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

Details

Stereochemistry ABSOLUTE
Molecular Formula 2C20H27NO2.C4H6O6
Molecular Weight 776.9546
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXILORPHAN TARTRATE

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.OC1=CC2=C(C[C@H]3N(CC4CC4)CC[C@@]25CCCC[C@@]35O)C=C1.OC6=CC7=C(C[C@H]8N(CC9CC9)CC[C@@]7%10CCCC[C@@]8%10O)C=C6

InChI

InChIKey=ONHZWTYSVRYZMM-HQLXQQFBSA-N
InChI=1S/2C20H27NO2.C4H6O6/c2*22-16-6-5-15-11-18-20(23)8-2-1-7-19(20,17(15)12-16)9-10-21(18)13-14-3-4-14;5-1(3(7)8)2(6)4(9)10/h2*5-6,12,14,18,22-23H,1-4,7-11,13H2;1-2,5-6H,(H,7,8)(H,9,10)/t2*18-,19+,20-;1-,2-/m111/s1

HIDE SMILES / InChI

Molecular Formula C20H27NO2
Molecular Weight 313.4339
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Oxilorphan (also known as levo-BC-2605) was developed as a long-acting, narcotic antagonist that has agonist properties. Oxilorphan is a partial agonist at the kappa-opioid receptor and antagonist of the mu-opioid receptor. During clinical trials, oxilorphan had led to dysphoria, which combined with its hallucinogenic effects, serves to limit its clinical usefulness. As a result, many patients who experienced these side effects refused to take additional doses in clinical trials.

Approval Year

PubMed

PubMed

TitleDatePubMed
Oxilorphan (l-N-cyclopropylmethyl-3,14-dihydroxymorphinan): a new synthetic narcotic antagonist.
1975 Apr
Patents

Sample Use Guides

In Vivo Use Guide
1, 2, 4, 6, and 8 mg in 30 normal subjects to determine the relation of single oral doses and toxicity
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:24:12 GMT 2023
Edited
by admin
on Fri Dec 15 15:24:12 GMT 2023
Record UNII
D9S0U9ELR7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXILORPHAN TARTRATE
Common Name English
MORPHINAN-3,14-DIOL, 17-(CYCLOPROPYLMETHYL)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (2:1) (SALT)
Systematic Name English
Code System Code Type Description
PUBCHEM
133083128
Created by admin on Fri Dec 15 15:24:12 GMT 2023 , Edited by admin on Fri Dec 15 15:24:12 GMT 2023
PRIMARY
FDA UNII
D9S0U9ELR7
Created by admin on Fri Dec 15 15:24:12 GMT 2023 , Edited by admin on Fri Dec 15 15:24:12 GMT 2023
PRIMARY
CAS
39695-17-5
Created by admin on Fri Dec 15 15:24:12 GMT 2023 , Edited by admin on Fri Dec 15 15:24:12 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY