U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Pharmacological profiles of opioid ligands at kappa opioid receptors.
2006 Jan 25

Sample Use Guides

Unknown
Route of Administration: Oral
Name Type Language
XORPHANOL
INN  
INN  
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
Created by admin on Fri Dec 15 16:40:44 GMT 2023 , Edited by admin on Fri Dec 15 16:40:44 GMT 2023
NCI_THESAURUS C1506
Created by admin on Fri Dec 15 16:40:44 GMT 2023 , Edited by admin on Fri Dec 15 16:40:44 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL2111060
Created by admin on Fri Dec 15 16:40:44 GMT 2023 , Edited by admin on Fri Dec 15 16:40:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID001018240
Created by admin on Fri Dec 15 16:40:44 GMT 2023 , Edited by admin on Fri Dec 15 16:40:44 GMT 2023
PRIMARY
PUBCHEM
5488631
Created by admin on Fri Dec 15 16:40:44 GMT 2023 , Edited by admin on Fri Dec 15 16:40:44 GMT 2023
PRIMARY
SMS_ID
100000079361
Created by admin on Fri Dec 15 16:40:44 GMT 2023 , Edited by admin on Fri Dec 15 16:40:44 GMT 2023
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NCI_THESAURUS
C152935
Created by admin on Fri Dec 15 16:40:44 GMT 2023 , Edited by admin on Fri Dec 15 16:40:44 GMT 2023
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INN
5269
Created by admin on Fri Dec 15 16:40:44 GMT 2023 , Edited by admin on Fri Dec 15 16:40:44 GMT 2023
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WIKIPEDIA
XORPHANOL
Created by admin on Fri Dec 15 16:40:44 GMT 2023 , Edited by admin on Fri Dec 15 16:40:44 GMT 2023
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EVMPD
SUB00118MIG
Created by admin on Fri Dec 15 16:40:44 GMT 2023 , Edited by admin on Fri Dec 15 16:40:44 GMT 2023
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CAS
77287-89-9
Created by admin on Fri Dec 15 16:40:44 GMT 2023 , Edited by admin on Fri Dec 15 16:40:44 GMT 2023
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FDA UNII
L415991P58
Created by admin on Fri Dec 15 16:40:44 GMT 2023 , Edited by admin on Fri Dec 15 16:40:44 GMT 2023
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