Scaline

Class of chemical compounds From Wikipedia, the free encyclopedia

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).[1][2][3][4][5][6][7]

Mescaline, the most well-known scaline psychedelic.

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 methoxy group at the 2 position instead of the 3 position of the phenyl ring, 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.

A closely related group is thioscalines, which are scalines in which one or more of the alkoxy groups are replaced with alkylthio groups.[16][1][3][7][15]

Use and effects

More information Compound, Chemical name ...
Doses and durations of scalines
CompoundChemical nameDoseDuration
α,α-Dideuteromescaline (α-D)3,4,5-Trimethoxy-α,α-dideuterophenethylamineUnknownUnknown
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: [1][3][16][7][17][18][15][19][8]
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More information Compound, Chemical name ...
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: [1][3][16][7][15]
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Interactions

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

Pharmacology

Pharmacodynamics

More information Compound, 5-HT1A ...
Serotonin receptor affinities (Ki, nM) of selected scalines (Jain et al., 2025)[20]
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––––
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Society and culture

Canada

Mescaline and 3,4,5-trimethoxyamphetamine (TMA) are the only scalines (and derivatives) that are controlled substances in Canada as of 2025.[21]

List of scalines

4-Substituted

4-Alkoxy-substituted

  • 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)
  • 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

Others

3- or 5-Extended

See also: TWEETIO § Scalines

3- or 5-Replaced

2- or 6-Substituted

N-Substituted

α- or β-Substituted

See also: 3C (psychedelics) and BOx (psychedelics)
  • BOM (β,3,4,5-tetramethoxyphenethylamine; β-methoxymescaline)
  • α-Ethylmescaline (AEM) (α-ethyl-3,4,5-trimethoxyphenethylamine)
  • β-HOM (3,4,5-trimethoxy-β-hydroxyphenethylamine; β-hydroxymescaline)
  • 3,4,5-Trimethoxyamphetamine (3,4,5-TMA; TMA; TMA-1; α-methylmescaline)

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)
  • DEMPDHPCA-M (DEMPDHPCA-mescaline; N,N-diethyl-1-methyl-5-(3,4,5-trimethoxyphenyl)-1,2,3,6-tetrahydropyridine-3-carboxamide)
  • Flyscaline (mescaline-FLY)
  • 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)

Other compounds

  • 4-D (4-trideuteromescaline; 4-trideuteromethoxy-3,5-methoxyphenethylamine)
  • 3,5-Dimethoxyphenethylamine (3,5-DMPEA; 4-desmethoxymescaline)
  • Alpha-D (α-D; 3,4,5-trimethoxy-α,α-dideuterophenethylamine; α,α-dideuteromescaline)
  • Beta-D (β-D; 3,4,5-trimethoxy-β,β-dideuterophenethylamine; β,β-dideuteromescaline)
  • Isomescaline (IM) (2,3,4-trimethoxyphenethylamine)
  • Lophophine (2C-MMDA; 5-methoxy-MDPEA; MMDPEA; 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)

Related compounds

See also

References

External links

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