Mescaline

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Mescaline
Mescaline Structural Formulae bondline.svg
Mescaline structure.png
Clinical data
Other namesMescalin; Mezcalin; Mezcaline; 3,4,5-Trimethoxyphenethylamine; 3,4,5-TMPEA; TMPEA
AHFS/Drugs.com mescaline
Routes of
administration 		Oral, smoking, insufflation, intravenous [1] [2]
Drug class Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Metabolism Oxidative deamination, N-acetylation, O-demethylation, conjugation, other pathways [4] [5]
Metabolites • 3,4,5-Trimethoxyphenyl-acetaldehyde [4] [1]
• 3,4,5-Trimethoxyphenylacetic acid [1]
• 3,4,5-Trimethoxyphenylethanol [5]
• Others [4] [5] [2]
Onset of action Oral: 0.5–3 hours [6] [1] [2]
Elimination half-life 3.6 hours [6] [7]
Duration of action ≥10–12 hours [6] [1] [2]
Excretion Urine (28–81% unchanged, 13–26% as TMPA) [1] [4] [5] [2]
Identifiers
  • 2-(3,4,5-trimethoxyphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.174 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H17NO3
Molar mass 211.261 g·mol−1
3D model (JSmol)
Density 1.067 g/cm3
Melting point 35 to 36 °C (95 to 97 °F)
Boiling point 180 °C (356 °F) at 12 mmHg
Solubility in water moderately soluble in water mg/mL (20 °C)
  • O(c1cc(cc(OC)c1OC)CCN)C
  • InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3 Yes check.svgY
  • Key:RHCSKNNOAZULRK-UHFFFAOYSA-N Yes check.svgY
   (verify)

Mescaline, also known as mescalin or mezcalin, [8] as well as 3,4,5-trimethoxyphenethylamine, is a naturally occurring psychedelic protoalkaloid of the substituted phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin. [4] [1] [6] [5] It binds to and activates certain serotonin receptors in the brain, producing hallucinogenic effects. [1] [6]

Contents

Biological sources

It occurs naturally in several species of cacti. It is also reported to be found in small amounts in certain members of the bean family, Fabaceae, including Senegalia berlandieri (syn. Acacia berlandieri), [9] although these reports have been challenged and have been unsupported in any additional analyses. [10]

Plant sourceAmount of mescaline
(% of dry weight)
Echinopsis lageniformis (Bolivian torch cactus, syns. Echinopsis scopulicola, Trichocereus bridgesii) [11] Average 0.56; 0.85 in one cultivar of Echinopsis scopulicola [11] [12]
Leucostele terscheckii (syns Echinopsis terscheckii, Trichocereus terscheckii) [13] 0.005 - 2.375 [14] [15]
Peyote cactus (Lophophora williamsii) [16] 0.01-5.5 [17]
Trichocereus macrogonus var. macrogonus (Peruvian torch, syns Echinopsis peruviana, Trichocereus peruvianus) [18] 0.01-0.05; [14] 0.24-0.81 [12]
Trichocereus macrogonus var. pachanoi (San Pedro cactus, syns Echinopsis pachanoi, Echinopsis santaensis, Trichocereus pachanoi) [19] 0.23-4.7; [12] 0.32 under its synonym Echinopsis santaensis [12]
Trichocereus uyupampensis (syn. Echinopsis uyupampensis)0.05 [12]
Trichocereus tacaquirensis (subsp. taquimbalensis syn. Trichocereus taquimbalensis)0.005-2.7 [20]
Trichocereus pachanoi in Peru Troncos de cactus Echinopsis pachanoi.jpg
Trichocereus pachanoi in Peru

As shown in the accompanying table, the concentration of mescaline in different specimens can vary largely within a single species. Moreover, the concentration of mescaline within a single specimen varies as well. [21]

