3C (3C-x), also known as4-substituted 3,5-dimethoxyamphetamines,substituted 3,4,5-trimethoxyamphetamine (3,4,5-TMA or TMA-1) analogues, or3C-scalines, is a general name for the family ofpsychedelicamphetamines containingmethoxy groups at the 3 and 5positions of thebenzene ring.[1][2] Thesecompounds areanalogues of3,4,5-trimethoxyamphetamine (3,4,5-TMA or TMA-1).[1][2]
The 3C drugs are not the amphetamine counterparts of the2C drugs, which are 4-substituted 2,5-dimethoxyphenethylamines.[1][2] Instead, theDOx drugs, which are 4-substituted 2,5-dimethoxyamphetamines, are the amphetamine counterparts of the 2C drugs.[1][2] The 3C drugs are the amphetamine counterparts ofsubstituted mescaline analogues (4-substituted 3,5-dimethoxyphenethylamines).[1][2] Moreover, in terms of naming with the "3C" prefix, the 3C drugs are generally actuallyderivatives of TMA-1 with the 4-positionmethoxy group extended rather than having any 4-positionsubstituent.[1][2] In this regard, they would be the 3,5-dimethoxyamphetamine counterparts of the2C-O (2,4,5-trimethoxyphenethylamine) drugs (e.g.,2C-O-4) and the2,4,5-trimethoxyamphetamine (2,4,5-TMA; TMA-2) derivatives (e.g.,MEM).[3][4]
3C drugs have been developed and/or studied byAlexander Shulgin[1][2] andDaniel Trachsel,[5][6][4][7] among others.[8][9] Thepharmacology of 3C drugs has been studied and described.[7][8]
| Compound | Chemical name | Dose | Duration | |
|---|---|---|---|---|
| TMA (3C-M) | 3,4,5-Trimethoxyamphetamine | 100–250 mg | 6–8 hours | |
| 3C-AL | 4-Allyloxy-3,5-dimethoxyamphetamine | 15–30 mg | 8–12 hours | |
| 3C-BZ | 4-Benzyloxy-3,5-dimethoxyamphetamine | 25–200 mg | 18–24 hours | |
| 3C-CPM | 4-Cyclopropylmethoxy-3,5-dimethoxyamphetamine | Unknown | Unknown | |
| 3C-DFE | 4-(2,2-Difluoroethoxy)-3,5-dimethoxyamphetamine | 22 mg | ~10 hours | |
| 3C-DFM | 4-(2,2-Difluoromethoxy)-3,5-dimethoxyamphetamine | Unknown | Unknown | |
| 3C-E | 4-Ethoxy-3,5-dimethoxyamphetamine | 30–60 mg | 8–12 hours | |
| 3C-FE | 4-(2-Fluoroethoxy)-3,5-dimethoxyamphetamine | >24 mg | Unknown | |
| 3C-FP | 4-(3-Fluoropropoxy)-3,5-dimethoxyamphetamine | ≥25 mg | ~8 hours | |
| 3C-IB | 4-Isobutoxy-3,5-dimethoxyamphetamine | Unknown | Unknown | |
| 3C-IP | 4-Isopropoxy-3,5-dimethoxyamphetamine | Unknown | Unknown | |
| 3C-MAL | 4-Methallyloxy-3,5-dimethoxyamphetamine | Unknown | Unknown | |
| 3C-P | 4-Propoxy-3,5-dimethoxyamphetamine | 20–40 mg | Unknown | |
| 3C-TFE | 4-(2,2,2-Trifluoroethoxy)-3,5-dimethoxyamphetamine | 30 mg | ~15 hours | |
| Refs:[10][2][1][11][4][5][7] | ||||
Table 4 Human potency data for selected hallucinogens. [...]