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Chemistry

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Also known as: 125494-59-9, Sibutramine hydrochloride monohydrate, Reductil, Sibutramine hydrochloride hydrate, Sibutramine hydrochloride [usan], Bts 54524

Molecular Formula

C₁₇H₂₉Cl₂NO

Molecular Weight

334.3 g/mol

InChI Key

KFNNPQDSPLWLCX-UHFFFAOYSA-N

FDA UNII

OGM0YHD1WF

Sibutramine Hydrochloride is the hydrochloride salt form of sibutramine, a phenethylamine derivative with appetite depressant property. Sibutramine hydrochloride metabolites M1 and M2 competitively inhibit the reuptake of norepinephrine, serotonin, and to a lesser degree dopamine by pre-synaptic nerve terminals, thereby promoting a sense of satiety, leading to a decrease in calorie intake, and possibly an increase in resting metabolic rate. This agent does not exhibit anticholinergic or antihistaminic effects.

1 2D Structure

Sibutramine Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[1-(4-chlorophenyl)cyclobutyl]-N,N,3-trimethylbutan-1-amine;hydrate;hydrochloride

2.1.2 InChI

InChI=1S/C17H26ClN.ClH.H2O/c1-13(2)12-16(19(3)4)17(10-5-11-17)14-6-8-15(18)9-7-14;;/h6-9,13,16H,5,10-12H2,1-4H3;1H;1H2

2.1.3 InChI Key

KFNNPQDSPLWLCX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)CC(C1(CCC1)C2=CC=C(C=C2)Cl)N(C)C.O.Cl

2.2 Other Identifiers

2.2.1 UNII

OGM0YHD1WF

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (r)-ddms

2. Bts 54 524

3. Bts 54524

4. Bts-54524

5. Di-desmethylsibutramine

6. Didesmethylsibutramine

7. Mono-desmethylsibutramine

8. N-1-(1-(4-chlorophenyl)cyclobutyl)-3-methylbutyl-n,n-dimethylamine Hcl

9. Reductil

10. Sibutramine

11. Sibutramine Hydrochloride

2.3.2 Depositor-Supplied Synonyms

1. 125494-59-9

2. Sibutramine Hydrochloride Monohydrate

3. Reductil

4. Sibutramine Hydrochloride Hydrate

5. Sibutramine Hydrochloride [usan]

6. Bts 54524

7. Ogm0yhd1wf

8. Bts-54524

9. Sibutramine (hydrochloride Monohydrate)

10. Sibutramine Hydrochloride Civ

11. 1-[1-(4-chlorophenyl)cyclobutyl]-n,n,3-trimethylbutan-1-amine;hydrate;hydrochloride

12. Sibutramine Hydrochloride Hydrate (jan)

13. Cyclobutanemethanamine, 1-(4-chlorophenyl)-n,n-dimethyl-alpha-(2-methylpropyl)-, Hydrochloride, Hydrate (1:1:1)

14. Sibutramine, Hydrochloride Monohydrate

15. Sibutramine Hydrochloride Hydrate [jan]

16. Unii-ogm0yhd1wf

17. Meridia (tn)

18. Sibutramine Hcl H2o

19. Cpd000472527

20. Schembl42301

21. (+-)-1-(p-chlorophenyl)-alpha-isobutyl-n,n-dimethylcyclobutanemethylamine Hydrochloride Monohydrate

22. Mls001424319

23. Sibutramine Hydrochloride,(s)

24. Chembl3989830

25. Sibutramine Hydrochloride (usp)

26. Dtxsid00925148

27. Kes-524

28. Bcp07236

29. Akos015855356

30. Ac-4218

31. Ccg-101169

32. Ks-1192

33. 1-[1-(4-chlorophenyl)cyclobutyl]-n,n,3-trimethyl-butan-1-amine Hydrate Hydrochloride

34. Sibutramine Hydrochloride [mart.]

35. Sibutramine Hydrochloride [vandf]

36. Bs164401

37. Cyclobutanemethanamine, 1-(4-chlorophenyl)-n,n-dimethyl-alpha-(2-methylpropyl)-, Hydrochloride, Monohydrate, (+-)-

38. Hy-14470

39. Smr000472527

40. 1-(1-(4-chlorophenyl)cyclobutyl)-n,n,3

41. Db-049918

42. Trimethylbutan-1-amine Hydrochloride Hydrate

43. 1-(1-(4-chlorophenyl)cyclobutyl)-n,n,3-

44. Ft-0651268

45. Sibutramine Hydrochloride Monohydrate- Bio-x

46. D02571

47. Sibutramine Hydrochloride [orange Book]

48. Sibutramine Hydrochloride [usp Impurity]

49. 485s007

50. A805388

51. Sibutramine Hydrochloride Monohydrate [mi]

52. Sibutramine Hydrochloride Monohydrate [hsdb]

53. Q27285644

54. Sibutramine Hydrochloride Monohydrate [who-dd]

55. Sibutramine Hydrochloride Monohydrate, >=98% (hplc), Solid

56. 1-[1-(4-chlorophenyl)cyclobutyl]-n,n,3-trimethyl-1-butanamine Hydrate Hydrochloride

57. N,n-dimethyl-1-[1-(4-chlorophenyl)-cyclobutyl]-3-methylbutylamine Hydrochloride Monohydrate

58. N,n-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine Hydrochloride Monohydrate

59. Sibutramine Hydrochloride Monohydrate 1.0 Mg/ml In Methanol (as Anhydrous Free Base)

60. (+/-)-1-(p-chlorophenyl)-.alpha.-isobutyl-n,n-dimethylcyclobutanemethylamine Hydrochloride Monohydrate

61. 1-[1-(4-chlorophenyl)cyclobutyl]-n,n,3-trimethylbutan-1-amine--hydrogen Chloride--water (1/1/1)

62. Cyclobutanemethanamine, 1-(4-chlorophenyl)-n,n-dimethyl-.alpha.-(2-methylpropyl)-, Hydrochloride, Hydrate (1:1:1)

63. Cyclobutanemethanamine, 1-(4-chlorophenyl)-n,n-dimethyl-a-(2-methylpropyl)-, Hydrochloride, Monohydrate, (+/-)-

64. Sibutramine Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₉Cl₂NO
Molecular Weight	334.3 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	5
Exact Mass	333.1626199 g/mol
Monoisotopic Mass	333.1626199 g/mol
Topological Polar Surface Area	4.2 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	275
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antidepressive Agents

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)

Appetite Depressants

Agents that are used to suppress appetite. (See all compounds classified as Appetite Depressants.)

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