Benzphetamine

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Benzphetamine
INN: Benzfetamine
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Clinical data
Trade namesDidrex, others
Other namesBenzfetamine; d-Benzphetamine; (+)-Benzphetamine; (S)-(+)-Benzphetamine; (S)-Benzphetamine; (2S)-N-Benzyl-N-methylamphetamine; dextro-N-Benzyl-N-methylamphetamine; N-Benzyldextromethamphetamine; (+)-N-Benzyl-N,α-dimethylphenethylamine
AHFS/Drugs.comProfessional Drug Facts
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Dependence
liability		High[1]
Routes of
administration		By mouth
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  • None
Legal status
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Pharmacokinetic data
Protein binding75–99%
Metabolites• Dextromethamphetamine
• Dextroamphetamine
Elimination half-life4–6 hours[3]
Identifiers
  • (2S)-N-Benzyl-N-methyl-1-phenylpropan-2-amine
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Chemical and physical data
FormulaC17H21N
Molar mass239.362 g·mol−1
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  • N(C)(Cc1ccccc1)[C@@H](C)Cc2ccccc2
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Benzphetamine, sold under the brand name Didrex among others, is an amphetamine-type stimulant and appetite suppressant used short-term for weight loss along with a doctor-approved, reduced-calorie diet, exercise, and behavioral program. It is prescribed for obesity to people who have been unable to lose weight through exercise and dieting alone. It is a prodrug of dextromethamphetamine and dextroamphetamine.[4][5][6]

Mechanism of Action

Benzphetamine promotes weight loss by reducing appetite and slightly increasing metabolism.[citation needed] It is the parent compound of clobenzorex, the latter of which is not subject to the Federal Analogue Act, nor scheduled per the Controlled Substances Act of 1970 in the USA.

Contraindications

Benzphetamine is contraindicated in patients with advanced arteriosclerosis, symptomatic cardiovascular disease, moderate to severe hypertension, hyperthyroidism, known hypersensitivity or idiosyncrasy to sympathomimetic amines, and glaucoma, or who have recently used a monoamine oxidase inhibitor (MAOI).[7] Benzphetamine should not be given to patients who are in an agitated state or who have a history of drug misuse.[8]

Pharmacology

Benzphetamine is a sympathomimetic amine and is classified as an anorectic.[9] The drug's main function is to reduce appetite, which in turn reduces caloric intake.[10][11]

Although the mechanism of action of the sympathomimetic appetite suppressants in the treatment of obesity is not fully known, these medications have pharmacological effects similar to those of amphetamines. Amphetamine and related sympathomimetic medications (such as benzphetamine) are thought to stimulate the release of norepinephrine and/or dopamine from storage sites in nerve terminals of the lateral hypothalamic feeding center, thereby producing a decrease in appetite. This release is mediated through the binding of benzphetamine to VMAT2 and inhibiting its function, causing a release of these neurotransmitters into the synaptic cleft through their reuptake transporters. Tachyphylaxis and tolerance have been demonstrated with all drugs of this class.[12][13]

Benzphetamine has a half-life of 4 to 6 hours.[3]

Society and culture

Names

Benzfetamine is the international nonproprietary name.[14]

United States

Benzphetamine is unique in its classification as a Schedule III substance in the United States, given that most members of the amphetamine family are classified in the more highly regulated Schedule II tier. Benzphetamine is metabolized by the human body into amphetamine and methamphetamine, making it a prodrug of the aforementioned molecules, as well as one of a number of substances that convert in vivo into a substance of higher addiction and abuse potential.[15] Clobenzorex, as previously stated, is completely uncontrolled by the Controlled Substances or Federal Analogue Acts, yet is an analog and derivative of benzphetamine.

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content."Benzphetamine". Toxnet. Archived from the original on 1 November 2018.
  2. ^ Page Module:Citation/CS1/styles.css has no content.Anvisa (24 July 2023). "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 português do Brasil). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
  3. ^ a b Page Module:Citation/CS1/styles.css has no content.Woo T (3 August 2015). Pharmacotherapeutics for Advanced Practice Nurse Prescribers (4th ed.). F.A. Davis Company. p. 226. ISBN 978-0-8036-3827-3.
  4. ^ Page Module:Citation/CS1/styles.css has no content.AHC Media, LLC (17 March 2014). Pediatric Trauma Care II: A clinical reference for physicians and nurses caring for the acutely injured child. AHC Media, LLC. pp. 118–. ISBN 978-1-934863-59-6.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Cody JT, Valtier S (1998). "Detection of amphetamine and methamphetamine following administration of benzphetamine". Journal of Analytical Toxicology. 22 (4): 299–309. doi:10.1093/jat/22.4.299. PMID 9681333.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Budd RD, Jain NC (1978). "Short Communication: Metabolism and Excretion of Benzphetamine: Sources of Error in Reporting Results". Journal of Analytical Toxicology. 2 (6): 241. doi:10.1093/jat/2.6.241.
  7. ^ Page Module:Citation/CS1/styles.css has no content."DailyMed - BENZPHETAMINE HYDROCHLORIDE tablet". dailymed.nlm.nih.gov. Retrieved 22 March 2025.
  8. ^ Page Module:Citation/CS1/styles.css has no content."Benzphetamine". Toxnet. Archived from the original on 1 November 2018.
  9. ^ Page Module:Citation/CS1/styles.css has no content.Valentine JL, Middleton R (April 2000). "GC-MS identification of sympathomimetic amine drugs in urine: rapid methodology applicable for emergency clinical toxicology". Journal of Analytical Toxicology. 24 (3): 211–222. doi:10.1093/jat/24.3.211. PMID 10774541.
  10. ^ Page Module:Citation/CS1/styles.css has no content."Benzphetamine (oral route)". Mayo Clinic. Retrieved 22 March 2025.
  11. ^ Page Module:Citation/CS1/styles.css has no content."Benzphetamine tablets". Cleveland Clinic.
  12. ^ Page Module:Citation/CS1/styles.css has no content."Vesicular Monoamine Transporter 2 (VMAT2) Inhibitors", LiverTox: Clinical and Research Information on Drug-Induced Liver Injury, Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases, 2012, PMID 31643515, retrieved 22 March 2025
  13. ^ Page Module:Citation/CS1/styles.css has no content.Bernstein AI, Stout KA, Miller GW (July 2014). "The vesicular monoamine transporter 2: an underexplored pharmacological target". Neurochemistry International. 73: 89–97. doi:10.1016/j.neuint.2013.12.003. PMC 5028832. PMID 24398404.
  14. ^ Page Module:Citation/CS1/styles.css has no content."Benzphetamine". Inxight Drugs. Retrieved 2 September 2024.
  15. ^ Page Module:Citation/CS1/styles.css has no content.Musshoff F (February 2000). "Illegal or legitimate use? Precursor compounds to amphetamine and methamphetamine". Drug Metabolism Reviews. 32 (1): 15–44. doi:10.1081/DMR-100100562. PMID 10711406. S2CID 20012024.

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