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
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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/10844103Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10844103
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10844103 |
13.0 nM [IC50] | ||
Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10844103 |
140.0 nM [IC50] | ||
Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10844103 |
8.9 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10844103
Rats were treated with (+)-DDMS at doses 2.5–10 mg/kg, i.p.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10844103
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
Edited
Fri Dec 15 22:26:03 GMT 2023
by
admin
on
Fri Dec 15 22:26:03 GMT 2023
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Record UNII |
B408000HRV
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Record Status |
Validated (UNII)
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Record Version |
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-
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B408000HRV
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DTXSID90177513
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9900576
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229639-56-9
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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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Related Record | Type | Details | ||
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RACEMATE -> ENANTIOMER |