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Clobenzorex

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Clobenzorex
Clinical data
Other namesN-(2-chlorobenzyl)amphetamine
AHFS/Drugs.comInternational 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 InfoCard100.033.108 Edit this at Wikidata
Chemical and physical data
FormulaC16H18ClN
Molar mass259.78 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 checkY
  • Key:LRXXRIXDSAEIOR-UHFFFAOYSA-N checkY
  (verify)

Clobenzorex (Asenlix, Dinintel, Finedal, Rexigen) is a stimulant drug of the amphetamine chemical class used as an appetite suppressant.[3] The drug is legally distributed in Mexico under the trade name Asenlix by Aventis.

Chemically, clobenzorex is an N-substituted amphetamine prodrug that is metabolized primarily into 4-hydroxyclobenzorex after ingestion; however, small amounts are also metabolized into dextroamphetamine.[4] In commercial production, clobenzorex is supplied as the hydrochloride salt in green-tinted capsules. The drug gained use as a prescription anorectic in the 1970s.

Chemistry

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Synthesis

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Thieme Synthesis:[5] Patent:[6] Radiolabelled:[7]

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).

Apparently, also made from the acid chloride, and reduction of the amide with lithium aluminium anhydride.[citation needed]

Detection in urine

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Clobenzorex can be detected in urine, which can cause false positives for workplace drug screening.[8] It is one of many drugs that can cause false positives for amphetamine urine drug screening.[9] It may be differentiated from amphetamine use through testing for metabolites such as 4-hydroxyclobenzorex[10] or enantiomeric analysis.[8]

Society and culture

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In Canada, Clobenzorex is not specifically listed in the CDSA, however due to structural similarities with norbenzphetamine, it is a schedule I under item 19(17).[citation needed]

In the UK it is a controlled drug (class B).[11] In Brazil it's a controlled prohibited psychotropic (class A3).[12]

The substance is not scheduled in the United States and is unaffected by the Federal Analogue Act as a derivative of Benzphetamine. Clobenzorex is legal in the United States of America. [13]

Clobenzorex is not controlled within the United States or subject to import controls. Importation of clobenzorex for personal use is lawful provided that is for use to treat a condition with no approved medications, unlawful marketing is not occurring in the U.S, not deemed hazardous to health for the treating the condition, and is verified as a continuation of a treatment plan that began in a foreign country.[14]

Recreational use

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The use of clobenzorex is banned by the World Anti-Doping Agency for use during sports competitions.[15]

See also

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References

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  1. ^ Boos T (April 6, 2023). "Clobenzorex Letter". Imgur. Archived from the original on July 11, 2023. Retrieved July 11, 2023.
  2. ^ 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.
  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. ^ 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 ...
  5. ^ 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.
  6. ^ GB 1123565, "New substituted benzylamines and their salts and process for preparation", issued 1968, assigned to Soc. Ind. Fabric. Antibiot. 
  7. ^ 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.
  8. ^ a b Houck MM (2018-01-02). Forensic Toxicology. Academic Press. pp. 245, 290. ISBN 978-0-12-800818-8.
  9. ^ 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.
  10. ^ 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.
  11. ^ "Misuse of Drugs Act 1971 (c. 38): SCHEDULE 2: Controlled Drugs". Office of Public Sector Information. Retrieved 15 June 2009.
  12. ^ 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.
  13. ^ Boos T (April 6, 2023). "Clobenzorex Letter". Imgur. Archived from the original on July 11, 2023. Retrieved July 11, 2023.
  14. ^ "Is it legal for me to personally import drugs?". FDA.gov. Food and Drug Administration. 28 June 2021. Retrieved 22 July 2021.
  15. ^ "World Anti-Doping Code International Standard Prohibited List 2023" (PDF). World Anti-Doping Agency. September 2022.
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