841

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.426797
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.59708244
• LogD (pH = 7.4): 1.3117145
• Log P: 3.2300963
• Molar Refractivity: 74.1902 cm^3
• Polarizability: 29.278252 Å^3
• Polar Surface Area: 46.25 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.77
• LOG S: -4.24
• Solubility (Water): 1.40e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.3

DETAILS

DrugBank - DB01209

• Drug Groups: approved
• Description: Dezocine is a partial opiate drug and is used for pain management. Dezocine is a very effective alternative to fentanyl when administered during outpatient laparoscopy, although is associated with an increased incidence of postoperative nausea.
• Indication: Indicated in the treatment of moderate to severe pain.
• Pharmacology: Dezocine is a parenteral narcotic analgesic possessing both agonist and antagonist activity. It is similar to morphine with respect to analgesic potency and onset and duration of action. The narcotic antagonist activity is greater than that of pentazocine.
• Toxicity: Symptoms of overdose include cold and clammy skin, confusion, nervousness, or severe restlessness, convulsions (seizures), severe dizziness, severe drowsiness, low blood pressure, pinpoint pupils of eyes, slow heartbeat, slow or troubled breathing and severe weakness.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, via conjugation (glucuronidation).
• Absorption: Rapid and complete following intramuscular administration.
• Half Life: Elimination half-life following intramuscular administration averages 2.2 hours. Elimination half-life following a 5mg intravenous dose averages 1.7 to 2.6 hours (range 0.6 to 4.4 hours) while a 10mg dose averages 2.4 to 2.6 hours (range 1.2 to 7.4 hours). In patients with hepatic cirrhosis, the half-life is increased by 30 to 50%.