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Phendimetrazine - Wikipedia

From Wikipedia, the free encyclopedia

Pharmaceutical drug

Pharmaceutical compound

Phendimetrazine, sold under the brand name Bontril among others, is a stimulant medication of the morpholine chemical class used as an appetite suppressant.[2]

Phendimetrazine tablets and capsules

Phendimetrazine functions as a prodrug of phenmetrazine; approximately 30 percent of an oral dose is converted into it. Phendimetrazine can essentially be thought of as an extended-release formulation of phenmetrazine with less potential for abuse. Phendimetrazine is an anorectic drug which acts as a norepinephrine-dopamine releasing agent (NDRA).[3]

As an amphetamine congener, its structure incorporates the backbone of methamphetamine, a potent CNS stimulant. While the addition of an N-methyl group to amphetamine significantly increases its potency and bioavailability, methylation of phenmetrazine renders the compound virtually inactive. However, phendimetrazine is a prodrug for phenmetrazine which acts as the active metabolite. Phendimetrazine possesses preferable pharmacokinetics over phenmetrazine as a therapeutic agent because its metabolization by demethylases produces a more steady and prolonged exposure of active drug within the body.[4] This decreases abuse potential as the peak blood-concentration of active phenmetrazine that's produced from a single dose of phendimetrazine is lower than a single therapeutically equivalent dose of phenmetrazine.

Indicated as a short-term secondary treatment for exogenous obesity, phendimetrazine immediate-release 35mg tablets are typically consumed one hour before meals, not to exceed three doses daily. Phendimetrazine is also manufactured as a 105mg extended-release capsule for once daily dosing, typically consumed 30 to 60 minutes before a morning meal. Whereas the immediate-release formulation has a maximum daily dosage of 210mg (6 tablets), the extended-release capsules have a maximum daily dosage of 105mg (one capsule).

According to the List of Psychotropic Substances under International Control published by the International Narcotics Control Board, phendimetrazine is a Schedule III controlled substance under the Convention on Psychotropic Substances.[5]

The reaction between N-methylethanolamine and 2-bromopropiophenone gives compound (3), which is reductively cyclized using formic acid to synthesize phendimetrazine.[6][7]

Society and culture[edit]

It is sold under various brand names including Bontril, Bontril PDM, Adipost, Anorex-SR, Appecon, Melfiat, Obezine, Phendiet, Plegine, Prelu-2, and Statobex.[8] [9]

  1. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  2. ^ Landau D, Jackson J, Gonzalez G (2008). "A case of demand ischemia from phendimetrazine". Cases J. 1 (1): 105. doi:10.1186/1757-1626-1-105. PMC 2531092. PMID 18710555.
  3. ^ Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates". Current Topics in Medicinal Chemistry. 6 (17): 1845–59. doi:10.2174/156802606778249766. PMID 17017961. Retrieved 5 May 2020.
  4. ^ Banks ML, Blough BE, Fennell TR, Snyder RW, Negus SS (June 2013). "Role of phenmetrazine as an active metabolite of phendimetrazine: evidence from studies of drug discrimination and pharmacokinetics in rhesus monkeys". Drug and Alcohol Dependence. 130 (1–3): 158–166. doi:10.1016/j.drugalcdep.2012.10.026. PMC 3616150. PMID 23211394.
  5. ^ "List of psychotropic substances under international control" (PDF). Archived from the original (PDF) on 31 August 2012. Retrieved 15 June 2005.
  6. ^ "Phendimetrazine". Thieme. Retrieved 30 June 2024.
  7. ^ Werner Heel and Karl Zeile, U.S. patent 2,997,469 (1961 to Ingelheim, Germany, assignors to C. H. Boehringer Sohn, Ingelheim, Germany, a partnership).
  8. ^ "Phendimetrazine Tartrate (Phendimetrazine Tartrate): Side Effects, Uses, Dosage, Interactions, Warnings". RxList. Retrieved 23 May 2025.
  9. ^ "Phendimetrazine (oral route)". Mayo Clinic. Retrieved 29 June 2025.
Stimulants Adamantanes Adenosine antagonists Alkylamines Ampakines Arylcyclohexylamines Benzazepines Cathinones Cholinergics Convulsants Eugeroics Oxazolines Phenethylamines Phenylmorpholines Piperazines Piperidines Pyrrolidines Racetams Tropanes Tryptamines Others ATC code

:

N06B Phenethylamines Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines
(and further-extended) Catecholamines
(and close relatives) Cyclized
phenethylamines Phenylalkylpyrrolidines 2-Benzylpiperidines
(phenidates) Phenylmorpholines
(phenmetrazines) Phenyloxazolamines
(aminorexes) Isoquinolines and
tetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted Related compounds

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