ALMITRINE Chemical Properties

Melting point:

181°

Density 

1.2278 (estimate)

form 

Solid

Safety Information

Toxicity

LD50 ipr-mus: 390 mg/kg DRFUD4 3,717,78

ALMITRINE Usage And Synthesis

Originator

Armanor ,Les Laboratoires Servier

Uses

Respiratory stimulant.

Definition

ChEBI: A triamino-1,3,5-triazine compound having allylamino substituents at the 2- and 4-positions and a 4-(bis(p-fluorophenyl)methyl)-1-piperazinyl group at the 6-position.

Manufacturing Process

A solution of 4,6-bis(allylamino)-2-chloro-s-triazine, melting point 204°C (Kofler) and dihydrochloride of 1-p,p'-difluorobenzhydryl piperazine, melting point 178°-180°C (capillary) in anhydrous dimethylformamide are heated under reflux. On completion of this operation the solvent is removed under vacuum and the residue taken up in a mixture of chloroform and of water (1:1). The organic phase is separated, and repeatedly extracted with aqueous N-methanesulphonic acid and the aqueous acidic layers separated. The aforementioned acidic solutions are then combined and rendered alkaline (pH 10) with dilute aqueous sodium hydroxide, the base extracted with ether, the extract dried over anhydrous potassium carbonate, and filtered. The etheral filtrate, upon evaporation yields the 2,4-bis(allylamino)-6-(4-(bis(pfluorophenyl) methyl)-1-piperazinyl)-s-triazine, melting point 175°-180°C.

brand name

Vectarion (Oril S.A., France).

Therapeutic Function

Respiratory stimulant

World Health Organization (WHO)

Peripheral neuropathy has been reported in a few patients receiving almitrine for long periods. The indications for treatment have consequently been restricted in the Federal Republic of Germany. Some other countries have advised doctors to maintain patients under close supervision throughout treatment and to restrict dosage to two out of every three months.

Pharmacology

Almitrine, like doxapram, increases the rate and depth of respiration. In addition, it is believed that it redistributes pulmonary blood circulation, increasing it in alveoli, which leads to relatively better pulmonary ventilation. It has a more prolonged effect than doxapram.

Safety Profile

Poison by intraperitoneal andintravenous routes. When heated to decomposition itemits very toxic fumes of F?? and NOx.

Synthesis

Almitrine, 2,4-bis (allylamino)-6-[4-[bis-(p-fluorophenyl)methyl]-1-piperazinyl]-s-triazine (8.2.6), is synthesized by reacting 1-[bis-(p-fluorophenyl)methyl]piperazine with cyanuric chloride, which gives 2,4-dichloro-6-[4-[bis-(p-fluorophenyl) methyl]-1-piperazinyl]-s-trazine (8.2.5). Reacting this with allylamine gives almitrine (8.2.6) [19¨C22].

ALMITRINE(27469-53-0)Related Product Information

• TRIAZINONE
• almitrine-raubasine
• TRIETAZINE-ETHYLAMINO
• Melamine hydrogen flouride
• 4,4'-Difluorobenzhydrylpiperazine
• 1-(4-FLUORO-ALPHA-PHENYLBENZYL)PIPERAZINE
• (R)-1-(4-Fluorophenyl)ethylamine
• 1-(1,3,5-TRIAZIN-2-YL)PIPERAZINE
• (S)-N-METHYL-1-(4-FLUOROPHENYL)ETHYLAMINE
• ALMITRINE BISMESYLATE,ALMITRINE DIMESYLATE,ALMITRINE DIMESILATE
• 1-(4-FLUOROBENZYL)PIPERAZINE
• (R)-N-METHYL-1-(4-FLUOROPHENYL)ETHYLAMINE
• 1-[1-(4-FLUORO-PHENYL)-ETHYL]-PIPERAZINE
• ALMITRINE
• (S)-1-(4-FLUOROPHENYL)ETHYLAMINE
• (4-fluorophenyl)(phenyl)methylamine