Scaline

A scaline, also known as a substituted mescaline analogue 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 methoxy group at the 2 position instead of the 3 position of the phenyl ring, 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 frequently 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.

A closely related group is thioscalines, which are compounds in which one or more of the methoxy groups of mescaline are replaced with alkylthio groups.

Use and effects

+ Compound Chemical name Dose Duration α,α-Dideuteromescaline (α-D) 3,4,5-Trimethoxy-α,α-dideuterophenethylamine 230 mg Unknown α,β-Dideuteromescaline (α,β-D) 3,4,5-Trimethoxy-α,β-dideuterophenethylamine 250 mg Unknown 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-Difluoroisopropoxy)-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-(trifluoromethoxy)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 Propynylscaline 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 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:

+ Compound Chemical name Dose Duration 3-Thioasymbescaline (3-TASB) 3-Ethylthio-4-ethoxy-5-methoxyphenethylamine ~160 mg 10–18 hours 4-Thioasymbescaline (4-TASB) 3-Ethoxy-4-ethylthio-5-methoxyphenethylamine 60–100 mg 10–15 hours 5-Thioasymbescaline (5-TASB) 3,4-Diethoxy-5-methylthiophenethylamine ~160 mg ~8 hours 4-Thiobuscaline (4-TB) 4-Butylthio-3,5-dimethoxyphenethylamine 60–120 mg ~8 hours 3-Thioescaline (3-TE) 3-Methylthio-4-ethoxy-5-methoxyphenethylamine 60–80 mg 8–12 hours 4-Thioescaline (4-TE) 4-Ethylthio-3,5-dimethoxyphenethylamine 20–30 mg 9–12 hours 2-Thioisomescaline (2-TIM) 2-Methylthio-3,4-dimethoxyphenethylamine >240 mg Unknown 3-Thioisomescaline (3-TIM) 3-Methylthio-2,4-dimethoxyphenethylamine >240 mg Unknown 4-Thioisomescaline (4-TIM) 4-Methylthio-2,3-dimethoxyphenethylamine >240 mg Unknown 3-Thiomescaline (3-TM) 3-Methylthio-4,5-dimethoxyphenethylamine 60–100 mg 8–12 hours 4-Thiomescaline (4-TM) 4-Methylthio-3,5-dimethoxyphenethylamine 20–40 mg 10–15 hours 3-Thiometaescaline (3-TME) 3-ethylthio-4,5-dimethoxyphenethylamine 60–100 mg 10–15 hours 4-Thiometaescaline (4-TME) 3-Ethoxy-4-methylthio-5-methoxyphenethylamine 60–100 mg 10–15 hours 5-Thiometaescaline (5-TME) 3-Ethoxy-4-methoxy-5-methylthiophenethylamine >200 mg Unknown 4-Thioproscaline (4-TP) 4-Propylthio-3,5-dimethoxyphenethylamine 20–25 mg 10–15 hours 3-Thiosymbescaline (3-TSB) 3-Ethoxy-5-ethylthio-4-methoxyphenethylamine >200 mg Unknown 4-Thiosymbescaline (4-TSB) 4-Methylthio-3,5-diethoxyphenethylamine >240 mg Unknown 3-Thiotrescaline (3-T-TRIS) 3-Ethylthio-4,5-Diethoxyphenethylamine >160 mg Unknown 4-Thiotrescaline (4-T-TRIS) 4-Ethylthio-3,5-diethoxyphenethylamine >200 mg Unknown Refs:

Interactions

Pharmacology Pharmacodynamics

+ Compound 5-HT1A 5-HT1B 5-HT1D 5-HT1E 5-HT2A 5-HT2B 5-HT2C 5-HT3 5-HT5A 5-HT6 5-HT7 Mescaline – – 794 – 1,950 398 – – – – – Escaline – – 724 – – 148 1,950 – – – – Isoproscaline – – 4,790 – 2,750 263 2,510 – – – – Cyclopropylmescaline – – – – – 234 955 – – – – Allylescaline – – – 490 2,450 245 1,320 – – – – Methallylescaline – – 2,750 – 955 110 324 – – – –

Society and culture Legal status Canada Mescaline and 3,4,5-trimethoxyamphetamine (TMA) are the only scalines (and derivatives) that are controlled substances in Canada as of 2025.

List of scalines 4-Substituted 4-Alkoxy-substituted 4-Methoxyescaline (4-MeO-E; MeOEtO) (3,5-dimethoxy-4-(2-methoxyethoxy)phenethylamine) Allylescaline (AL) (4-allyloxy-3,5-dimethoxyphenethylamine) Amylescaline (4-n-amyloxy-3,5-dimethoxyphenethylamine) Benzscaline (BZ) (4-benzyloxy-3,5-dimethoxyphenethylamine) Buscaline (B) (4-butoxy-3,5-dimethoxyphenethylamine) Cyclopropylmescaline (CPM) (4-cyclopropylmethoxy-3,5-dimethoxyphenethylamine) Cycloproscaline (CP) (4-cyclopropoxy-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) Phescaline (4-phenoxy-3,5-dimethoxyphenethylamine) Propynylscaline (4-propynyloxy-3,5-dimethoxyphenethylamine) Proscaline (P) (4-propoxy-3,5-dimethoxyphenethylamine) Septylescaline (4-n-heptyloxy-3,5-dimethoxyphenethylamine) Trifluoroescaline (TFE) (multiple forms) Trifluoromescaline (TFM) (4-trifluoromethoxy-3,5-dimethoxyphenethylamine) Trifluoroproscaline (TFP) (multiple forms) Viscaline (4-vinyl-3,5-dimethoxyphenethylamine)

4-Alkylthio-substituted 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)

Others Biscaline (4-phenyl-3,5-dimethoxyphenethylamine) 4-Bromomescaline (4-Br-3,5-DMPEA) (4-bromo-3,5-dimethoxyphenethylamine) 4-Desmethylmescaline (desmethyl) (4-hydroxy-3,5-dimethoxyphenethylamine) 4-Desoxymescaline (desoxy) (4-methyl-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-Bromo-6-chloromescaline (2-bromo-6-chloro-3,4,5-trimethoxyphenethylamine) 2-Bromo-6-methylmescaline (2-bromo-6-methyl-3,4,5-trimethoxyphenethylamine) 2-Bromomescaline (2-bromo-3,4,5-trimethoxyphenethylamine) 2-Chloromescaline (2-chloro-3,4,5-trimethoxyphenethylamine) 2-Iodomescaline (2-iodo-3,4,5-trimethoxyphenethylamine) 2-Methylmescaline (2-methyl-3,4,5-trimethoxyphenethylamine) 2,6-Dibromomescaline (2,6-dibromo-3,4,5-trimethoxyphenethylamine) 2,6-Dichloromescaline (2,6-dichloro-3,4,5-trimethoxyphenethylamine) 2,6-Dimethylmescaline (2,6-dimethyl-3,4,5-trimethoxyphenethylamine) 2,3,4,5,6-Pentamethoxyphenethylamine (PeMPEA; 2,6-dimethoxymescaline) 2,3,4,5-Tetramethoxyphenethylamine (TeMPEA; TeMPEA-1; 2-methoxymescaline)

N-Substituted