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Scaline

Class of chemical compounds

Wikipedia contributorsAdapted for Fathomly · View authors
5 min read
Source updated September 13, 2026
Image credit is listed at the end of this article.

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.

01Use and effects

Doses and durations of scalines
CompoundChemical nameDoseDuration
α,α-Dideuteromescaline (α-D)3,4,5-Trimethoxy-α,α-dideuterophenethylamine230 mgUnknown
α,β-Dideuteromescaline (α,β-D)3,4,5-Trimethoxy-α,β-dideuterophenethylamine250 mgUnknown
β,β-Dideuteromescaline (β-D)3,4,5-Trimethoxy-β,β-dideuterophenethylamine200-400 mg12 hours
4-Desoxymescaline (DESOXY)4-Methyl-3,5-dimethoxyphenethylamine40-120 mg6-8 hours
4-O-Desmethylmescaline (DESMETHYL)4-Hydroxy-3,5-dimethoxyphenethylamineUnknownUnknown
4-Trideuteromescaline (4-D)4-Trideuteromethoxy-3,5-dimethoxyphenethylamine200-400 mg12 hours
Allylescaline (AL)4-Allyloxy-3,5-dimethoxyphenethylamine20-35 mg8-12 hours
Asymbescaline (ASB)3,4-Diethoxy-5-methoxyphenethylamine200-280 mg10-15 hours
Benzscaline (BZ)4-Benzyloxy-3,5-dimethoxyphenethylamineUnknownUnknown
Biscaline (BI)4-Phenyl-3,5-dimethoxyphenethylamineUnknownUnknown
Buscaline (B)4-Butoxy-3,5-dimethoxyphenethylamine>150 mgSeveral hours
Cyclopropylmescaline (CPM)4-Cyclopropylmethoxy-3,5-dimethoxyphenethylamine60-80 mg12-18 hours
Cycloproscaline (CP)4-Cyclopropoxy-3,5-dimethoxyphenethylamine≥60 mg≥6 hours
Difluoroescaline (DFE)4-(2,2-Difluoroethoxy)-3,5-dimethoxyphenethylamine40-80 mg6-12 hours
Difluoroisoproscaline (DFIP)4-(1,3-Difluoroisopropoxy)-3,5-dimethoxyphenethylamineUnknownUnknown
Difluoromescaline (DFM)4-Difluoromethoxy-3,5-dimethoxyphenethylamine50-100 mg12-18 hours
Escaline (E)4-Ethoxy-3,5-dimethoxyphenethylamine40-60 mg8-12 hours
Fluoroescaline (FE)4-(2-Fluoroethoxy)-3,5-dimethoxyphenethylamine≥75 mg~6 hours
Fluoroisoproscaline (FIP)4-(1-Fluoroisopropoxy)-3,5-dimethoxyphenethylamineUnknownUnknown
Fluoromescaline (FM)4-Fluoromethoxy-3,5-dimethoxyphenethylamineUnknownUnknown
Fluoroproscaline (FP)4-(3-Fluoropropoxy)-3,5-dimethoxyphenethylamine60-150 mg3-5 hours
Isobuscaline (IB)4-Isobutoxy-3,5-dimethoxyphenethylamine60-100 mg10-14 hours
Isomescaline (IM)2,3,4-Trimethoxyphenethylamine>400 mgUnknown
Isoproscaline (IP)4-Isopropoxy-3,5-dimethoxyphenethylamine40-80 mg10-16 hours
Mescaline (M)3,4,5-Trimethoxyphenethylamine200-400 (50-800) mg10-12 (6-14) hours
Metadifluoromescaline (MDFM)3-(Difluoromethoxy)-4,5-dimethoxyphenylethylamine≥85 mg~8 hours
Metatrifluoromescaline (MTFM)3,4-Dimethoxy-5-(trifluoromethoxy)phenethylamineUnknownUnknown
Metaescaline (ME)3-Ethoxy-4,5-dimethoxyphenethylamine200-350 mg8-12 hours
Metaproscaline (MP)3,4-Dimethoxy-5-propoxyphenethylamine>240 mgUnknown
Methallylescaline (MAL)4-Methallyloxy-3,5-dimethoxyphenethylamine40-65 mg12-16 hours
Phenescaline (PE)4-Phenethyloxy-3,5-dimethoxyphenethylamine>150 mgUnknown
Phescaline (PH)4-Phenoxy-3,5-dimethoxyphenethylamineUnknownUnknown
Propynylscaline4-Propynyloxy-3,5-dimethoxyphenethylamine≥80 mg8-12 hours
Proscaline (P)4-Propoxy-3,5-dimethoxyphenethylamine30-60 mg8-12 hours
sec-Buscaline (SBU)4-sec-Butoxy-3,5-dimethoxyphenethylamineUnknownUnknown
Symbescaline (SB)4-Methoxy-3,5-diethoxyphenethylamine>240 mgUnknown
tert-Buscaline (TBU)4-tert-Butoxy-3,5-dimethoxyphenethylamineUnknownUnknown
Trescaline (TRIS)3,4,5-Triethoxyphenethylamine>240 mgUnknown
Trifluoroescaline (TFE)4-(2,2,2-Trifluoroethoxy)-3,5-dimethoxyphenethylamine35-65 mg12-18 hours
Trifluoroisoproscaline (TFIP)4-(1,1,1-Trifluoroisopropoxy)-3,5-dimethoxyphenethylamineUnknownUnknown
Trifluoromescaline (TFM)4-(Trifluoromethoxy)-3,5-dimethoxyphenethylamine15-40 mg14-24 hours
Trifluoroproscaline (TFP)4-(3,3,3-Trifluoropropoxy)-3,5-dimethoxyphenethylamine≥60 mgUnknown
Viscaline (V)4-Vinyl-3,5-dimethoxyphenethylamineUnknownUnknown
Refs:
Doses and durations of thioscalines
CompoundChemical nameDoseDuration
3-Thioasymbescaline (3-TASB)3-Ethylthio-4-ethoxy-5-methoxyphenethylamine~160 mg10-18 hours
4-Thioasymbescaline (4-TASB)3-Ethoxy-4-ethylthio-5-methoxyphenethylamine60-100 mg10-15 hours
5-Thioasymbescaline (5-TASB)3,4-Diethoxy-5-methylthiophenethylamine~160 mg~8 hours
4-Thiobuscaline (4-TB)4-Butylthio-3,5-dimethoxyphenethylamine60-120 mg~8 hours
3-Thioescaline (3-TE)3-Methylthio-4-ethoxy-5-methoxyphenethylamine60-80 mg8-12 hours
4-Thioescaline (4-TE)4-Ethylthio-3,5-dimethoxyphenethylamine20-30 mg9-12 hours
2-Thioisomescaline (2-TIM)2-Methylthio-3,4-dimethoxyphenethylamine>240 mgUnknown
3-Thioisomescaline (3-TIM)3-Methylthio-2,4-dimethoxyphenethylamine>240 mgUnknown
4-Thioisomescaline (4-TIM)4-Methylthio-2,3-dimethoxyphenethylamine>240 mgUnknown
3-Thiomescaline (3-TM)3-Methylthio-4,5-dimethoxyphenethylamine60-100 mg8-12 hours
4-Thiomescaline (4-TM)4-Methylthio-3,5-dimethoxyphenethylamine20-40 mg10-15 hours
3-Thiometaescaline (3-TME)3-ethylthio-4,5-dimethoxyphenethylamine60-100 mg10-15 hours
4-Thiometaescaline (4-TME)3-Ethoxy-4-methylthio-5-methoxyphenethylamine60-100 mg10-15 hours
5-Thiometaescaline (5-TME)3-Ethoxy-4-methoxy-5-methylthiophenethylamine>200 mgUnknown
4-Thioproscaline (4-TP)4-Propylthio-3,5-dimethoxyphenethylamine20-25 mg10-15 hours
3-Thiosymbescaline (3-TSB)3-Ethoxy-5-ethylthio-4-methoxyphenethylamine>200 mgUnknown
4-Thiosymbescaline (4-TSB)4-Methylthio-3,5-diethoxyphenethylamine>240 mgUnknown
3-Thiotrescaline (3-T-TRIS)3-Ethylthio-4,5-Diethoxyphenethylamine>160 mgUnknown
4-Thiotrescaline (4-T-TRIS)4-Ethylthio-3,5-diethoxyphenethylamine>200 mgUnknown
Refs:

