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Not to be confused with mezcal or mesclun.
Mescaline Structural Formula.svg
Clinical data
AHFS/ mescaline
  • US: C (Risk not ruled out)
Routes of
Oral, intravenous
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Biological half-life 6 hours
Synonyms 3,4,5-trimethoxyphenethylamine
CAS Number
PubChem CID
ECHA InfoCard 100.000.174
Chemical and physical data
Formula C11H17NO3
Molar mass 211.257 g/mol
3D model (Jmol)
Boiling point 180 °C (356 °F)


It occurs naturally in the peyote cactus (Lophophora williamsii),[1] the San Pedro cactus (Echinopsis pachanoi),[2] the Peruvian torch (Echinopsis peruviana),[3] and in a number of other members of the Cactaceae plant family. It is also found in small amounts in certain members of the Fabaceae (bean) family, including Acacia berlandieri.[4]

History and use[edit]





Potential medical usage[edit]


Notable users[edit]

Biosynthesis of mescaline[edit]

Mescaline biosynthetic pathways.svg

Mescaline is biosynthesized from tyrosine or a hydroxylated phenylalanine. In Lophophora williamsii (Peyote), dopamine converts into mescaline in a biosynthetic pathway involving m-O-methylation and aromatic hydroxylation.[23]



Synthetic mescaline[edit]


Mescaline was first synthesized in 1919 by Ernst Späth from 3,4,5-trimethoxybenzoyl chloride.[27] Subsequent to this, numerous approaches utilizing different starting materials have been developed. Notable examples include the following:



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 to not be subject to metabolism by CYP2D6[44] and between 20% and 50% of mescaline is excreted in the urine unchanged, and the rest being excreted as the carboxylic acid form of mescaline, a likely result of MAO degradation.[45] 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).

Behavioral and non-behavioral effects[edit]


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. Aldous Huxley described these self-transforming amorphous shapes as like animated stained glass illuminated from light coming through the eyelids. Like LSD, mescaline induces distortions of form and kaleidoscopic experiences but they manifest more clearly with eyes closed and under low lighting conditions.[citation needed]

As with LSD, synesthesia can occur especially with the help of music.[47] An unusual but unique characteristic of mescaline use is the "geometricization" of three-dimensional objects. The object can appear flattened and distorted, similar to the presentation of a Cubist painting.[48]

Mescaline elicits a pattern of sympathetic arousal, with the peripheral nervous system being a major target for this substance.[47] Effects typically begin a while after ingestion, and may last a long time depending on dosage.

Mechanism of action[edit]


Mescaline acts similarly to other psychedelic agents.[49] It binds to and activates the serotonin 5-HT2A receptor with a high affinity.[50] How activating the 5-HT2A receptor leads to psychedelia is still unknown, but it is likely that somehow it involves excitation of neurons in the prefrontal cortex.[51] Mescaline is also known to bind to and activate the serotonin 5-HT2C receptor.[52]

Difluoromescaline and trifluoromescaline are more potent than mescaline, as is its amphetamine homologue trimethoxyamphetamine.[53][54]


United States[edit]

In the United States, mescaline was made illegal in 1970 by the Comprehensive Drug Abuse Prevention and Control Act.[55] The drug was prohibited internationally by the 1971 Convention on Psychotropic Substances[56] and is categorized as a Schedule I hallucinogen by the CSA. Mescaline is legal only for certain religious groups (such as the Native American Church) and in scientific and medical research. In 1990, the Supreme Court ruled that the state of Oregon could bar 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. However, in a subsequent case, the Court held that the government had not carried the burden under the Religious Freedom Restoration Act of showing a compelling interest that allowed no exception to the ban on the use of the drug to accommodate a sincere religious practice.[57] Thus, the current state of the law is that, while the federal government may not restrict use of peyote in ceremony, individual states do have a right to restrict its use.[58] 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.[59]


United Kingdom[edit]


Other countries[edit]

Mescaline is considered a schedule 9 substance in Australia under the Poisons Standard (October 2015).[61] 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." [61]

The peyote cacti and other mescaline-containing plants such as San Pedro are illegal in Western Australia, Queensland, and the Northern Territory, whilst in other states such as Tasmania, Victoria and New South Wales, they are legal for ornamental and gardening purposes.

In Canada, France, The Netherlands and Germany, mescaline in raw form and dried mescaline-containing cacti are considered an illegal drug. 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.[1] In Canada, mescaline is classified as a schedule III drug under the Controlled Drugs and Substances Act, whereas peyote is exempt.[62]

In Russia mescaline, its derivatives and mescaline-containing plants are banned as narcotic drugs (Schedule I).[63]

See also[edit]


  3. ^ Ogunbodede, Olabode; McCombs, Douglas; Trout, Keeper; Daley, Paul; Terry, Martin (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): 356–362. doi:10.1016/j.jep.2010.07.021. 
  4. ^ Forbes, T.D.A.; Clement, B.A. "Chemistry of Acacia's from South Texas" (PDF). Texas A&M Agricultural Research & Extension Center at Uvalde. Archived from the original (PDF) on 2012. 
  5. ^ El-Seedi HR, De Smet PA, Beck O, Possnert G, Bruhn JG (October 2005). "Prehistoric peyote use: alkaloid analysis and radiocarbon dating of archaeological specimens of Lophophora from Texas" (PDF). J Ethnopharmacol. 101 (1–3): 238–42. doi:10.1016/j.jep.2005.04.022. PMID 15990261. 
  7. ^ Giannini, AJ; Slaby, AE; Giannini, MC (1982). Handbook of Overdose and Detoxification Emergencies. New Hyde Park, NY.: Medical Examination Publishing Company. ISBN 978-0-87488-182-0. 
  8. ^ "Arthur Heffter". Character Vaults. Retrieved 9 January 2013. 
  9. ^ Manske, R. H. F.; Holmes, H. L., eds. (1953). "Mescaline (3,4,5-Trimethoxyphenethylamine)". The Alkaloids. 3. Academic Press. pp. 324–328. 
  14. ^ Giannini, A James (1997). Drugs of Abuse (Second ed.). Los Angeles: Practice Management Information Corp. ISBN 1-57066-053-0. 
  17. ^ Dixit, Jay (23 June 2008). "George Carlin's Last Interview". Psychology Today. 
  18. ^ Rolling Stone 1989, Santana at Woodstock
  19. ^ Ward Kimball's Final Farewell, Hogan's Alley #11
  22. ^ "When Sartre Talked to Crabs (It Was Mescaline)". The New York Times. 2009-11-14. ISSN 0362-4331. Retrieved 2016-11-11. 
  24. ^ a b Kulma, Anna; Szopa, Jan (March 2007). "Catecholamies are active compounds in plants". Plant Science. 172 (3): 433–440. doi:10.1016/j.plantsci.2006.10.013. 
  25. ^ Rosengarten, H; Friedhoff, A. J. (1976). "A review of recent studies of the biosynthesis and excretion of hallucinogens formed by methylation of neurotransmitters or related substances". Schizophrenia Bulletin. 2 (1): 90–105. doi:10.1093/schbul/2.1.90. PMID 779022. 
  26. ^ Mescaline, Peyote, San Pedro Cactus
  27. ^ Späth, Ernst (1919). "Über dieAnhalonium-Alkaloide". Monatshefte für Chemie und verwandte Teile anderer Wissenschaften. 40 (2): 129–154. doi:10.1007/BF01524590. 
  28. ^ Slotta, K. H.; Heller, H. (1930). "Über β-Phenyl-äthylamine, I. Mitteil.: Mezcalin und mezcalin-ähnliche Substanzen". Berichte der deutschen chemischen Gesellschaft (A and B Series). 63 (11): 3029–3044. doi:10.1002/cber.19300631117. 
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  30. ^ Kindler, Karl; Peschke, Wilhelm (1932). "Über neue und über verbesserte Wege zum Aufbau von pharmakologisch wichtigen Aminen VI. Über Synthesen des Meskalins". Archiv der Pharmazie. 270 (7): 410–413. doi:10.1002/ardp.19322700709. 
