Mescaline

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Summary sheet: Mescaline
Mescaline
Mescaline.svg
Chemical Nomenclature
Common names Mescaline
Substitutive name 3,4,5-Trimethoxyphenethylamine
Systematic name 2-(3,4,5-Trimethoxyphenyl)ethanamine
Class Membership
Psychoactive class Psychedelic
Chemical class Phenethylamine
Routes of Administration

WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.



Oral
Dosage
Threshold 50 mg
Light 100 - 200 mg
Common 200 - 400 mg
Strong 400 - 800 mg
Heavy 800 mg+
Duration
Total 8 - 14 hours
Onset 45 - 90 minutes
Come up 60 - 120 minutes
Peak 4 - 6 hours
Offset 2 - 3 hours
After effects 6 - 36 hours









DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.

Interactions
DOx
25x-NBOMe
2C-x
2C-T-x
5-MeO-xxT
Cannabis
Amphetamines
Cocaine
MAOIs
Tramadol
ΑMT

3,4,5-Trimethoxyphenethylamine (also known as mescaline) is a naturally-occurring classical psychedelic substance of the phenethylamine class.[1] It occurs naturally in the peyote cactus (Lophophora williamsii),[2] San Pedro cactus (Echinopsis pachanoi),[3] Peruvian Torch cactus (Echinopsis peruviana) as well as the Cactaceae plant and the Fabaceae bean families.[4] It is one of the oldest known hallucinogens and the parent compound of the psychedelic phenethylamines, one of the two major subclasses of psychedelic compounds (along with tryptamines).

Mescaline was first isolated from peyote in 1897 by the German chemist Arthur Heffter.[5] The ritual use of the peyote cactus has occurred for at least 5700 years by Native Americans in Mexico and other mescaline-containing cacti such as the San Pedro have a long history of use in the South American continent, from Peru to Ecuador.[6] Mescaline is an important part of the life's work of the American chemist Alexander Shulgin, who used it as a starting point for synthesizing dozens of novel psychedelic compounds that are documented in his 1991 book PiHKAL ("Phenethylamines I Have Known and Loved").[7]

Subjective effects include open and closed-eye visuals, time distortion, enhanced introspection, conceptual thinking, euphoria, and ego loss. Mescaline is generally considered to be one of the most gentle, insightful, and euphoric psychedelics. It is known for placing greater emphasis on bodily and tactile sensations (sometimes compared to MDMA) than psychedelic tryptamines like psilocybin or DMT, which tend to have a more frenetic headspace and dynamic visual geometry. It is considered to be one of the best agents for psychedelic therapy due to its mellow, organic, yet complex character. Synthetic mescaline is highly sought after by connoisseurs and is typically produced in limited batches, owing to its low potency and relatively high production cost.

Unlike other highly prohibited substances, mescaline has not been proven to be physiologically toxic or addictive.[8] Nevertheless, adverse psychological reactions such as anxiety, paranoia, delusions, and psychosis can still always occur, particularly among those predisposed to mental disorders.[9] Additionally, it should be noted that in street markets terms like "mescaline" or "synthetic mescaline" are commonly used as deceptive labels for other psychedelics (e.g. 2C-x, DOx, or 25x-NBOMe) that are typically more dangerous.[citation needed] It is highly advised to use harm reduction practices if using this substance.

History and culture

The ritual use of the Peyote cactus has occurred for at least 5700 years by Native Americans in Mexico. Upon early contact, Europeans noted the use of Peyote in Native American religious ceremonies. Additionally, alternative mescaline-containing cacti such as the San Pedro have a long history of use in the South American continent, spanning from Peru to Ecuador.[6] The principal psychoactive component in both Peyote and San Pedro, mescaline, was first isolated and identified in 1897 by the German chemist Arthur Heffter[5] and first synthesized in 1919 by Ernst Späth.[10] It was one of the first psychedelics to be experimented with by Western intellectuals like Aldous Huxley, who famously described its effects in the 1954 essay "The Doors of Perception".[citation needed]

In traditional peyote preparations, the top of the cactus is cut at ground level, leaving the large tap roots to grow new 'heads'. These 'heads' are then dried to make disc-shaped buttons and the buttons are chewed to produce the effects or soaked in water to drink. In modern times, users will often grind it into a powder and pour it into gel capsules to avoid having to come into contact with the bitter taste of the cactus. The usual human dose is 200–400 milligrams of mescaline sulfate or 178–356 milligrams of mescaline hydrochloride.[7] The average 76 mm (3.0 in.) button contains about 25 mg mescaline.[11]

Mescaline is an important part of the life's work of Alexander Shulgin, a psychedelic chemist and researcher. Shulgin used mescaline as a starting point for synthesizing dozens of novel psychedelic phenethylamine compounds such as the 2C-x and DOx families. It is a member of the so-called "magical half-dozen" which refers to Shulgin's self-rated most important phenethylamine compounds with psychedelic activity, all of which except mescaline he developed and synthesized himself. They are found within the first book of PiHKAL, and are as follows: Mescaline, DOM, 2C-B, 2C-E, 2C-T-2 and 2C-T-7.[12]

Chemistry

Mescaline, or 3,4,5-trimethoxyphenethylamine, is a substituted phenethylamine featuring a phenyl ring bound to an amino -NH2 group through an ethyl chain. Mescaline contains three methoxy functional groups CH3O- which are attached to carbons R3, R4, and R5 of the phenyl ring.

Mescaline has a number of structural analogs, which include but are not limited to: proscaline, escaline, and methallylescaline. It is also the synthetic starting point of the 2C-x and DOx family of psychedelic phenethylamines. 2C-x compounds like 2C-B (also known as bromomescaline) produce mescaline-like psychedelic effects but with greater potency and a reduced duration. DOx compounds (e.g. DOM, DOB) have a significantly extended duration and more stimulant effects.

Pharmacology

Further information: Serotonergic psychedelic

Mescaline acts similarly to other psychedelic agents.[13] It binds to and activates the serotonin 5-HT2A receptor with a high affinity.[14] How activating the 5-HT2A receptor leads to psychedelia is still unknown, but it likely somehow involves excitation of neurons in the prefrontal cortex.[15] Mescaline is also known to bind to and activate the serotonin 5-HT2C receptor.[16]

Subjective effects

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), a research literature based on collected anecdotal reports and the personal experiences of PsychonautWiki contributors. As a result, they should be regarded with a healthy degree of skepticism. It is worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce a full spectrum of effects. Likewise, adverse effects become much more likely with higher doses and may include addiction, serious injury, or death ☠.

Physical effects
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Visual effects
Eye.svg

Cognitive effects
User.svg

Multi-sensory effects
Gears.svg

Transpersonal effects
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Experience reports

Anecdotal reports which describe the effects of this compound within our experience index include:

Additional experience reports can be found here:

Natural sources

Flowering San Pedro, an entheogenic cactus that has been used for over 3,000 years[17]

Toxicity and harm potential

The toxicity and long-term health effects of recreational mescaline use does not appear to have been studied in any scientific context and the exact toxic dose is unknown. However, there are no known fatal overdoses within the scientific literature.

Anecdotal reports suggest that there are no negative health effects attributed to simply trying mescaline by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed).

Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

It is strongly recommended that one use harm reduction practices when using this substance.

Dependence and abuse potential

Mescaline is not habit-forming, and the desire to use it can actually decrease with use. It is most often self-regulating.

Tolerance to the effects of mescaline is built almost immediately after ingestion. After that, it takes about 3 days for the tolerance to be reduced to half and 7 days to be back at baseline (in the absence of further consumption). Mescaline presents cross-tolerance with all psychedelics, meaning that after the consumption of mescaline all psychedelics will have a reduced effect.[27]

Dangerous interactions

Although many psychoactive substances are reasonably safe to use on their own, they can suddenly become dangerous or even life-threatening when combined with other substances. The following list includes some known dangerous combinations (although it is not guaranteed to include all of them). Independent research (e.g. Google, DuckDuckGo) should always be conducted to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

  • DOx
  • 25x-NBOMe
  • 2C-x
  • 2C-T-x
  • 5-MeO-xxT - The 5-MeO class of tryptamines can be unpredictable in their interactions
  • Cannabis - Cannabis has an unexpectedly strong and somewhat unpredictable synergy with psychedelics.
  • Amphetamines - The focus and anxiety caused by stimulants is magnified by psychedelics and results in an increased risk of thought loops
  • Cocaine - The focus and anxiety caused by stimulants is magnified by psychedelics and results in an increased risk of thought loops
  • MAOIs
  • Tramadol - This combination can cause seizures due to the lowering of the threshold by Tramadol and the potential of Mescaline to cause seziures.
  • ΑMT

Legal status

Internationally, mescaline is classified as a Schedule I controlled substance under the United Nations 1971 Convention on Psychotropic Substances, meaning that international trade in mescaline is supposed to be closely monitored and its use is supposed to be restricted to scientific research and medical use. Natural materials containing mescaline, including peyote, are not regulated under the 1971 Psychotropic Convention.[28]

  • Australia: Peyote cacti and other mescaline-containing plants, such as San Pedro, are illegal in Western Australia, Queensland, and the Northern Territory. In other states such as Victoria and New South Wales, they are legal for ornamental and gardening purposes.[citation needed]
  • Brazil: Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.[29]
  • Canada: Mescaline is classified as a Schedule III drug under the Controlled Drugs and Substances Act. Peyote is listed as an exemption.[30] Other mescaline containing plants are presumably illegal to possess outside of ornamental and gardening purposes.
  • Germany: Mescaline is controlled under Anlage I BtMG[31] (Narcotics Act, Schedule I), former: Opiumgesetz (Opium Act) as of February 25, 1967.[32] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[33]
  • The Netherlands: Mescaline in its raw form and dried mescaline-containing cacti are considered an illegal drug. However, anyone may grow and use peyote without restriction as it is specifically exempt from legislation.[citation needed]
  • Switzerland: Mescaline is a controlled substance specifically named under Verzeichnis D.[34]
  • United Kingdom: Mescaline in purified powder form is a Class A drug. However, dried cactus can be bought and sold legally.[35]
  • United States: Mescaline was made illegal in 1970 by the Comprehensive Drug Abuse Prevention and Control Act.[36] The drug 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. 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.[citation needed]

