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 family.[4] It is one of the oldest known hallucinogens and is also the prototype of the psychedelic phenethylamines, one of the two major subclasses of psychedelics (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 mescaline as a starting point for synthesizing dozens of novel psychedelic compounds that he documented in the 1991 book PiHKAL ("Phenethylamines I Have Known and Loved").

Subjective effects include open and closed-eye visuals, time distortion, enhanced introspection, conceptual thinking, euphoria, and ego loss. Mescaline is considered to be one of the most gentle, insightful, and euphoric psychedelics, known for its greater emphasis on bodily and tactile sensations (sometimes compared to MDMA) than tryptamine psychedelics like psilocybin or DMT, which tend to have a more dynamic/frenetic headspace and visual geometry. It is considered to be one of the best agents for psychedelic therapy due to its gentle, organic nature. Synthetic mescaline is highly sought after and is typically produced in limited batches for connoisseurs, 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.[7] Nevertheless, adverse psychological reactions such as anxiety, paranoia, delusions, and psychosis can still always occur, particularly among those predisposed to mental disorders.[8] 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.[9] 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.[10] 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 literature based on anecdotal reports and the personal experiences of PsychonautWiki contributors. As a result, they should be treated with a healthy amount of skepticism. It is worth noting that these effects will not necessarily occur in a consistent or reliable manner, although higher doses are more likely to induce the full spectrum of effects. Likewise, adverse effects become much more likely with higher doses and may include serious injury or death.

Physical effects
Child.svg

    • Stimulation - Mescaline is usually considered to be very energetic and stimulating without being forced. For example, when taken in any environment it will usually encourage physical activities such as running, walking, climbing or dancing. In comparison, other more commonly used psychedelics such as psilocin are generally sedating and relaxed.
    • Spontaneous bodily sensations - The "body high" of mescaline can be described as proportionally intense in comparison to its accompanying visual and cognitive effects. It is manifested in a number of forms including an intense soft, warm glow that grows over the body and is capable of becoming extremely physically euphoric. This is most similar to MDMA and psilocin and is consistently manifested throughout the experience. This is contrasted by an intensely pleasurable yet sharp, cold electric tingling sensation which moves up and down the body. This is most similar to LSD and is also consistently manifested throughout the experience. The final physical effect noticed throughout the experience is an intense energetic pins and needles sensation that manifests itself in the form of a continuously shifting and tingling sensation that travels up and down the body in spontaneous waves. This is most similar to 2C-B and is not entirely consistent throughout the experience.
      • Physical euphoria - Relative to other psychedelics, mescaline has been noted for the bodily or physically euphoric aspect that is vaguely reminiscent of other phenethylamines like MDA.
    • Nausea - Nausea is commonly reported when consumed in moderate to high doses and either passes instantly once the user has vomited or gradually fades by itself as the peak sets in.
    • Increased salivation - This effect, while uncommon, seems to be less pronounced than it is with psilocin and other tryptamines and usually does not persist throughout the experience.
    • Tactile enhancement - Feelings of enhanced tactile sensations are consistently present at moderate levels. If Level 8A geometry is reached, an intense sensation of suddenly becoming aware of and being able to feel every single nerve ending across a person's entire body all at once is consistently present.
    • Appetite suppression
    • Bodily control enhancement
    • Stamina enhancement
    • Olfactory enhancement
    • Frequent urination
    • Increased heart rate
    • Increased libido
    • Muscle contractions
    • Pupil dilation
    • Seizure - A rarely observed effect but is thought to be able to happen in those predisposed to them, especially while in physically taxing conditions such as being dehydrated, fatigued, undernourished, or overheated.[citation needed]

Visual effects
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Cognitive effects
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Auditory effects
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Multi-sensory effects
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    • Synaesthesia - In its fullest manifestation, this is a very rare and non-reproducible effect. Increasing the dosage can increase the likelihood of this occurring, but seems to only be a prominent part of the experience among those who are already predisposed to synaesthetic states.

