XORPHANOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H31NO
Molecular Weight	337.4983
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12[C@@H](C)CC(=C)C[C@@]13CCN(CC4CCC4)[C@@H]2CC5=CC=C(O)C=C35

InChI

InChIKey=AZJPPZHRNFQRRE-AZIXLERZSA-N

InChI=1S/C23H31NO/c1-15-10-16(2)22-21-11-18-6-7-19(25)12-20(18)23(22,13-15)8-9-24(21)14-17-4-3-5-17/h6-7,12,16-17,21-22,25H,1,3-5,8-11,13-14H2,2H3/t16-,21+,22-,23+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H31NO
Molecular Weight	337.4983
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4039650 | https://www.ncbi.nlm.nih.gov/pubmed/6135994 | https://adisinsight.springer.com/drugs/800003663

Xorphanol (also known as TR5379M) is a full κ-opioid receptor agonist and is a partial agonist at μ opioid receptor. Clinically, xorphanol was studied as an orally active analgesic that provided effective pain relief but showed low physical dependence liability. Further development of this drug was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Activation profiles of opioid ligands in HEK cells expressing delta opioid receptors.	2002 Nov 18	12437765
Activity of opioid ligands in cells expressing cloned mu opioid receptors.	2003 Jan 4	12513698
Pharmacological profiles of opioid ligands at kappa opioid receptors.	2006 Jan 25	16433932

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:40:44 GMT 2023` Edited by `admin` on `Fri Dec 15 16:40:44 GMT 2023`
Record UNII	L415991P58
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

XORPHANOL

Official Name

English

xorphanol [INN]

Common Name

English

17-(CYCLOBUTYLMETHYL)-8.BETA.-METHYL-6-METHYLENEMORPHINAN-3-OL

Systematic Name

English

TR 5379

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C241