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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=C(C=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

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

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, (+)-
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
(+)-SKF-10047
Code English
(+)-N-ALLYLNORMETAZOCINE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID90207344
Created by admin on Sat Dec 16 17:36:14 GMT 2023 , Edited by admin on Sat Dec 16 17:36:14 GMT 2023
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CAS
58640-82-7
Created by admin on Sat Dec 16 17:36:14 GMT 2023 , Edited by admin on Sat Dec 16 17:36:14 GMT 2023
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FDA UNII
YR49MN7Q8G
Created by admin on Sat Dec 16 17:36:14 GMT 2023 , Edited by admin on Sat Dec 16 17:36:14 GMT 2023
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PUBCHEM
3036222
Created by admin on Sat Dec 16 17:36:14 GMT 2023 , Edited by admin on Sat Dec 16 17:36:14 GMT 2023
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