Clobenzorex

Last updated

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 (marketed as Asenlix by Aventis; generic trade names include Dinintel, Finedal, Rexigen, and Itravil) is an N-substituted amphetamine salt, anorectic, and stimulant prodrug of dextroamphetamine. Within hours of ingestion, clobenzorex metabolizes into 4-hydroxyclobenzorex and d-amphetamine. [2] [3]

Contents

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).

Detection in urine

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 over the counter under trade names including Asenlix and Itravil. [7]

United Kingdom

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

United States

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

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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