Clobenzorex

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Clobenzorex
Clobenzorex structure.svg
Clinical data
Other namesN-(2-chlorobenzyl)amphetamine
AHFS/Drugs.com International Drug Names
Routes of
administration 		Oral
ATC code
Legal status
Legal status
Identifiers
  • N-(2-chlorobenzyl)-1-phenylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.033.108 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H18ClN
Molar mass 259.78 g·mol−1
3D model (JSmol)
  • Clc1ccccc1CNC(C)Cc2ccccc2
  • InChI=1S/C16H18ClN/c1-13(11-14-7-3-2-4-8-14)18-12-15-9-5-6-10-16(15)17/h2-10,13,18H,11-12H2,1H3 Yes check.svgY
  • Key:LRXXRIXDSAEIOR-UHFFFAOYSA-N Yes check.svgY
   (verify)

Clobenzorex is a central nervous system stimulant and anorectic drug, chemically classified as an N-substituted amphetamine and a phenethylamine. Marketed by Aventis under the trade name Asenlix in India, Mexico, Honduras, and other parts of Latin America.

Contents

A prodrug of amphetamine, clobenzorex is metabolized within hours of ingestion into 4-hydroxyclobenzorex and, in smaller amounts, amphetamine. [2] [3]

Chemistry

Synthesis

Thieme Synthesis: Patent: Radiolabelled: Clobenzorex synthesis.svg
Thieme Synthesis: Patent: Radiolabelled:

Condensation between amphetamine (1) and 2-chlorobenzaldehyde (2) gives a Schiff-base, CID:135056236 (3). Subsequent reduction with sodium borohydride completed the synthesis of clobenzorex (4).

Urinalysis

Clobenzorex can be detected by urine drug screening. [7] It is one of many drugs that can cause a positive result for amphetamine in urine drug screening. [8] It may be differentiated from use of amphetamine itself through testing for metabolites such as 4-hydroxyclobenzorex [9] or enantiomeric analysis. [7]

Brazil

In Brazil, clobenzorex is a controlled prohibited psychotropic (class A3). [10]

Canada

In Canada, clobenzorex is not specifically listed per the Controlled Drugs and Substances Act.[ citation needed ]

Mexico

In Mexico, clobenzorex is available for sale over the counter at many Mexican pharmacies under the primary brand Asenlix, as well as generic trade names like Dinintel, Finedal, Rexigen, Itravil, all of which are available via prescription in India, and OTC in Mexico and Honduras, typically used as an appetite suppressant. [7]

United Kingdom

In the United Kingdom, clobenzorex is a controlled drug (class B). [11]

United States

Clobenzorex is not controlled under the Controlled Substances Act of 1970 nor is it controlled under the Federal Analogue Act, as it is a derivative of benzphetamine. [12] It is not subject to import controls and is legal to import and possess for personal medical use, provided all of the following conditions are met: [13]

  1. It is used to treat a condition with no FDA-approved medications or an orphan drug does not effectively treat a condition, and the risks of use have not been determined to outweigh to benefits of treatment;
  2. is not being deceptively and unlawfully marketed; and
  3. is part of an ongoing medical treatment plan that began in a foreign country.

World Anti-Doping Agency

The use of clobenzorex is banned by the World Anti-Doping Agency for use during sports competitions as an athletic performance enhancer ("doping"). [14]

See also

References

  1. ↑ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ↑ Cody JT (2005). "Amphetamines: methods of forensic analysis.". In Smith F, Athanaselis SS (eds.). Handbook of Forensic Drug Analysis. Elsevier. pp. 357–451 (430). ISBN   978-0-08-047289-8. Amphetamine produced from the metabolism of clobenzorex has been shown to be the d-enantiomer only ...
  3. ↑ Young R, Darmani NA, Elder EL, Dumas D, Glennon RA (February 1997). "Clobenzorex: evidence for amphetamine-like behavioral actions". Pharmacology, Biochemistry, and Behavior. 56 (2): 311–316. doi:10.1016/s0091-3057(96)00329-2. PMID   9050090. S2CID   37062225.
  4. ↑ Boissier JR, Ratouis R, Dumont C (January 1966). "[New derivatives of phenylisopropylamine: synthesis and study of their anorexic activity]". Annales Pharmaceutiques Françaises (in French). 24 (1): 57–68. PMID   5910702.
  5. ↑ GB 1123565,"New substituted benzylamines and their salts and process for preparation",issued 1968, assigned to Soc. Ind. Fabric. Antibiot.
  6. ↑ Lintermans J, Benakis A, Ratouis R (July 1970). "Synthèse du chlorhydrate de (+)-N-(o-chlorobenzyl) α-methyl phénéthylamine marqué en position 7 par 14C (chlorhydrate de clobenzorex)". Journal of Labelled Compounds. 6 (3): 289–297. doi:10.1002/jlcr.2590060310.
  7. 1 2 3 Houck MM (2018-01-02). Forensic Toxicology. Academic Press. pp. 245, 290. ISBN   978-0-12-800818-8.
  8. ↑ Poag ME, Rubinstein M, Bernstein CA (2018-02-23). On Call Psychiatry E-Book: On Call Series. Elsevier Health Sciences. p. 304. ISBN   978-0-323-54721-5.
  9. ↑ Cody JT, Valtier S (2001-04-01). "Amphetamine, Clobenzorex, and 4-Hydroxyclobenzorex Levels Following Multidose Administration of Clobenzorex". Journal of Analytical Toxicology. 25 (3): 158–165. doi: 10.1093/jat/25.3.158 . ISSN   0146-4760. PMID   11327347.
  10. ↑ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-09-28.
  11. ↑ "Misuse of Drugs Act 1971 (c. 38): SCHEDULE 2: Controlled Drugs". Office of Public Sector Information. Retrieved 15 June 2009.
  12. ↑ Boos T (April 6, 2023). "Clobenzorex Letter". Imgur. Archived from the original on July 11, 2023. Retrieved July 11, 2023.
  13. ↑ "Is it legal for me to personally import drugs?". FDA.gov. Food and Drug Administration. 28 June 2021. Archived from the original on 2 February 2022. Retrieved 22 July 2021.
  14. ↑ "World Anti-Doping Code International Standard Prohibited List 2023" (PDF). World Anti-Doping Agency . September 2022.
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