Phendimetrazine

Overview

Phendimetrazine, sold under the brand name Bontril among others, is a stimulant medication of the morpholine chemical class used as an appetite suppressant.[1] WP

Pharmacology

Pharmacology

Phendimetrazine functions as a prodrug of phenmetrazine; approximately 30% 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).[2] WP

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. 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.[3] WP

Indicated as a short-term secondary treatment for exogenous obesity, phendimetrazine immediate-release 35 mg tablets are typically consumed one hour before meals, not to exceed three doses daily. Phendimetrazine is also manufactured as a 105 mg 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 210 mg (6 tablets), the extended-release capsules have a maximum daily dosage of 105 mg (one capsule). WP⚠ Wikipedia itself has flagged this text: citation needed.

Legal status

Legality

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.[4] WP

Brand names

It is sold under various brand names including Bontril, Bontril PDM, Adipost, Anorex-SR, Appecon, Melfiat, Obezine, Phendiet, Plegine, Prelu-2, and Statobex.[5][6] WP

Chemistry

Formula

C12H17NO PC

CAS number

634-03-7 PC

Molar mass (g/mol)

191.27 PC

IUPAC name (computed by PubChem)

(2S,3S)-3,4-dimethyl-2-phenylmorpholine PC

SMILES

C[C@H]1[C@@H](OCCN1C)C2=CC=CC=C2 PC

InChIKey

MFOCDFTXLCYLKU-CMPLNLGQSA-N PC

PubChem CID

30487

IUPAC name

3,4-dimethyl-2-phenylmorpholine WP

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Landau D, Jackson J, Gonzalez G. A case of demand ischemia from phendimetrazine. Cases J. 2008. doi:10.1186/1757-1626-1-105 · PMID 18710555 · PMC2531092
2. Journal / agency Rothman RB, Baumann MH. Therapeutic potential of monoamine transporter substrates. Current Topics in Medicinal Chemistry. 2006. doi:10.2174/156802606778249766 · PMID 17017961
3. Journal / agency Banks ML, Blough BE, Fennell TR, Snyder RW, Negus SS. Role of phenmetrazine as an active metabolite of phendimetrazine: evidence from studies of drug discrimination and pharmacokinetics in rhesus monkeys. Drug and Alcohol Dependence. June 2013. doi:10.1016/j.drugalcdep.2012.10.026 · PMID 23211394 · PMC3616150
4. Other List of psychotropic substances under international control
5. Other Phendimetrazine Tartrate (Phendimetrazine Tartrate): Side Effects, Uses, Dosage, Interactions, Warnings
6. Other Phendimetrazine (oral route)

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.