Asubstituted mescaline analogue, also known as ascaline and typically but not always a4-substituted 3,5-dimethoxyphenethylamine, is ananalogue of thephenethylamineserotonergic psychedelicmescaline (3,4,5-trimethoxyphenethylamine).[1][2][3][4][5][6][7]
Other related compounds include the2C (4-substituted 2,5-dimethoxyphenethylamine) andDOx (4-substituted 2,5-dimethoxyamphetamine)compounds as well as3,4,5-trimethoxyamphetamine (TMA) and other4-substituted 3,5-dimethoxyamphetamines (3C drugs).[1][2][3][4] They are also mescaline analogues, but the 2C and DOx drugs have a third methoxy group in the 2 position instead of the 3 position while TMA is anamphetamine rather than a phenethylamine.[1][2][3][4]
Thepharmacology of mescaline analogues has been studied.[8][9][10] Mescaline analogues, or 4-substituted 3,5-dimethoxyphenethylamines specifically, tend to be much lesspotent than the 2C and DOx drugs.[1][3][2] This relates to the fact that the 2,4,5-substitution pattern tends to be optimal in terms ofreceptor affinity and potency.[1][11] However, mescaline analogues are frequently much more potent than mescaline.[1][3]
Substituted mescaline analogues have been extensively characterized byAlexander Shulgin and described in his books such asPiHKAL (Phenethylamines I Have Known and Loved)[6] andThe Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds[7] as well as in hisliterature reviews.[1][3][4][5] They have also been studied byDavid E. Nichols[12][13][14] andDaniel Trachsel,[15][8][10] among other researchers.
| Compound | Chemical name | Dose | Duration | |
|---|---|---|---|---|
| β,β-Dideuteromescaline (β-D) | 3,4,5-Trimethoxy-β,β-dideuterophenethylamine | 200–400 mg | 12 hours | |
| 4-Desoxymescaline (DESOXY) | 4-Methyl-3,5-dimethoxyphenethylamine | 40–120 mg | 6–8 hours | |
| 4-O-Desmethylmescaline (DESMETHYL) | 4-Hydroxy-3,5-dimethoxyphenethylamine | Unknown | Unknown | |
| 4-Trideuteromescaline (4-D) | 4-Trideuteromethoxy-3,5-dimethoxyphenethylamine | 200–400 mg | 12 hours | |
| Allylescaline (AL) | 4-Allyloxy-3,5-dimethoxyphenethylamine | 20–35 mg | 8–12 hours | |
| Asymbescaline (ASB) | 3,4-Diethoxy-5-methoxyphenethylamine | 200–280 mg | 10–15 hours | |
| Benzscaline (BZ) | 4-Benzyloxy-3,5-dimethoxyphenethylamine | Unknown | Unknown | |
| Biscaline (BI) | 4-Phenyl-3,5-dimethoxyphenethylamine | Unknown | Unknown | |
| Buscaline (B) | 4-Butoxy-3,5-dimethoxyphenethylamine | >150 mg | Several hours | |
| Cyclopropylmescaline (CPM) | 4-Cyclopropylmethoxy-3,5-dimethoxyphenethylamine | 60–80 mg | 12–18 hours | |
| Cycloproscaline (CP) | 4-Cyclopropoxy-3,5-dimethoxyphenethylamine | ≥60 mg | ≥6 hours | |
| Difluoroescaline (DFE) | 4-(2,2-Difluoroethoxy)-3,5-dimethoxyphenethylamine | 40–80 mg | 6–12 hours | |
| Difluoroisoproscaline (DFIP) | 4-(1,3-Difluoropropoxy)-3,5-dimethoxyphenethylamine | Unknown | Unknown | |
| Difluoromescaline (DFM) | 4-Difluoromethoxy-3,5-dimethoxyphenethylamine | 50–100 mg | 12–18 hours | |
| Escaline (E) | 4-Ethoxy-3,5-dimethoxyphenethylamine | 40–60 mg | 8–12 hours | |
| Fluoroescaline (FE) | 4-(2-Fluoroethoxy)-3,5-dimethoxyphenethylamine | ≥75 mg | ~6 hours | |
| Fluoroisoproscaline (FIP) | 4-(1-Fluoroisopropoxy)-3,5-dimethoxyphenethylamine | Unknown | Unknown | |
