phendimetrazine

Chemical Properties

Pale Yellow Oil

Originator

Plegine, Ayerst, US ,1961

Uses

An Amphetamine derivative. Controlled substance (stimulant).

Definition

ChEBI: Phendimetrazine is a member of morpholines.

Manufacturing Process

A mixture of 61 grams 1-phenyl-1-oxo-2-(N-methyl-N-ethanolamino)-propane hydrochloride and 100 cc 98-100% formic acid was refluxed at the boiling point at atmospheric pressure for 45 minutes on an oil bath. Thereafter, the oil bath temperature was increased to 180°C and as much of the excess unreacted formic acid as possible was distilled off. A vigorous evolution of carbon dioxide developed during the distillation, which ceased after approximately 45 additional minutes. The honey-yellow syrup which remained as the distillation residue was worked up by admixing it with about six volumes of water and adjusting the aqueous mixture to alkaline reaction with concentrated sodium hydroxide. An oily phase separated out which was extracted with ether. The ether extract was washed with water and dried over potassium carbonate. The solvent was distilled off and the distillation residue was fractionally distilled in vacuo. The base boils at 132°-133°C at 12 mm. The yield was 93% of theory. Reaction with tartaric acid gave the final product.
The starting material is produced by reacting propiophenone with bromine and then reacting the α-bromopropiophenone produced with 2methylaminomethanol.

brand name

Bontril (Mallinckrodt); Bontril (Valeant); Melfiat (Numark);Adipo ii;Amphasub;Anoxine-t;Arcotrol;Di-ap-trol;Dital;Dyrexan-od;Elphemet;Fringanor;Hyrex-105;Obe-del;Obesan-x;Obex la;Obex-la;Obezine;Panrexin-m;Plegline;Pt-1-5;Reducto;Reton;S 7;Sly-ll;Slyn-ll;Sprx 105;Statobex-d;Stodex;Symetra;Trimcaps;Trimstat;Trimtabs;Weighttrol.

Therapeutic Function

Antiobesity

World Health Organization (WHO)

Phendimetrazine, a sympathomimetic amine, was introduced in 1961 for use as an anorexic agent. It retains a place in the treatment of obesity. However, since it has been subject to abuse and because dependence can occur, phendimetrazine is controlled under Schedule IV of the 1971 Convention on Psychotropic Substances. (Reference: (UNCPS4) United Nations Convention on Psychotropic Substances (IV), , , 1971)