History and use

Peyote has been used for at least 5,700 years by Indigenous peoples of the Americas in Mexico. [2] [22] Europeans recorded use of peyote in Native American religious ceremonies upon early contact with the Huichol people in Mexico. [23] Other mescaline-containing cacti such as the San Pedro have a long history of use in South America, from Peru to Ecuador. [24] [25] [26] [27] While religious and ceremonial peyote use was widespread in the Aztec empire and northern Mexico at the time of the Spanish conquest, religious persecution confined it to areas near the Pacific coast and up to southwest Texas. However, by 1880, peyote use began to spread north of South-Central America with "a new kind of peyote ceremony" inaugurated by the Kiowa and Comanche people. These religious practices, incorporated legally in the United States in 1920 as the Native American Church, have since spread as far as Saskatchewan, Canada. [22]

In traditional peyote preparations, the top of the cactus is cut off, leaving the large tap root along with a ring of green photosynthesizing area to grow new heads. These heads are then dried to make disc-shaped buttons. Buttons are chewed to produce the effects or soaked in water to drink. However, the taste of the cactus is bitter, so modern users will often grind it into a powder and pour it into capsules to avoid having to taste it. The typical dosage is 200–400 milligrams of mescaline sulfate or 178–356 milligrams of mescaline hydrochloride. [28] [29] The average 76 mm (3.0 in) peyote button contains about 25 mg mescaline. [30] Some analyses of traditional preparations of San Pedro cactus have found doses ranging from 34 mg to 159 mg of total alkaloids, a relatively low and barely psychoactive amount. It appears that patients who receive traditional treatments with San Pedro ingest sub-psychoactive doses and do not experience psychedelic effects. [31]

Botanical studies of peyote began in the 1840s and the drug was listed in the Mexican pharmacopeia. [5] The first of mescal buttons was published by John Raleigh Briggs in 1887. [5] Mescaline was first isolated and identified in 1896 or 1897 by the German chemist Arthur Heffter and his colleagues. [5] [2] [32] He showed that mescaline was exclusively responsible for the psychoactive or hallucinogenic effects of peyote. [5] However, other components of peyote, such as hordenine, pellotine, and anhalinine, are also active. [5] Mescaline was first synthesized in 1919 by Ernst Späth. [2] [33]

In 1955, English politician Christopher Mayhew took part in an experiment for BBC's Panorama , in which he ingested 400 mg of mescaline under the supervision of psychiatrist Humphry Osmond. Though the recording was deemed too controversial and ultimately omitted from the show, Mayhew praised the experience, calling it "the most interesting thing I ever did". [34]

Studies of the potential therapeutic effects of mescaline started in the 1950s. [5]

The mechanism of action of mescaline, activation of the serotonin 5-HT2A receptors, became known in the 1990s. [5]

Potential medical usage

Mescaline has a wide array of suggested medical usage, including treatment of depression, anxiety, PTSD, [35] and alcoholism. [36] However, its status as a Schedule I controlled substance in the Convention on Psychotropic Substances limits availability of the drug to researchers. Because of this, very few studies concerning mescaline's activity and potential therapeutic effects in people have been conducted since the early 1970s. [37] [38] [39]

Behavioral and non-behavioral effects

Mescaline induces a psychedelic state comparable to those produced by LSD and psilocybin, but with unique characteristics. [39] Subjective effects may include altered thinking processes, an altered sense of time and self-awareness, and closed- and open-eye visual phenomena. [40]

Prominence of color is distinctive, appearing brilliant and intense. Recurring visual patterns observed during the mescaline experience include stripes, checkerboards, angular spikes, multicolor dots, and very simple fractals that turn very complex. The English writer Aldous Huxley described these self-transforming amorphous shapes as like animated stained glass illuminated from light coming through the eyelids in his autobiographical book The Doors of Perception (1954). Like LSD, mescaline induces distortions of form and kaleidoscopic experiences but they manifest more clearly with eyes closed and under low lighting conditions. [41]

Heinrich Klüver coined the term "cobweb figure" in the 1920s to describe one of the four form constant geometric visual hallucinations experienced in the early stage of a mescaline trip: "Colored threads running together in a revolving center, the whole similar to a cobweb". The other three are the chessboard design, tunnel, and spiral. Klüver wrote that "many 'atypical' visions are upon close inspection nothing but variations of these form-constants." [42]

As with LSD, synesthesia can occur especially with the help of music. [43] An unusual but unique characteristic of mescaline use is the "geometrization" of three-dimensional objects. The object can appear flattened and distorted, similar to the presentation of a Cubist painting. [44]

Mescaline elicits a pattern of sympathetic arousal, with the peripheral nervous system being a major target for this substance. [43]

According to a research project in the Netherlands, ceremonial San Pedro use seems to be characterized by relatively strong spiritual experiences, and low incidence of challenging experiences. [45]

Chemistry

Mescaline, also known as 3,4,5-trimethoxyphenethylamine (3,4,5-TMPEA), is a substituted phenethylamine derivative. [46] [5] It is closely structurally related to the catecholamine neurotransmitters dopamine, norepinephrine, and epinephrine. [46]

The drug is relatively hydrophilic with low fat solubility. [5] Its predicted log P (XLogP3) is 0.7. [46]

Biosynthesis

Mescaline is biosynthesized from tyrosine, which, in turn, is derived from phenylalanine by the enzyme phenylalanine hydroxylase. In Lophophora williamsii (Peyote), dopamine converts into mescaline in a biosynthetic pathway involving m-O-methylation and aromatic hydroxylation. [47]

Tyrosine and phenylalanine serve as metabolic precursors towards the synthesis of mescaline. Tyrosine can either undergo a decarboxylation via tyrosine decarboxylase to generate tyramine and subsequently undergo an oxidation at carbon 3 by a monophenol hydroxylase or first be hydroxylated by tyrosine hydroxylase to form L-DOPA and decarboxylated by DOPA decarboxylase. These create dopamine, which then experiences methylation by a catechol-O-methyltransferase (COMT) by an S-adenosyl methionine (SAM)-dependent mechanism. The resulting intermediate is then oxidized again by a hydroxylase enzyme, likely monophenol hydroxylase again, at carbon 5, and methylated by COMT. The product, methylated at the two meta positions with respect to the alkyl substituent, experiences a final methylation at the 4 carbon by a guaiacol-O-methyltransferase, which also operates by a SAM-dependent mechanism. This final methylation step results in the production of mescaline.

Phenylalanine serves as a precursor by first being converted to L-tyrosine by L-amino acid hydroxylase. Once converted, it follows the same pathway as described above. [48] [49]

Biosynthesis of mescaline Mescaline biosynthetic pathways.svg
Biosynthesis of mescaline

Laboratory synthesis

Laboratory synthetic mescaline biosynthesized from peyote -- this was the first psychedelic compound to be extracted and isolated Synthetic mescaline powder i2001e0151 ccby3.jpg
Laboratory synthetic mescaline biosynthesized from peyote — this was the first psychedelic compound to be extracted and isolated
Dried Peyote (Lophophora williamsii), containing around 5-6% mescaline by weight Dried Peyote.jpg
Dried Peyote (Lophophora williamsii), containing around 5-6% mescaline by weight

Mescaline was first synthesized in 1919 by Ernst Späth from 3,4,5-trimethoxy­benzoyl chloride. [33] Several approaches using different starting materials have been developed since, including the following:

Pharmacology

Pharmacodynamics

Mescaline activities
Target Affinity (Ki, nM)
5-HT1A 1,841–4,600
5-HT1B >10,000
5-HT1D >10,000
5-HT1E 5,205
5-HT1F ND
5-HT2A 550–17,400 (Ki)
88–10,000 (EC50 Tooltip half-maximal effective concentration)
56–107% (Emax Tooltip maximal efficacy)
5-HT2B 793–800 (Ki)
>20,000 (EC50)
5-HT2C 300–17,000
20–114 (EC50)
22–95 (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A >10,000
5-HT6 >10,000
5-HT7 >10,000
α1A >15,000
α1B >10,000
α1D ND
α2A 1,400–8,930
α2B >10,000
α2C 745
β1–β2 >10,000
D1 >10,000
D2 >10,000
D3 >17,000
D4 >10,000
D5 >10,000
H1–H4 >10,000
M1–M5 >10,000
TAAR1 3,300 (Ki) (rat)
11,000 (Ki) (mouse)
>10,000 (EC50) (human)
I1 2,678
σ1–σ2 >10,000
SERT Tooltip Serotonin transporter>30,000 (Ki)
367,000 (IC50 Tooltip half-maximal inhibitory concentration)
NET Tooltip Norepinephrine transporter>30,000 (Ki)
>900,000 (IC50)
DAT Tooltip Dopamine transporter>30,000 (Ki)
841,000 (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [66] [67] [6] [1]
[68] [69] [70] [71]

