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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H27NO2
Molecular Weight 313.4339
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXILORPHAN

SMILES

[H][C@@]12CC3=C(C=C(O)C=C3)[C@]4(CCCC[C@@]14O)CCN2CC5CC5

InChI

InChIKey=STBZIDOIKQNFCQ-HSALFYBXSA-N
InChI=1S/C20H27NO2/c22-16-6-5-15-11-18-20(23)8-2-1-7-19(20,17(15)12-16)9-10-21(18)13-14-3-4-14/h5-6,12,14,18,22-23H,1-4,7-11,13H2/t18-,19+,20-/m1/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

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 15:14:25 UTC 2023
Edited
by admin
on Fri Dec 15 15:14:25 UTC 2023
Record UNII
9Y9J2J74TO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXILORPHAN
INN   USAN  
INN   USAN  
Official Name English
LEVO-BC-2605
Code English
OXILORPHAN [USAN]
Common Name English
MORPHINAN-3,14-DIOL, 17-(CYCLOPROPYLMETHYL)-
Systematic Name English
oxilorphan [INN]
Common Name English
(-)-17-(CYCLOPROPYLMETHYL)MORPHINAN-3,14-DIOL
Systematic Name English
Code System Code Type Description
INN
3560
Created by admin on Fri Dec 15 15:14:25 UTC 2023 , Edited by admin on Fri Dec 15 15:14:25 UTC 2023
PRIMARY
PUBCHEM
5361090
Created by admin on Fri Dec 15 15:14:25 UTC 2023 , Edited by admin on Fri Dec 15 15:14:25 UTC 2023
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ChEMBL
CHEMBL2106993
Created by admin on Fri Dec 15 15:14:25 UTC 2023 , Edited by admin on Fri Dec 15 15:14:25 UTC 2023
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WIKIPEDIA
Oxilorphan
Created by admin on Fri Dec 15 15:14:25 UTC 2023 , Edited by admin on Fri Dec 15 15:14:25 UTC 2023
PRIMARY
CAS
42281-59-4
Created by admin on Fri Dec 15 15:14:25 UTC 2023 , Edited by admin on Fri Dec 15 15:14:25 UTC 2023
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SMS_ID
100000083044
Created by admin on Fri Dec 15 15:14:25 UTC 2023 , Edited by admin on Fri Dec 15 15:14:25 UTC 2023
PRIMARY
FDA UNII
9Y9J2J74TO
Created by admin on Fri Dec 15 15:14:25 UTC 2023 , Edited by admin on Fri Dec 15 15:14:25 UTC 2023
PRIMARY
ECHA (EC/EINECS)
255-749-8
Created by admin on Fri Dec 15 15:14:25 UTC 2023 , Edited by admin on Fri Dec 15 15:14:25 UTC 2023
PRIMARY
NCI_THESAURUS
C174594
Created by admin on Fri Dec 15 15:14:25 UTC 2023 , Edited by admin on Fri Dec 15 15:14:25 UTC 2023
PRIMARY
MESH
C008732
Created by admin on Fri Dec 15 15:14:25 UTC 2023 , Edited by admin on Fri Dec 15 15:14:25 UTC 2023
PRIMARY
EVMPD
SUB09530MIG
Created by admin on Fri Dec 15 15:14:25 UTC 2023 , Edited by admin on Fri Dec 15 15:14:25 UTC 2023
PRIMARY
EPA CompTox
DTXSID001009897
Created by admin on Fri Dec 15 15:14:25 UTC 2023 , Edited by admin on Fri Dec 15 15:14:25 UTC 2023
PRIMARY
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY