Nhcho

aCH3 CH3 CH3

Currently, mecamylamine is the only ganglioblocker used for general hypertension; however, the need has declined because of the possibility of addiction and the introduction of many other antihypertensive drugs into medical practice. Synonyms of this drug are meva-sine, inversine, and others.

Trimethaphan: Trimethaphan, D-3,4-(1,3-dibenzyl-2-oxoimidazolidino)-1,2-trimethylen-thiophanium D-camphorsulfonate (14.2.12), is an intermediate product of biotin (vitamin H) synthesis. It is synthesized from fumaric acid, the bromination of which leads to meso-dibromosuccinic acid (14.2.3). Reacting this with benzylamine gives 2,3-to-(ben-zylamino)succinic acid (14.2.4), which when treated with phosgene gives 1,3-dibenzyl-2-oxoimidazolidin-4,5-dicarboxylic acid (14.2.5). Dehydration of this product produces the corresponding imidazoline derivative of succinic acid (14.2.6). Reduction of this using zinc in acetic acid and subsequent treatment with hydrogen sulfide gives 1,3-dibenzyl-2,5-dioxotetrahydrothieno[3,4]imidazoline (14.2.7), which is reacted with 3-ethoxypropyl-magnesiumbromide. The resulting carbinol (14.2.8) undergoes acidic dehydration to (14.2.9) and is further reduced (having formed a double bond) by hydrogen using Raney nickel as a catalyst. Cleavage of the ester bond in the resulting product (14.2.10) with the help of hydrogen bromide in acetic acid gives 3,4-(1,3-dibenzyl-2-oxoimidazolidino)-1,2-trimethylenthiophanium bromide (14.2.11), the treatment of which with silver D-cam-phorsulfonate gives trimethaphan (14.2.12) [34-38].

H COOH C=C HOOC H

Br Br C6H5-CH2-NHNH-CH2-C6H5 Br2 I I C6H5-CH2-NH2 I I COCI2 -H—C—C—H -H—C—C—H -»

II II

HOOC COOH HOOC COOH

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