Editing 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 = <!-- Clinical data -->
| pronounce = 
| tradename = Didrex, Recede
| Drugs.com = {{drugs.com|ppa|benzphetamine}}
| MedlinePlus = 
| DailyMedID = Benzphetamine
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU_comment = 
| pregnancy_category = 
| dependency_liability = High<ref>{{cite web|url= http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+3294|title= Benzphetamine|author= <!--Staff writer(s); no by-line.-->|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}}</ref>
| addiction_liability = 
| routes_of_administration = [[Oral administration|By mouth]]
| class = 
| ATC_prefix = None
| ATC_suffix = 
| ATC_supplemental = <!-- Legal status -->
| legal_AU = S4
| legal_AU_comment = 
| legal_BR = F2
| legal_BR_comment = <ref>{{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}}</ref>
| legal_CA = Schedule I
| legal_DE = Anlage I
| legal_US = Schedule III
| legal_UK = Class C
| legal_EU = 
| legal_EU_comment = 
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment = 
| legal_status = <!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 75–99%
| metabolism = 
| metabolites = • [[Dextromethamphetamine]]<br />• [[Dextroamphetamine]]
| onset = 
| elimination_half-life = 4–6 hours<ref name="Woo2015" />
| duration_of_action = 
| excretion = <!-- Identifiers -->
| 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; (2''S'')-''N''-Benzyl-''N''-methylamphetamine; ''dextro''-''N''-Benzyl-''N''-methylamphetamine; ''N''-Benzyldextromethamphetamine; (+)-''N''-Benzyl-''N'',α-dimethylphenethylamine

<!-- Chemical data -->| IUPAC_name = (2''S'')-''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 [[anorectic|appetite suppressant]] used short-term for [[weight loss]] along with a doctor-approved, reduced-[[calorie]] [[dieting|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]].<ref name="LLC2014">{{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–}}</ref><ref>{{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 }}</ref><ref>{{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 }}</ref>

==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 [[controlled substance|scheduled]] per the [[Controlled Substances Act of 1970]].

==Contraindications==
Benzphetamine is [[contraindication|contraindicated]] in patients with advanced [[arteriosclerosis]], [[symptom|symptomatic]] [[cardiovascular disease]], moderate to severe [[hypertension]], [[hyperthyroidism]], known [[hypersensitivity]] or idiosyncrasy to [[sympathomimetic amine]]s, and [[glaucoma]], or who have recently used a [[monoamine oxidase inhibitor]] (MAOI).<ref>{{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}}</ref> Benzphetamine should not be given to patients who are in an [[psychomotor agitation|agitated]] state or who have a history of [[drug misuse]].<ref>{{cite web|url= http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+3294|title= Benzphetamine|author= <!--Staff writer(s); no by-line.-->|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}}</ref>

==Pharmacology==
Benzphetamine is a [[sympathomimetic]] [[amine]] and is classified as an [[anorectic]].<ref>{{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 }}</ref> The drug's main function is to reduce appetite, which in turn reduces caloric intake.<ref>{{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}}</ref><ref>{{Cite web |title=Benzphetamine tablets |url=https://my.clevelandclinic.org/health/drugs/19071-benzphetamine-tablets |website=Cleveland Clinic}}</ref>

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|VMAT<sub>2</sub>]] 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.<ref>{{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}}</ref><ref>{{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 }}</ref>

Benzphetamine has a [[metabolic half life|half-life]] of 4 to 6{{nbsp}}hours.<ref name="Woo2015">{{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}}</ref>

==Society and culture==
===Names===
Benzfetamine is the [[international nonproprietary name]].<ref>{{cite web | title=Benzphetamine | website=Inxight Drugs | url=https://drugs.ncats.io/substance/0M3S43XK27 | access-date=2 September 2024}}</ref>

===Legal status===
====United States====
Benzphetamine is unique in its classification as a [[Controlled Substances Act#Schedule III controlled substances|Schedule III]] substance in the United States, given that most members of the amphetamine family are classified in the more highly regulated [[Controlled Substances Act#Schedule II controlled substances|Schedule II]] tier. Benzphetamine is metabolized by the human body into [[amphetamine]] and [[methamphetamine]], making it a [[prodrug]]s 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.<ref name="pmid10711406">{{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 }}</ref> [[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}}
{{Portal bar | Medicine}}
{{Authority control}}

[[Category:Anti-obesity drugs]]
[[Category:Anorectics]]
[[Category:Benzyl compounds]]
[[Category:Norepinephrine-dopamine releasing agents]]
[[Category:Prodrugs]]
[[Category:Stimulants]]
[[Category:Substituted amphetamines]]
[[Category:Sympathomimetic amines]]
[[Category:Sympathomimetics]]