Chlorosibutramine

Last updated
Chlorosibutramine
Chlorosibutramine structure.png
Identifiers
  • 1-(1-(3,4-dichlorophenyl)cyclobutyl)-N,N,3-trimethylbutan-1-amine
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
Formula C17H25Cl2N
Molar mass 314.29 g·mol−1
3D model (JSmol)
  • CC(C)CC(C1(CCC1)C2=CC(=C(C=C2)Cl)Cl)N(C)C
  • InChI=1S/C17H25Cl2N/c1-12(2)10-16(20(3)4)17(8-5-9-17)13-6-7-14(18)15(19)11-13/h6-7,11-12,16H,5,8-10H2,1-4H3
  • Key:AYHHTXUMSBRQFM-UHFFFAOYSA-N

Chlorosibutramine is an analogue of the anorectic drug sibutramine, which has been sold as an ingredient in weight loss products sold as dietary supplements, first detected in South Korea in 2013. [1] [2] [3] It is illegal in South Korea. [4]

See also

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Desmethylsibutramine 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.

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Didesmethylsibutramine is an active metabolite of the anorectic drug sibutramine that has been identified as an adulterant in weight loss supplements. Data on the activity of didesmethylsibutramine in humans is limited, although a case of psychosis associated with didesmethylsibutramine use was reported in 2019.

<span class="mw-page-title-main">Chlorosipentramine</span> Chemical compound

Chlorosipentramine is an analogue of the anorectic drug sibutramine, which has been sold as an ingredient in weight loss products sold as dietary supplements, first detected in South Korea in 2017. It is one of a number of sibutramine derivatives which have been sold in grey-market weight loss products since sibutramine itself was taken off the market due to safety concerns. Others include desmethylsibutramine, didesmethylsibutramine, homosibutramine, chlorosibutramine, and benzylsibutramine. Chlorosipentramine is illegal in South Korea along with other related compounds.

References

  1. Kim JW, Kweon SJ, Park SK, Kim JY, Lee JH, Han KM, Cho S, Kim J, Han SY, Kim HJ, Kim WS (2013). "Isolation and identification of a sibutramine analogue adulterated in slimming dietary supplements". Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment. 30 (7): 1221–9. doi:10.1080/19440049.2013.793826. PMID   23799645. S2CID   28127025.
  2. Yun J, Shin KJ, Choi J, Jo CH (May 2018). "Isolation and structural characterization of a novel sibutramine analogue, chlorosipentramine, in a slimming dietary supplement, by using HPLC-PDA, LC-Q-TOF/MS, FT-IR, and NMR". Forensic Science International. 286: 199–207. doi:10.1016/j.forsciint.2018.03.021. PMID   29602147.
  3. 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.
  4. "Anti-obesity drugs and their analogues: Chlorosibutramine" (PDF). FAOLEX Database. Food and Agriculture Organization of the United Nations.