Mescaline

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Mescaline
Mescaline Structural Formulae bondline.svg
Mescaline structure.png
Clinical data
Other namesMescalin; Mezcalin; 3,4,5-Trimethoxyphenethylamine; TMPEA; Peyote
AHFS/Drugs.com mescaline
Routes of
administration 		Oral, intravenous
Drug class Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 3.6 hours
Duration of action 11 hours
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 or mescalin or mezcalin [2] (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. It binds to and activates certain serotonin receptors in the brain, producing hallucinogenic effects. [3]

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), [4] although these reports have been challenged and have been unsupported in any additional analyses. [5]

Plant sourceAmount of mescaline
(% of dry weight)
Echinopsis lageniformis (Bolivian torch cactus, syns. Echinopsis scopulicola, Trichocereus bridgesii) [6] Average 0.56; 0.85 in one cultivar of Echinopsis scopulicola [6] [7]
Leucostele terscheckii (syns Echinopsis terscheckii, Trichocereus terscheckii) [8] 0.005 - 2.375 [9] [10]
Peyote cactus (Lophophora williamsii) [11] 0.01-5.5 [12]
Trichocereus macrogonus var. macrogonus (Peruvian torch, syns Echinopsis peruviana, Trichocereus peruvianus) [13] 0.01-0.05; [9] 0.24-0.81 [7]
Trichocereus macrogonus var. pachanoi (San Pedro cactus, syns Echinopsis pachanoi, Echinopsis santaensis, Trichocereus pachanoi) [14] 0.23-4.7; [7] 0.32 under its synonym Echinopsis santaensis [7]
Trichocereus uyupampensis (syn. Echinopsis uyupampensis)0.05 [7]
Trichocereus tacaquirensis (subsp. taquimbalensis syn. Trichocereus taquimbalensis)0.005-2.7 [15]

density of mescaline: 1.067g/mL [16]

solubility of mescaline in water: moderately soluble in water [17]

Trichocereus pachanoi in Peru Troncos de cactus Echinopsis pachanoi.jpg
Trichocereus pachanoi in Peru

As can be observed from the table above, 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. [18]

History and use

Peyote has been used for at least 5,700 years by Indigenous peoples of the Americas in Mexico. [19] Europeans noted use of peyote in Native American religious ceremonies upon early contact, [20] notably by the Huichol people in Mexico. Other mescaline-containing cacti such as the San Pedro have a long history of use in South America, from Peru to Ecuador. [21] [22] [23] [24] 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. [19]

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 contemporary users will often grind it into a powder and pour it into capsules to avoid having to taste it. The usual human dosage is 200–400 milligrams of mescaline sulfate or 178–356 milligrams of mescaline hydrochloride. [25] [26] The average 76 mm (3.0 in) peyote button contains about 25 mg mescaline. [27] 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. [28]

Mescaline was first isolated and identified in 1897 by the German chemist Arthur Heffter [29] and first synthesized in 1919 by Ernst Späth. [30]

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". [31]

Potential medical usage

Mescaline has a wide array of suggested medical usage, including treatment of depression, anxiety, PTSD, [32] and alcoholism. [33] 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 humans have been conducted since the early 1970s. [34] [35] [36]

Behavioral and non-behavioral effects

Mescaline induces a psychedelic state comparable to those produced by LSD and psilocybin, but with unique characteristics. [36] Subjective effects may include altered thinking processes, an altered sense of time and self-awareness, and closed- and open-eye visual phenomena. [37]

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. [38]

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." [39]

As with LSD, synesthesia can occur especially with the help of music. [40] 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. [41]

Mescaline elicits a pattern of sympathetic arousal, with the peripheral nervous system being a major target for this substance. [40]

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. [42]

Chemistry

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. [43]

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. [44] [45]

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. [30] Subsequent to this, numerous approaches utilizing different starting materials have been developed. Notable examples include the following:

Pharmacology

Pharmacodynamics

Mechanism of action

Mescaline binding affinities
TargetAffinity (Ki, μM)
5-HT1A 1.8–4.6
5-HT1B >10
5-HT1D >10
5-HT1E 5.2
5-HT2A 0.55–17.4
5-HT2B 0.79–0.80
5-HT2C 0.30–17
5-HT3 >10
5-HT5A >10
5-HT6 >10
5-HT7 >10
α1A >15
α1B >10
α2A 1.4–8.9
α2B >10
α2C 0.75
β1 >10
β2 >10
D1 >14
D2 >10
D3 >17
D4 >10
D5 >10
TAAR1 3.3–11 (mouse/rat)
I1 2.7
σ1 >10
σ2 >10
SERT Tooltip Serotonin transporter>30
NET Tooltip Norepinephrine transporter>30
DAT Tooltip Dopamine transporter>30
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [62] [63] [64] [65]

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. [44]

In humans, mescaline acts similarly to other psychedelic agents. [66] It acts as an agonist, [67] binding to and activating the serotonin 5-HT2A receptor. [68] [69] 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. [70] 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. [71] 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. [70] [62] [65] [72]

Tolerance builds with repeated usage, lasting for a few days. Mescaline causes cross-tolerance with other serotonergic psychedelics such as LSD and psilocybin. [73]

The LD50 of mescaline has been measured in various animals: 212 mg/kg i.p. (mice), 132 mg/kg i.p. (rats), and 328 mg/kg i.p. (guinea pigs). For humans, the LD50 of mescaline has been reported to be approximately 880 mg/kg. [74]

Mescaline is a relatively low-potency psychedelic, with active doses in the hundreds of milligrams and micromolar affinities for the serotonin 5-HT2A receptor. [75] [70] 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). [70] There have been efforts to develop more potent analogues of mescaline. [75] Difluoro­mescaline and trifluoro­mescaline are more potent than mescaline, as is its amphetamine homologue trimethoxy­amphetamine (TMA). [76] [77] Escaline and proscaline are also both more potent than mescaline, showing the importance of the 4-position substituent with regard to receptor binding. [78]

Pharmacokinetics

About half the initial dosage is excreted after six hours, but some studies suggest that it is not metabolized at all before excretion. Mescaline appears not to be subject to metabolism by CYP2D6 [79] 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 MAO degradation. [80]

The previously reported half-life of mescaline was 6 hours, however new study published in 2023 reported 3.6 hours. [69] The higher estimate is believed to be due to small sample numbers and collective measurement of metabolite. [81]

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. [82] The drug is prohibited internationally by the 1971 Convention on Psychotropic Substances. [83] 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. [84] Synthetic mescaline, but not mescaline derived from cacti, was officially decriminalized in the state of Colorado by ballot measure Proposition 122 in November 2022. [85]

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. [86]

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. [87]

Australia

Mescaline is considered a schedule 9 substance in Australia under the Poisons Standard (February 2020). [88] 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." [88]

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. [11] In Canada, mescaline is classified as a schedule III drug under the Controlled Drugs and Substances Act, whereas peyote is exempt. [89]

In Russia mescaline, its derivatives and mescaline-containing plants are banned as narcotic drugs (Schedule I). [90]

Notable users

See also

Related Research Articles

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References

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  2. ↑ "Mescaline". PubChem. U.S. National Library of Medicine. Retrieved 22 October 2024.
  3. ↑ Vamvakopoulou IA, Narine KA, Campbell I, Dyck JR, Nutt DJ (January 2023). "Mescaline: The forgotten psychedelic". Neuropharmacology. 222: 109294. doi:10.1016/j.neuropharm.2022.109294. PMID   36252614.
  4. ↑ Forbes TD, Clement BA. "Chemistry of Acacia's from South Texas" (PDF). Texas A&M Agricultural Research & Extension Center at Uvalde. Archived from the original (PDF) on 15 May 2011.
  5. ↑ "Acacia species with data conflicts". sacredcacti.com. 16 January 2015. Retrieved 13 March 2021.
  6. 1 2 Bury B (2 August 2021). "Could Synthetic Mescaline Protect Declining Peyote Populations?". Chacruna. Retrieved 2 November 2021.
  7. 1 2 3 4 5 Ogunbodede O, McCombs D, Trout K, Daley P, Terry M (September 2010). "New mescaline concentrations from 14 taxa/cultivars of Echinopsis spp. (Cactaceae) ("San Pedro") and their relevance to shamanic practice". Journal of Ethnopharmacology. 131 (2). Elsevier BV: 356–362. doi:10.1016/j.jep.2010.07.021. PMID   20637277.
  8. ↑ "Cardon Grande (Echinopsis terscheckii)". Desert-tropicals.com. Archived from the original on 5 April 2015. Retrieved 14 January 2015.
  9. 1 2 "Partial List of Alkaloids in Trichocereus Cacti". Thennok.org. Archived from the original on 11 February 2009. Retrieved 22 December 2017.
  10. ↑ "Forbidden Fruit Archives". Archived from the original on 28 November 2005.
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