  31. ^ Benington, Fred; Morin, Richard (1951). "An Improved Synthesis of Mescaline". Journal of the American Chemical Society. 73 (3): 1353–1353. doi:10.1021/ja01147a505. 
  32. ^ Shulgin, Alexander; Shulgin, Ann (1991). PiHKAL: A Chemical Love Story. Lafayette, CA: Transform Press. p. 703. ISBN 9780963009609. 
  33. ^ Hahn, Georg; Rumpf, Fritz (1938). "Über β-[Oxy-phenyl]-äthylamine und ihre Umwandlungen, V. Mitteil.: Kondensation von Oxyphenyl-äthylaminen mit α-Ketonsäuren". Berichte der deutschen chemischen Gesellschaft (A and B Series). 71 (10): 2141–2153. doi:10.1002/cber.19380711022. 
  35. ^ Ramirez, F.; Erne, Max (1950). "Über die Reduktion von β-Nitrostyrolen mit Lithiumaluminiumhydrid". Helvetica Chimica Acta. 33 (4): 912–916. doi:10.1002/hlca.19500330420. 
  36. ^ Szyszka, G.; Slotta, K. H. (1933). "Über β-Phenyl-äthylamine.III. Mitteilung: Neue Darstellung von Mescalin". Journal für Praktische Chemie. 137 (9–12): 339–350. doi:10.1002/prac.19331370907. 
  37. ^ Burger, Alfred; Ramirez, Fausto A. (1950). "The Reduction of Phenolic β-Nitrostyrenes by Lithium Aluminum Hydride". Journal of the American Chemical Society. 72 (6): 2781–2782. doi:10.1021/ja01162a521. 
  38. ^ Hahn, Georg; Wassmuth, Heinrich (1934). "Über β-[Oxyphenyl]-äthylamine und ihre Umwandlungen, I. Mitteil.: Synthese des Mezcalins". Berichte der deutschen chemischen Gesellschaft (A and B Series). 67 (4): 696–708. doi:10.1002/cber.19340670430. 
  39. ^ Makepeace, Tsao (1951). "A New Synthesis of Mescaline". Journal of the American Chemical Society. 71 (11): 5495–5496. doi:10.1021/ja01155a562. 
  40. ^ Dornow, Alfred; Petsch, Günther (1952). "Über die Darstellung des Oxymezcalins und Mezcalins 2. Mitteilung". Archiv der Pharmazie. 285 (7): 323–326. doi:10.1002/ardp.19522850704. 
  42. ^ Banholzer, K.; Campbell, Tod W.; Schmid, H. (1952). "Notiz über eine neue Synthese von Mezcalin, N-Methyl- und N-Dimethylmezcalin". Helvetica Chimica Acta. 35 (5): 1577–1581. doi:10.1002/hlca.19520350519. 
  43. ^ Smith, Michael Valentine. "Psychedelics and Society". Retrieved 6 April 2012. 
  46. ^ Kovacic, Peter; Somanathan, Ratnasamy (1 January 2009). "Novel, unifying mechanism for mescaline in the central nervous system". Oxidative Medicine and Cellular Longevity. 2 (4): 181–190. doi:10.4161/oxim.2.4.9380. ISSN 1942-0900. 
  48. ^ Giannini, A. James; Slaby, Andrew E. (1989). Drugs of Abuse. Oradell, NJ.: Medical Economics Books. pp. 207–239. ISBN 978-0-87489-499-8. 
  50. ^ Monte AP, Waldman SR, Marona-Lewicka D, et al. (September 1997). "Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives". J. Med. Chem. 40 (19): 2997–3008. doi:10.1021/jm970219x. PMID 9301661. 
  52. ^ "Neuropharmacology of Hallucinogens". 27 March 2009. Retrieved 7 September 2011. 
  59. ^ "State v. Mooney". Retrieved 5 October 2012. 
  61. ^ a b Poisons Standard October 2015.
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  63. ^

External links[edit]