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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H23NO.ClH
Molecular Weight 293.832
Optical Activity ( + )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

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

SMILES

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

InChI

InChIKey=ZTGMHFIGNYXMJV-XSCGHNKWSA-N
InChI=1S/C17H23NO.ClH/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;1H/t12-,16+,17+;/m1./s1

HIDE SMILES / InChI

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
Agonist and antagonist actions of morphine-like drugs on the guinea-pig isolated ileum.
1966 Sep
SKF-10,047 reverses stress-induced motor suppression: interaction with dopaminergic system.
1994 Jul 21
Effects of (+)SKF 10047, a sigma-1 selective agonist, on isolation-induced aggression in male mice.
2006 Nov

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
Name Type Language
ALAZOCINE HYDROCHLORIDE, (+)-
Common Name English
(+)-N-ALLYL-N-NORMETAZOCINE HYDROCHLORIDE
Common Name English
(+)-SKF-10047 HYDROCHLORIDE
Code English
2,6-METHANO-3-BENZAZOCIN-8-OL, 1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(2-PROPEN-1-YL)-, HYDROCHLORIDE (1:1), (2S,6S,11S)-
Systematic Name English
Code System Code Type Description
FDA UNII
J9S5L9NLC3
Created by admin on Sat Dec 16 15:19:00 GMT 2023 , Edited by admin on Sat Dec 16 15:19:00 GMT 2023
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CAS
133005-41-1
Created by admin on Sat Dec 16 15:19:00 GMT 2023 , Edited by admin on Sat Dec 16 15:19:00 GMT 2023
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PUBCHEM
13286169
Created by admin on Sat Dec 16 15:19:00 GMT 2023 , Edited by admin on Sat Dec 16 15:19:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID70474678
Created by admin on Sat Dec 16 15:19:00 GMT 2023 , Edited by admin on Sat Dec 16 15:19:00 GMT 2023
PRIMARY