Mescaline

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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	?
Chemical data
Formula	C₁₁H₁₇N O₃
Mol. mass	211.26 g/mol
SMILES	search in 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

Mescaline (3,4,5-trimethoxyphenethylamine) is a hallucinogenic alkaloid of the phenethylamine class.

It occurs naturally in the peyote cactus (Lophophora williamsii), the San Pedro cactus (Echinopsis pachanoi) and the Peruvian Torch cactus (Echinopsis peruviana), and it is also found in a number of other members of the Cactaceae. Mescaline was first isolated and identified in 1897 by the German Arthur Heffter and first synthesized in 1919 by Ernst Späth.

1 Usage and history
- 1.1 Dosage and effects
2 Pharmacokinetics
3 Legal status
4 Chemistry
5 Effects and side effects
6 Analogs
7 See also
8 External links
9 References
10 Categorization

[edit] Usage and history

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.

[edit] Dosage and effects

For the drug to take effect, 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 incredibly bitter and repulsive, 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 0.3–0.5 grams of pure mescaline, with the effects lasting for up to 12 hours. Hallucinations occur at 300-600mg, which is the equivalent to approximately 20 mescal buttons. Users typically experience visual hallucinations and radically altered states of consciousness, often experienced as pleasurable and illuminating but occasionally is accompanied by feelings of anxiety or revulsion. Like all psychedelic hallucinogens, mescaline is not physically addictive. In addition, mescaline containing cacti can induce severe vomiting and nausea.

[edit] Pharmacokinetics

[Referenced from Rostock, D. T. (2003, Spring). Pharmacological constituents of mescaline and salvinorin-A. University of Idaho, Department of Psychology.]

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

Crystals: 212mg/kg i.p. (mice)

Crystals: 132 mg/kg i.p. (rats)

Crystals: 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. About half the initial dosage is excreted after 6 hours, but some studies suggest that it is not metabolized at all before excretion.

Slow tolerance builds with repeated usage, and it is suggested that a cross tolerance can be developed with LSD.

[edit] Legal status

In the US it was made illegal in 1970 by the Comprehensive Drug Abuse Prevention and Control Act. It was prohibited internationally by the 1971 Convention on Psychotropic Substances [1] and is categorized as a Schedule I hallucinogen by the CSA. Mescaline is only legal for certain natives. Penalties for manufacture or sale can be as high as five years in jail and a fine of $15000, with a penalty of up to one year and fine of $5000 for possession.

In the underground economy of the late 1960's mescaline was widely sold. Much of the purported mescaline actually was not mescaline, but an unknown fraction was other psychedelics, mostly LSD. Quality control in an underground, and later illegal, product can be problematic. Most people trusted their dealers, and most dealers trusted their chemists. Many of these chemists had studied in good universities, but universities offered few courses in the chemistry of psychedelic drugs, much less offering PhD's for developing new methods of synthesizing them.

[edit] Chemistry

A common synthetic approach starts from 3,4,5-trimethoxybenzaldehyde. The chemical make-up is C₁₁H₁₇NO₃ (PiHKAL entry). It is also synthesized from syringaldehyde, vanillin, and gallic acid. 3,4,5-trimethoxynitrostyrene can be reduced to mescaline using catalytic hydrogenation.