QUADAZOCINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H37NO2
Molecular Weight	383.5668
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CC3=C(C=C(O)C=C3)[C@](C)(CCN1C)[C@]2(C)CCC(=O)CCC4CCCC4

InChI

InChIKey=LOYWOYCPSWPKFH-DSNGMDLFSA-N

InChI=1S/C25H37NO2/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/h9,11,17-18,23,28H,4-8,10,12-16H2,1-3H3/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

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

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 `Fri Dec 15 16:17:37 UTC 2023` Edited by `admin` on `Fri Dec 15 16:17:37 UTC 2023`
Record UNII	X9BMD58553
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

QUADAZOCINE

Official Name

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*))-

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)-

Systematic 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

Common Name

English

quadazocine [INN]

Common Name

English

Quadazocine [WHO-DD]

Common Name

English

WIN-44441

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C67413