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-HT2A 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]
List of desoxyscalines
[edit]Phenethylamines (desoxyscalines)
[edit]- Desoxymescaline (D; DESOXY; 4-methylmescaline; 4-methyl-3,5-dimethoxyphenethylamine)
- Desoxyescaline (DE; 4-ethylmescaline; 4-ethyl-3,5-dimethoxyphenethylamine)
- Desoxyproscaline (DP; 4-propylmescaline; 4-propyl-3,5-dimethoxyphenethylamine)
- Desoxyisoproscaline (DIP; 4-isopropylmescaline; 4-isopropyl-3,5-dimethoxyphenethylamine)
- Desoxyallylescaline (DAL; 4-allylmescaline; 4-allyl-3,5-dimethoxyphenethylamine)
- Desoxymethallylescaline (DMAL; 4-methallylmescaline; 4-methallyl-3,5-dimethoxyphenethylamine)
- Desoxyvinylscaline (DV; 4-vinylmescaline; 4-vinyl-3,5-dimethoxyphenethylamine)
- Desoxyethynylscaline (DYN; 4-ethynylmescaline; 4-ethynyl-3,5-dimethoxyphenethylamine)
- Desoxybromoscaline (DBR; 4-bromomescaline; 4-bromo-3,5-dimethoxyphenethylamine)
- Desoxydifluorovinylscaline (DDFV; 4-(2,2-difluorovinyl)mescaline; 4-(2,2-difluorovinyl)-3,5-dimethoxyphenethylamine)
- Desoxytrifluoromescaline (DTFM; 4-(trifluoromethyl)mescaline; 4-(trifluoromethyl)-3,5-dimethoxyphenethylamine)
- Desoxytrifluoroescaline (DTFE; 4-(2,2,2-trifluoroethyl)mescaline; 4-(2,2,2-trifluoroethyl)-3,5-dimethoxyphenethylamine)
- Desoxydimethylvinylscaline (DDMV; 4-(2,2-dimethylvinyl)mescaline; 4-(2,2-dimethylvinyl)-3,5-dimethoxyphenethylamine)
- Desoxybutadienylscaline (DBD; 4-(buta-1,3-dienyl)mescaline; 4-(buta-1,3-dienyl)-3,5-dimethoxyphenethylamine)
- Biscaline (4-phenylmescaline; 4-phenyl-3,5-dimethoxyphenethylamine)
Desoxymescaline (D)
Desoxyescaline (DE)
Desoxyproscaline (DP)
Desoxyisoproscaline (DIP)
Desoxyallylescaline (DAL)
Desoxymethallylescaline (DMAL)
Desoxyvinylscaline (DV)
Desoxyethynylscaline (DYN)
Desoxybromoscaline (DBR)
Desoxydifluorovinylscaline (DDFV)
Desoxytrifluoromescaline (DTFM)
Desoxytrifluoroescaline (DTFE)
Desoxydimethylvinylscaline (DDMV)
E-Desoxybutadienylscaline (E-DBD)
Z-Desoxybutadienylscaline (Z-DBD)
Amphetamines (3C-desoxyscalines)
[edit]- 3C-D (3C-desoxymescaline; 4-methyl-3,5-dimethoxyamphetamine)
- 3C-DE (3C-desoxyescaline; 4-ethyl-3,5-dimethoxyamphetamine)
- 3C-DP (3C-desoxyproscaline; 4-propyl-3,5-dimethoxyamphetamine)
- 3C-DAL (3C-desoxyallylescaline; 4-allyl-3,5-dimethoxyamphetamine)
- 3C-DV (3C-desoxyvinylscaline; 4-vinyl-3,5-dimethoxyamphetamine)
- 3C-DBR (3C-desoxybromoscaline; 4-bromo-3,5-dimethoxyamphetamine)
- 4-I-3,5-DMA (3C-desoxyiodoscaline; 4-iodo-3,5-dimethoxyamphetamine)
- 3C-DDFV (3C-desoxydifluorovinylscaline; 4-(2,2-difluorovinyl)-3,5-dimethoxyamphetamine)
- 3C-DTFE (3C-desoxytrifluoroescaline; 4-(2,2,2-trifluoroethyl)-3,5-dimethoxyamphetamine)
- 3C-DDMV (3C-desoxydimethylvinylscaline; 4-(2,2-dimethylvinyl)-3,5-dimethoxyamphetamine)
- 3C-DBD (3C-desoxybutadienylscaline; 4-(buta-1,3-dienyl)-3,5-dimethoxyamphetamine)
- 3C-DPV (3C-desoxyphenylvinylscaline; 4-(2-phenylvinyl)-3,5-dimethoxyamphetamine)
- 4-PhPr-3,5-DMA (4-(3-phenylpropyl)-3,5-dimethoxyamphetamine)
References
[edit]- 1 2 3 4 5 6 7 8 9 10 11 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 740–744. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
[Translated:] Compounds 154-155 contain a halogen atom instead of the 4-alkyloxy group found in many known mescaline analogues. 4-BR (154) was tested by Nichols and Dyer for the correlation between lipophilicity and 5-HT agonist activity [103]. The 3C analogue 4-BR-3,5-DMA (155) was described by Shulgin for its activity in humans [19]; at a dose of 4-10 mg, no significant effects were observed (a certain, undefined effect was present for 8-12 h), but there were indications of analgesic effects. However, these could not be confirmed in an animal study [19]. [...] Shulgin investigated the effects of desoxymescaline (DESOXY; 164) in humans [19]. He mentions a dosage of 40-120 mg and a duration of action of 6-8 hours. The psychedelic color display of mescaline (1) does not appear to be present; however, the imagery induced by music with closed eyes was clearly evident. The initial results from DESOXY (164) suggest that further interesting substances of this type are possible. What would other homo-scalines without the oxygen in the 4-position show in vitro and in vivo? The substance desoxyescalin (DE; 166) is, at least sterically speaking, closer to mescaline (1) than DESOXY (164). Many other potentially interesting deoxy compounds are conceivable, such as 167-174, and it would be quite exciting to have the in vitro and in vivo data at hand to learn more about the properties of the 3,4,5-trisubstituted phenylalkylamines. Here, too, 3C analogs would be conceivable, a currently completely unexplored class. What would happen if one of the two MeO groups in DESOXY (164) or in 166-174 were replaced by an EtO, MeS, or EtS substituent? This results in countless theoretical combinations!
- 1 2 3 4 5 6 7 8 9 10 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
- 1 2 3 4 5 6 7 US patent 20230285327, Daniel Trachsel; Matthias Emanuel Liechti & Felix Lustenberger, "Desoxyscaline derivatives with modified mescaline-like action", published 14 September 2023, assigned to Mind Medicine, Inc. Data table
- ↑ WO 2022/192781, Kruegel AC, "Phenalkylamines and methods of making and using the same", published 15 September 2022, assigned to Gilgamesh Pharmaceuticals, Inc.
