Sibutramine hydrochloride
- CAS No.
- 84485-00-7
- Chemical Name:
- Sibutramine hydrochloride
- Synonyms
- SIBUTRAMINE HCL;REDUCTIL;MERIDIA;Yeduc;tdfeind;BTS 54524;SIBUTRAMING;Sidwtramine;xibuqyumiine;Unii-ogm0yhd1wf
- CBNumber:
- CB3783665
- Molecular Formula:
- C17H27Cl2N
- Molecular Weight:
- 316.31
- MDL Number:
- MFCD00897667
- MOL File:
- 84485-00-7.mol
| Melting point | 190-200°C |
|---|---|
| storage temp. | room temp |
| solubility | Soluble to 5 mM in water and to 100 mM in DMSO |
| form | Powder |
| CAS DataBase Reference | 84485-00-7(CAS DataBase Reference) |
| FDA UNII | 9GG866ZP1E |
Sibutramine hydrochloride Chemical Properties,Uses,Production
Weight loss pills
Sibutramine hydrochloride is a weight loss drug, it is hydrochloride salt form of sibutramine , and the pharmacological effects are fully consistent with of sibutramine , but the stability and solubility are better than sibutramine.
Sibutramine hydrochloride is firstly used to treat depression, in their clinical application process , people find that the effect of weight loss is significantly stronger than the effect of the antidepressant . On one hand ,by inhibiting the reuptake of serotonin, which makes the body reduce hunger, it can suppress appetite and control caloric intake effectively ; on the other hand, by activating the adrenergic receptors, which increases adipose tissue consumption, it can increase metabolism and energy consumption;it has obvious weight loss effect, but it may cause endangering serious side effects such as high blood pressure, high heart rate, anorexia, insomnia, abnormal liver function.
The above information is edited by the chemicalbook of Tian Ye.
Precautions
Sibutramine hydrochloride belongs to the serotonin and norepinephrine reuptake inhibitors, it has the dual role of inhibiting appetite and enhancing metabolism, it can be used for the treatment of obesity which diet and exercise can not control.
There are many taboos in clinical practice of sibutramine hydrochloride , for example, patients with severe hypertension or patients with severe liver and kidney dysfunction, or patients with angle-closure glaucoma and women after childbirth, should not use it . Because the physiological effects of 16 years old or younger minors have not yet been confirmed, use of it should be prohibited. Also doses should be strictly controlled by users, the recommended starting dose is 10 mg per day for adults, the maximum should not exceed 15 mg. If there is overdose, patients should go to hospital for treatment, there is no specific antidote, only symptomatic treatment can be taken in clinic.
Uses
It is used as an antidepressant.
Originator
Meridia,Abbott Laboratories,USA
Uses
Anorexic; antidepressant.
Uses
Sibutramine Hydrochloride is a 5-HT and noradrenaline reuptake inhibitor.
Uses
Sibutramine hydrochloride monohydrate was used as standard to screen dietary supplements for sibutramine using ion mobility spectrometer.1
Manufacturing Process
A solution of 4-chlorobenzyl cyanide and 1,3-dibromopropane in dry
dimethylsulfoxide was added dropwise under nitrogen to a stirred mixture of
sodium hydride dispersed in mineral oil and dimethylsulfoxide at a
temperature in the range 30° to 35°C. The mixture was stirred at room
temperature for 2 h and propan-2-ol and then water were added dropwise.
The mixture was filtered through a diatomaceous earth sold under the
Registered Trade Mark CELITE and the solid residue washed with ether. The
ether layer was separated, washed with water, dried and evaporated. 1-(4-
Chlorophenyl)-1-cyclobutanecarbonitrile was isolated by distillation.
1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile (37.6 g) was added to a solution
of potassium hydroxide (32.4 g) in diethyleneglycol (370 ml) and the mixture
heated under reflux for three and a 0.5 h The reaction mixture was poured
into an ice/water mixture and the resulting solution was washed with ether.
The aqueous layer was added to a mixture of concentrated hydrochloric acid
(100 ml) and ice and the resulting precipitate of 1-(4-chlorophenyl)-1-
cyclobutanecarboxylic acid (melting point 86°-88°C) collected, washed with
water and dried.
1-(4-Chlorophenyl)-1-cyclobutane carboxylic acid (10.5 g) was heated under
reflux with thionyl chloride (20 ml) for 2.5 h. Excess thionyl chloride was
evaporated off and the acid chloride of the above acid distilled (boiling point
82°-96°C /0.2 mm Hg). A solution of the acid chloride in dry tetrahydrofuran
was added slowly to the product of the reaction of magnesium turnings and
ethyl bromide in dry tetrahydrofuran. Water was added followed by 5 N
hydrochloric acid with cooling. The reaction mixture was extracted with ether,
washed with water, sodium bicarbonate solution, dried. The solvent was
removed by evaporation and 1-isobutyl-1-(4-chlorophenyl)cyclobutane
obtained by distillation. The 1-isobutyl-1-(4-chlorophenyl)cyclobutane,
diethylene glycoldimethyl ether, water and concentrated hydrochloric acid
were mixed and heated under reflux. The mixture was poured into water
aqueous NaOH was added and the product extracted into ether. Evaporation
gave a dark oil. A sample of this oil, water and formic acid were mixed and
formaldehyde added. The mixture was heated under reflux and then
concentrated hydrochloric acid and propan-2-ol were added. Evaporation to dryness gave N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]isobutyl
hydrochloride as a white solid.
brand name
Meridia (Abbott).
Therapeutic Function
Antidepressant, Anorexic
Biological Activity
5-HT and noradrenalin re-uptake inhibitor (SNRI). Produces weight loss in rats via inhibition of food intake and increased energy expenditure. Antidepressant.
Biochem/physiol Actions
Sibutramine is a serotonin and noradrenaline reuptake inhibitor (SNRI). It is an antiobesity drug, which decreases calorie intake and increases energy expanditure. Sibutramine antagonizes MPTP-induced dopamine depletion in mouse brain.
Sibutramine hydrochloride Preparation Products And Raw materials
Raw materials
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