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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H22ClN.ClH
Molecular Weight 288.256
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

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

SMILES

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

InChI

InChIKey=KHRVYINTXCWNRF-UQKRIMTDSA-N
InChI=1S/C15H22ClN.ClH/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;1H/t14-;/m0./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 (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.
Name Type Language
DIDESMETHYLSIBUTRAMINE HYDROCHLORIDE, (S)-
Common Name English
CYCLOBUTANEMETHANAMINE, 1-(4-CHLOROPHENYL)-.ALPHA.-(2-METHYLPROPYL)-, HYDROCHLORIDE, (.ALPHA.S)-
Common Name English
CYCLOBUTANEMETHANAMINE, 1-(4-CHLOROPHENYL)-.ALPHA.-(2-METHYLPROPYL)-, HYDROCHLORIDE (1:1), (.ALPHA.S)-
Systematic Name English
Code System Code Type Description
CAS
262854-36-4
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
11601691
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
O492E9070X
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