Desoxyscaline

A desoxyscaline, also known as a desoxygenated scaline and a type of 4-substituted 3,5-dimethoxyphenethylamine, is an analogue of the phenethylamine psychedelic drug mescaline in which the methoxy group at the 4 position has been replaced with a non-alkoxy substituent (e.g., an alkyl, halo, or other substituent).^[1][2][3] They are desoxygenated analogues of the scalines like mescaline and are also positional isomers of the 2C psychedelics.^[1][2][3] Major examples of desoxyscalines include desoxymescaline ("desoxy" or 4-methylmescaline), a positional isomer of 2C-D, and desoxybromoscaline (4-bromomescaline), a positional isomer of 2C-B.^[1][2][3] 3C-Desoxyscalines, for instance 3C-DBR (4-Br-3,5-DMA), which is a positional isomer of DOB, are the amphetamine (3C) derivatives of the desoxyscalines.^[1][2][3]

In contrast to the scalines and 2Cs, the desoxyscalines and 3C-desoxyscalines have been very little-explored.^[1][2][3] Alexander Shulgin reported in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved) that desoxymescaline is active as a psychedelic drug in humans, with several-fold greater potency than mescaline, but with lighter as well as distinct hallucinogenic effects, at least at the doses tested.^[1][2] Desoxybromoscaline was also mentioned, but was not tested.^[1][2] However, its amphetamine analogue, 3C-DBR (4-Br-3,5-DMA), was found to produce unusual effects including analgesia and tactile anesthesia among others, but induced no clear hallucinogenic effects.^[1][2] These effects occurred at relatively low doses, with higher doses not being tested.^[1][2]

Other desoxyscalines and 3C-desoxyscalines besides the preceding compounds have largely not been explored.^[1][2] However, Daniel Trachsel and colleagues named many additional desoxyscalines in their 2013 book Phenethylamine: von der Struktur zur Funktion (Phenethylamines: From Structure to Function) and expressed that this structural scaffold would be an exciting area of investigation.^[1] Subsequently, Trachsel and Matthias Liechti and colleagues, in association with Mind Medicine (now Definium Therapeutics), defined more compounds of this family in a 2023 patent, and showed that many of them are potent serotonin 5-HT_2A receptor agonists with the potential for activity as psychedelic drugs.^[3] Andrew Kruegel in association with Gilgamesh Pharmaceuticals has also patented and described a few compounds of this group.^[4]