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Benzphetamine

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Chemical compound
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Pharmaceutical compound
Benzphetamine
INN: Benzfetamine
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
License data
Dependence
liability
High[1]
Routes of
administration
By mouth
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Protein binding75–99%
MetabolitesDextromethamphetamine
Dextroamphetamine
Eliminationhalf-life4–6 hours[3]
Identifiers
  • (2S)-N-Benzyl-N-methyl-1-phenylpropan-2-amine
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC17H21N
Molar mass239.362 g·mol−1
3D model (JSmol)
  • N(C)(Cc1ccccc1)[C@@H](C)Cc2ccccc2
  • InChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1 checkY
  • Key:YXKTVDFXDRQTKV-HNNXBMFYSA-N checkY
  (verify)

Benzphetamine, sold under the brand nameDidrex among others, is anamphetamine-type stimulant andappetite suppressant used short-term forweight loss along with a doctor-approved, reduced-caloriediet,exercise, and behavioral program. It is prescribed forobesity to people who have been unable to lose weight through exercise and dieting alone. It is aprodrug ofdextromethamphetamine anddextroamphetamine.[4][5][6]

Mechanism of Action

[edit]

Benzphetamine promotes weight loss by reducing appetite and slightly increasingmetabolism.[citation needed] It is the parent compound ofclobenzorex, the latter of which is not subject to theFederal Analogue Act, norscheduled per theControlled Substances Act of 1970.

Contraindications

[edit]

Benzphetamine iscontraindicated in patients with advancedarteriosclerosis,symptomaticcardiovascular disease, moderate to severehypertension,hyperthyroidism, knownhypersensitivity or idiosyncrasy tosympathomimetic amines, andglaucoma, or who have recently used amonoamine oxidase inhibitor (MAOI).[7] Benzphetamine should not be given to patients who are in anagitated state or who have a history ofdrug misuse.[8]

Pharmacology

[edit]

Benzphetamine is asympathomimeticamine and is classified as ananorectic.[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 ofnorepinephrine and/ordopamine 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 toVMAT2 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 ahalf-life of 4 to 6 hours.[3]

Society and culture

[edit]

Names

[edit]

Benzfetamine is theinternational nonproprietary name.[14]

Legal status

[edit]

United States

[edit]

Benzphetamine is unique in its classification as aSchedule III substance in the United States, given that most members of the amphetamine family are classified in the more highly regulatedSchedule II tier. Benzphetamine is metabolized by the human body intoamphetamine andmethamphetamine, making it aprodrugs the aforementioned molcecules, as well as one of a number of substances that convertin vivo conversion 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

[edit]
  1. ^"Benzphetamine".Toxnet.Archived from the original on 1 November 2018.
  2. ^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 Brazilian Portuguese).Diário Oficial da União (published 25 July 2023).Archived from the original on 27 August 2023. Retrieved27 August 2023.
  3. ^abWoo 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. ^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. ^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. ^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. ^"DailyMed - BENZPHETAMINE HYDROCHLORIDE tablet".dailymed.nlm.nih.gov. Retrieved22 March 2025.
  8. ^"Benzphetamine".Toxnet.Archived from the original on 1 November 2018.
  9. ^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. ^"Benzphetamine (oral route)".Mayo Clinic. Retrieved22 March 2025.
  11. ^"Benzphetamine tablets".Cleveland Clinic.
  12. ^"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, retrieved22 March 2025
  13. ^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. ^"Benzphetamine".Inxight Drugs. Retrieved2 September 2024.
  15. ^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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