Scaline

, the most well-known scaline psychedelic. 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.…

, the most well-known scaline psychedelic. 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

Interactions

Pharmacology

Pharmacodynamics

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

N-Acetylmescaline (N-acetyl-3,4,5-trimethoxyphenethylamine) N-Formylmescaline (N-formyl-3,4,5-trimethoxyphenethylamine) N,N-Diformylmescaline (N,N-diformyl-3,4,5-trimethoxyphenethylamine) Mescaloruvic acid (N-(1-carboxyethyl)mescaline; N-(1-carboxyethyl)-3,4,5-trimethoxyphenethylamine) Mescaloxylic acid (N-carboxymethylmescaline; N-carboxymethyl-3,4,5-trimethoxyphenethylamine) N-Methylmescaline (M-M) (N-methyl-3,4,5-trimethoxyphenethylamine) M-NDEPA (N-diethylaminocarbonylethyl-3,4,5-trimethoxyamphetamine) 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; N,N-dimethyl-3,4,5-trimethoxyphenethylamine)

α- or β-Substituted

α-Ethylmescaline (AEM) (α-ethyl-3,4,5-trimethoxyphenethylamine) β-Hydroxymescaline (β-HOM; mescalol) (3,4,5-trimethoxy-β-hydroxyphenethylamine) β-Methoxymescaline (BOM) (β,3,4,5-tetramethoxyphenethylamine) 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) 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

3-Methoxy-4,5-dihydroxyphenethylamine (4-O-,5-O-didesmethylmescaline) 3,5-Dimethoxyphenethylamine (3,5-DMPEA; 4-desmethoxymescaline) Dimetofrine (3,5-dimethoxy-4,β-dihydroxy-N-methylphenethylamine; β-hydroxy-N-methyl-4-O-desmethylmescaline) 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

3,4-Dimethoxyphenethylamine (DMPEA; 3,4-DMPEA; homoveratrylamine; 3-desmethoxymescaline) 3-Methoxy-4-ethoxyphenethylamine (MEPEA; 3-desmethoxyescaline) 3-Methoxy-4-allyloxyphenethylamine (MAPEA; 3-desmethoxyallylescaline) 3-Methoxy-4-propoxyamphetamine (POMA; 3-desmethoxyproscaline)

See also

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

References

External links

Isomer Design Scalines - Wikipedia Massviews Analysis (Wikipedia Page Views of Individual Scalines)

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