In plants, mescaline may be the end-product of a pathway utilizing catecholamines as a method of stress response, similar to how animals may release such compounds and others such as cortisol when stressed. The in vivo function of catecholamines in plants has not been investigated, but they may function as antioxidants, as developmental signals, and as integral cell wall components that resist degradation from pathogens. The deactivation of catecholamines via methylation produces alkaloids such as mescaline. [48]

In humans, mescaline acts similarly to other psychedelic agents. [72] It acts as an agonist, [73] binding to and activating the serotonin 5-HT2A receptor. [74] [75] Its EC50 Tooltip half-maximal effective concentration at the serotonin 5-HT2A receptor is approximately 10 μM and at the serotonin 5-HT2B receptor is greater than 20 μM. [1] How activating the 5-HT2A receptor leads to psychedelic effects is still unknown, but it is likely that somehow it involves excitation of neurons in the prefrontal cortex. [76] In addition to the serotonin 5-HT2A and 5-HT2B receptors, mescaline is also known to bind to the serotonin 5-HT2C receptor and a number of other targets. [1] [70] [68] [77]

Mescaline lacks affinity for the monoamine transporters, including the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT) (Ki = >30 μM). [1] However, mescaline has been found to increase levels of the major serotonin metabolite 5-hydroxyindoleacetic acid (5-HIAA) at high doses in rodents. [1] [5] [2] [78] This finding suggests that mescaline may inhibit the reuptake and/or induce the release of serotonin at such doses. [1] [5] [79] However, this possibility has not yet been further assessed or demonstrated. [1] Besides serotonin, mescaline may also weakly induce the release of dopamine, but this is probably of modest significance. [5] [2] [80] In accordance, there is no evidence of it showing addiction or dependence. [2] [5] The monoamine-releasing effects of mescaline are likely related to its structural similarity to substituted amphetamines and related compounds. [2] [5]

Tolerance builds with repeated usage, lasting for a few days. Mescaline causes cross-tolerance with other serotonergic psychedelics such as LSD and psilocybin. [81]

The LD50 of mescaline has been measured in various animals: 212–315 mg/kg i.p. (mice), 132–410 mg/kg i.p. (rats), 328 mg/kg i.p. (guinea pigs), 54 mg/kg in dogs, and 130 mg/kg i.v. in rhesus macaques. [2] [82] For humans, the LD50 of mescaline has been reported to be approximately 880 mg/kg. [82] It has been said that it would be very difficult to consume enough mescaline to cause death in humans. [2]

Mescaline is a relatively low-potency psychedelic, with active doses in the hundreds of milligrams and micromolar affinities for the serotonin 5-HT2A receptor. [4] [1] For comparison, psilocybin is approximately 20-fold more potent (doses in the tens of milligrams) and lysergic acid diethylamide (LSD) is approximately 2,000-fold more potent (doses in the tens to hundreds of nanograms). [1] There have been efforts to develop more potent analogues of mescaline. [4] Difluoro­mescaline and trifluoro­mescaline are more potent than mescaline, as is its amphetamine homologue trimethoxy­amphetamine (TMA). [83] [84] Escaline and proscaline are also both more potent than mescaline, showing the importance of the 4-position substituent with regard to receptor binding. [85]

Pharmacokinetics

About half the initial dosage is excreted after 6 hours, but some studies suggest that it is not metabolized at all before excretion. Mescaline appears not to be subject to metabolism by CYP2D6 [86] and between 20% and 50% of mescaline is excreted in the urine unchanged, with the rest being excreted as the deaminated-oxidised-carboxylic acid form of mescaline, a likely result of monoamine oxidase (MAO) degradation. [87] However, the enzymes mediating the oxidative deamination of mescaine are controversial. [2] MAO, diamine oxidase (DAO), and/or other enzymes may be involved or responsible. [2]

The previously reported elimination half-life of mescaline was originally reported to be 6 hours, but a new study published in 2023 reported a half-life of 3.6 hours. [7] [75] The higher estimate is believed to be due to small sample numbers and collective measurement of mescaline metabolites. [7]

Mescaline appears to have relatively poor blood–brain barrier permeability due to its low lipophilicity. [5] [2] However, it is still able to cross into the central nervous system and produce psychoactive effects at sufficienty high doses. [5] [2]

Active metabolites of mescaline may contribute to its psychoactive effects. [5] [2]

United States

In the United States, mescaline was made illegal in 1970 by the Comprehensive Drug Abuse Prevention and Control Act, categorized as a Schedule I hallucinogen. [88] The drug is prohibited internationally by the 1971 Convention on Psychotropic Substances. [89] Mescaline is legal only for certain religious groups (such as the Native American Church by the American Indian Religious Freedom Act of 1978) and in scientific and medical research. In 1990, the Supreme Court ruled that the state of Oregon could ban the use of mescaline in Native American religious ceremonies. The Religious Freedom Restoration Act (RFRA) in 1993 allowed the use of peyote in religious ceremony, but in 1997, the Supreme Court ruled that the RFRA is unconstitutional when applied against states.[ citation needed ] Many states, including the state of Utah, have legalized peyote usage with "sincere religious intent", or within a religious organization,[ citation needed ] regardless of race. [90] Synthetic mescaline, but not mescaline derived from cacti, was officially decriminalized in the state of Colorado by ballot measure Proposition 122 in November 2022. [91]

While mescaline-containing cacti of the genus Echinopsis are technically controlled substances under the Controlled Substances Act, they are commonly sold publicly as ornamental plants. [92]

United Kingdom

In the United Kingdom, mescaline in purified powder form is a Class A drug. However, dried cactus can be bought and sold legally. [93]

Australia

Mescaline is considered a schedule 9 substance in Australia under the Poisons Standard (February 2020). [94] A schedule 9 substance is classified as "Substances with a high potential for causing harm at low exposure and which require special precautions during manufacture, handling or use. These poisons should be available only to specialised or authorised users who have the skills necessary to handle them safely. Special regulations restricting their availability, possession, storage or use may apply." [94]

Other countries

In Canada, France, The Netherlands and Germany, mescaline in raw form and dried mescaline-containing cacti are considered illegal drugs. However, anyone may grow and use peyote, or Lophophora williamsii, as well as Echinopsis pachanoi and Echinopsis peruviana without restriction, as it is specifically exempt from legislation. [16] In Canada, mescaline is classified as a schedule III drug under the Controlled Drugs and Substances Act, whereas peyote is exempt. [95]

In Russia mescaline, its derivatives and mescaline-containing plants are banned as narcotic drugs (Schedule I). [96]

Notable users

See also

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<span class="mw-page-title-main">25-NB</span> Family of serotonergic psychedelics

The 25-NB (25x-NBx) series, or NBOMe series, also known as the N-benzylphenethylamines, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C family. They act as selective agonists of the serotonin 5-HT2A receptor. The 25-NB family is unique relative to other classes of psychedelics in that they are, generally speaking, extremely potent and relatively selective for the 5-HT2A receptor. Use of NBOMe series drugs has caused many deaths and hospitalisations since the drugs popularisation in the 2010s. This is primarily due to their high potency, unpredictable pharmacokinetics, and sellers passing off the compounds in the series as LSD.

A trip killer, or hallucinogen antidote, is a drug that aborts or reduces the effects of a hallucinogenic drug experience. As there are different types of hallucinogens that work in different ways, there are different types of trip killers. They can completely block or reduce the effects of hallucinogens or they can simply provide anxiety relief and sedation. Examples of trip killers, in the case of serotonergic psychedelics, include serotonin receptor antagonists, like antipsychotics and certain antidepressants, and benzodiazepines. Trip killers are sometimes used by recreational psychedelic users as a form of harm reduction to manage so-called bad trips, for instance difficult experiences with prominent anxiety. They can also be used clinically to manage effects of hallucinogens, like anxiety and psychomotor agitation, for instance in the emergency department.

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