clobenzorex

{{Infobox drug

| verifiedrevid = 437142503

| IUPAC_name = N-(2-chlorobenzyl)-1-phenylpropan-2-amine

| image = Clobenzorex_structure.svg

| tradename =

| Drugs.com = {{drugs.com|international|clobenzorex}}

| pregnancy_category =

| legal_AU =

| legal_BR = F2

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}

| legal_CA = Schedule I

| legal_CA_comment =

| legal_US = Unscheduled

| legal_UK = Class B

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 13364-32-4

| ATC_prefix = A08

| ATC_suffix = AA08

| PubChem = 71675

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 64732

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4A5352XI2A

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07115

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1213251

| C = 16

| H = 18

| Cl = 1

| N = 1

| smiles = Clc1ccccc1CNC(C)Cc2ccccc2

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = LRXXRIXDSAEIOR-UHFFFAOYSA-N

| synonyms = N-(2-chlorobenzyl)amphetamine

}}

Clobenzorex is a central nervous system stimulant and anorectic drug, chemically classified as an N-substituted amphetamine and a phenethylamine. Marketed by Aventis under the trade name Asenlix in India, Mexico, Honduras, and other parts of Latin America.

A prodrug of amphetamine, clobenzorex is metabolized within hours of ingestion into 4-hydroxyclobenzorex and, in smaller amounts, amphetamine.{{cite book | vauthors = Cody JT | chapter = Amphetamines: methods of forensic analysis. | veditors = Smith F, Athanaselis SS| title = Handbook of Forensic Drug Analysis. | date = 2005 | pages = 357–451 (430) | publisher = Elsevier | chapter-url = https://books.google.com/books?id=8JsQgRO3QcwC&dq=Clobenzorex+metabolism&pg=PA430 | quote = Amphetamine produced from the metabolism of clobenzorex has been shown to be the d-enantiomer only ... | isbn = 978-0-08-047289-8 }}{{cite journal | vauthors = Young R, Darmani NA, Elder EL, Dumas D, Glennon RA | title = Clobenzorex: evidence for amphetamine-like behavioral actions | journal = Pharmacology, Biochemistry, and Behavior | volume = 56 | issue = 2 | pages = 311–316 | date = February 1997 | pmid = 9050090 | doi = 10.1016/s0091-3057(96)00329-2 | s2cid = 37062225 }}

Chemistry

=Synthesis=

File:Clobenzorex synthesis.svg

Condensation between amphetamine (1) and 2-chlorobenzaldehyde (2) gives a Schiff-base, [https://pubchem.ncbi.nlm.nih.gov/compound/135056236 CID:135056236] (3). Subsequent reduction with sodium borohydride completed the synthesis of clobenzorex (4).

= Urinalysis =

Clobenzorex can be detected by urine drug screening.{{Cite book | vauthors = Houck MM |url=https://books.google.com/books?id=icS3CgAAQBAJ&dq=Clobenzorex+urine&pg=PA290 |title=Forensic Toxicology |date=2018-01-02 |publisher=Academic Press |isbn=978-0-12-800818-8 |pages=245, 290 |language=en}} It is one of many drugs that can cause a positive result for amphetamine in urine drug screening.{{Cite book | vauthors = Poag ME, Rubinstein M, Bernstein CA |url= https://books.google.com/books?id=9vVNDwAAQBAJ&dq=Clobenzorex+urine&pg=PA304 |title=On Call Psychiatry E-Book: On Call Series |date=2018-02-23 |publisher=Elsevier Health Sciences |isbn=978-0-323-54721-5 |pages=304 |language=en}} It may be differentiated from use of amphetamine itself through testing for metabolites such as 4-hydroxyclobenzorex{{Cite journal | vauthors = Cody JT, Valtier S |date=2001-04-01 |title=Amphetamine, Clobenzorex, and 4-Hydroxyclobenzorex Levels Following Multidose Administration of Clobenzorex |journal=Journal of Analytical Toxicology |language=en |volume=25 |issue=3 |pages=158–165 |doi=10.1093/jat/25.3.158 |pmid=11327347 |issn=0146-4760|doi-access=free }} or enantiomeric analysis.

Legal Status

=Brazil=

In Brazil, clobenzorex is a controlled prohibited psychotropic (class A3).{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-09-28 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}

=Canada=

In Canada, clobenzorex is not specifically listed per the Controlled Drugs and Substances Act.{{Citation needed|date=March 2025}}

=Mexico=

In Mexico, clobenzorex is available for sale over the counter at many Mexican pharmacies under the primary brand Asenlix, as well as generic trade names like Dinintel, Finedal, Rexigen, Itravil, all of which are available via prescription in India, and OTC in Mexico and Honduras, typically used as an appetite suppressant.

=United Kingdom=

In the United Kingdom, clobenzorex is a controlled drug (class B).{{cite web |url=http://www.legislation.gov.uk/ukpga/1971/38/schedule/2 |title=Misuse of Drugs Act 1971 (c. 38): SCHEDULE 2: Controlled Drugs |publisher=Office of Public Sector Information |access-date=15 June 2009 }}

=United States=

Clobenzorex is not controlled under the Controlled Substances Act of 1970 nor is it controlled under the Federal Analogue Act, as it is a derivative of benzphetamine. {{Cite web |last=Boos |first=Terrence |date=April 6, 2023 |title=Clobenzorex Letter |url=https://imgur.io/MDUoDT4 |archive-url=https://megalodon.jp/2023-0711-1602-12/https://imgur.io:443/MDUoDT4 |archive-date=July 11, 2023 |access-date=July 11, 2023 |website=Imgur}} It is not subject to import controls and is legal to import and possess for personal medical use, provided all of the following conditions are met:{{cite web |date=28 June 2021 |title=Is it legal for me to personally import drugs? |url=https://www.fda.gov/about-fda/fda-basics/it-legal-me-personally-import-drugs |archive-url=https://web.archive.org/web/20220202183358/https://www.fda.gov/about-fda/fda-basics/it-legal-me-personally-import-drugs |archive-date=2 February 2022 |access-date=22 July 2021 |website=FDA.gov |publisher=Food and Drug Administration}}

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; and
is part of an ongoing medical treatment plan that began in a foreign country.

=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").{{Cite web |date=September 2022 |title=World Anti-Doping Code International Standard Prohibited List 2023 |url=https://www.wada-ama.org/sites/default/files/2022-09/2023list_en_final_9_september_2022.pdf |website=World Anti-Doping Agency}}