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).^{[1][2][3][4][5][6][7]}

Mescaline.

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).^[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 an amphetamine rather than a phenethylamine.^[1][2][3][4]

The pharmacology of mescaline analogues has been studied.^[8][9][10] Mescaline analogues, or 4-substituted 3,5-dimethoxyphenethylamines specifically, tend to be much less potent 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 of receptor affinity and potency.^[1][11] However, mescaline analogues are frequently much more potent than mescaline.^[1][3]

Substituted mescaline analogues have been extensively characterized by Alexander Shulgin and described in his books such as PiHKAL (Phenethylamines I Have Known and Loved)^[6] and The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds^[7] as well as in his literature reviews.^[1][3][4][5] They have also been studied by David E. Nichols^[12][13][14] and Daniel Trachsel,^[15][8][10] among other researchers.

Use and effects

Doses and durations of scalines

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]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

List of substituted mescaline analogues

4-Substituted

• 4-D (4-trideuteromethoxy-3,5-methoxyphenethylamine)
• 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-bromo-3,4,5-trimethoxyphenethylamine)
• 2-Chloromescaline (2-chloro-3,4,5-trimethoxyphenethylamine)^[20]
• 2,6-Dibromomescaline (2,6-dibromo-3,4,5-trimethoxyphenethylamine)^[21]
• 2,6-Dichloromescaline (2,6-dichloro-3,4,5-trimethoxyphenethylamine)^[22]
• 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

See also: 3C (psychedelics)

• 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)
• Beta-D (3,4,5-trimethoxy-β-dideuterophenethylamine; β-dideuteromescaline)
• Bromojimscaline (1-(7-bromo-4,5,6-trimethoxy-2,3-dihydro-1H-inden-1-yl)methanamine)
• Bromotomscaline (1-(5-bromo-2,3,4-trimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanamine)
• 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)

See also

• Substituted methoxyphenethylamine
• 3C (psychedelics) (4-substituted 3,5-dimethoxyamphetamines)
• PiHKAL (Phenethylamines I Have Known and Loved)
• The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds