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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, (R)-

SMILES

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

InChI

InChIKey=KHRVYINTXCWNRF-PFEQFJNWSA-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-;/m1./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 (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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:26:04 GMT 2023
Edited
by admin
on Sat Dec 16 11:26:04 GMT 2023
Record UNII
YWP9I7EXUM
Record Status Validated (UNII)
Record Version
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Name Type Language
DIDESMETHYLSIBUTRAMINE HYDROCHLORIDE, (R)-
Common Name English
CYCLOBUTANEMETHANAMINE, 1-(4-CHLOROPHENYL)-.ALPHA.-(2-METHYLPROPYL)-, HYDROCHLORIDE, (.ALPHA.R)-
Common Name English
CYCLOBUTANEMETHANAMINE, 1-(4-CHLOROPHENYL)-.ALPHA.-(2-METHYLPROPYL)-, HYDROCHLORIDE (1:1), (.ALPHA.R)-
Systematic Name English
((R)-1-(1-(4-CHLOROPHENYL)CYCLOBUTYL)-3-METHYLBUTAN-1-YL)AMINE HYDROCHLORIDE
Systematic Name English
Code System Code Type Description
PUBCHEM
9900575
Created by admin on Sat Dec 16 11:26:04 GMT 2023 , Edited by admin on Sat Dec 16 11:26:04 GMT 2023
PRIMARY
CAS
262854-35-3
Created by admin on Sat Dec 16 11:26:04 GMT 2023 , Edited by admin on Sat Dec 16 11:26:04 GMT 2023
PRIMARY
FDA UNII
YWP9I7EXUM
Created by admin on Sat Dec 16 11:26:04 GMT 2023 , Edited by admin on Sat Dec 16 11:26:04 GMT 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER