Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Mescaline: Difference between pages

{{Short description|Naturally occurring psychedelic compound}}

{{Distinguish|mezcal|mesclun|mexamine}}

{{Use dmy dates|date=October 2020}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Infobox drug

| Watchedfields = changed

| verifiedrevid = 477169864

| drug_name =

| type =

| IUPAC_name = 2-(3,4,5-trimethoxyphenyl)ethanamine

| image = Mescaline Structural Formulae bondline.svg

| alt =

| caption =

| image2 = File:Mescaline structure.png

<!--Clinical data-->| Drugs.com = {{drugs.com|parent|mescaline}}

| pregnancy_US = C

| MedlinePlus =

| licence_EU =

| licence_US =

| pregnancy_AU =

| pregnancy_category =

| legal_AU = Schedule 9

| legal_BR = F2

| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>

| legal_CA = Schedule III (Except peyote)

| legal_DE = Anlage I

| legal_UK = Class A

| legal_UK_comment = (Plants containing mescaline legal)

| legal_US = Schedule I

| legal_UN = P I

| legal_status =

| routes_of_administration = [[wikt:oral|Oral]], intravenous

<!--Pharmacokinetic data-->| elimination_half-life = 6 hours

<!--Identifiers-->| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 54-04-6

| ATC_prefix = None

| PubChem = 4076

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| DrugBank =

| ChemSpiderID = 3934

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = RHO99102VC

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C06546

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 28346

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 26687

<!--Chemical data-->

| C = 11

| H = 17

| N = 1

| O = 3

| smiles = O(c1cc(cc(OC)c1OC)CCN)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{Stdinchicite|correct|chemspider}}

| StdInChIKey = RHCSKNNOAZULRK-UHFFFAOYSA-N

| synonyms = 3,4,5-Trimethoxyphenethylamine, TMPEA, Peyote

| melting_point = 35

| melting_high = 36

| boiling_point = 180

| boiling_notes = at 12 mmHg

}}

'''Mescaline''' or '''mescalin''' ('''3,4,5-trimethoxyphenethylamine''') is a [[natural product|naturally occurring]] [[psychedelic drug|psychedelic]] [[alkaloid|protoalkaloid]] of the [[substituted phenethylamine]] class, known for its [[hallucinogen]]ic effects comparable to those of [[lysergic acid diethylamide|LSD]] and [[psilocybin]].

==Biological sources==

It occurs naturally in several species of [[Psychoactive cactus|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''),<ref name="chem">{{Cite web |title=Chemistry of Acacia's from South Texas |publisher=Texas A&M Agricultural Research & Extension Center at Uvalde |url=http://uvalde.tamu.edu/pdf/chemtdaf.pdf |archive-url=https://web.archive.org/web/20110515034950/http://uvalde.tamu.edu/pdf/chemtdaf.pdf |archive-date=15 May 2011 | vauthors = Forbes TD, Clement BA |url-status=dead }}</ref> although these reports have been challenged and have been unsupported in any additional analyses.<ref>{{Cite web |url=https://sacredcacti.com/blog/acacia/ |title=Acacia species with data conflicts |publisher=sacredcacti.com |date=16 January 2015 |access-date=13 March 2021 }}</ref>

{|class="wikitable"

|-

!Plant source

!Amount of Mescaline<br /> (% of dry weight)

|-

|''[[Echinopsis lageniformis]]'' (Bolivian torch cactus, syns. ''Echinopsis scopulicola'', ''Trichocereus bridgesii'')<ref>{{Cite web | vauthors = Bury B |date=2021-08-02 |title=Could Synthetic Mescaline Protect Declining Peyote Populations? |url= https://chacruna.net/synthetic_mescaline_protect_declining_peyote_populations/ |access-date=2021-11-02 |website=Chacruna |language=en-US}}</ref>||0.25-0.56; 0.85 under its synonym ''Echinopsis scopulicola''<ref name="Ogunbodede McCombs Trout Daley"/>

|-

|''[[Leucostele terscheckii]]'' (syns ''Echinopsis terscheckii'', ''Trichocereus terscheckii'')<ref>{{cite web|url=http://www.desert-tropicals.com/Plants/Cactaceae/Echinopsis_terscheckii.html|title=Cardon Grande (Echinopsis terscheckii)|publisher=Desert-tropicals.com|access-date=14 January 2015|archive-date=5 April 2015|archive-url=https://web.archive.org/web/20150405113718/http://www.desert-tropicals.com/Plants/Cactaceae/Echinopsis_terscheckii.html|url-status=dead}}</ref> || 0.005 - 2.375<ref name="nook2"/><ref name="netfirms">[http://entheogen.netfirms.com/articles/articles/Narcotic_Cacti.html Forbidden Fruit Archives] {{webarchive|url=https://web.archive.org/web/20051128031148/http://entheogen.netfirms.com/articles/articles/Narcotic_Cacti.html |date=2005-11-28 }}</ref>

|-

|[[Peyote]] cactus (''Lophophora williamsii'')<ref name="Bib">{{Cite book |title=Drug Identification Bible |publisher=Amera-Chem, Inc. |year=2007 |isbn=978-0-9635626-9-2 |location=Grand Junction, CO}}</ref>||0.01-5.5<ref name="Lophwilliamsii MollyT">{{cite journal | vauthors = Klein MT, Kalam M, Trout K, Fowler N, Terry M | title=Mescaline Concentrations in Three Principal Tissues of Lophophora williamsii (Cactaceae): Implications for Sustainable Harvesting Practices | journal=Haseltonia | publisher=Elsevier BV | volume=131 | issue=2 | year=2015 | issn= | doi=10.2985/026.020.0107| pages=34–42| s2cid=32474292 }}</ref>

|-

|''[[Trichocereus macrogonus]]'' var. ''macrogonus'' (Peruvian torch, syns ''Echinopsis peruviana'', ''Trichocereus peruvianus'')<ref name="OgunMcCoTrouDale10">{{cite journal | vauthors = Ogunbodede O, McCombs D, Trout K, Daley P, Terry M | title = New mescaline concentrations from 14 taxa/cultivars of Echinopsis spp. (Cactaceae) ("San Pedro") and their relevance to shamanic practice | journal = Journal of Ethnopharmacology | volume = 131 | issue = 2 | pages = 356–362 | date = September 2010 | pmid = 20637277 | doi = 10.1016/j.jep.2010.07.021 }}</ref>||0.01-0.05;<ref name="nook2">{{cite web|url=http://www.thenook.org/archives/tek/alklist.htm|title=Partial List of Alkaloids in Trichocereus Cacti|publisher=Thennok.org|access-date=22 December 2017|archive-date=11 February 2009|archive-url=https://web.archive.org/web/20090211110045/http://thenook.org/archives/tek/alklist.htm|url-status=dead}}</ref> 0.24-0.81<ref name="Ogunbodede McCombs Trout Daley"/>

|-

|[[Trichocereus macrogonus var. pachanoi|''Trichocereus macrogonus'' var. ''pachanoi'']] (San Pedro cactus, syns ''Echinopsis pachanoi'', ''Echinopsis santaensis'', ''Trichocereus pachanoi'')<ref>{{cite journal | vauthors = Crosby DM, McLaughlin JL | title = Cactus alkaloids. XIX. Crystallization of mescaline HCl and 3-methoxytyramine HCl from Trichocereus pachanoi | journal = Lloydia | volume = 36 | issue = 4 | pages = 416–418 | date = December 1973 | pmid = 4773270 | url = http://catbull.com/alamut/Bibliothek/1973_d.m._crosby_8158_1.pdf | access-date = 13 December 2013 }}</ref> ||0.23-4.7;<ref name="Ogunbodede McCombs Trout Daley">{{cite journal | vauthors = Ogunbodede O, McCombs D, Trout K, Daley P, Terry M | title = New mescaline concentrations from 14 taxa/cultivars of Echinopsis spp. (Cactaceae) ("San Pedro") and their relevance to shamanic practice | journal = Journal of Ethnopharmacology | volume = 131 | issue = 2 | pages = 356–362 | date = September 2010 | pmid = 20637277 | doi = 10.1016/j.jep.2010.07.021 | publisher = Elsevier BV }}</ref> 0.32 under its synonym ''Echinopsis santaensis''<ref name="Ogunbodede McCombs Trout Daley"/>

|-

|''[[Trichocereus uyupampensis]]'' (syn. ''Echinopsis uyupampensis'')||0.05<ref name="Ogunbodede McCombs Trout Daley"/>

|}

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. In columnar species like ''E. lageniformis'', ''E. pachanoi'' and ''E. peruviana'', the concentration of mescaline is highest at the top while in ''L. williamsii'', mescaline appears to concentrate mainly at the sides of the cactus.<ref>{{Cite journal |last=Van Der Sypt |first=Frederick |date=2022-04-03 |title=Validation and exploratory application of a simple, rapid and economical procedure (MESQ) for the quantification of mescaline in fresh cactus tissue and aqueous cactus extracts |url=https://zenodo.org/records/6409376 |journal=PhytoChem & BioSub Journal |doi=10.5281/zenodo.6409376}}</ref>

== History and use==

[[Peyote]] has been used for at least 5,700 years by [[Indigenous peoples of the Americas]] in Mexico.<ref name=prehistoric>{{cite journal | vauthors = El-Seedi HR, De Smet PA, Beck O, Possnert G, Bruhn JG | title = Prehistoric peyote use: alkaloid analysis and radiocarbon dating of archaeological specimens of Lophophora from Texas | journal = Journal of Ethnopharmacology | volume = 101 | issue = 1–3 | pages = 238–242 | date = October 2005 | pmid = 15990261 | doi = 10.1016/j.jep.2005.04.022 }}</ref> Europeans noted use of peyote in Native American religious ceremonies upon early contact,<ref>{{cite book | vauthors = Ruiz de Alarcón H |title= Treatise on the Heathen Superstitions that Today Live Among the Indians Native to this New Spain, 1629 |date=1984 |publisher=University of Oklahoma Press |isbn=978-0806120317}}</ref> notably by the [[Huichol people|Huichols]] in Mexico. Other mescaline-containing cacti such as the San Pedro have a long history of use in South America, from Peru to Ecuador.<ref>{{Cite journal | vauthors = Socha DM, Sykutera M, Orefici G |date=2022-12-01 |title=Use of psychoactive and stimulant plants on the south coast of Peru from the Early Intermediate to Late Intermediate Period |journal=Journal of Archaeological Science |language=en |volume=148 |pages=105688 |doi=10.1016/j.jas.2022.105688 |bibcode=2022JArSc.148j5688S |s2cid=252954052 |issn=0305-4403|doi-access=free }}</ref><ref>{{cite journal | vauthors = Bussmann RW, Sharon D | title = Traditional medicinal plant use in Northern Peru: tracking two thousand years of healing culture | journal = Journal of Ethnobiology and Ethnomedicine | volume = 2 | pages = 47 | date = November 2006 | pmid = 17090303 | pmc = 1637095 | doi = 10.1186/1746-4269-2-47 | doi-access = free }}</ref><ref name=":0">{{cite journal | vauthors = Armijos C, Cota I, González S | title = Traditional medicine applied by the Saraguro yachakkuna: a preliminary approach to the use of sacred and psychoactive plant species in the southern region of Ecuador | journal = Journal of Ethnobiology and Ethnomedicine | volume = 10 | pages = 26 | date = February 2014 | pmid = 24565054 | pmc = 3975971 | doi = 10.1186/1746-4269-10-26 | doi-access = free }}</ref><ref>{{Cite journal | vauthors = Samorini G |date=2019-06-01 |title=The oldest archeological data evidencing the relationship of Homo sapiens with psychoactive plants: A worldwide overview |url=https://akjournals.com/view/journals/2054/3/2/article-p63.xml |journal=Journal of Psychedelic Studies |language=en |volume=3 |issue=2 |pages=63–80 |doi=10.1556/2054.2019.008|s2cid=135116632 |doi-access=free }}</ref> 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, has since spread as far as Saskatchewan, Canada.<ref name=prehistoric/>

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.<ref>{{Cite web |url=http://www.erowid.org/library/books_online/pihkal/pihkal096.shtml |title=#96 M – Mescaline (3,4,5-Trimethoxyphenethylamine) |work=PIHKAL |publisher=Erowid.org |access-date=7 September 2011 }}</ref><ref>{{cite journal | vauthors = Uthaug MV, Davis AK, Haas TF, Davis D, Dolan SB, Lancelotta R, Timmermann C, Ramaekers JG | title = The epidemiology of mescaline use: Pattern of use, motivations for consumption, and perceived consequences, benefits, and acute and enduring subjective effects | journal = Journal of Psychopharmacology | volume = 36 | issue = 3 | pages = 309–320 | date = March 2022 | pmid = 33949246 | pmc = 8902264 | doi = 10.1177/02698811211013583 }}</ref> The average {{convert|76|mm|in|abbr=on}} peyote button contains about 25&nbsp;mg mescaline.<ref>{{Cite book|title=Handbook of Overdose and Detoxification Emergencies |location=New Hyde Park, NY. |publisher=Medical Examination Publishing Company |year=1982 |isbn=978-0-87488-182-0 | vauthors = Giannini AJ, Slaby AE, Giannini MC }}</ref>

Mescaline was first isolated and identified in 1897 by the German chemist [[Arthur Heffter]]<ref name="Erowid-Heffter">{{Cite web |url=http://www.erowid.org/culture/characters/heffter_arthur/heffter_arthur.shtml |title=Arthur Heffter |work=Character Vaults |publisher=Erowid.org |access-date=9 January 2013 }}</ref> and first synthesized in 1919 by [[Ernst Späth]].<ref name = "Späth_1919">{{cite journal| vauthors = Späth E |title=Über dieAnhalonium-Alkaloide I. Anhalin und Mezcalin|journal=Monatshefte für Chemie und Verwandte Teile Anderer Wissenschaften|date=February 1919|volume=40|issue=2|pages=129–154|doi=10.1007/BF01524590|s2cid=104408477|language=de|issn=0343-7329}}</ref>

In 1955, English politician [[Christopher Mayhew]] took part in an experiment for [[BBC]]'s ''[[Panorama (TV series)|Panorama]]'', in which he ingested 400&nbsp;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".<ref>{{Cite web |url=http://sotcaa.net/hiddenarchive/mayhew01.html |title=Panorama: The Mescaline Experiment |date=February 2005 |archive-url=https://web.archive.org/web/20120726183523/http://sotcaa.net/hiddenarchive/mayhew01.html |archive-date=26 July 2012 }}</ref>

=== Potential medical usage ===

Mescaline has a wide array of suggested medical usage, including treatment of alcoholism<ref>{{Cite web |url=https://abcnews.go.com/blogs/health/2012/03/09/could-lsd-treat-alcoholism/ |title=Could LSD treat alcoholism? |publisher=abcnews.go.com |date=9 March 2012 |access-date=5 October 2012 }}</ref> and depression.<ref>{{Cite web |url=http://news.discovery.com/human/magic-mushrooms-depression-122301.html |title=Magic Mushrooms could treat depression |publisher=news.discovery.com |date=23 January 2012 |access-date=9 January 2013 }}</ref> 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.<ref>{{Cite web | vauthors = Carpenter DE |date=2021-07-08 |title=Mescaline is Resurgent (Yet Again) As a Potential Medicine |url=https://www.lucid.news/mescaline-is-resurgent-yet-again-as-a-potential-medicine/ |access-date=2022-02-28 |website=Lucid News |language=en-US}}</ref><ref>{{cite journal | vauthors = Agin-Liebes G, Haas TF, Lancelotta R, Uthaug MV, Ramaekers JG, Davis AK | title = Naturalistic Use of Mescaline Is Associated with Self-Reported Psychiatric Improvements and Enduring Positive Life Changes | journal = ACS Pharmacology & Translational Science | volume = 4 | issue = 2 | pages = 543–552 | date = April 2021 | pmid = 33860184 | pmc = 8033766 | doi = 10.1021/acsptsci.1c00018 }}</ref><ref name=":1">{{cite journal | vauthors = Bender E | title = Finding medical value in mescaline | journal = Nature | volume = 609 | issue = 7929 | pages = S90–S91 | date = September 2022 | pmid = 36171368 | doi = 10.1038/d41586-022-02873-8 | bibcode = 2022Natur.609S..90B | s2cid = 252548055 | doi-access = }}</ref>

== Biosynthesis ==

Mescaline is [[biosynthesis|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.<ref>{{Cite book |title=Medicinal Natural Products: A Biosynthetic Approach | vauthors = Dewick PM |location=United Kingdom |publisher=John Wiley & Sons |pages=335–336 |year=2009 |isbn=978-0-471-49641-0 }}</ref>

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|''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 <small>L</small>-tyrosine by [[L-amino acid hydroxylase]]. Once converted, it follows the same pathway as described above.<ref name="10.1016/j.plantsci.2006.10.013"/><ref>{{cite journal | vauthors = Rosengarten H, Friedhoff AJ | title = A review of recent studies of the biosynthesis and excretion of hallucinogens formed by methylation of neurotransmitters or related substances | journal = Schizophrenia Bulletin | volume = 2 | issue = 1 | pages = 90–105 | year = 1976 | pmid = 779022 | doi = 10.1093/schbul/2.1.90 | doi-access = }}</ref>

:[[File:Mescaline biosynthetic pathways.svg|thumb|left|400px|Biosynthesis of mescaline]]{{clear left}}

===Laboratory synthesis===

[[File:Synthetic mescaline powder i2001e0151 ccby3.jpg|right|thumb|Laboratory synthetic mescaline biosynthesized from {{nowrap|peyote{{hsp}}{{mdash}}{{hsp}}}}this was the first psychedelic compound to be extracted and isolated<ref>{{cite web|url=https://www.mescaline.com/exp/|title=Mescaline : D M Turner|website=www.mescaline.com}}</ref>]]

[[File:Dried Peyote.jpg|thumb|250px|Dried Peyote (''Lophophora williamsii''), containing around 5-6% mescaline by weight]]

Mescaline was first synthesized in 1919 by [[Ernst Späth]] from 3,4,5-trimethoxy{{shy}}benzoyl chloride.<ref name = "Späth_1919" /> Subsequent to this, numerous approaches utilizing different starting materials have been developed. Notable examples include the following:

* [[Hofmann rearrangement]] of 3,4,5-trimethoxy{{shy}}phenyl{{shy}}propionamide.<ref>{{cite journal | vauthors = Slotta KH, Heller H |title=Über β-Phenyl-äthylamine, I. Mitteil.: Mezcalin und mezcalin-ähnliche Substanzen |journal= Berichte der Deutschen Chemischen Gesellschaft (A and B Series) |year=1930 |volume=63 |issue=11 |pages=3029–3044 |doi=10.1002/cber.19300631117 }}</ref>

* [[Cyanohydrin reaction]] between [[potassium cyanide]] and [[3,4,5-trimethoxybenzaldehyde|3,4,5-trimethoxy{{shy}}benz{{shy}}aldehyde]] followed by [[acetylation]] and [[Organic redox reaction|reduction]].<ref>{{cite journal| vauthors = Amos D |title= Preparation of Mescaline from Eucalypt Lignin|journal=Australian Journal of Pharmacy |date=1964 |volume=49 |page=529 |url=https://www.erowid.org/archive/rhodium/chemistry/mescalyptus.html}}</ref><ref>{{cite journal| vauthors = Kindler K, Peschke W |title=Über neue und über verbesserte Wege zum Aufbau von pharmakologisch wichtigen Aminen VI. Über Synthesen des Meskalins|journal=Archiv der Pharmazie|year=1932|volume=270|issue=7|pages=410–413|doi=10.1002/ardp.19322700709|s2cid=93188741 }}</ref>

* [[Henry reaction]] of 3,4,5-trimethoxy{{shy}}benz{{shy}}aldehyde with [[nitromethane]] followed by [[Reduction of nitro compounds|nitro compound reduction]] of ω-nitro{{shy}}trimethoxy{{shy}}styrene.<ref>{{cite journal| vauthors = Benington F, Morin R |title=An Improved Synthesis of Mescaline|journal=Journal of the American Chemical Society|year=1951|volume=73|issue=3|pages=1353|doi=10.1021/ja01147a505}}</ref><ref>{{cite book| vauthors = Shulgin A, Shulgin A |title=PiHKAL: A Chemical Love Story|year=1991|publisher=Transform Press|location=Lafayette, CA|isbn=9780963009609|page=703|url=https://books.google.com/books?id=O8AdHBGybpcC&q=9780963009609}}</ref><ref>{{cite journal| vauthors = Hahn G, Rumpf F |title=Über β-[Oxy-phenyl]-äthylamine und ihre Umwandlungen, V. Mitteil.: Kondensation von Oxyphenyl-äthylaminen mit α-Ketonsäuren|journal=Berichte der Deutschen Chemischen Gesellschaft (A and B Series)|year=1938|volume=71|issue=10|pages=2141–2153|doi=10.1002/cber.19380711022}}</ref><ref>{{cite journal| vauthors = Toshitaka O, Hiroaka A |title=Synthesis of Phenethylamine Derivatives as Hallucinogen|journal=Japanese Journal of Toxicology and Environmental Health|date=1992|volume=38|issue=6|pages=571–580|doi=10.1248/jhs1956.38.571 |url=https://nootropicsfrontline.com/wp-content/uploads/2021/07/wiki_ohshita1992.pdf |archive-url=https://ghostarchive.org/archive/20221009/https://nootropicsfrontline.com/wp-content/uploads/2021/07/wiki_ohshita1992.pdf |archive-date=2022-10-09 |url-status=live|access-date=20 June 2014|doi-access=free}}</ref><ref>{{cite journal| vauthors = Ramirez F, Erne M |title=Über die Reduktion von β-Nitrostyrolen mit Lithiumaluminiumhydrid|journal=Helvetica Chimica Acta|date=1950|volume=33|issue=4|pages=912–916|doi=10.1002/hlca.19500330420}}</ref><ref>{{cite journal| vauthors = Szyszka G, Slotta KH |title=Über β-Phenyl-äthylamine.III. Mitteilung: Neue Darstellung von Mescalin|journal=Journal für Praktische Chemie|date=1933|volume=137|issue=9–12|pages=339–350|doi=10.1002/prac.19331370907}}</ref><ref>{{cite journal| vauthors = Burger A, Ramirez FA |title=The Reduction of Phenolic β-Nitrostyrenes by Lithium Aluminum Hydride|journal=Journal of the American Chemical Society|date=1950|volume=72|issue=6|pages=2781–2782|doi=10.1021/ja01162a521}}</ref>

* [[Ozonolysis]] of [[elemicin]] followed by [[reductive amination]].<ref>{{cite journal| vauthors = Hahn G, Wassmuth H |title=Über β-[Oxyphenyl]-äthylamine und ihre Umwandlungen, I. Mitteil.: Synthese des Mezcalins|journal=Berichte der Deutschen Chemischen Gesellschaft (A and B Series)|year=1934|volume=67|issue=4|pages=696–708|doi=10.1002/cber.19340670430}}</ref>

* [[Carbonyl reduction#Ester reduction|Ester reduction]] of [[Eudesmic acid]]'s [[methyl group|methyl]] [[ester]] followed by [[halogenation]], [[Kolbe nitrile synthesis]], and [[nitrile reduction]].<ref name="Makepeace, Tsao 1951 5495–5496">{{cite journal| vauthors = Makepeace T |title=A New Synthesis of Mescaline|journal=Journal of the American Chemical Society|year=1951|volume=71|issue=11|pages=5495–5496|doi=10.1021/ja01155a562}}</ref><ref>{{cite journal| vauthors = Dornow A, Petsch G |title=Über die Darstellung des Oxymezcalins und Mezcalins 2. Mitteilung|journal=[[Archiv der Pharmazie]]|year=1952|volume=285|issue=7|pages=323–326|doi=10.1002/ardp.19522850704|s2cid=97553172 }}</ref><ref>{{cite book| vauthors = Ikan R |title=Natural Products: A Laboratory Guide 2nd Ed|year=1991|publisher=Academic Press, Inc.|location=San Diego|isbn=978-0123705518|pages=232–235|url=https://books.google.com/books?id=B7P8HQimBAIC&pg=PA243}}</ref>

* [[Amide reduction]] of 3,4,5-trimethoxy{{shy}}phenyl{{shy}}acetamide.<ref>{{cite journal| vauthors = Banholzer K, Campbell TW, Schmid H |title=Notiz über eine neue Synthese von Mezcalin, N-Methyl- und N-Dimethylmezcalin|journal=Helvetica Chimica Acta|date=1952|volume=35|issue=5|pages=1577–1581|doi=10.1002/hlca.19520350519}}</ref>

*Reduction of 3,4,5-trimethoxy{{shy}}(2-nitrovinyl)benzene with lithium aluminum hydride.<ref name = "Kovacic_2009" />

* Treatment of tricarbonyl-(η6-1,2,3-trimethoxy{{shy}}benzene) chromium complex with acetonitrile carbanion in [[Tetrahydrofuran|THF]] and iodine, followed by reduction of the nitrile with lithium aluminum hydride.<ref name="Makepeace, Tsao 1951 5495–5496"/>

==Pharmacokinetics==

[[Drug tolerance|Tolerance]] builds with repeated usage, lasting for a few days. Mescaline causes cross-tolerance with other [[serotonergic psychedelics]] such as [[lysergic acid diethylamide|LSD]] and [[psilocybin]].<ref>{{Cite web |url=http://www.erowid.org/archive/rhodium/chemistry/psychedelicchemistry/chapter1.html |title=Psychedelics and Society | vauthors = Smith MV |publisher=Erowid.org |access-date=6 April 2012 }}</ref>

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]]<ref name="pmid9264312">{{cite journal | vauthors = Wu D, Otton SV, Inaba T, Kalow W, Sellers EM | title = Interactions of amphetamine analogs with human liver CYP2D6 | journal = Biochemical Pharmacology | volume = 53 | issue = 11 | pages = 1605–1612 | date = June 1997 | pmid = 9264312 | doi = 10.1016/S0006-2952(97)00014-2 }}</ref> 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.<ref name="pmid14814616">{{cite journal | vauthors = Cochin J, Woods LA, Seevers MH | title = The absorption, distribution and urinary excretion of mescaline in the dog | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 101 | issue = 2 | pages = 205–209 | date = February 1951 | pmid = 14814616 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=14814616 }}</ref> The [[Median lethal dose|LD₅₀]] of mescaline has been measured in various animals: 212&nbsp;mg/kg i.p. (mice), 132&nbsp;mg/kg i.p. (rats), and 328&nbsp;mg/kg i.p. (guinea pigs). For humans, the [[median lethal dose|LD₅₀]] of mescaline has been reported to be approximately 880&nbsp;mg/kg.<ref>{{cite journal|vauthors=Buckingham J|title=Mescaline|journal=Dictionary of Natural Products|pages=254–260|date=2014 }}</ref>

== Behavioral and non-behavioral effects ==

Mescaline induces a [[Psychedelic experience|psychedelic state]] comparable to those produced by [[LSD]] and [[psilocybin]], but with unique characteristics.<ref name=":1" /> Subjective effects may include altered thinking processes, an altered sense of time and self-awareness, and closed- and open-eye visual phenomena.<ref name = "Kovacic_2009">{{cite journal | vauthors = Kovacic P, Somanathan R | title = Novel, unifying mechanism for mescaline in the central nervous system: electrochemistry, catechol redox metabolite, receptor, cell signaling and structure activity relationships | journal = Oxidative Medicine and Cellular Longevity | volume = 2 | issue = 4 | pages = 181–190 | date = 1 January 2009 | pmid = 20716904 | pmc = 2763256 | doi = 10.4161/oxim.2.4.9380 }}</ref>

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 [[Kaleidoscope|kaleidoscopic]] experiences but they manifest more clearly with [[Closed-eye hallucination|eyes closed]] and under low lighting conditions.<ref>{{Cite book| vauthors = Freye E |title=Pharmacology and Abuse of Cocaine, Amphetamines, Ecstasy and Related Designer Drugs: A Comprehensive Review on their Mode of Action, Treatment of Abuse and Intoxication|collaboration=Joseph V. Levy|publisher=Springer Science & Business Media|year=2009|isbn=978-90-481-2447-3|pages=227}}</ref>

[[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."<ref>{{Cite book |title=A Dictionary of Hallucations |location=Oradell, NJ. |publisher=Springer |year=2010|pages=102}}</ref>

As with LSD, [[synesthesia]] can occur especially with the help of music.<ref name="Diaz">{{Cite book |title=How Drugs Influence Behavior | vauthors = Diaz J |location=Englewood Cliffs |publisher=Prentice Hall |year=1996 |isbn=978-0-02-328764-0 }}</ref> 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 [[Cubism|Cubist]] painting.<ref>{{Cite book |title=Drugs of Abuse |location=Oradell, NJ. |publisher=Medical Economics Books |year=1989 |pages=207–239 |isbn=978-0-87489-499-8 | vauthors = Giannini AJ, Slaby AE }}</ref>

Mescaline elicits a pattern of sympathetic arousal, with the [[peripheral nervous system]] being a major target for this substance.<ref name="Diaz"/>

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.<ref>{{Cite journal | vauthors = Bohn A, Kiggen MH, Uthaug MV, van Oorsouw KI, Ramaekers JG, van Schie HT |date=2022-12-05 |title=Altered States of Consciousness During Ceremonial San Pedro Use |journal=The International Journal for the Psychology of Religion |language=en |volume=33 |issue=4 |pages=309–331 |doi=10.1080/10508619.2022.2139502 |issn=1050-8619|doi-access=free |hdl=2066/285968 |hdl-access=free }}</ref>

== Mechanism of action ==

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 [[antioxidant]]s, 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.<ref name="10.1016/j.plantsci.2006.10.013">{{cite journal |title=Catecholamies are active compounds in plants |date=March 2007 |journal=Plant Science |volume=172 |issue=3 |pages=433–440 |doi=10.1016/j.plantsci.2006.10.013 | vauthors = Kulma A, Szopa J }}</ref>

In humans, mescaline acts similarly to other psychedelic agents.<ref name="pmid14761703">{{cite journal | vauthors = Nichols DE | title = Hallucinogens | journal = Pharmacology & Therapeutics | volume = 101 | issue = 2 | pages = 131–181 | date = February 2004 | pmid = 14761703 | doi = 10.1016/j.pharmthera.2003.11.002 }}</ref> It acts as an agonist,<ref name="pmid2707301">{{cite journal | vauthors = Appel JB, Callahan PM | title = Involvement of 5-HT receptor subtypes in the discriminative stimulus properties of mescaline | journal = European Journal of Pharmacology | volume = 159 | issue = 1 | pages = 41–46 | date = January 1989 | pmid = 2707301 | doi = 10.1016/0014-2999(89)90041-1 }}</ref> binding to and activating the [[serotonin]] [[5-HT2A receptor|5-HT_2A receptor]] with a high [[affinity (pharmacology)|affinity]].<ref name="pmid9301661">{{cite journal | vauthors = Monte AP, Waldman SR, Marona-Lewicka D, Wainscott DB, Nelson DL, Sanders-Bush E, Nichols DE | title = Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives | journal = Journal of Medicinal Chemistry | volume = 40 | issue = 19 | pages = 2997–3008 | date = September 1997 | pmid = 9301661 | doi = 10.1021/jm970219x | citeseerx = 10.1.1.690.9370 }}</ref> How activating the 5-HT_2A receptor leads to psychedelia is still unknown, but it is likely that somehow it involves excitation of neurons in the [[prefrontal cortex]].<ref name="pmid17535909">{{cite journal | vauthors = Béïque JC, Imad M, Mladenovic L, Gingrich JA, Andrade R | title = Mechanism of the 5-hydroxytryptamine 2A receptor-mediated facilitation of synaptic activity in prefrontal cortex | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 104 | issue = 23 | pages = 9870–9875 | date = June 2007 | pmid = 17535909 | pmc = 1887564 | doi = 10.1073/pnas.0700436104 | doi-access = free | bibcode = 2007PNAS..104.9870B }}</ref> Mescaline is also known to have even greater [[Ligand (biochemistry)|binding affinity]] for the serotonin [[5-HT2C receptor|5-HT_2C receptor]].<ref>{{Cite web |url=http://www.erowid.org/psychoactives/pharmacology/pharmacology_article1.shtml |title=Neuropharmacology of Hallucinogens |publisher=Erowid.org |date=27 March 2009 |access-date=7 September 2011 }}</ref>

{| class="wikitable"

|-

! Binding sites

! Binding affinity Ki (μM)<ref name="pmid27216487">{{cite journal | vauthors = Rickli A, Moning OD, Hoener MC, Liechti ME | title = Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens | journal = European Neuropsychopharmacology | volume = 26 | issue = 8 | pages = 1327–1337 | date = August 2016 | pmid = 27216487 | doi = 10.1016/j.euroneuro.2016.05.001 | s2cid = 6685927 | url = http://edoc.unibas.ch/53326/1/20170117174852_587e4af45b658.pdf }}</ref>

|-

| 5-HT_1A

| 4.6

|-

| 5-HT_2A

| 6.3

|-

| 5-HT_2C

| 17

|-

| α_1A

| >15

|-

| α_2A

| 1.4

|-

| TAAR₁

| 3.3

|}

Difluoro{{shy}}mescaline and [[Trifluoromescaline|trifluoro{{shy}}mescaline]] are more potent than mescaline, as is its amphetamine [[Homologous series|homologue]] [[Trimethoxyamphetamine|trimethoxy{{shy}}amphetamine]].<ref>{{cite journal | vauthors = Trachsel D | title = Fluorine in psychedelic phenethylamines | journal = Drug Testing and Analysis | volume = 4 | issue = 7–8 | pages = 577–590 | year = 2012 | pmid = 22374819 | doi = 10.1002/dta.413 | url = http://bitnest.ca/external.php?id=%257DbxUgXXCNAUj%257E%257E%2507 | url-status = dead | archive-url = https://web.archive.org/web/20130603150127/http://bitnest.ca/external.php?id=%257DbxUgXXCNAUj%257E%257E%2507 | archive-date = 2013-06-03 }}</ref><ref>{{Cite web | vauthors = Shulgin A |title=#157 TMA - 3,4,5-TRIMETHOXYAMPHETAMINE |url=https://www.erowid.org/library/books_online/pihkal/pihkal157.shtml |work=PiHKAL: A Chemical Love Story |publisher=Erowid.org |access-date=9 January 2013 }}</ref> [[Escaline]] and [[proscaline]] are also both more potent than mescaline, showing the importance of the 4-position substituent with regard to receptor binding.<ref name="pmid3952123">{{cite journal | vauthors = Nichols DE | title = Studies of the relationship between molecular structure and hallucinogenic activity | journal = Pharmacology, Biochemistry, and Behavior | volume = 24 | issue = 2 | pages = 335–340 | date = February 1986 | pmid = 3952123 | doi = 10.1016/0091-3057(86)90362-x | s2cid = 30796368 }}</ref>

== Legality ==

=== United States ===

In the United States, mescaline was made illegal in 1970 by the [[Controlled Substances Act|Comprehensive Drug Abuse Prevention and Control Act]], categorized as a Schedule I hallucinogen.<ref>{{cite web |url=http://www.usdoj.gov/dea/pubs/scheduling.html |title=Drug Scheduling |access-date=2 November 2007 |author=United States Department of Justice |author-link=United States Department of Justice |archive-url=https://web.archive.org/web/20081020210309/http://www.usdoj.gov/dea/pubs/scheduling.html |archive-date=20 October 2008 |url-status=dead}}</ref> The drug is prohibited internationally by the 1971 [[Convention on Psychotropic Substances]].<ref>{{cite web|url=http://www.incb.org/pdf/e/list/green.pdf |title=List of psychotropic substances under international control |publisher=[[International Narcotics Control Board]] |access-date=27 January 2008 |url-status=dead |archive-url=https://web.archive.org/web/20051205125434/http://www.incb.org/pdf/e/list/green.pdf |archive-date=5 December 2005 }}</ref> 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 of the United States|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|date=August 2018}} Many states, including the state of [[Utah]], have legalized peyote usage with "sincere religious intent", or within a religious organization,{{Citation needed|date=October 2012}} regardless of race.<ref>{{cite web |url=http://www.utcourts.gov/opinions/supopin/mooney062204.htm |title=State v. Mooney |publisher=utcourts.gov |access-date=5 October 2012}}</ref> Synthetic mescaline, but not mescaline derived from cacti, was officially decriminalized in the state of Colorado by ballot measure Proposition 122 in November 2022.<ref>{{cite web | url=https://ballotpedia.org/Colorado_Proposition_122,_Decriminalization_and_Regulated_Access_Program_for_Certain_Psychedelic_Plants_and_Fungi_Initiative_(2022) | title=Colorado Proposition 122, Decriminalization and Regulated Access Program for Certain Psychedelic Plants and Fungi Initiative (2022) }}</ref>

While mescaline-containing cacti of the genus ''[[Echinopsis]]'' are technically controlled substances under the [[Controlled Substances Act]], they are commonly sold publicly as [[ornamental plant]]s.<ref>{{cite book | vauthors = Gupta RC |title=Veterinary Toxicology: Basic and Clinical Principles |date=2018 |publisher=Academic Press |isbn=9780123704672 |pages=363–390 |edition=Third }}</ref>

=== 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.<ref>{{Cite web |url=http://www.erowid.org/plants/cacti/cacti_law2.shtml |title=2007 U.K. Trichocereus Cacti Legal Case Regina v. Saul Sette |publisher=Erowid.org |date=June 2007 |access-date=6 April 2012 }}</ref>

=== Australia ===

Mescaline is considered a schedule 9 substance in Australia under the [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard (February 2020)]].<ref name="Poisons Stanrard">[https://www.legislation.gov.au/Details/F2020C00148 Poisons Standard February 2020]. comlaw.gov.au</ref> 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."<ref name="Poisons Stanrard" />

=== 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.<ref name=Bib/> In Canada, mescaline is classified as a schedule III drug under the [[Controlled Drugs and Substances Act]], whereas peyote is exempt.<ref>{{cite web |url=http://laws-lois.justice.gc.ca/Search/Search.aspx?txtS3archA11=mescaline&txtT1tl3=%22Controlled+Drugs+and+Substances+Act%22&h1ts0n1y=0&ddC0nt3ntTyp3=Acts. |title=Justice Laws Search |publisher=laws-lois.justice.gc.ca |access-date=5 October 2012}}</ref>

In Russia mescaline, its derivatives and mescaline-containing plants are banned as narcotic drugs (Schedule I).<ref>{{cite web|url=http://base.garant.ru/12112176/|title=Постановление Правительства РФ от 30.06.1998 N 681 "Об утверждении перечня наркотических средств, психотропных веществ и их прекурсоров, подлежащих контролю в Российской Федерации" (с изменениями и дополнениями) - ГАРАНТ|website=base.garant.ru}}</ref>

{{See also|Legal status of psychoactive cactus by country}}

== Notable users ==

* [[Antonin Artaud]] wrote 1947's ''The Peyote Dance'', where he describes his peyote experiences in Mexico a decade earlier.<ref>{{Cite magazine | vauthors = Doyle P |date=2019-05-20 |title=Patti Smith Channels French Poet Antonin Artaud on Peyote |url=https://www.rollingstone.com/music/music-news/watch-patti-smith-channel-french-poet-antonin-artaud-on-peyote-837533/ |access-date=2022-04-03 |magazine=Rolling Stone |language=en-US}}</ref>

* [[Jerry Garcia]] took peyote prior to forming [[The Grateful Dead]] but later switched to [[LSD]] and [[N,N-Dimethyltryptamine|DMT]] since they were easier on the stomach.

* [[Allen Ginsberg]] took peyote. Part II of his poem "Howl" was inspired by a peyote vision that he had in San Francisco.<ref>{{Cite magazine |date=1968-08-10 |title=The Father of Flower Power |url=http://www.newyorker.com/magazine/1968/08/17/paterfamilias-i |access-date=2022-04-03 |magazine=The New Yorker |language=en-US}}</ref>

* [[Ken Kesey]] took peyote prior to writing ''[[One Flew Over the Cuckoo's Nest (novel)|One Flew Over the Cuckoo's Nest]]''.

* [[Jean-Paul Sartre]] took mescaline shortly before the publication of his first book, ''[[The Imaginary (Sartre)|L'Imaginaire]]''; he had a bad trip during which he imagined that he was menaced by sea creatures. For many years following this, he persistently thought that he was being followed by lobsters, and became a patient of [[Jacques Lacan]] in hopes of being rid of them. Lobsters and crabs figure in his novel ''[[Nausea (novel)|Nausea]]''.

* [[Havelock Ellis]] was the author of one of the first written reports to the public about an experience with mescaline (1898).<ref>{{cite book | chapter-url = https://archive.org/stream/contemporaryrev23unkngoog#page/n142/mode/2up | vauthors = Ellis H | chapter = Mescal: A New Artificial Paradise | title = The Contemporary Review | volume = LXXIII | date = 1898 }}</ref><ref name =rudgley1993>{{cite book| vauthors = Rudgley R | date=1993 | title=The Alchemy of Culture: Intoxicants in Society |chapter=VI | publisher=British Museum Press | isbn=978-0-7141-1736-2}}</ref><ref>{{cite book | vauthors = Giannini AJ |title=Drugs of Abuse |edition=Second |location=Los Angeles |publisher=Practice Management Information Corp |year=1997 |isbn=978-1-57066-053-5 }}</ref>

*[[Stanisław Ignacy Witkiewicz]], Polish writer, artist and philosopher, experimented with mescaline and described his experience in a 1932 book ''Nikotyna Alkohol Kokaina Peyotl Morfina Eter''.<ref name="Witkiewicz">{{cite book | vauthors = Witkiewicz SI, Biczysko S | title = Nikotyna, alkohol, kokaina, peyotl, morfina, eter+ appendix. | date = 1932 | location = Warsaw | publisher = Drukarnia Towarzystwa Polskiej Macierzy Szkolnej | url = https://pl.wikisource.org/wiki/Nikotyna_Alkohol_Kokaina_Peyotl_Morfina_Eter_%2B_Appendix}}</ref>

* [[Aldous Huxley]] described his experience with mescaline in the essay "[[The Doors of Perception]]" (1954).

* [[Jim Carroll]] in ''[[The Basketball Diaries (book)|The Basketball Diaries]]'' described using peyote that a friend smuggled from Mexico.

* [[Hunter S. Thompson]] wrote an extremely detailed account of his first use of mescaline in "First Visit with Mescalito", and it appeared in his book ''[[Songs of the Doomed]]'', as well as featuring heavily in his novel ''[[Fear and Loathing in Las Vegas]]''.

* Psychedelic research pioneer [[Alexander Shulgin]] said he was first inspired to explore psychedelic compounds by a mescaline experience.<ref>{{Cite web |title=Alexander Shulgin: why I discover psychedelic substances |year=1996 |work=Luc Sala interview |url=https://www.youtube.com/watch?v=QD260LPqHKA&t=3m18s |archive-url=https://ghostarchive.org/varchive/youtube/20211211/QD260LPqHKA| archive-date=2021-12-11 |url-status=live|location=Mexico }}{{cbignore}}</ref> In 1974, Shulgin synthesized [[2C-B]], a psychedelic phenylethylamine derivative, structurally similar to mescaline,<ref>{{cite journal | vauthors = Papaseit E, Farré M, Pérez-Mañá C, Torrens M, Ventura M, Pujadas M, de la Torre R, González D | title = Acute Pharmacological Effects of 2C-B in Humans: An Observational Study | language = English | journal = Frontiers in Pharmacology | volume = 9 | pages = 206 | date = 2018 | pmid = 29593537 | pmc = 5859368 | doi = 10.3389/fphar.2018.00206 | doi-access = free }}</ref> and one of Shulgin's self-rated most important phenethylamine compounds together with Mescaline, [[2C-E]], [[2C-T-7]], and [[2C-T-2]].<ref>{{Cite web |date=2019-12-02 |title=Mescaline |url=https://psychedelicreview.com/compound/mescaline/ |access-date=2023-10-30 |website=Psychedelic Science Review |language=en-US}}</ref>

* [[Bryan Wynter]] produced ''Mars Ascends'' after trying the substance for the first time.<ref>{{cite book | vauthors = Bird M | title = 100 Ideas that Changed Art. | location = London | publisher = Laurence King Publishing | date = 2012 }}</ref>

* [[George Carlin]] mentioned mescaline use during his youth while being interviewed in 2008.<ref>{{cite web | vauthors = Dixit J |date=23 June 2008 |title=George Carlin's Last Interview |work=Psychology Today |url=http://www.psychologytoday.com/blog/brainstorm/200806/george-carlins-last-interview?page=4}}</ref>

* [[Carlos Santana]] told about his mescaline use in a 1989 ''[[Rolling Stone]]'' interview.<ref>{{cite magazine | vauthors = Greene A | title = Dazed and Confused: 10 Classic Drugged-Out Shows | magazine = Rolling Stone | date = 1989 | url = https://www.rollingstone.com/music/pictures/10-classic-drugged-out-performances-from-santana-to-green-day-20130606/1-santana-at-woodstock-1969-mescaline-0973315 | quote = Santana at Woodstock, 1969 - Mescaline }}</ref>

* Disney animator [[Ward Kimball]] described participating in a study of mescaline and peyote conducted by [[University of California, Los Angeles|UCLA]] in the 1960s.<ref>{{cite web |url=http://cartoonician.com/ward-kimballs-final-farewell/ |title=Ward Kimball's Final Farewell |date=4 March 2016 |publisher=cartoonician.com |access-date=4 March 2016|archive-url=https://web.archive.org/web/20160306095332/http://cartoonician.com/ward-kimballs-final-farewell/|archive-date=6 March 2016|url-status=dead}}</ref>

* [[Michael Cera]] used real mescaline for the movie ''[[Crystal Fairy & the Magical Cactus]]'', as expressed in an interview.<ref>{{cite news| url=http://www.huffingtonpost.com/2013/07/10/michael-cera-drugs-mescaline-crystal-fairy_n_3575056.html | work=Huffington Post | vauthors = Boardman M | title=Michael Cera Took Drugs On-Camera | date=10 July 2013}}</ref>

* [[Philip K. Dick]] was inspired to write ''[[Flow My Tears, the Policeman Said]]'' after taking mescaline.<ref>{{Cite web|url=http://www.philipkdickfans.com/mirror/websites/pkdweb/FLOW%20MY%20TEARS.HTM|title=FLOW MY TEARS |publisher=www.philipkdickfans.com|access-date=2018-05-04}}</ref>

* [[Arthur Kleps]], a psychologist turned drug legalization advocate and writer whose Neo-American Church defended use of marijuana and hallucinogens such as LSD and peyote for spiritual enlightenment and exploration, bought, in 1960, by mail from Delta Chemical Company in New York 1 g of mescaline sulfate and took 500&nbsp;mg. He experienced a psychedelic trip that caused profound changes in his life and outlook.

== See also ==

* [[List of psychedelic plants]]

* [[Methallylescaline]]

* [[Psychedelic experience]]

* [[Psychoactive drug]]

* [[Entheogen]]

* ''[[The Doors of Perception]]''

** [[Mind at Large]] (concept in ''The Doors of Perception'')

* ''[[The Psychedelic Experience: A Manual Based on the Tibetan Book of the Dead]]''

== References ==

{{Reflist|30em}}

== Further reading ==

{{refbegin}}

* {{cite book | vauthors = Jay M | date = 2019 | title = Mescaline: A Global History of the First Psychedelic | publisher = Yale University Press }}

* {{cite book | vauthors = Klüver H | author-link = Heinrich Klüver | date = 1942 | chapter = Mechanisms of hallucinations. | veditors = [[Quinn McNemar|McNemar Q]], Merrill MA | title = Studies in personality | pages = 175–207 | publisher = McGraw-Hill | chapter-url = https://maps.org/research-archive/psychedelicreview/n07/n07041klu.pdf }}

* {{cite book | vauthors = Pollan M | author-link = Michael Pollan | date = 2021 | title = This Is Your Mind on Plants | publisher = Penguin Press | isbn = 9780593296905 }}

{{refend}}

== External links ==

{{Commons}}

* [https://web.archive.org/web/20090326163130/http://drugabuse.gov/Infofacts/hallucinogens.html National Institutes of Health – National Institute on Drug Abuse Hallucinogen InfoFacts]

* [http://www.erowid.org/chemicals/mescaline/mescaline.shtml Mescaline] at [[Erowid]]

* [https://psychonautwiki.org/wiki/Mescaline Mescaline] at PsychonautWiki

* [http://www.erowid.org/library/books_online/pihkal/pihkal096.shtml PiHKAL entry]

* [http://pihkal.info/read.php?domain=pk&id=96 Mescaline entry in PiHKAL • info]

* {{YouTube|Hd4rgyZzseY|Film of Christopher Mayhew's mescaline experiment}}

* [https://web.archive.org/web/20060215094333/http://diseyes.lycaeum.org/cact/final.htm Mescaline: The Chemistry and Pharmacology of its Analogs], an essay by [[Alexander Shulgin]]

* [http://www.houstonpress.com/2008-02-14/news/mescaline-on-the-mexican-border/ Mescaline on the Mexican Border]

{{Hallucinogens}}

{{Serotonergics}}

{{Phenethylamines}}

[[Category:Alkaloids found in Fabaceae]]

[[Category:Cacti]]

[[Category:Entheogens]]

[[Category:Mescalines]]

[[Category:Native American Church]]

[[Category:Phenethylamine alkaloids]]

[[Category:Serotonin receptor agonists]]