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

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H23NO
Molecular Weight 257.3706
Optical Activity ( + )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALAZOCINE, (+)-

SMILES

C[C@@H]1[C@@H]2CC3=CC=C(O)C=C3[C@@]1(C)CCN2CC=C

InChI

InChIKey=LGQCVMYAEFTEFN-DQYPLSBCSA-N
InChI=1S/C17H23NO/c1-4-8-18-9-7-17(3)12(2)16(18)10-13-5-6-14(19)11-15(13)17/h4-6,11-12,16,19H,1,7-10H2,2-3H3/t12-,16+,17+/m1/s1

HIDE SMILES / InChI

Molecular Formula C17H23NO
Molecular Weight 257.3706
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7957624 | https://www.ncbi.nlm.nih.gov/pubmed/23139844

(+)-SKF-10,047 is a sigma-opioid receptor agonist. (+)-SKF-10,047 is distinct from its (-)-enantiomer in binding pattern and associated behavioural effects. (+)-SKF-10,047 stress-induced motor suppression, while its (-)-optical isomer was inactive. Besides activation of sigma-1 receptor, (+)-SKF-10,047 is inhibitor of Na(V)1.2 and Na(V)1.4 channels.

CNS Activity

Curator's Comment: Known to be CNS penetrant in rats. Human data not available.

Originator

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Sigma-1 receptor agonists directly inhibit Nav1.2/1.4 channels.
2012
Effects of (+)SKF 10047, a sigma-1 selective agonist, on isolation-induced aggression in male mice.
2006-11
SKF-10,047 reverses stress-induced motor suppression: interaction with dopaminergic system.
1994-07-21
Agonist and antagonist actions of morphine-like drugs on the guinea-pig isolated ileum.
1966-09

Sample Use Guides

To evaluate effect of (+)-SKF-10,047 on conditioned fear stress, the drug was administered subcutaneously at 20 min before motility was measured in the test trial. (+)-SKF-10,047 (3 and 6 mg/kg) dose-dependently attenuated the conditioned fear stress.
Route of Administration: Other
Inhibition of sigma opioid receptor from guinea brains was studied using radioligand binding assay, with 3H-SKF10047 used as a radioligand. (+)-SKF-10,047 displaces [3H]-(+)*SKF10047 with Ki of 18 nM
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:20:09 GMT 2025
Edited
by admin
on Wed Apr 02 09:20:09 GMT 2025
Record UNII
YR49MN7Q8G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(+)-SKF-10047
Preferred Name English
ALAZOCINE, (+)-
Common Name English
2,6-METHANO-3-BENZAZOCIN-8-OL, 1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(2-PROPEN-1-YL)-, (2S,6S,11S)-
Systematic Name English
(+)-N-ALLYLNORMETAZOCINE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID90207344
Created by admin on Wed Apr 02 09:20:09 GMT 2025 , Edited by admin on Wed Apr 02 09:20:09 GMT 2025
PRIMARY
CAS
58640-82-7
Created by admin on Wed Apr 02 09:20:09 GMT 2025 , Edited by admin on Wed Apr 02 09:20:09 GMT 2025
PRIMARY
FDA UNII
YR49MN7Q8G
Created by admin on Wed Apr 02 09:20:09 GMT 2025 , Edited by admin on Wed Apr 02 09:20:09 GMT 2025
PRIMARY
PUBCHEM
3036222
Created by admin on Wed Apr 02 09:20:09 GMT 2025 , Edited by admin on Wed Apr 02 09:20:09 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT