Mescaline

Mescaline
Clinical data


AHFS/Drugs.com	mescaline
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	, intravenous
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule III DE: Anlage I (Controlled) UK: Class A US: Schedule I
Pharmacokinetic data
Biological half-life	6 hours
Identifiers
IUPAC name 2-(3,4,5-trimethoxyphenyl)ethanamine
Synonyms	3,4,5-trimethoxyphenethylamine
CAS Number	54-04-6^Y
PubChem (CID)	4076
ChemSpider	3934^Y
UNII	RHO99102VC^Y
KEGG	C06546^Y
ChEBI	CHEBI:28346^Y
ChEMBL	CHEMBL26687^Y
ECHA InfoCard	100.000.174
Chemical and physical data
Formula	C₁₁H₁₇NO₃
Molar mass	211.257 g/mol
3D model (Jmol)	Interactive image
Melting point	35 to 36 °C (95 to 97 °F)
Boiling point	180 °C (356 °F)
SMILES O(c1cc(cc(OC)c1OC)CCN)C
InChI InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3^Y Key:RHCSKNNOAZULRK-UHFFFAOYSA-N^Y

Mescaline, or 3,4,5-trimethoxyphenethylamine, is a naturally occurring psychedelic alkaloid of the phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin.

It occurs naturally in the peyote cactus (Lophophora williamsii), the San Pedro cactus (Echinopsis pachanoi), the Peruvian torch (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.

Peyote has been used for at least 5700 years by Native Americans in Mexico. 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 off, leaving the large tap root along with a ring of green photosynthesizing area to grow new heads. These heads are then dried to make disc-shaped buttons. Buttons are chewed to produce the effects or soaked in water to drink. However, the taste of the cactus is bitter, so contemporary 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. The average 76 mm (3.0 in) button contains about 25 mg mescaline.

Mescaline was first isolated and identified in 1897 by the German chemist Arthur Heffter and first synthesized in 1919 by Ernst Späth.

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Wikipedia