Clobenzorex

Clobenzorex (Asenlix, Dinintel, Finedal, Rexigen) is a stimulant drug of the amphetamine chemical class used as an appetite suppressant.^[2] The drug is legally distributed in Mexico under the trade name Asenlix by Aventis.

Clobenzorex

Clinical data
Other names	N-(2-chlorobenzyl)amphetamine
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	A08AA08 (WHO)
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] CA: Schedule I UK: Class B US: Unscheduled
Identifiers
IUPAC name N-(2-chlorobenzyl)-1-phenylpropan-2-amine
CAS Number	13364-32-4 Y
PubChem CID	71675
ChemSpider	64732 Y
UNII	4A5352XI2A
KEGG	D07115 Y
ChEMBL	ChEMBL1213251 Y
CompTox Dashboard (EPA)	DTXSID7048409
ECHA InfoCard	100.033.108
Chemical and physical data
Formula	C16H18ClN
Molar mass	259.78 g·mol−1
3D model (JSmol)	Interactive image
SMILES Clc1ccccc1CNC(C)Cc2ccccc2
InChI 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 Y Key:LRXXRIXDSAEIOR-UHFFFAOYSA-N Y
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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.^[3] 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

Synthesis

Thieme Synthesis:^[4] Patent:^[5] Radiolabelled:^[6]

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

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]

Society and culture

Legal status

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).^[10] In Brazil it's a controlled prohibited psychotropic (class A3).^[11]

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. ^[12]

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.^[13]

Recreational use

The use of clobenzorex is banned by the World Anti-Doping Agency for use during sports competitions.^[14]

See also

• Benzphetamine
• MDBZ
• N-Benzyl-2C-B

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. 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.
3. 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 ...
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. 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. "Misuse of Drugs Act 1971 (c. 38): SCHEDULE 2: Controlled Drugs". Office of Public Sector Information. Retrieved 15 June 2009.
11. 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.
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. Retrieved 22 July 2021.
14. "World Anti-Doping Code International Standard Prohibited List 2023" (PDF). World Anti-Doping Agency. September 2022.