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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 of XORPHANOL

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Oral
Substance Class Chemical
Record UNII
L415991P58
Record Status Validated (UNII)
Record Version