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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H22ClN
Molecular Weight 251.795
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIDESMETHYLSIBUTRAMINE, (S)-

SMILES

CC(C)C[C@H](N)C1(CCC1)C2=CC=C(Cl)C=C2

InChI

InChIKey=WQSACWZKKZPCHN-AWEZNQCLSA-N
InChI=1S/C15H22ClN/c1-11(2)10-14(17)15(8-3-9-15)12-4-6-13(16)7-5-12/h4-7,11,14H,3,8-10,17H2,1-2H3/t14-/m0/s1

HIDE SMILES / InChI

Molecular Formula C15H22ClN
Molecular Weight 251.795
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12423077 | https://www.ncbi.nlm.nih.gov/pubmed/20195828

(-)-DDMS (S-Didesmethylsibutramine, (S)-DDMS) is one of sibutramine active metabolites. Sibutramine is widely used in the treatment of obesity. Sibutramine acts by inhibiting the reuptake of serotonin and noradrenaline in synapses, thereby enhancing both satiety and energy expenditure. In preclinical models (S)-Didesmethylsibutramine affected locomotor behavior and the Porsolt test but appeared to be completely inactive on food intake. (S)-enantiomers of didesmethylsibutramine may, to some extent, contribute to sibutramine’s side effect profile.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
62.0 nM [IC50]
4300.0 nM [IC50]
12.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Enantioselective behavioral effects of sibutramine metabolites.
2000 May 26
Patents

Patents

Sample Use Guides

Rats were treated with (-)-DDMS at doses 2.5–10 mg/kg, i.p.
Route of Administration: Intraperitoneal
Synaptosomes (isolated from male Wistar rat hypothalamus, whole brain, or corpus striatum) and monoamines were prepared in Krebs’ buffer, which was oxygenated and then incubated in a deep well plates. Uptake was performed by incubating the synaptosomes in the presence and absence of each of the test compounds ((-)-DDMS or (+)-DDMS). Uptake was then stopped by filtration through a unifilter 96-well plate, which was washed with Krebs buffer in order to eliminate the free radiolabeled monoamine. Radioactivity taken up by synaptosomes was retained on the filter and then measured with a microplate scintillation counter.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:11:31 GMT 2023
Edited
by admin
on Sat Dec 16 11:11:31 GMT 2023
Record UNII
8T426BV34Q
Record Status Validated (UNII)
Record Version
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Name Type Language
DIDESMETHYLSIBUTRAMINE, (S)-
Common Name English
(S)-DIDESMETHYLSIBUTRAMINE
Common Name English
(-)-DIDESMETHYLSIBUTRAMINE
Common Name English
CYCLOBUTANEMETHANAMINE, 1-(4-CHLOROPHENYL)-.ALPHA.-(2-METHYLPROPYL)-, (.ALPHA.S)-
Systematic Name English
(.ALPHA.S)-1-(4-CHLOROPHENYL)-.ALPHA.-(2-METHYLPROPYL)CYCLOBUTANEMETHANAMINE
Common Name English
S-(-)-DI-DESMETHYLSIBUTRAMINE
Common Name English
Code System Code Type Description
CAS
229639-57-0
Created by admin on Sat Dec 16 11:11:31 GMT 2023 , Edited by admin on Sat Dec 16 11:11:31 GMT 2023
PRIMARY
PUBCHEM
9794968
Created by admin on Sat Dec 16 11:11:31 GMT 2023 , Edited by admin on Sat Dec 16 11:11:31 GMT 2023
PRIMARY
FDA UNII
8T426BV34Q
Created by admin on Sat Dec 16 11:11:31 GMT 2023 , Edited by admin on Sat Dec 16 11:11:31 GMT 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER