Substituted Mescaline Analogue
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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 Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...
serotonergic psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...
mescaline Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...
(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 third methoxy group in the 2 position instead of the 3 position while TMA is an
amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...
rather than a phenethylamine. The
pharmacology Pharmacology is the science of drugs and medications, including a substance's origin, composition, pharmacokinetics, pharmacodynamics, therapeutic use, and toxicology. More specifically, it is the study of the interactions that occur betwee ...
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 In chemistry, biochemistry, and pharmacology, a dissociation constant (''K''D) is a specific type of equilibrium constant that measures the propensity of a larger object to separate (dissociate) reversibly into smaller components, as when a Complex ...
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 ''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...
'' (''Phenethylamines I Have Known and Loved'') and '' The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds'' as well as in his
literature review A literature review is an overview of previously published works on a particular topic. The term can refer to a full scholarly paper or a section of a scholarly work such as books or articles. Either way, a literature review provides the rese ...
s. They have also been studied by David E. Nichols and Daniel Trachsel, among other researchers.


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) * 2,6-Dibromomescaline (2,6-dibromo-3,4,5-trimethoxyphenethylamine) * 2,6-Dichloromescaline (2,6-dichloro-3,4,5-trimethoxyphenethylamine) * 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

* 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) * Flyscaline (mescaline-FLY) * Isomescaline (IM) (2,3,4-trimethoxyphenethylamine) * Jimscaline (1-(4,5,6-trimethoxy-2,3-dihydro-1''H''-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 .2.0cta-1,3,5-trien-7-yl)methylamine)


See also

* Substituted methoxyphenethylamine * 3C (psychedelics) (4-substituted 3,5-dimethoxyamphetamines) * ''
PiHKAL ''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...
'' (''Phenethylamines I Have Known and Loved'') * '' The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds''


References


External links


Isomer Design
{{Chemical classes of psychoactive drugs Alexander Shulgin Chemical classes of psychoactive drugs Psychedelic phenethylamines Scalines