Trazium
Chemical compound
Trazium (EGYT-3,615) is an antidepressant drug which was never marketed. It has psychostimulant-like effects and its actions appear to be mediated by the dopaminergic and adrenergic systems. It was formulated as a salt with ethanesulfonic acid and given the generic name trazium esilate (INN).
01Synthesis
Precursors: Background literature:
Ex 5: The Grignard reaction between para-chlorophenylmagnesium bromide and 1-cyanoisoquinoline [1198-30-7] (1) gave 1-(4-chlorobenzoyl)isoquinoline, PC12243105 (2). The reaction of this with O-tosylhydroxylamine [52913-14-1] gives (2-aminoisoquinolin-2-ium-1-yl)-(4-chlorophenyl)methanone;4-methylbenzenesulfonate, PC23311140 (3). The reaction of this a mixture of formamide and phosphoryl chloride gave the ring. The addition of perchloric acid led to 1-(4-Chlorophenyl)[1,2,4]triazino[6,1-a]isoquinolin-5-ium perchlorate [82319-70-8] (4). The reaction of this with triethylammonium bromide is said to give (4).
Patent:
Ex 1: 1-(4-chlorophenyl)-as-triazino[6,1-a]isoquinolinium-bromide [82319-85-5] (1) is reacted with an aqueous solution of acetonitrile to give the title compound. Ex 2: Treatment with ethanesulfonic acid in acetonitrile then prepares the esilate salt.
Sources and credits
This article is adapted from the Wikipedia article “Trazium”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Trazium.png by Chemgirl131 at en.wikipedia, Public domain
- Trazium precursor patent.svg by Mo18ekula, CC0
- Trazium synthesis.svg by Mo18ekula, CC0
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