# Substituted mescaline analogue

A substituted mescaline analogue, also known as a scaline and typically but not always a 4-substituted 3,5-dimethoxyphenethylamine, is an analogue of the phenethylamine serotonergic psychedelic mescaline (3,4,5-trimethoxyphenethylamine).
Other related compounds include the 2C (4-substituted 2,5-dimethoxyphenethylamine) and DOx (4-substituted 2,5-dimethoxyamphetamine) compounds as well as 3,4,5-trimethoxyamphetamine (TMA) and other 4-substituted 3,5-dimethoxyamphetamines (3C drugs). 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 an amphetamine rather than a phenethylamine.
The pharmacology of mescaline analogues has been studied. Mescaline analogues, or 4-substituted 3,5-dimethoxyphenethylamines specifically, tend to be much less potent than the 2C and DOx drugs. This relates to the fact that the 2,4,5-substitution pattern tends to be optimal in terms of receptor affinity and potency. However, mescaline analogues are not infrequently much more potent than mescaline.
Substituted mescaline analogues have been extensively characterized by Alexander Shulgin and described in his books such as PiHKAL (Phenethylamines I Have Known and Loved) and The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds as well as in his literature reviews. They have also been studied by David E. Nichols and Daniel Trachsel, among other researchers.

## List of substituted mescaline analogues
### 4-Substituted

* Allylescaline (AL) (4-allyloxy-3,5-dimethoxyphenethylamine)
* Amylescaline (4-n-amyloxy-3,5-dimethoxyphenethylamine)
* Benzscaline (BZ) (4-benzyloxy-3,5-dimethoxyphenethylamine)
* Biscaline (4-phenyl-3,5-dimethoxyphenethylamine)
* Buscaline (B) (4-butoxy-3,5-dimethoxyphenethylamine)
* Cyclopropylmescaline (CPM) (4-cyclopropylmethoxy-3,5-dimethoxyphenethylamine)
* Cycloproscaline (CP) (4-cyclopropoxy-3,5-dimethoxyphenethylamine)
* 4-Desmethylmescaline (DESMETHYL) (4-hydroxy-3,5-dimethoxyphenethylamine)
* 4-Desoxymescaline (4-methyl-3,5-dimethoxyphenethylamine)
* Difluoroescaline (DFE) (multiple forms)
* Difluoroisoproscaline (DFIP) (multiple forms)
* Difluoromescaline (DFM) (4-difluoromethoxy-3,5-dimethoxyphenethylamine)
* Escaline (E) (4-ethoxy-3,5-dimethoxyphenethylamine)
* Fluoroescaline (FE) (multiple forms)
* Fluoromescaline (FM) (4-fluoromethoxy-3,5-dimethoxyphenethylamine)
* Fluoroproscaline (FP) (multiple forms)
* Hexylescaline (4-n-hexyloxy-3,5-dimethoxyphenethylamine)
* Isobuscaline (IB) (4-isobutoxy-3,5-dimethoxyphenethylamine)
* Isoproscaline (IP) (4-isopropoxy-3,5-dimethoxyphenethylamine)
* Methallylescaline (MAL) (4-methylallyloxy-3,5-dimethoxyphenethylamine)
* Phenescaline (4-phenylethoxy-3,5-dimethoxyphenethylamine)
* Propynylmescaline (4-propynyloxy-3,5-dimethoxyphenethylamine)
* Proscaline (P) (4-propoxy-3,5-dimethoxyphenethylamine)
* Septylescaline (4-n-heptyloxy-3,5-dimethoxyphenethylamine)
* 4-Thiobuscaline (4-TB) (4-butylthio-3,5-dimethoxyphenethylamine)
* 4-Thioescaline (4-TE) (4-ethylthio-3,5-dimethoxyphenethylamine)
* 4-Thiomescaline (4-TM) (4-methylthio-3,5-dimethoxyphenethylamine)
* 4-Thioproscaline (4-TP) (4-propylthio-3,5-dimethoxyphenethylamine)
* Trifluoroescaline (TFE) (multiple forms)
* Trifluoromescaline (TFM) (4-trifluoromethoxy-3,5-dimethoxyphenethylamine)
* Trifluoroproscaline (TFP) (multiple forms)
* Viscaline (4-vinyl-3,5-dimethoxyphenethylamine)

### 3- or 5-Extended

* Asymbescaline (ASB) (3,4-diethoxy-5-methoxyphenethylamine)
* Metadifluoromescaline (MDFM) (3,4-dimethoxy-5-difluoromethoxyphenethylamine)
* Metaescaline (ME) (3-ethoxy-4,5-dimethoxyphenethylamine)
* Metaproscaline (MP) (3,4-dimethoxy-5-propoxyphenethylamine)
* Symbescaline (SB) (4-methoxy-3,5-diethoxyphenethylamine)
* 4-Thioasymbescaline (4-TASB) (4-ethylthio-3-ethoxy-5-methoxyphenethylamine)
* 4-Thiometaescaline (4-TME) (4-methylthio-3-ethoxy-5-methoxyphenethylamine)
* 4-Thiosymbescaline (4-TSB) (4-methylthio-3,5-diethoxyphenethylamine)
* 4-Thiotrescaline (4-T-TRIS; 4-thiotrisescaline) (4-ethylthio-3,5-diethoxyphenethylamine)
* Trescaline (TRIS; trisescaline) (3,4,5-triethoxyphenethylamine)

### 3- or 5-Replaced

* 3-Desmethylmescaline (3-DESMETHYL) (3,4-dimethoxy-5-hydroxyphenethylamine)
* 3-Thioasymbescaline (3-TASB) (3-ethylthio-4-ethoxy-5-methoxyphenethylamine)
* 5-Thioasymbescaline (5-TASB) (3,4-diethoxy-5-methylthiophenethylamine)
* 3-Thioescaline (3-TE) (3-methoxy-4-ethoxy-5-methylthiophenethylamine)
* 3-Thiomescaline (3-TM) (3,4-dimethoxy-5-methylthiophenethylamine)
* 3-Thiometaescaline (3-TME) (3-ethylthio-4,5-dimethoxyphenethylamine)
* 5-Thiometaescaline (5-TME) (3-ethoxy-4-methoxy-5-methylthiophenethylamine)
* 3-Thiosymbescaline (3-TSB) (3-ethoxy-4-methoxy-5-ethylthiophenethylamine)
* 3-Thiotrescaline (3-T-TRIS; 3-thiotrisescaline) (3,4-diethoxy-5-ethylthiophenethylamine)
* 3,4,5-Trideoxymescaline (TMePEA) (3,4,5-trimethylphenethylamine)

### 2- or 6-Substituted

* 2-Bromomescaline (2-Br-M) (2-bromo-3,4,5-trimethoxyphenethylamine)
* 2,3,4,5,6-Pentamethoxyphenethylamine (PeMPEA)
* 2,3,4,5-Tetramethoxyphenethylamine (TeMPEA; TeMPEA-1)
* 2,3,5,6-Tetramethoxyphenethylamine (TeMPEA-3)

### N-Substituted

* N-Methylmescaline (M-M) (N-methyl-3,4,5-trimethoxyphenethylamine)
* NBOMe-escaline (N-(2-methoxybenzyl)-4-ethoxy-3,5-dimethoxyphenethylamine)
* NBOMe-mescaline (N-(2-methoxybenzyl)-3,4,5-trimethoxyphenethylamine)
* Trichocereine (MM-M) (N,N-dimethylmescaline)

### α or β-substituted

* BOM (β,3,4,5-tetramethoxyphenethylamine)
* α-Ethylmescaline (AEM) (α-ethyl-3,4,5-trimethoxyphenethylamine)
* 3,4,5-Trimethoxyamphetamine (3,4,5-TMA; TMA; TMA-1; α-methylmescaline)

### Other compounds

* 3,5-Dimethoxyphenethylamine (3,5-DMPEA; 4-desmethoxymescaline)
* Flyscaline (mescaline-FLY)
* Isomescaline (IM) (2,3,4-trimethoxyphenethylamine)
* Jimscaline (1-(4,5,6-trimethoxy-2,3-dihydro-1H-inden-1-yl)methylamine)
* Lophophine (3-methoxy-4,5-methylenedioxyphenethylamine)
* 2-Thioisomescaline (2-TIM) (2-methylthio-3,4-dimethoxyphenethylamine)
* 3-Thioisomescaline (3-TIM) (3-methylthio-2,4-dimethoxyphenethylamine)
* 4-Thioisomescaline (4-TIM) (4-methylthio-2,4-dimethoxyphenethylamine)
* Tomscaline (1-(2,3,4-trimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methylamine)