Clobenzorex
 | |
| Clinical data | |
|---|---|
| Other names | N-(2-chlorobenzyl)amphetamine |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Oral |
| ATC code | |
| Legal status | |
| Legal status |
|
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.033.108 |
| Chemical and physical data | |
| Formula | C16H18ClN |
| Molar mass | 259.78 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (verify) | |
Clobenzorex is an N-substituted amphetamine hydrochloride salt marketed as Asenlix by drug manufacturer Aventis in Mexico, in addition to other trade names. The substance has been used increasingly since the 1970s as an appetite suppressant and stimulant, and is a minor prodrug of dextroamphetamine; clobenzorex primarily metabolizes upon ingestion into into 4-hydroxyclobenzorex, while small amounts convert into d-amphetamine within hours.[2][3]
Chemistry
[edit]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]
Legal Status
[edit]Brazil
[edit]In Brazil, clobenzorex is a controlled prohibited psychotropic (class A3).[10]
Canada
[edit]In Canada, clobenzorex is not specifically listed per the Controlled Drugs and Substances Act.[citation needed]
Mexico
[edit]In Mexico, clobenzorex is available over the counter under trade names including Asenlix, Dinintel, Finedal, Rexigen, and Itravil. [7]
United Kingdom
[edit]In the United Kingdom, clobenzorex is a controlled drug (class B).[11]
United States
[edit]Clobenzorex is neither scheduled under the Controlled Substances Act of 1970 nor classified as a benzphetamine derivative by the Federal Analogue Act,[12] and is not subject to import controls, effectively making it legal to import and possess for personal use insofar as the following criteria is met:[13]
- 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
- is not being deceptively and unlawfully marketed
- is part of an ongoing medical treatment plan that began in a foreign country
World Anti-Doping Agency
[edit]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
[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.
- ^ 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 ...
- ^ 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.
- ^ 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 c 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.
- ^ 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.
- ^ "Misuse of Drugs Act 1971 (c. 38): SCHEDULE 2: Controlled Drugs". Office of Public Sector Information. Retrieved 15 June 2009.
- ^ Boos T (April 6, 2023). "Clobenzorex Letter". Imgur. Archived from the original on July 11, 2023. Retrieved July 11, 2023.
- ^ "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.
- ^ "World Anti-Doping Code International Standard Prohibited List 2023" (PDF). World Anti-Doping Agency. September 2022.