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Benzphetamine

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Benzphetamine
INN: Benzfetamine
Clinical data
Trade namesDidrex, Recede
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
Elimination half-life4–6 hours[3]
Identifiers
  • (2S)-N-Benzyl-N-methyl-1-phenylpropan-2-amine
CAS Number
PubChem CID
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 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]

It primarily promotes weight loss through reduced appetite, but also slightly increases metabolism.[citation needed]

Contraindications

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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). Benzphetamine should not be given to patients who are in an agitated state or who have a history of drug misuse.[7]

Pharmacology

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Benzphetamine is a sympathomimetic amine and is classified as an anorectic.[8] The drug's main function is to reduce appetite, which in turn reduces caloric intake.[medical citation needed]

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.[medical citation needed]

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

Society and culture

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Names

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Benzfetamine is the international nonproprietary name.[9]

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Benzphetamine is unique in its classification as a Schedule III drug in the United States. (Most members of the amphetamine family are classified in the more highly regulated Schedule II.) Benzphetamine is metabolized by the human body into amphetamine and methamphetamine, making it one of a number of drugs to undergo in vivo conversion to a substance of higher addiction and abuse potential.[10]

References

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  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. Retrieved 27 August 2023.
  3. ^ a b Woo T (3 August 2015). Pharmacotherapeutics for Advanced Practice Nurse Prescribers, 4th Edition. F.A. Davis Company. p. 226. ISBN 978-0-8036-3827-3.{{cite book}}: CS1 maint: overridden setting (link)
  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. ^ "Benzphetamine". Toxnet. Archived from the original on 1 November 2018.
  8. ^ 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.
  9. ^ "Benzphetamine". Inxight Drugs. Retrieved 2 September 2024.
  10. ^ 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.