Dezocine

Title: Dezocine
CAS Registry Number: 53648-55-8
CAS Name: (5R,11S,13S)-13-Amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-5,11-methanobenzocyclodecen-3-ol
Manufacturers' Codes: Wy-16225
Trademarks: Dalgan (Wyeth)
Molecular Formula: C16H23NO
Molecular Weight: 245.36
Percent Composition: C 78.32%, H 9.45%, N 5.71%, O 6.52%
Literature References: Synthetic opiate agonist-antagonist. Prepn: M. E. Freed et al., DE 2159324 (1972 to Am. Home Products), C.A. 79, 53094w (1973); eidem, J. Med. Chem. 16, 595 (1973). Pharmacology: J. L. Malis et al., J. Pharmacol. Exp. Ther. 194, 488 (1975). Metabolism: S. F. Sisenwine, C. O. Tio, Drug Metab. Dispos. 9, 37 (1981). Pharmacokinetics: S. F. Sisenwine et al., ibid. 10, 366 (1982). Clinical studies: W. Oosterlinck, A. Verbaeys, Curr. Med. Res. Opin. 6, 472 (1980); J. W. Downing et al., Br. J. Anaesth. 53, 59 (1981).
Derivative Type: Hydrobromide salt
Molecular Formula: C15H23NO.HBr
Molecular Weight: 314.26
Percent Composition: C 57.33%, H 7.70%, N 4.46%, O 5.09%, Br 25.43%
Properties: Crystalline powder, mp 269-270°. pH (2% aq soln): 4.6. Soly in water: >20 mg/ml. LD50 in female mice, rats (mg/kg): 313, 232 orally; 129, 270 i.m. (Malis).
Melting point: mp 269-270°
Toxicity data: LD50 in female mice, rats (mg/kg): 313, 232 orally; 129, 270 i.m. (Malis)
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).
DFDD DFDT d-Fenchone D-Fucose D-Galactosamine

Dezocine
Dezocine.svg
Systematic (IUPAC) name
(5R,11S,13R)-13-Amino-5-methyl-5,6,7,8,9,10,11,12-octahydro-5,11-methanobenzo[10]annulen-3-ol
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Legal status Discontinued[1]
Routes Intravenous
Pharmacokinetic data
Metabolism Hepatic
Half-life 2.2 hours
Identifiers
CAS number 53648-55-8 YesY
ATC code N02AX03
PubChem CID 3033053
DrugBank DB01209
ChemSpider 2297867 YesY
UNII VHX8K5SV4X YesY
KEGG D00838 YesY
ChEBI CHEBI:4474 YesY
ChEMBL CHEMBL1685 YesY
Synonyms WY-16,225
Chemical data
Formula C16H23NO 
Mol. mass 245.36 g/mol
 N (what is this?)  (verify)

Dezocine (DalganTM WY16225)is an opiate analgesic. First synthesized in 1970,[2] it acts at mu-, delta-, and kappa-opioid receptors. Dezocine acts as a mixed agonist/antagonist of opioid receptors. It is related to pentazocine, with a similar profile of effects that include analgesic action and euphoria at low doses,[3] but produces dysphoria and hallucinations at high doses, most likely due to action at κ-opioid receptors.[4][5]