Mescaline

Mescaline
Clinical data
Other names	M; Mescalin; Mezcalin; Mezcaline; Meskalin; Mezkalin; 3,4,5-Trimethoxyphenethylamine; 3,4,5-TMPEA; TMPEA; O,O-Dimethyl-5-methoxydopamine; 2C-TMA; EA-1306; NSC-30419; JOUR-5700; JOUR5700; BMND04; BMND06; BMND09
AHFS/Drugs.com	mescaline
Routes of; administration	Oral, smoking, insufflation, intravenous
Drug class	Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule III , except peyote; DE: Anlage I (Authorized scientific use only); UK: Class A (Plants containing mescaline legal); US: Schedule I (with religious use exceptions); UN: P I (psychoactive cactus like peyote or san pedro uncontrolled);
Pharmacokinetic data
Bioavailability	Unknown (but ≥53%)
Protein binding	Unknown (but appears minimal)
Metabolism	Oxidative deamination, N-acetylation, O-demethylation, conjugation, other pathways
Metabolites	• 3,4,5-Trimethoxyphenyl-acetaldehyde; • 3,4,5-Trimethoxyphenylacetic acid; • 3,4,5-Trimethoxyphenylethanol; • Others
Onset of action	Oral: 0.5–0.9 hours (range 0.1–2.7 hours); IVTooltip Intravenous injection: <10 minutes
Elimination half-life	3.6 hours (range 2.6–5.3 hours)
Duration of action	6.4–14 hours (range 3.0–22 hours)
Excretion	Urine (≥92%; 28–60% unchanged, ≥27–31% as TMPAA, 5% as N-Ac-3,4-DiMeO-5-OH-PEA, <0.1% as NAMTooltip N-acetylmescaline)
Identifiers
	IUPAC name 2-(3,4,5-trimethoxyphenyl)ethanamine;
CAS Number	54-04-6 ;
PubChem CID	4076;
DrugBank	DB19083;
ChemSpider	3934 ;
UNII	RHO99102VC;
KEGG	C06546 ;
ChEBI	CHEBI:28346 ;
ChEMBL	ChEMBL26687 ;
PDB ligand	A1AFW (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID80202303 ;
ECHA InfoCard	100.000.174
Chemical and physical data
Formula	C11H17NO3
Molar mass	211.261 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.067 g/cm3
Melting point	35 to 36 °C (95 to 97 °F)
Boiling point	180 °C (356 °F) at 12 mmHg
Solubility in water	moderately soluble in water mg/mL (20 °C)
	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 ; Key:RHCSKNNOAZULRK-UHFFFAOYSA-N ;
	(verify)

Mescaline, also known in chemical terms as 3,4,5-trimethoxyphenethylamine, is a naturally occurring psychedelic drug and alkaloid of the phenethylamine and scaline families found in certain cacti like peyote (Lophophora williamsii) and the San Pedro cactus (Echinopsis pachanoi, others).

The drug is used recreationally, spiritually, and medically, with psychedelic effects occurring at doses of 100 to 800 mg (as its hydrochloride salt) orally and it can be used in pure form or in the form of mescaline-containing cacti. Mescaline induces a psychedelic experience characterized by visual changes, altered perception of time, space, and self, synesthesia, and spiritual experiences, with an onset of 30 to 60 minutes, a time to peak of 2 to 4 hours, and a duration that increases with dose and ranges from 6 to 14 hours.

Mescaline primarily acts as a partial agonist at serotonin 5-HT_2A receptors, with varying affinity and efficacy across multiple other receptors and targets. The serotonin 5-HT_2A receptor antagonist ketanserin blocks mescaline's psychoactive effects. Mescaline is a relatively hydrophilic compound structurally related to dopamine, first synthesized in 1919, with numerous synthetic methods and potent analogues developed since. It occurs naturally in various cacti species, with concentrations varying widely, and is biosynthesized in plants from amino acids like phenylalanine and tyrosine.

The practice of humans consuming mescaline-containing cacti dates back over 6,000 years. Peyote cacti were studied scientifically in the 1800s, culminating in the isolation of mescaline as the active psychedelic constituent in cacti, legal recognition of religious use, and ongoing exploration of the therapeutic potential of mescaline and other analogues. Mescaline was the first psychedelic compound to be characterized by the Western world and has been referred to as the "first psychedelic".

Mescaline and the cacti that produce it are largely illegal worldwide, though exceptions exist for religious, scientific, or ornamental use, and the compound has influenced many notable cultural figures, for instance Aldous Huxley and Alexander Shulgin among others. Very few studies of mescaline in people have been conducted since the early 1970s. However, the drug is now being studied in terms of its effects and for potential medical use once again as of the early 2020s.