XORPHANOL MESYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H31NO.CH4O3S
Molecular Weight	433.604
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=VRWTWCLVCNQJGM-ZBWZZBALSA-N

InChI=1S/C23H31NO.CH4O3S/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;1-5(2,3)4/h6-7,12,16-17,21-22,25H,1,3-5,8-11,13-14H2,2H3;1H3,(H,2,3,4)/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

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/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 15:48:55 UTC 2023` Edited by `admin` on `Fri Dec 15 15:48:55 UTC 2023`
Record UNII	A88BIS7IBB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

XORPHANOL MESYLATE

Official Name

English

XORPHANOL MESYLATE [USAN]

Common Name

English

TR-5379M

Code

English

17-(Cyclobutylmethyl)-8β-methyl-6-methylenemorphinan-3-ol methanesulfonate (salt)

Common Name

English

XORPHANOL MESILATE

Common Name

English

MORPHINAN-3-OL, 17-(CYCLOBUTYLMETHYL)-8-METHYL-6-METHYLENE-, (8.BETA.)-, METHANESULPHONATE (SALT)

Common Name

English

MORPHINAN-3-OL, 17-(CYCLOBUTYLMETHYL)-8-METHYL-6-METHYLENE-, (8.BETA.)-, METHANESULFONATE (SALT)

Common Name

English

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

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C241