Mescaline

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Not to be confused with mesclun.



Mescaline
Systematic (IUPAC) name
3,4,5-trimethoxy-phenethylamine or 2-(3,4,5-trimethoxyphenyl) ethanamine
Identifiers
CAS number	54-04-6
ATC code	?
PubChem	4076
Chemical data
Formula	C₁₁H₁₇N O₃
Mol. mass	211.26 g/mol
SMILES	eMolecules & PubChem
Physical data
Melt. point	183–186 °C (361–367 °F) (Sulfate dihydrate)
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	X(AU) X(US)
Legal status	Prohibited (S9)(AU) Schedule III(CA) Class A(UK) Schedule I(US)
Routes	Oral, Intravenous

Mescaline (3,4,5-trimethoxyphenethylamine) is a naturally-occurring psychedelic alkaloid of the phenethylamine class. It is mainly used as a recreational drug, an entheogen, and a tool to supplement various types of practices for transcendence, including in meditation, psychonautics, and legal psychedelic psychotherapy, whether self administered or not.

It occurs naturally in the peyote cactus (Lophophora williamsii), the San Pedro cactus (Echinopsis pachanoi) and the Peruvian Torch cactus (Echinopsis peruviana), and in a number of other members of the Cactaceae. It is also found in small amounts in certain members of the Fabaceae (bean family), including Acacia berlandieri.^[1] Mescaline was first isolated and identified in 1897 by the German Arthur Heffter and first synthesized in 1919 by Ernst Späth.

1 History and Usage
2 Pharmacokinetics
3 Behavioral and Non-behavioral Effects
4 Mode of Action
5 Legal status
6 Analogs
7 See also
8 References
- 8.1 Notes
- 8.2 General References
9 External links

[edit] History and Usage

The use of peyote in Native American religious ceremonies has been noted since the earliest European contact, notably by the Huichols in Mexico, but other cacti such as the San Pedro have been used in different regions, from Peru to Ecuador.

Aldous Huxley experimented with the use of mescaline. So did Aleister Crowley as reported in his diary, as well as the famous sex psychologist Havelock Ellis.

In traditional peyote preparations, the top of the cactus is cut from the roots, and dried to make disk-shaped buttons. It is chewed to produce its effect 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 fill them in capsules to avoid having to taste it. The effective human dosage is 300–500 milligrams of pure mescaline. Hallucinations occur at 300–600mg, which is the equivalent to approximately 20 mescal buttons.

[edit] Pharmacokinetics

Although the ED₅₀ is variable with dosage and individual, the LD₅₀ has been measured in various animals and is reported as follows:

212 mg/kg i.p. (mice)
132 mg/kg i.p. (rats)
328 mg/kg i.p. (guinea pigs)

It is reported that mescaline is 1000-3000 times less potent than LSD, and 30 times less potent than psilocybin^{[citation needed]}. About half the initial dosage is excreted after 6 hours, but some studies suggest that it is not metabolized at all before excretion.

Tolerance builds with repeated usage, and it is suggested that a cross-tolerance can be developed with LSD and psilocin.^[2]

[edit] Behavioral and Non-behavioral Effects

Hallucinations produced by mescaline are somewhat different from those of LSD. Hallucinations are consistent with actual experience, but are typically intensifications of the stimulus properties of objects and sounds. Prominence of color is distinctive, appearing brilliant and intense. Unlike LSD, mescaline does not induce distortions of form or kaleidoscopic experiences. However, like LSD, synesthesia can occur.^[2]

Mescaline elicits a pattern of sympathetic arousal, with the peripheral nervous system being a major target for this drug.^[2]

Effects last for up to 12 hours^[2].

[edit] Mode of Action

Mescaline is a sympathomimetic of the neurotransmitter, norepinephrine. However, mescaline does not affect 5-HT2 receptors as LSD and psilocin are known to do. In the periphery, mescaline blocks the release of acetylcholine in muscle^[2] and also affects potassium conductance.

[edit] Legal status

In the US it was made illegal in 1970 by the Comprehensive Drug Abuse Prevention and Control Act.^[3] It was prohibited internationally by the 1971 Convention on Psychotropic Substances^[4] and is categorized as a Schedule I hallucinogen by the CSA. Mescaline is only legal for certain natives (such as those involved in the Native American Church). 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 powder form, although dried cactus can be bought and sold legally, unlike raw "magic" mushrooms, which are now illegal)^[5], 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.