Benzphetamine
{{Short description|Chemical compound}}
{{Global|date=March 2025}}
{{Use dmy dates|date=September 2024}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{drugbox
| Verifiedfields = verified
| verifiedrevid = 459955085
| INN = Benzfetamine
| image = Benzphetamine.svg
| width = 250px
| alt =
| image2 = Benzphetamine-MV.png
| width2 = 225px
| alt2 =
| pronounce =
| tradename = Didrex, Recede
| Drugs.com = {{drugs.com|ppa|benzphetamine}}
| MedlinePlus =
| DailyMedID = Benzphetamine
| pregnancy_AU =
| pregnancy_AU_comment =
| pregnancy_category =
| addiction_liability =
| routes_of_administration = By mouth
| class =
| ATC_prefix = None
| ATC_suffix =
| ATC_supplemental =
| legal_AU = S4
| legal_AU_comment =
| 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_DE = Anlage I
| legal_US = Schedule III
| legal_UK = Class C
| legal_EU =
| legal_EU_comment =
| legal_UN =
| legal_UN_comment =
| legal_status =
| bioavailability =
| protein_bound = 75–99%
| metabolism =
| metabolites = • Dextromethamphetamine
• Dextroamphetamine
| onset =
| elimination_half-life = 4–6 hours
| duration_of_action =
| excretion =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 156-08-1
| CAS_supplemental =
| PubChem = 5311017
| IUPHAR_ligand =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00865
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4470556
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0M3S43XK27
| KEGG = D07514
| KEGG2 = D07515
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 3044
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 3545985
| NIAID_ChemDB =
| PDB_ligand =
| synonyms = Benzfetamine; d-Benzphetamine; (+)-Benzphetamine; (S)-(+)-Benzphetamine; (S)-Benzphetamine; (2S)-N-Benzyl-N-methylamphetamine; dextro-N-Benzyl-N-methylamphetamine; N-Benzyldextromethamphetamine; (+)-N-Benzyl-N,α-dimethylphenethylamine
| IUPAC_name = (2S)-N-Benzyl-N-methyl-1-phenylpropan-2-amine
| C = 17
| H = 21
| N = 1
| SMILES = N(C)(Cc1ccccc1)[C@@H](C)Cc2ccccc2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YXKTVDFXDRQTKV-HNNXBMFYSA-N
}}
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.{{cite book|author=AHC Media, LLC|title=Pediatric Trauma Care II: A clinical reference for physicians and nurses caring for the acutely injured child|url=https://books.google.com/books?id=9fucAwAAQBAJ&pg=PA118|date=17 March 2014|publisher=AHC Media, LLC|isbn=978-1-934863-59-6|pages=118–}}{{cite journal | vauthors = Cody JT, Valtier S | title = Detection of amphetamine and methamphetamine following administration of benzphetamine | journal = Journal of Analytical Toxicology | volume = 22 | issue = 4 | pages = 299–309 | year = 1998 | pmid = 9681333 | doi = 10.1093/jat/22.4.299 | doi-access = free }}{{cite journal | vauthors = Budd RD, Jain NC | doi = 10.1093/jat/2.6.241| title = Short Communication: Metabolism and Excretion of Benzphetamine: Sources of Error in Reporting Results| journal = Journal of Analytical Toxicology| volume = 2| issue = 6| pages = 241| year = 1978 }}
Mechanism of Action
Benzphetamine promotes weight loss by reducing appetite and slightly increasing metabolism.{{Citation needed|date=September 2024}} 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.
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).{{Cite web |title=DailyMed - BENZPHETAMINE HYDROCHLORIDE tablet |url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=14d4589d-7f1c-4b6e-9557-59dad39b0960&audience=consumer |access-date=2025-03-22 |website=dailymed.nlm.nih.gov}} Benzphetamine should not be given to patients who are in an agitated state or who have a history of drug misuse.{{cite web|url= http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+3294|title= Benzphetamine|author= |website= Toxnet|archive-url= https://web.archive.org/web/20181101101226/https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+3294|archive-date= 2018-11-01|url-status= dead}}
Pharmacology
Benzphetamine is a sympathomimetic amine and is classified as an anorectic.{{cite journal | vauthors = Valentine JL, Middleton R | title = GC-MS identification of sympathomimetic amine drugs in urine: rapid methodology applicable for emergency clinical toxicology | journal = Journal of Analytical Toxicology | volume = 24 | issue = 3 | pages = 211–222 | date = April 2000 | pmid = 10774541 | doi = 10.1093/jat/24.3.211 }} The drug's main function is to reduce appetite, which in turn reduces caloric intake.{{Cite web |title=Benzphetamine (oral route) |url=https://www.mayoclinic.org/drugs-supplements/benzphetamine-oral-route/description/drg-20070952 |access-date=2025-03-22 |website=Mayo Clinic |language=en}}{{Cite web |title=Benzphetamine tablets |url=https://my.clevelandclinic.org/health/drugs/19071-benzphetamine-tablets |website=Cleveland Clinic}}
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.{{Citation |title=Vesicular Monoamine Transporter 2 (VMAT2) Inhibitors |date=2012 |work=LiverTox: Clinical and Research Information on Drug-Induced Liver Injury |url=https://www.ncbi.nlm.nih.gov/books/NBK548187/ |access-date=2025-03-22 |place=Bethesda (MD) |publisher=National Institute of Diabetes and Digestive and Kidney Diseases |pmid=31643515}}{{cite journal | vauthors = Bernstein AI, Stout KA, Miller GW | title = The vesicular monoamine transporter 2: an underexplored pharmacological target | journal = Neurochemistry International | volume = 73 | pages = 89–97 | date = July 2014 | pmid = 24398404 | pmc = 5028832 | doi = 10.1016/j.neuint.2013.12.003 }}
Benzphetamine has a half-life of 4 to 6{{nbsp}}hours.{{cite book | vauthors = Woo T |date= 2015-08-03|title= Pharmacotherapeutics for Advanced Practice Nurse Prescribers | edition = 4th |page= 226|publisher= F.A. Davis Company |isbn=978-0-8036-3827-3}}
Society and culture
=Names=
=Legal status=
==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 prodrugs the aforementioned molcecules, as well as one of a number of substances that convert in vivo conversion into a substance of higher addiction and abuse potential.{{cite journal | vauthors = Musshoff F | title = Illegal or legitimate use? Precursor compounds to amphetamine and methamphetamine | journal = Drug Metabolism Reviews | volume = 32 | issue = 1 | pages = 15–44 | date = February 2000 | pmid = 10711406 | doi = 10.1081/DMR-100100562 | s2cid = 20012024 }} Clobenzorex, as previously stated, is completely uncontrolled by the Controlled Substances or Federal Analogue Acts, yet is an analog and derivative of benzphetamine.
References
{{Reflist}}
{{Antiobesity preparations}}
{{Monoamine releasing agents}}
{{Phenethylamines}}
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Category:Norepinephrine-dopamine releasing agents
Category:Substituted amphetamines