Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H22ClN.C4H6O6 |
| Molecular Weight | 401.882 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H]([C@H](O)C(O)=O)C(O)=O.CC(C)C[C@@H](N)C1(CCC1)C2=CC=C(Cl)C=C2
InChI
InChIKey=ZGVBAFVARMNSSD-FYEOGULHSA-N
InChI=1S/C15H22ClN.C4H6O6/c1-11(2)10-14(17)15(8-3-9-15)12-4-6-13(16)7-5-12;5-1(3(7)8)2(6)4(9)10/h4-7,11,14H,3,8-10,17H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t14-;1-,2-/m10/s1
DescriptionCurator'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
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
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.
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DTXSID50725170
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259729-93-6
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HQ81B20FW4
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11246629
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admin on Fri Dec 15 17:37:17 GMT 2023 , Edited by admin on Fri Dec 15 17:37:17 GMT 2023
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SUBSTANCE RECORD
