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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, (R)-

SMILES

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

InChI

InChIKey=WQSACWZKKZPCHN-CQSZACIVSA-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-/m1/s1

HIDE SMILES / InChI

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 (R-Didesmethylsibutramine , (R)-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 (R)-enantiomer of Didesmethylsibutramine was clearly more potent than the (S)-enantiomers and (R)-didesmethylsibutramine shows some activity in all tests. (S)-didesmethylsibutramine affected locomotor behavior and the Porsolt test but appeared to be completely inactive on food intake. R-Didesmethylsibutramine is more potent than sibutramine in depressing food intake and decreasing body weight, suggest that these enantioselective metabolites might be safer and more effective than sibutramine as potential therapies for obesity.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
13.0 nM [IC50]
140.0 nM [IC50]
8.9 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
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.
Name Type Language
DIDESMETHYLSIBUTRAMINE, (R)-
Common Name English
CYCLOBUTANEMETHANAMINE, 1-(4-CHLOROPHENYL)-.ALPHA.-(2-METHYLPROPYL)-, (.ALPHA.R)-
Common Name English
R-(+)-DI-DESMETHYLSIBUTRAMINE
Common Name English
DIDESMETHYLSIBUTRAMINE, (+)-
Common Name English
(1R)-1-(1-(4-CHLOROPHENYL)CYCLOBUTYL)-3-METHYLBUTAN-1-AMINE
Systematic Name English
Code System Code Type Description
FDA UNII
B408000HRV
Created by admin on Fri Dec 15 22:26:03 GMT 2023 , Edited by admin on Fri Dec 15 22:26:03 GMT 2023
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EPA CompTox
DTXSID90177513
Created by admin on Fri Dec 15 22:26:03 GMT 2023 , Edited by admin on Fri Dec 15 22:26:03 GMT 2023
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PUBCHEM
9900576
Created by admin on Fri Dec 15 22:26:03 GMT 2023 , Edited by admin on Fri Dec 15 22:26:03 GMT 2023
PRIMARY
CAS
229639-56-9
Created by admin on Fri Dec 15 22:26:03 GMT 2023 , Edited by admin on Fri Dec 15 22:26:03 GMT 2023
PRIMARY