| Fluoromescaline (FM) | 4-Fluoromethoxy-3,5-dimethoxyphenethylamine | Unknown | Unknown | |
| Fluoroproscaline (FP) | 4-(3-Fluoropropoxy)-3,5-dimethoxyphenethylamine | 60–150 mg | 3–5 hours | |
| Isobuscaline (IB) | 4-Isobutoxy-3,5-dimethoxyphenethylamine | 60–100 mg | 10–14 hours | |
| Isomescaline (IM) | 2,3,4-Trimethoxyphenethylamine | >400 mg | Unknown | |
| Isoproscaline (IP) | 4-Isopropoxy-3,5-dimethoxyphenethylamine | 40–80 mg | 10–16 hours | |
| Mescaline (M) | 3,4,5-Trimethoxyphenethylamine | 200–400 (50–800) mg | 10–12 (6–14) hours | |
| Metadifluoromescaline (MDFM) | 3-(Difluoromethoxy)-4,5-dimethoxyphenylethylamine | ≥85 mg | ~8 hours | |
| Metatrifluoromescaline (MTFM) | 3,4-Dimethoxy-5-(trifluoroisopropoxy)phenethylamine | Unknown | Unknown | |
| Metaescaline (ME) | 3-Ethoxy-4,5-dimethoxyphenethylamine | 200–350 mg | 8–12 hours | |
| Metaproscaline (MP) | 3,4-Dimethoxy-5-propoxyphenethylamine | >240 mg | Unknown | |
| Methallylescaline (MAL) | 4-Methallyloxy-3,5-dimethoxyphenethylamine | 40–65 mg | 12–16 hours | |
| Phenescaline (PE) | 4-Phenethyloxy-3,5-dimethoxyphenethylamine | >150 mg | Unknown | |
| Phescaline (PH) | 4-Phenoxy-3,5-dimethoxyphenethylamine | Unknown | Unknown | |
| Propynylmescaline | 4-Propynyloxy-3,5-dimethoxyphenethylamine | ≥80 mg | 8–12 hours | |
| Proscaline (P) | 4-Propoxy-3,5-dimethoxyphenethylamine | 30–60 mg | 8–12 hours | |
| sec-Buscaline (SBU) | 4-sec-Butoxy-3,5-dimethoxyphenethylamine | Unknown | Unknown | |
| Symbescaline (SB) | 4-Methoxy-3,5-diethoxyphenethylamine | >240 mg | Unknown | |
| tert-Buscaline (TBU) | 4-tert-Butoxy-3,5-dimethoxyphenethylamine | Unknown | Unknown | |
| Thioasymbescaline (TASB) | 3-Ethoxy-4-ethylthio-5-methoxyphenethylamine | 60–100 mg | 10–15 hours | |
| Thiobuscaline (TB) | 4-Butylthio-3,5-dimethoxyphenethylamine | 60–120 mg | ~8 hours | |
| Thioescaline (TE) | 4-Ethylthio-3,5-dimethoxyphenethylamine | 20–30 mg | 9–12 hours | |
| Thioisomescaline (TIM) | 2,3-Dimethoxy-4-methylthiophenethylamine | >240 mg | Unknown | |
| Thiomescaline (TM) | 4-Methylthio-3,5-dimethoxyphenethylamine | 20–40 mg | 10–15 hours | |
| Thiometaescaline (TME) | 3-Ethoxy-4-methylthio-5-methoxyphenethylamine | 60–100 mg | 10–15 hours | |
| Thioproscaline (TP) | 4-Propylthio-3,5-dimethoxyphenethylamine | 20–25 mg | 10–15 hours | |
| Thiosymbescaline (TSB) | 4-Methylthio-3,5-diethoxyphenethylamine | >240 mg | Unknown | |
| Thiotrescaline (T-TRIS) | 4-Ethylthio-3,5-diethoxyphenethylamine | >200 mg | Unknown | |
| Trescaline (TRIS) | 3,4,5-Triethoxyphenethylamine | >240 mg | Unknown | |
| Trifluoroescaline (TFE) | 4-(2,2,2-Trifluoroethoxy)-3,5-dimethoxyphenethylamine | 35–65 mg | 12–18 hours | |
| Trifluoroisoproscaline (TFIP) | 4-(1,1,1-Trifluoroisopropoxy)-3,5-dimethoxyphenethylamine | Unknown | Unknown | |
| Trifluoromescaline (TFM) | 4-(Trifluoromethoxy)-3,5-dimethoxyphenethylamine | 15–40 mg | 14–24 hours | |
| Trifluoroproscaline (TFP) | 4-(3,3,3-Trifluoropropoxy)-3,5-dimethoxyphenethylamine | ≥60 mg | Unknown | |
| Viscaline (V) | 4-Vinyl-3,5-dimethoxyphenethylamine | Unknown | Unknown | |
| Refs:[1][3][16][7][17][18][15][19][8] | ||||
Table 4 Human potency data for selected hallucinogens. [...]