02Pharmacology

Pharmacodynamics

Serotonin receptor affinities (Ki, nM) of selected scalines (Jain et al., 2025)
Compound5-HT1A5-HT1B5-HT1D5-HT1E5-HT2A5-HT2B5-HT2C5-HT35-HT5A5-HT65-HT7
Mescaline, , 794, 1,950398, , , , ,
Escaline, , 724, , 1481,950, , , ,
Isoproscaline, , 4,790, 2,7502632,510, , , ,
Cyclopropylmescaline, , , , , 234955, , , ,
Allylescaline, , , 4902,4502451,320, , , ,
Methallylescaline, , 2,750, 955110324, , , ,

03Society 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.

04List of scalines

4-Substituted

4-Alkoxy-substituted

4-Alkylthio-substituted

Others

3- or 5-Extended

3- or 5-Replaced

2- or 6-Substituted

N-Substituted

α- or β-Substituted

Cyclized

  • 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)
  • Hemi-flyscaline (mescaline-hemiFLY)
  • Jimscaline (1-(4,5,6-trimethoxy-2,3-dihydro-1H-inden-1-yl)methylamine)
  • Tomscaline (1-(2,3,4-trimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methylamine)
  • UCD0120-M (UCD0120-mescaline; N,N-diethyl-1-methyl-5-(3,4,5-trimethoxyphenyl)-1,2,3,6-tetrahydropyridine-3-carboxamide)

Deuterated

  • 2,6-D (2,6-dideuteromescaline; 2,6-dideutero-3,4,5-trimethoxyphenethylamine)
  • 3,5-D (3,5-di(trideutero)mescaline; 4-methoxy-3,5-di(trideuteromethoxy)phenethylamine)
  • 4-D (4-trideuteromescaline; 4-trideuteromethoxy-3,5-methoxyphenethylamine)
  • Alpha-D (α-D; 3,4,5-trimethoxy-α,α-dideuterophenethylamine; α,α-dideuteromescaline)
  • Alpha,Beta-D (α,β-D; 3,4,5-trimethoxy-α,β-dideuterophenethylamine; α,β-dideuteromescaline)
  • Beta-D (β-D; 3,4,5-trimethoxy-β,β-dideuterophenethylamine; β,β-dideuteromescaline)

Other compounds

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Sources and credits

This article is adapted from the Wikipedia article “Scaline”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.

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Related topics

Substituted methoxyphenethylamine

Methoxyphenethylamines, as well as methoxyamphetamines (MAs) in the case of the amphetamine (α-methylphenethylamine) homologues, are substituted phenethylamines with one or more methoxy groups. In some cases, one or more of the methoxy groups may also be extended to form other alkoxy and related groups such as ethoxy or propoxy.

3C (psychedelics)

3C, also known as 4-substituted 3,5-dimethoxyamphetamines, substituted 3,4,5-trimethoxyamphetamine (3,4,5-TMA or TMA-1) analogues, or 3C-scalines, is a general name for the family of psychedelic amphetamines containing methoxy groups at the 3 and 5 positions of the benzene ring. These compounds are analogues of 3,4,5-trimethoxyamphetamine (3,4,5-TMA or TMA-1).

Desoxyscaline

A desoxyscaline, also known as a desoxygenated scaline and a type of 4-substituted 3,5-dimethoxyphenethylamine, is an analogue of the phenethylamine psychedelic drug mescaline in which the methoxy group at the 4 position has been replaced with a non-alkoxy substituent. They are desoxygenated analogues of the scalines like mescaline and are also positional isomers of the 2C psychedelics.