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

Further information: Responsible use § Hallucinogens

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 are 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 quickly become dangerous or even life-threatening when combined with other substances. The list below includes some known dangerous combinations (although it cannot be 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 interactions listed 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

See also: Psychedelic cacti § 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.115.011478 Freely accessible. eISSN 1521-0081. ISSN 0031-6997. OCLC 00824083. PMC 4813425 Freely 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. ↑ Lüscher, Christian; Ungless, Mark A. (2006). "The Mechanistic Classification of Addictive Drugs". PLOS Medicine. 3 (11). doi:10.1371/journal.pmed.0030437 Freely accessible. eISSN 1549-1676. ISSN 1549-1277. OCLC 54674092. PMC 1635740 Freely accessible. PMID 17105338. 
  8. ↑ 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. 
  9. ↑ 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. 
  10. ↑ Alexander Shulgin; Ann Shulgin (1991). "#96. M". PiHKAL: A Chemical Love Story. United States: Transform Press. ISBN 0963009605. OCLC 1166889264. 
  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.0700436104 Freely accessible. eISSN 1091-6490. ISSN 0027-8424. OCLC 43473694. PMC 1887564 Freely accessible. PMID 17535909. 
  16. ↑ "BILZoR" (February 2004). "The Neuropharmacology of Hallucinogens: a brief introduction". v1. Erowid. Retrieved September 30, 2020. 
  17. ↑ Richard Rudgley (1998). "San Pedro Cactus". The Encyclopedia of Psychoactive Substances. London: Little, Brown and Company. ISBN 0316643475. 
  18. ↑ 18.00 18.01 18.02 18.03 18.04 18.05 18.06 18.07 18.08 18.09 18.10 "Visionary Cactus Guide: Cactus Botany". Erowid. Retrieved January 14, 2015. 
  19. ↑ 19.0 19.1 19.2 Keeper Trout & friends (2014). "Cactus Chemistry By Species" (PDF). Mydriatic Productions. Archived from the original (PDF) on July 11, 2016. 
  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. 
  21. ↑ 21.0 21.1 21.2 21.3 "Partial List of Alkaloids in Trichocereus Cacti". The Nook. Archived from the original on December 30, 2019. 
  22. ↑ "Trichocereus spp". a1b2c3.com. Retrieved September 30, 2020. 
  23. ↑ "Echinopsis tacaquirensis ssp. taquimbalensis". Desert Tropicals. Retrieved 14 January 2015. [dead link]
  24. ↑ "Cardon Grande (Echinopsis terscheckii)". Desert Tropicals. Retrieved 14 January 2015. [dead link]
  25. ↑ "Austrocylindropuntia cylindrica". Desert Tropicals. [dead link]
  26. ↑ Philippe Faucon. "Cane Cholla". Desert-Tropicals. Archived from the original on January 9, 2019. 
  27. ↑ Michael Valentine Smith. "Psychedelics and Society". Psychedelic Chemistry. Erowid. Retrieved September 30, 2020. 
  28. ↑ "Convention On Psychotropic Substances, 1971" (PDF). United Nations Office on Drugs and Crime. OCLC 977159148. Retrieved January 3, 2020. 
  29. ↑ "RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016" (in Portuguese). Agência Nacional de Vigilância Sanitária (Anvisa) [National Sanitary Surveillance Agency]. December 5, 2016. Retrieved January 8, 2020. 
  30. ↑ "Schedule III". Controlled Drugs and Substances Act (S.C. 1996, c. 19). Government of Canada. Retrieved January 1, 2020. 
  31. ↑ "Gesetz über den Verkehr mit Betäubungsmitteln: Anlage I" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019. 
  32. ↑ "Vierte Verordnung über die den Betäubungsmitteln gleichgestellten Stoffe" (PDF). Bundesgesetzblatt Teil I: 1967 Nr. 10 (in German). Bundesanzeiger Verlag. February 24, 1967. p. 197. ISSN 0341-1095. OCLC 924790029. 
  33. ↑ "Gesetz über den Verkehr mit Betäubungsmitteln: § 29" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019. 
  34. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020. 
  35. ↑ Regina v. Saul Sette (June 2007). "2007 U.K. Trichocereus Cacti Legal Case". Erowid Extracts. Vol. 12. Erowid. Retrieved September 30, 2020. 
  36. ↑ "Controlled Substance Schedules". Diversion Control Devision. Retrieved September 30, 2020. 
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