See also

External links

References

  1. Nichols, David E. (2016). Barker, Eric L., ed. "Psychedelics". Pharmacological Reviews. 68 (2): 264–355. doi:10.1124/pr.115.011478Freely accessible. eISSN 1521-0081. ISSN 0031-6997. OCLC 00824083. PMC 4813425Freely accessible. PMID 26841800. 
  2. Drug Identification Bible. Grand Junction, CO: Amera-Chem. 2007. ISBN 0-9635626-9-X. OCLC 180867436. 
  3. Crosby, D. M.; McLaughlin, J. L. (1973). "Cactus Alkaloids. XIX. Crystallization of Mescaline HCl and 3-Methoxytyramine HCl from Trichocereus pachanoi" (PDF). Lloydia. 36 (4): 416–418. ISSN 0024-5461. OCLC 1606095. PMID 4773270. 
  4. Forbes, T. D. A.; Clement, B. A. (1998). "Chemistry of Acacia's from South Texas" (PDF). Uvalde, Texas: Texas A&M Agricultural Research and Extension Center. 
  5. 5.0 5.1 "Arthur Heffter". Erowid Character Vaults. August 9, 1998. Retrieved September 30, 2020. 
  6. 6.0 6.1 El-Seedi, H. R.; De Smet, P. A. G. M.; Beck, O.; Possnert, G.; Bruhn, J. G. (2005). "Prehistoric peyote use: Alkaloid analysis and radiocarbon dating of archaeological specimens of Lophophora from Texas". Journal of Ethnopharmacology. 101 (1–3): 238–242. doi:10.1016/j.jep.2005.04.022. eISSN 1872-7573. ISSN 0378-8741. OCLC 04649997. PMID 15990261. 
  7. 7.0 7.1 Alexander Shulgin; Ann Shulgin (1991). "#96. M". PiHKAL: A Chemical Love Story. United States: Transform Press. ISBN 0963009605. OCLC 1166889264. 
  8. Lüscher, Christian; Ungless, Mark A. (2006). "The Mechanistic Classification of Addictive Drugs". PLOS Medicine. 3 (11). doi:10.1371/journal.pmed.0030437Freely accessible. eISSN 1549-1676. ISSN 1549-1277. OCLC 54674092. PMC 1635740Freely accessible. PMID 17105338. 
  9. Strassmann, Rick (1984). "Adverse reactions to psychedelic drugs. A review of the literature". Journal of Nervous and Mental Disease. 172 (10): 577–595. doi:10.1097/00005053-198410000-00001. ISSN 0022-3018. OCLC 1754691. PMID 6384428. 
  10. Manske, R. H. F.; Holmes, H. L. (1953). "Mescaline (3,4,5-Trimethoxyphenethylamine)". The Alkaloids. III. New York: Academic Press. pp. 324–328. ISBN 0080865275. OCLC 281698426. 
  11. Giannini, A. J.; Slaby, A. E.; Giannini, M. C. (1982). Handbook of Overdose and Detoxification Emergencies. New Hyde Park, NY: Medical Examination Publishing Company. ISBN 978-0-87488-182-0. OCLC 9084341. 
  12. Alexander Shulgin; Ann Shulgin (1991). PiHKAL: A Chemical Love Story. United States: Transform Press. ISBN 0963009605. OCLC 1166889264. 
  13. Nichols, David E. (2004). "Hallucinogens". Pharmacology & Therapeutics. 101 (2): 131–181. doi:10.1016/j.pharmthera.2003.11.002. eISSN 1879-016X. ISSN 0163-7258. OCLC 04981366. PMID 14761703. 
  14. Monte, A. P.; Waldman, S. R.; Marona-Lewicka, D.; Wainscott, D. B.; Nelson, D. L.; Sanders-Bush, E.; Nichols, D. E. (1997). "Dihydrobenzofuran Analogues of Hallucinogens. 4. Mescaline Derivatives". Journal of Medicinal Chemistry. 40 (19): 2997–3008. doi:10.1021/jm970219x. eISSN 1520-4804. ISSN 0022-2623. OCLC 39480771. PMID 9301661. 
  15. Béïque, J.-C.; Imad, M.; Mladenovic, L.; Gingrich, J. A.; Andrade, R. (2007). "Mechanism of the 5-hydroxytryptamine 2A receptor-mediated facilitation of synaptic activity in prefrontal cortex". Proceedings of the National Academy of Sciences of the United States of America. 104 (23): 9870–9875. doi:10.1073/pnas.0700436104Freely accessible. eISSN 1091-6490. ISSN 0027-8424. OCLC 43473694. PMC 1887564Freely accessible. PMID 17535909. 
  16. "BILZoR" (February 2004). "The Neuropharmacology of Hallucinogens: a brief introduction". v1. Erowid. Retrieved September 30, 2020. 
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  20. 20.0 20.1 20.2 20.3 Michael S. Smith (June 1998). "Narcotic and Hallucinogenic Cacti of the New World". Forbidden Fruit Archives. Archived from the original on May 12, 2008. 
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  25. "Austrocylindropuntia cylindrica". Desert Tropicals. [dead link]
  26. Philippe Faucon. "Cane Cholla". Desert-Tropicals. Archived from the original on January 9, 2019. 
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