Mescaline

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Mescaline
File:Mescaline Structural Formulae.png
File:Mescaline-3d-CPK.png
Systematic (IUPAC) name
2-(3,4,5-trimethoxyphenyl)ethanamine
Clinical data
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration
Oral, Intravenous
Legal status
Legal status
Pharmacokinetic data
Biological half-life 6 hours
Identifiers
CAS Number 54-04-6
ATC code none
PubChem CID 4076
ChemSpider 3934
Synonyms 3,4,5-trimethoxyphenethylamine
Chemical data
Formula C11H17NO3
Molar mass 211.257 g/mol[[Script error: No such module "String".]]
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Physical data
Melting point 183 to 186 °C (361 to 367 °F) (Sulfate dihydrate)
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Mescaline or 3,4,5-trimethoxyphenethylamine is a naturally-occurring psychedelic alkaloid of the phenethylamine class used mainly as an entheogen.

It occurs naturally in the peyote cactus (Lophophora williamsii),[1] the San Pedro cactus (Echinopsis pachanoi) and the Peruvian Torch cactus (Echinopsis peruviana), 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.[2] Mescaline was first isolated and identified in 1897 by the German Arthur Heffter and first synthesized in 1919 by Ernst Späth.

File:Mescaline Powder.jpg
Naturally derived mescaline powder extract.

History and usage

Peyote has been used for over 3000 years by Native Americans in Mexico.[1] Europeans noted use of peyote in Native American religious ceremonies upon early contact, notably by the 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.

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 disk-shaped buttons. Buttons are chewed to produce the effects or soaked in water for an intoxicating drink. However, the taste of the cactus is bitter, so users will often grind it into a powder and pour it in 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.[3] The average 3 inch button contains about 25 mg mescaline.[4]

Aldous Huxley described his experience with mescaline in The Doors of Perception. Aleister Crowley reported using mescaline in his diary. The sex psychologist Havelock Ellis also tried mescaline. Mescaline may have played a part in the development of the Cubist school of abstract art, when George Braque and Pablo Picasso published the "Cubist Manifesto" they described design paradigms which were similar to visual experiences induced by mescaline and other rare drugs known to the South American Islanders.[5] Hunter S. Thompson recounted his use of mescaline in Fear and Loathing in Las Vegas.

Pharmacokinetics

Tolerance builds with repeated usage, lasting for a few days. Mescaline causes cross-tolerance with LSD and other psychedelics.

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[6] 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.[7]

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

The visual distortions produced by mescaline are somewhat different from those of LSD. The subjective "visuals" are not true Hallucinations as they are consistent with actual experience and typically intensifications of the different stimulus (objects and sounds), not the appearance of non existent fanciful objects or actions that the user believes are real. Prominence of color is distinctive, appearing brilliant and intense. Placing a strobing light in front of closed eyelids can produce brilliant visual effects at the peak of the experience[citation needed]. Recurring visual patterns observed during the mescaline experience include stripes, checkerboards, angular spikes, multicolored dots, and very simple fractals which 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 which manifest more clearly with eyes closed and under low lighting conditions; however, all of these visual descriptions are purely subjective. Research into the root causes for the patterns associated with mescaline, LSD and DMT have given rise to mathematical theories that explain the biological processes that are disrupted by molecules like mescaline.[8]

As with LSD, synesthesia can occur especially with the help of music.[9] 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.[10]

Mescaline elicits a pattern of sympathetic arousal, with the peripheral nervous system being a major target for this drug.[9] Effects last for up to 12 hours.[9]

Mode of action

Mescaline acts similarly to other psychedelic agents.[11] It binds to and activates the serotonin 5-HT2A receptor with a high affinity as a partial agonist.[12] How activating the 5-HT2A receptor leads to psychedelia is still unknown, but it likely somehow involves excitation of neurons in the prefrontal cortex.[13]

Legality

In the US, mescaline was made illegal in 1970 by the Comprehensive Drug Abuse Prevention and Control Act.[14] It was prohibited internationally by the 1971 Convention on Psychotropic Substances[15] and is categorized as a Schedule I hallucinogen by the CSA. Mescaline is only legal 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 in 1993 allowed the use of peyote in religious ceremony but in 1997, the Supreme Court ruled that RFRA was unconstitutional when applied against states. However, a subsequent ruling in 2006 held that RFRA was constitutional when applied against the federal government.[16] 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 it.[17] Penalties for manufacture or sale can be as high as five years in prison and a fine of $15,000, with a penalty of up to one year and fine of $5000 for possession.

In the UK, mescaline is a Class A drug (in purified powder form, although dried cactus can be bought and sold legally, unlike raw "magic" mushrooms, which are now illegal),[18] and so carries the following penalties. For possession: up to seven years in prison or an unlimited fine or both. For dealing: up to life in prison or an unlimited fine or both.

In Australia the peyote cacti and mescaline are strictly illegal

In Canada, mescaline in raw form is considered an illegal drug. However, anyone may grow and use peyote, or Lophophora williamsii, without restriction, as it is specifically exempt from legislation.[1]

See also

References

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External links

br:Meskalin

bg:Мескалин ca:Mescalina cs:Mezkalin da:Meskalin de:Mescalin es:Mescalina fa:مسکالین fr:Mescaline gl:Mescalina hr:Meskalin io:Meskalino it:Mescalina he:מסקלין lv:Meskalīns lt:Meskalinas hu:Meszkalin nl:Mescaline ja:メスカリン no:Meskalin pl:Meskalina pt:Mescalina ro:Mescalină ru:Мескалин simple:Mescaline sk:Meskalín sr:Мескалин sh:Meskalin fi:Meskaliini sv:Meskalin tr:Meskalin

zh:麦司卡林
  1. 1.0 1.1 1.2 Drug Identification Bible. Grand Junction, CO: Amera-Chem, Inc. 2007. ISBN 0-9635626-9-X. 
  2. Chemistry of Acacia's from South Texas
  3. http://www.erowid.org/library/books_online/pihkal/pihkal096.shtml
  4. AJ Giannini, AE Slaby, MC Giannini. Handbook of Overdose and Detoxification Emergencies.New Hyde Park, NY. Medical Examination Publishing/Excerpta Medica Company,1982.
  5. AJ Giannini. Drugs of Abuse—Second Edition. Los Angeles, Practice Management Information Corp., 1997.
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  8. [1], Biological Cybernetics 1979.
  9. 9.0 9.1 9.2 Diaz, Jaime. How Drugs Influence Behavior. Englewood Cliffs: Prentice Hall, 1996
  10. AJ Giannini, AE Slaby. Drugs of Abuse. Oradell, NJ. Medical Economics Books,1989, pp.207-239.
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  14. United States Department of Justice. "Drug Scheduling". Retrieved 2007-11-02. 
  15. "List of psychotropic substances under international control" (PDF). International Narcotics Control Board. Retrieved 2008-01-27. 
  16. [http://caselaw.lp.findlaw.com/cgi-bin/getcase.pl?court=US&navby=case&vol=000&invol=04-1084 GONZALES, ATTORNEY GENERAL, et al. v. O CENTRO ESPIRITA BENEFICENTE UNIAO DO VEGETAL et al.]
  17. "Uses Drugs of Abuse—Origins and Effects - Hallucinogens". 
  18. "2007 U.K. Trichocereus Cacti Legal Case Regina v. Saul Sette".