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 3,4,5-Trimethoxyamphetamine (TMA, TMA-1, or 3,4,5-TMA), also known as α-methylmescaline or mescalamphetamine, is a psychedelic drug of the substituted phenethylamine, phenethylamine and substituted amphetamine, amphetamine families. It is one of ...

(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 Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

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 David Earl Nichols (born December 23, 1944, Covington, Kentucky) is an American pharmacologist and medicinal chemist. Previously the Robert C. and Charlotte P. Anderson Distinguished Chair in Pharmacology at Purdue University, Nichols has worke ...

and

Daniel Trachsel Daniel Trachsel is a Swiss people, Swiss chemist who studies psychedelic drug, psychedelics and entactogens. He has developed and published on a large number of novel psychedelic and entactogen chemical compound, compounds, including their psycho ...

, among other researchers.

List of substituted mescaline analogues

4-Substituted

* 4-D (4-trideuteromethoxy-3,5-methoxyphenethylamine) *

Allylescaline Allylescaline (4-allyloxy-3,5-dimethoxyphenethylamine) is a lesser-known psychedelic drug. It is closely related in structure to mescaline. Allylescaline was first synthesized by Otakar Leminger in 1972. The compound was later synthesized by Ale ...

(AL) (4-allyloxy-3,5-dimethoxyphenethylamine) * Amylescaline (4-''n''-amyloxy-3,5-dimethoxyphenethylamine) *

Benzscaline Benzscaline (BZ), also known as 4-benzyloxy-3,5-dimethoxyphenethylamine (4-BzlO-3,5-DMPEA), is a serotonin receptor agonist and possible serotonergic psychedelic of the phenethylamine and scaline families. It is a potent serotonin 5-HT2A rece ...

(BZ) (4-benzyloxy-3,5-dimethoxyphenethylamine) *

Biscaline Biscaline, also known as 3,5-dimethoxy-4-phenylphenethylamine, is a monoamine receptor modulator of the phenethylamine family. It is the analogue of mescaline (3,4,5-dimethoxyphenethylamine) in which the methoxy group at the 4 position has been ...

(4-phenyl-3,5-dimethoxyphenethylamine) *

Buscaline Buscaline (3,5-dimethoxy-4-butoxyphenethylamine) is a chemical compound prepared as a possible psychedelic drug. It is an analog of mescaline. Buscaline was first synthesized by Alexander Shulgin. In his book ''PiHKAL'', the minimum dosage is li ...

(B) (4-butoxy-3,5-dimethoxyphenethylamine) *

Cyclopropylmescaline Cyclopropylmescaline (CPM or 4-cyclopropylmethoxy-3,5-dimethoxyphenethylamine) is a lesser-known psychedelic drug. CPM was first synthesized by Alexander Shulgin. In his book ''PiHKAL'', the dosage range is listed as 60–80 mg and the durati ...

(CPM) (4-cyclopropylmethoxy-3,5-dimethoxyphenethylamine) * Cycloproscaline (CP) (4-cyclopropoxy-3,5-dimethoxyphenethylamine) *

4-Desmethylmescaline 4-''O''-Desmethylmescaline, also known as 3,5-dimethoxy-4-hydroxyphenethylamine, 3,5-dimethoxytyramine, or DESMETHYL, is an alkaloid and drug of the phenethylamine and scaline families related to mescaline. It is the analogue of mescaline in w ...

(DESMETHYL) (4-hydroxy-3,5-dimethoxyphenethylamine) *

4-Desoxymescaline 4-Desoxymescaline, or 4-methyl-3,5-dimethoxyphenethylamine, is a mescaline analogue related to other psychedelic phenethylamines. It is commonly referred to as DESOXY. DESOXY was discovered by Alexander Shulgin and published in his book ''PiHKAL ...

(4-methyl-3,5-dimethoxyphenethylamine) * Difluoroescaline (DFE) (multiple forms) * Difluoroisoproscaline (DFIP) (multiple forms) * Difluoromescaline (DFM) (4-difluoromethoxy-3,5-dimethoxyphenethylamine) *

Escaline Escaline (E), also known as 3,5-dimethoxy-4-ethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. It is the 4- ethoxy analogue of mescaline (3,4,5-trimethoxyphenethylamine) and the pheneth ...

(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 Isoproscaline or 4-isopropoxy-3,5-dimethoxyphenethylamine is an analog of mescaline. It is closely related to proscaline and was first synthesized by David E. Nichols. It produces hallucinogenic, psychedelic, and entheogenic effects. Chemistry ...

(IP) (4-isopropoxy-3,5-dimethoxyphenethylamine) *

Methallylescaline Methallylescaline, abbreviated as MAL and also known as 4-methylallyloxy-3,5-dimethoxyphenethylamine, is a lesser-known psychedelic drug. It is the 4-methyl analog of allylescaline. MAL was first synthesized by Alexander Shulgin. It has been sold ...

(MAL) (4-methylallyloxy-3,5-dimethoxyphenethylamine) *

Phenescaline Phenescaline, or 3,5-dimethoxy-4-phenylethoxyphenethylamine, is a lesser-known psychedelic drug. It is an analogue of mescaline. Alexander Shulgin first synthesized Phenescaline. In his book '' PiHKAL (Phenethylamines i Have Known And Loved)'', ...

(4-phenylethoxy-3,5-dimethoxyphenethylamine) * Propynylmescaline (4-propynyloxy-3,5-dimethoxyphenethylamine) *

Proscaline Proscaline (4-propoxy-3,5-dimethoxyphenethylamine or 4-propoxy-3,5-DMPEA) is a Psychedelic drug, psychedelic and hallucinogenic drug. It has structural properties similar to the drugs mescaline, isoproscaline, and escaline. In ''PiHKAL'', Alexan ...

(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 Trifluoromescaline (TF-M) is a derivative of the phenethylamine hallucinogen mescaline, which has a trifluoromethoxy group replacing the central methoxy group of mescaline. Trifluoromescaline was found to be one of the most potent compounds in t ...

(TFM) (4-trifluoromethoxy-3,5-dimethoxyphenethylamine) * Trifluoroproscaline (TFP) (multiple forms) * Viscaline (4-vinyl-3,5-dimethoxyphenethylamine)

3- or 5-Extended

Asymbescaline Asymbescaline (3,4-diethoxy-5-methoxyphenethylamine) is a lesser-known psychedelic drug. It is a homolog of mescaline. Asymbescaline was first synthesized by Alexander Shulgin. In his book ''PiHKAL'', the dosage range is listed as 200–280 ...

(ASB) (3,4-diethoxy-5-methoxyphenethylamine) * Metadifluoromescaline (MDFM) (3,4-dimethoxy-5-difluoromethoxyphenethylamine) *

Metaescaline Metaescaline (3,4-dimethoxy-5-ethoxyphenethylamine) is a lesser-known psychedelic drug. It is an analog of mescaline. Metaescaline was first synthesized by Alexander Shulgin. In his book ''PiHKAL'', the dosage range is listed as 200–350 mg ...

(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 TME, or thio metaescaline, is a series of lesser-known psychedelic drugs similar in structure to mescaline. Their structures are based on that of metaescaline. They were first synthesized by Alexander Shulgin and recorded in his book '' PiHKAL (Ph ...

(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 TASB, or thioasymbescaline, is a series of lesser-known psychedelic drugs similar in structure to asymbescaline and to mescaline. They were first synthesized by Alexander Shulgin and written up in his book '' PiHKAL (Phenethylamines i Have Known An ...

(3-TASB) (3-ethylthio-4-ethoxy-5-methoxyphenethylamine) *

5-Thioasymbescaline TASB, or thioasymbescaline, is a series of lesser-known psychedelic drugs similar in structure to asymbescaline and to mescaline. They were first synthesized by Alexander Shulgin and written up in his book '' PiHKAL (Phenethylamines i Have Known An ...

(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 2,3,4,5-Tetramethoxyphenethylamine (TeMPEA) is a drug of the phenethylamine family related to mescaline (3,4,5-trimethoxyphenethylamine) and the 2C drugs (4-substituted 2,5-dimethoxyphenethylamines). It was reported to be twice as potent as mes ...

(TeMPEA; TeMPEA-1) *

2,3,5,6-Tetramethoxyphenethylamine 2,3,5,6-Tetramethoxyphenethylamine (2,3,5,6-TeMPEA), also known as TeMPEA-3, is a drug of the phenethylamine family related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine). It is one of the possible positional isomers of tetram ...

(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 α-Ethylmescaline (AEM or 3,4,5-trimethoxy-α-ethylphenethylamine) is a lesser-known psychedelic drug. It is an analog of mescaline. AEM was first synthesized by Alexander Shulgin. In his book ''PiHKAL'', the minimum dosage is listed as 220 ...

(AEM) (α-ethyl-3,4,5-trimethoxyphenethylamine) *

3,4,5-Trimethoxyamphetamine 3,4,5-Trimethoxyamphetamine (TMA, TMA-1, or 3,4,5-TMA), also known as α-methylmescaline or mescalamphetamine, is a psychedelic drug of the substituted phenethylamine, phenethylamine and substituted amphetamine, amphetamine families. It is one of ...

(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 Jimscaline (C-(4,5,6-trimethoxyindan-1-yl)methanamine) is a conformationally-restricted derivative of the cactus-derived hallucinogen mescaline, which was reported in 2006 by a team at Purdue University led by David E. Nichols. It acts as a po ...

(1-(4,5,6-trimethoxy-2,3-dihydro-1''H''-inden-1-yl)methylamine) *

Lophophine Lophophine, also known as 3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA), is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine family. It is the α-demethylated homologue of MMDA, and is also closely related t ...

(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)

References

External links

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