QUADAZOCINE MESYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H37NO2.CH4O3S
Molecular Weight	479.672
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(O)(=O)=O.CN1CC[C@@]2(C)C3=CC(O)=CC=C3C[C@@H]1[C@@]2(C)CCC(=O)CCC4CCCC4

InChI

InChIKey=OKLHDYDHKBFXCK-HIYIHDMKSA-N

InChI=1S/C25H37NO2.CH4O3S/c1-24-14-15-26(3)23(16-19-9-11-21(28)17-22(19)24)25(24,2)13-12-20(27)10-8-18-6-4-5-7-18;1-5(2,3)4/h9,11,17-18,23,28H,4-8,10,12-16H2,1-3H3;1H3,(H,2,3,4)/t23-,24+,25-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C25H37NO2
Molecular Weight	383.5668
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	CH4O3S
Molecular Weight	96.106
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14622776 | https://www.ncbi.nlm.nih.gov/pubmed/10435403 | https://www.ncbi.nlm.nih.gov/pubmed/12681522

Quadazocine is a substituted hexahydro-2,6-methano-3-benzazocine patented by Sterling Drug Inc. as analgesics and narcotic antagonist. Quadazocine is a potent antagonist of μ opioid receptor, less potent antagonist of κ and δ opioid receptors. In monkeys for whom responding was reinforced by food delivery, quadazocine blocks the rate-decreasing effects of the µ-agonists alfentanil and fentanyl with greater potency than it blocked the rate-decreasing effects of the κ-agonists U69,593

Originator

Approval Year

PubMed

Title	Date	PubMed
Sex differences in opioid antinociception in rhesus monkeys: antagonism of fentanyl and U50,488 by quadazocine.	2002-06	14622776
Effects of flupenthixol and quadazocine on self-administration of speedball combinations of cocaine and heroin by rhesus monkeys.	1999-10	10481841
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications.	1998-03	9686407

Patents

Sample Use Guides

In Vivo Use Guide

rhesus monkey: 0.32, 1, or 3.2 mg/kg

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:16:52 GMT 2025` Edited by `admin` on `Mon Mar 31 18:16:52 GMT 2025`
Record UNII	582SS143QX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

QUADAZOCINE MESYLATE

Official Name

English

QUADAZOCINE MESILATE

Preferred Name

English

3-PENTANONE, 1-CYCLOPENTYL-5-((2R,6S,11S)-1,2,3,4,5,6-HEXAHYDRO-8-HYDROXY-3,6,11-TRIMETHYL-2,6-METHANO-3-BENZAZOCIN-11-YL)-, METHANESULFONATE (SALT)

Common Name

English

(-)-(2R,6S,11S)-1-CYCLOPENTYL-5-(1,2,3,4,5,6-HEXAHYDRO-8-HYDROXY-3,6,11-TRIMETHYL-2,6-METHANO-3-BENZAZOCIN-11-YL)-3-PENTANONE METHANESULFONATE (SALT)

Common Name

English

Quadazocine mesilate [WHO-DD]

Common Name

English

3-PENTANONE, 1-CYCLOPENTYL-5-((2R,6S,11S)-1,2,3,4,5,6-HEXAHYDRO-8-HYDROXY-3,6,11-TRIMETHYL-2,6-METHANO-3-BENZAZOCIN-11-YL)-, METHANESULPHONATE (SALT)

Common Name

English

(-)-(2R,6S,11S)-1-CYCLOPENTYL-5-(1,2,3,4,5,6-HEXAHYDRO-8-HYDROXY-3,6,11-TRIMETHYL-2,6-METHANO-3-BENZAZOCIN-11-YL)-3-PENTANONE METHANESULPHONATE (SALT)

Common Name

English

WIN-44441-3

Code

English

3-PENTANONE, 1-CYCLOPENTYL-5-(1,2,3,4,5,6-HEXAHYDRO-8-HYDROXY-3,6,11-TRIMETHYL-2,6-METHANO-3-BENZAZOCIN-11-YL)-, (2R-(2.ALPHA.,6.ALPHA.,11S*))-, METHANESULFONATE (SALT)

Common Name

English

3-PENTANONE, 1-CYCLOPENTYL-5-((2R,6S,11S)-1,2,3,4,5,6-HEXAHYDRO-8-HYDROXY-3,6,11-TRIMETHYL-2,6-METHANO-3-BENZAZOCIN-11-YL)-, METHANESULFONATE (1:1)

Systematic Name

English

WIN 44,441-3

Code

English

3-PENTANONE, 1-CYCLOPENTYL-5-(1,2,3,4,5,6-HEXAHYDRO-8-HYDROXY-3,6,11-TRIMETHYL-2,6-METHANO-3-BENZAZOCIN-11-YL)-, (2R-(2.ALPHA.,6.ALPHA.,11S*))-, METHANESULPHONATE (SALT)

Common Name

English

QUADAZOCINE MESYLATE [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413