Dezocine

Dezocine

Systematic (IUPAC) name
(5R,11S)- 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
Pregnancy cat.	?
Legal status	?
Routes	Oral
Pharmacokinetic data
Metabolism	Hepatic
Half-life	2.2 hours
Identifiers
CAS number	53648-55-8 Y
ATC code	N02AX03
PubChem	CID 3033053
DrugBank	APRD00912
ChemSpider	2297867 Y
UNII	VHX8K5SV4X Y
KEGG	D00838 Y
ChEBI	CHEBI:4474 Y
ChEMBL	CHEMBL1685 Y
Synonyms	WY-16,225
Chemical data
Formula	C16H23NO
Mol. mass	245.36 g/mol
SMILES	eMolecules & PubChem
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 Y Key:VTMVHDZWSFQSQP-VBNZEHGJSA-N Y
N(what is this?)  (verify)

Dezocine (Dalgan) was developed by American Home Products^[1] and is an opioid analgesic related to pentazocine, with a similar profile of effects that include analgesic action and euphoria at low doses,^[2] but produces dysphoria and hallucinations at high doses, most likely due to action at κ-opioid receptors.^[3][4]

Dezocine has been found to be an effective painkiller comparable to meperidine (pethidine),^[5] and so is a more effective analgesic than pentazocine, but causes relatively more respiratory depression than pentazocine.^[6] It is a useful drug for the treatment of pain,^[7] but side effects such as dizziness limit its clinical application,^[8] and it can produce opioid withdrawal syndrome in patients already dependent on other opioids.^[9]

Dezocine is unusual among opioids as it is one of the only primary amines known to be an active opioid (along with bisnortilidine, an active metabolite of tilidine). It is a mixed agonist-antagonist as with other drugs in this class,^[10] and despite having a stronger respiratory depressant effect than morphine, dezocine shows a ceiling effect on its respiratory depressive action so above a certain dose this effect does not get any more severe.^[11]

See also

• Benzomorphan

References

1. ^ DE Patent 2159324
2. ^ Zacny JP, Lichtor JL, de Wit H. Subjective, behavioral, and physiologic responses to intravenous dezocine in healthy volunteers. Anesthesia and Analgesia. 1992 Apr;74(4):523-30.
3. ^ Jacobs AM, Youngblood F. Opioid receptor affinity for agonist-antagonist analgesics. Journal of the American Podiatric Medical Association. 1992 Oct;82(10):520-4.
4. ^ Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J. Pharmacological profiles of opioid ligands at kappa opioid receptors. BMC Pharmacology. 2006 Jan 25;6:3.
5. ^ Camu F, Gepts E. Analgesic properties of dezocine for relief of postoperative pain. Acta Anaesthesiologica Belgica. 1979;30 Suppl:183-91.
6. ^ Wuest HP, Bellville JW. The respiratory effects of dezocine and pentazocine in man. Journal of Clinical Pharmacology. 1979 Apr;19(4):205-10.
7. ^ O'Brien JJ, Benfield P. Dezocine. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1989 Aug;38(2):226-48.
8. ^ Oosterlinck W, Verbaeys A. Preliminary clinical experience with dezocine, a new potent analgesic. Current Medical Research and Opinion. 1980;6(7):472-4.
9. ^ Strain EC, Preston KL, Liebson IA, Bigelow GE. Opioid antagonist effects of dezocine in opioid-dependent humans. Clinical Pharmacology and Therapeutics. 1996 Aug;60(2):206-17.
10. ^ Young AM, Stephens KR, Hein DW, Woods JH. Reinforcing and discriminative stimulus properties of mixed agonist-antagonist opioids. Journal Pharmacology and Experimental Therapeutics. 1984 Apr;229(1):118-26.
11. ^ Romagnoli A, Keats AS. Ceiling respiratory depression by dezocine. Clinical Pharmacology and Therapeutics. 1984 Mar;35(3):367-73.