Sibutramine

Base Information Edit

Chemical Name:Sibutramine
CAS No.:106650-56-0
Molecular Formula:C17H26ClN
Molecular Weight:279.853
Hs Code.:2921499090
European Community (EC) Number:600-761-4
UNII:WV5EC51866
DSSTox Substance ID:DTXSID1023578
Nikkaji Number:J247.963J
Wikipedia:Sibutramine
Wikidata:Q424151
NCI Thesaurus Code:C75965
Pharos Ligand ID:WTC152NY3JSF
Metabolomics Workbench ID:43334
ChEMBL ID:CHEMBL1419
Mol file:106650-56-0.mol

Synonyms:(R)-DDMS;BTS 54 524;BTS 54524;BTS-54524;di-desmethylsibutramine;didesmethylsibutramine;Meridia;mono-desmethylsibutramine;N-1-(1-(4-chlorophenyl)cyclobutyl)-3-methylbutyl-N,N-dimethylamine HCl;Reductil;sibutramine;sibutramine hydrochloride

This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Sibutramine Edit

Chemical Property:

Appearance/Colour:Yellowish solid
Vapor Pressure:7.45E-05mmHg at 25°C
Melting Point:191-192 °C
Boiling Point:342.6 °C at 760 mmHg
PKA:9.69±0.50(Predicted)
Flash Point:161 °C
PSA：3.24000
Density:1.031 g/cm³
LogP:4.73800
Water Solubility.:2.9 mg/mL
XLogP3:5.4
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:5
Exact Mass:279.1753775
Heavy Atom Count:19
Complexity:275

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Drug Classes:Weight Loss Agents
Canonical SMILES:CC(C)CC(C1(CCC1)C2=CC=C(C=C2)Cl)N(C)C
Recent ClinicalTrials:Efficacy and Safety of Sibutramin-containing Drugs in Patient With Alimentary Obesity
Recent EU Clinical Trials:TRATAMIENTO MULTIDISCIPLINARIO DE LA OBESIDAD MóRBIDA: MEDICAMENTOS, TERAPIA DE COMPORTAMIENTO, APOYO NUTRICIONAL Y ACTIVIDAD FíSICA. ESTDIO TRAMOMTANA
Indications It is suitable for the treatment of obesity which can’t be tackled through diet control or exercise. The treatment includes weight loss and maintenance of weight loss. The treatment should be applied in combination with low-calorie diet and exercise. It is recommended for being applied to the treatment of obesity patients with the body mass index being greater than or equal to 30kg/m2 or being equal to or greater than 27kg/m2 but accompanied with other risk factors such as hypertension, diabetes and dyslipidemia. The recommended starting amount is 10mg, qd. It can be used in single administration in the morning or be subject administration together with food. If the weight loss is less than expected, after four weeks, the dose can be adjusted to 15 mg per day. If the patient can’t tolerate the dose of 10 mg, the dose can be reduced to 5mg. The dose should be adjusted based on the patient's blood pressure and heart rate. It is not recommended for using the dose of over 15 mg/d.
Uses It is 5-HT reuptake inhibitors and can be used for the treatment of obesity. It can be used as an antidepressant. Anorexic; antidepressant.
Production method Mix p-Chlorobenzene, acetonitrile and KOH at 25%: slowly add drop wise of 1, 3-dibromopropane. After the completion of the dropping, continue for stirring of 1h; add distilled water and further extracted with ethyl acetate. The extract was washed with water, brine and dried. It is then filtered, concentrated under reduced pressure and distilled, collect the 160 ℃/2.13kPa fraction to obtain the compound (Ⅰ) with the yield being 73% to 74%. The magnesium sheet was dissolved in anhydrous THF. Add drop wise of isobutyl bromide followed by reaction of 1h. Then slowly add drop wise of the anhydrous THF solution of compound (I). After the completion of dropping, reflux for 4h and cool to room temperature. Add them drop wise into the isopropanol solution of KBH4, reflux for 4h. Cool, add water and extract with ethyl acetate. The extract was washed by water, brine and dried. It is then filtered with the filtrate being concentrated under reduced pressure before distillation. Collect the 170 ℃/0.67kPa fraction to obtain the compound (II) with the yield being 76% to 79%. Compound (II), formic acid and the 1/2 formaldehyde solution were stirred at 90~92 ℃ for 1h. Further add another part of 1/2 formaldehyde solution and reaction was continued for 1h. Cool to room temperature and slowly pour into the crushed ice solution of sodium hydroxide, then extract with diethyl ether. The extract was washed with saturated brine, washed, and dried. Then it is filtered with the filtrate being concentrated to give khaki sibutramine with the yield of 94%. The analytical sample can be subject to recrystallization of diethyl ether with the m.p. of 52~53 ℃. Sibutramine was dissolved in methanol, add concentrated hydrochloric acid for reaction at 50~60'C for 10min. Recover the methanol under reduced pressure until a small volume was crystallized, add water and stir, and cool at ice bath. Filter and wash to obtain the crude product of sibutramine hydrochloride. Use methanol-water of crystallization to obtain the white crystals of sibutramine hydrochloride with the melting point of 194 ℃ and yield of 83%.
Therapeutic Function Antidepressant, Anorexic

Technology Process of Sibutramine

There total 16 articles about Sibutramine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.4%

: 84485-00-7,154752-45-1
sibutramine hydrochloride

: 106650-56-0
sibutramine

Guidance literature:: With sodium carbonate;
DOI:10.1016/j.tetasy.2015.04.007

Reference yield: 98.0%

: C₁₅H₁₉ClN^(1-)*Cl^(1-)*Mg⁽²⁺⁾

: 106650-56-0,84467-54-9
didesmethylsibutramine

Guidance literature:: With borane-THF; benzene-1,2-dicarboxylic acid; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1016/S0040-4039(02)01905-6