Clobenzorex
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| Other names | N-(2-chlorobenzyl)amphetamine |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Oral |
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| ECHA InfoCard | 100.033.108 |
| Chemical and physical data | |
| Formula | C16H18ClN |
| Molar mass | 259.78 g·mol−1 |
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Clobenzorex (primarily branded Asenlix) is a stimulant drug of the amphetamine chemical class in use since the 1970s as an anorectic and appetite suppressant.[2]
The drug is legally distributed in Mexico under the trade name Asenlix' (manufactured by Aventis), although generic brands exist includingDinintel, Finedal, Rexigen, and Ivotril).
Chemistry
[edit]Chemically, clobenzorex is an N-substituted amphetamine prodrug that is metabolized primarily into 4-hydroxyclobenzorex after ingestion, with small amounts also metabolized into dextroamphetamine.[3] In commercial production, clobenzorex is supplied as the hydrochloride salt in green-tinted capsules.
Synthesis
[edit]
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
[edit]Clobenzorex can be detected in urine, which can cause false positives for workplace drug screening.[7] It is one of many drugs that can cause false positives for amphetamine urine drug screening.[8] It may be differentiated from amphetamine use through testing for metabolites such as 4-hydroxyclobenzorex[9] or enantiomeric analysis.[7]
Recreational use
[edit]The use of clobenzorex is banned by the World Anti-Doping Agency for use during sports competitions.[10]
Legal Status
[edit]United States of America
[edit]Clobenzorex is legal in the United States for personal possession,[11] as it is not specifically restricted by the Controlled Substances Act of 1970, nor is it regulated as a derivative of benzphetamine under the Federal Analogue Act.
Clobenzorex is not approved for medical use by the U.S. Food and Drug Administration, and hence is neither prescribed nor available for sale over the counter or behind the counter, as is the case with sales of ephedrine and pseudoephedrine products in the U.S. since 2006.
U.S. Customs and Border Patrol does not control or limit imports of clobenzorex for personal when alternative approved treatments are unavailable; or in the case of an orphan drug, often obscure, rarely stocked, or limited in quantity, if not unavailable. Likewise, the U.S. Drug Enforcement Administration does not interfere in the personal use of clobenzorex when the medication has been prescribed or refilled by a foreign-licensed health care provider or dispensed at a non-U.S. pharmacy. [dead link][citation needed]
Canada
[edit]In Canada, clobenzorex is not specifically listed in the CDSA, however due to structural similarity with nor benzphetamine, it is schedule I under item 19(17).[citation needed]
United Kingdom
[edit]In the United Kingdom, clobenzorex is a Class B controlled drug.[12] In Brazil it's a controlled prohibited psychotropic (class A3).[13]
See also
[edit]References
[edit]- ^ 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.
- ^ 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.
- ^ 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 ...
- ^ 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.
- ^ GB 1123565, "New substituted benzylamines and their salts and process for preparation", issued 1968, assigned to Soc. Ind. Fabric. Antibiot.
- ^ 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.
- ^ a b Houck MM (2018-01-02). Forensic Toxicology. Academic Press. pp. 245, 290. ISBN 978-0-12-800818-8.
- ^ 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.
- ^ 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.
- ^ "World Anti-Doping Code International Standard Prohibited List 2023" (PDF). World Anti-Doping Agency. September 2022.
- ^ Boos T (April 6, 2023). "Clobenzorex Letter". Imgur. Archived from the original on July 11, 2023. Retrieved July 11, 2023.
- ^ "Misuse of Drugs Act 1971 (c. 38): SCHEDULE 2: Controlled Drugs". Office of Public Sector Information. Retrieved 15 June 2009.
- ^ 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.