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Clobenzorex

From Wikipedia, the free encyclopedia

Pharmaceutical compound
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
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.033.108Edit 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 is acentral nervous systemstimulant andanorectic drug,chemically classified as anN-substituted amphetamine and aphenethylamine.Marketed by Aventis under thetrade nameAsenlix in India, Mexico, Honduras, and other parts ofLatin America.

Aprodrug ofamphetamine, clobenzorex is metabolized within hours of ingestion into 4-hydroxyclobenzorex and, in smaller amounts, amphetamine.[2][3]

Chemistry

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Synthesis

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

Condensation betweenamphetamine (1) and2-chlorobenzaldehyde (2) gives aSchiff-base,CID:135056236 (3). Subsequent reduction withsodium borohydride completed the synthesis of clobenzorex (4).

Urinalysis

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Clobenzorex can bedetected by urine drug screening.[7] It is one of many drugs that can cause a positive result for amphetamine in urine drug screening.[8] It may be differentiated from use of amphetamine itself through testing for metabolites such as 4-hydroxyclobenzorex[9] orenantiomeric analysis.[7]

Legal Status

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Brazil

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In Brazil, clobenzorex is acontrolled prohibited psychotropic (class A3).[10]

Canada

[edit]

In Canada, clobenzorex is not specifically listed per theControlled Drugs and Substances Act.[citation needed]

Mexico

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In Mexico, clobenzorex is available for saleover the counter at many Mexican pharmacies under the primary brandAsenlix, as well as generictrade names likeDinintel,Finedal,Rexigen,Itravil, all of which are available via prescription in India, and OTC in Mexico and Honduras, typically used as anappetite suppressant.[7]

United Kingdom

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In theUnited Kingdom, clobenzorex is acontrolled drug (class B).[11]

United States

[edit]

Clobenzorex is not controlled under theControlled Substances Act of 1970 nor is it controlled under theFederal Analogue Act, as it is a derivative ofbenzphetamine.[12] 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:[13]

  1. It is used to treat a condition with noFDA-approved medications or anorphan drug does not effectively treat a condition, and therisks of use have not been determined to outweigh to benefits of treatment;
  2. is not being deceptively and unlawfully marketed; and
  3. 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 theWorld Anti-Doping Agency foruse during sports competitions as an athletic performance enhancer ("doping").[14]

See also

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References

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  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. Retrieved2023-08-27.
  2. ^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 thed-enantiomer only ...
  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. ^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. ^abcHouck 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. ^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. Retrieved2023-09-28.
  11. ^"Misuse of Drugs Act 1971 (c. 38): SCHEDULE 2: Controlled Drugs". Office of Public Sector Information. Retrieved15 June 2009.
  12. ^Boos T (April 6, 2023)."Clobenzorex Letter".Imgur. Archived fromthe original on July 11, 2023. RetrievedJuly 11, 2023.
  13. ^"Is it legal for me to personally import drugs?".FDA.gov. Food and Drug Administration. 28 June 2021. Archived fromthe original on 2 February 2022. Retrieved22 July 2021.
  14. ^"World Anti-Doping Code International Standard Prohibited List 2023"(PDF).World Anti-Doping Agency. September 2022.
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