Basic information Safety Supplier Related

1-[1-(4-Chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride

Basic information Safety Supplier Related

1-[1-(4-Chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride Basic information

Product Name:
1-[1-(4-Chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride
Synonyms:
  • N-DI-DESMETHYL SIBUTRAMINE HCL
  • N-DI-DESMETHYL SIBUTRAMINE HYDROCHLORIDE
  • 1-[1-(4-CHLOROPHENYL)CYCLOBUTYL]-3-METHYLBUTYLAMINE HCL
  • 1-[1-(4-Chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride
  • Sibutramine Impurity 1
  • 1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutan-1-amine,hydrochloride
  • N,N-Didesmethyl Sibutramine HCl
  • 1-(4-CHLOROPHENYL)-BETA-(2-METHYLPROPYL)CYCLOBUTANEMETHANAMINE HYDROCHLORIDE
CAS:
84484-78-6
MF:
C15H23Cl2N
MW:
288.26
Mol File:
84484-78-6.mol
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1-[1-(4-Chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride Chemical Properties

Melting point:
160 - 166°C
storage temp. 
Desiccate at RT
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Solid
color 
White to Off-White
Stability:
Hygroscopic
CAS DataBase Reference
84484-78-6(CAS DataBase Reference)
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1-[1-(4-Chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride Usage And Synthesis

Uses

A metabolite of Sibutramine, a serotonin and noradrenaline reuptake inhibitor (SNR). Decreases calorie intake and increases energy expenditure.

Uses

A metabolite of Sibutramine, a serotonin and noradrenaline reuptake inhibitor (SNR). Decreases calorie intake and increases energy expenditure.

Biological Activity

Potently active primary amine metabolite of sibutramine (1-(4-Chlorophenyl)-N,N-dimethyl-a-(2-methylpropyl)cyclobutanemethanamine hydrochloride ) that exhibits a similar pharmacological profile to the parent compound. Inhibits serotonin and noradrenalin reuptake more potently than sibutramine in vitro . In vivo, reduces food intake in rodents following i.c.v. administration and increases energy expenditure via thermogenesis.

in vitro

simultaneous application of bts 54-505 with 5-ht resulted in a prolongation of the recovery time from the 5-ht-mediated suppression of discharge activity. bts 54-505 also prolonged the recovery time from a na-mediated potentiation of firing. these effects on recovery time are attributed to the inhibition of uptake of both 5-ht and na by bts 54-505. the amplitude of the response to 5-ht or na was unaffected by co-ejection of bts 54-505 [1].

in vivo

the secondary (bts 54-354) and primary (bts 54-505) amine metabolites of sibutramine hcl exhibit similar in vivo pharmacological activity to the parent compound. thus, each compound displays potent activity in acute behavioural models predictive of antidepressant effects and a comparable ability to inhibit the uptake of monoamines [2].

IC 50

0.066 μm for noradrenaline uptake; 5.1 μm for 5-ht uptake; 0.31 μm for dopamine uptake

References

[1] scott g, luscombe gp, mason r. the effects of bts 54-505, a metabolite of sibutramine, on monoamine and excitatory amino acid-evoked responses in the rat dorsolateral geniculate nucleus in vivo. br j pharmacol. 1994 jan;111(1):97-102.
[2] luscombe gp, hopcroft rh, thomas pc, buckett wr. the contribution of metabolites to the rapid and potent down-regulation of rat cortical beta-adrenoceptors by the putative antidepressant sibutramine hydrochloride. neuropharmacology. 1989 feb;28(2):129-34.

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