Desmethylsibutramine

Desmethylsibutramine
Identifiers
	IUPAC name 1-[1-(4-chlorophenyl)cyclobutyl]-N,3-dimethylbutan-1-amine;
CAS Number	168835-59-4 ;
PubChem CID	10199199;
CompTox Dashboard (EPA)	DTXSID701314239 ;
Chemical and physical data
Formula	C16H24ClN
Molar mass	265.83 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)CC(C1(CCC1)C2=CC=C(C=C2)Cl)NC;
	InChI InChI=1S/C16H24ClN/c1-12(2)11-15(18-3)16(9-4-10-16)13-5-7-14(17)8-6-13/h5-8,12,15,18H,4,9-11H2,1-3H3; Key:PLXKZKLXYHLWHR-UHFFFAOYSA-N;

Desmethylsibutramine (Norsibutramine, BTS-54354) is an active metabolite of the anorectic drug sibutramine. It is a more potent monoamine reuptake inhibitor than sibutramine and has been sold as an ingredient in weight loss products sold as dietary supplements, along with related compounds such as the N-ethyl and 3,4-dichloro derivatives.^[1]^[2]^[3]^[4]^[5]

References

^ Glick SD, Haskew RE, Maisonneuve IM, Carlson JN, Jerussi TP (May 2000). "Enantioselective behavioral effects of sibutramine metabolites". European Journal of Pharmacology. 397 (1): 93–102. doi:10.1016/s0014-2999(00)00216-8. PMID 10844103.
^ Park SR, Lee JG, Roh SH, Kim G, Kwon CH, Park HR, et al. (2012). "Determination of PDE-5 inhibitors and appetite suppressants in adulterated dietary supplements using LC/PDA and LC/MS". Food Additives & Contaminants. Part B, Surveillance. 5 (1): 29–32. doi:10.1080/19393210.2012.656706. PMID 24779692. S2CID 21389290.
^ Reeuwijk NM, Venhuis BJ, de Kaste D, Hoogenboom RL, Rietjens IM, Martena MJ (2014). "Active pharmaceutical ingredients detected in herbal food supplements for weight loss sampled on the Dutch market". Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment. 31 (11): 1783–1793. doi:10.1080/19440049.2014.958574. PMID 25247833. S2CID 24272967.
^ Zeng Y, Xu Y, Kee CL, Low MY, Ge X (2016). "Analysis of 40 weight loss compounds adulterated in health supplements by liquid chromatography quadrupole linear ion trap mass spectrometry". Drug Testing and Analysis. 8 (3–4): 351–6. doi:10.1002/dta.1846. PMID 26305055. S2CID 47560433.
^ Jeong D, Choe S, Lee S, Kim KM, Pyo J (January 2021). "Metabolic analysis of the illegal analogues of anti-obesity drugs using LC-Q-TOF-MS/MS". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 1163: 122502. doi:10.1016/j.jchromb.2020.122502. PMID 33412503. S2CID 231195145.

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[1] Glick SD, Haskew RE, Maisonneuve IM, Carlson JN, Jerussi TP (May 2000). "Enantioselective behavioral effects of sibutramine metabolites". European Journal of Pharmacology. 397 (1): 93–102. doi:10.1016/s0014-2999(00)00216-8. PMID 10844103.

[2] Park SR, Lee JG, Roh SH, Kim G, Kwon CH, Park HR, et al. (2012). "Determination of PDE-5 inhibitors and appetite suppressants in adulterated dietary supplements using LC/PDA and LC/MS". Food Additives & Contaminants. Part B, Surveillance. 5 (1): 29–32. doi:10.1080/19393210.2012.656706. PMID 24779692. S2CID 21389290.

[3] Reeuwijk NM, Venhuis BJ, de Kaste D, Hoogenboom RL, Rietjens IM, Martena MJ (2014). "Active pharmaceutical ingredients detected in herbal food supplements for weight loss sampled on the Dutch market". Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment. 31 (11): 1783–1793. doi:10.1080/19440049.2014.958574. PMID 25247833. S2CID 24272967.

[pmid26305055-4] Zeng Y, Xu Y, Kee CL, Low MY, Ge X (2016). "Analysis of 40 weight loss compounds adulterated in health supplements by liquid chromatography quadrupole linear ion trap mass spectrometry". Drug Testing and Analysis. 8 (3–4): 351–6. doi:10.1002/dta.1846. PMID 26305055. S2CID 47560433.

[5] Jeong D, Choe S, Lee S, Kim KM, Pyo J (January 2021). "Metabolic analysis of the illegal analogues of anti-obesity drugs using LC-Q-TOF-MS/MS". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 1163: 122502. doi:10.1016/j.jchromb.2020.122502. PMID 33412503. S2CID 231195145.

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Identifiers

IUPAC name 1-[1-(4-chlorophenyl)cyclobutyl]-N,3-dimethylbutan-1-amine
CAS Number	168835-59-4^Y
PubChem CID	10199199
CompTox Dashboard (EPA)	DTXSID701314239
Chemical and physical data
Formula	C₁₆H₂₄ClN
Molar mass	265.83 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(C)CC(C1(CCC1)C2=CC=C(C=C2)Cl)NC
InChI InChI=1S/C16H24ClN/c1-12(2)11-15(18-3)16(9-4-10-16)13-5-7-14(17)8-6-13/h5-8,12,15,18H,4,9-11H2,1-3H3 Key:PLXKZKLXYHLWHR-UHFFFAOYSA-N

Desmethylsibutramine

See also

References