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4-O-Desmethylmescaline

Pharmaceutical compound From Wikipedia, the free encyclopedia

4-O-Desmethylmescaline
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4-O-Desmethylmescaline, also known as 3,5-dimethoxy-4-hydroxyphenethylamine, 3,5-dimethoxytyramine, or DESMETHYL, is an alkaloid and drug of the phenethylamine and scaline families related to mescaline.[1][2] It is the analogue of mescaline in which the methyl ether at the 4-position hydroxyl group has been removed.[1][2]

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The compound occurs naturally in various cacti species, for instance those of the genera Lophophora, Trichocereus, Opuntia, and Stenocereus, among others.[1] It also occurs in certain Acacia species.[1] 4-O-Desmethylmescaline may be a biosynthetic precursor of mescaline in cacti and is also known to be a minor metabolite of mescaline.[1][3][4]

It is known to be pharmacologically active in cats, including producing catatonia and a hypokinetic rigid syndrome similarly to large doses of mescaline.[1][5] According to Alexander Shulgin, the effects of 4-O-desmethylmescaline in humans are unknown, and it is unclear whether it might have psychedelic effects similarly to mescaline.[1] However, according to John Raymond Smythies, 4-O-desmethylmescaline has no hallucinogenic activity, although this conclusion was based on the Winter and Flataker rope-climbing test in rats (where mescaline is active, 3,4-dimethoxyphenethylamine is 50% as active as mescaline, and 4-O-desmethylmescaline is completely inactive), rather than on tests in humans.[6][5][7][8]

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