File:Mescaline_Structural_Formulae_bondline.svg · Wikimedia Commons · See Wikimedia Commons
mescaline
Sign in to saveAlso known as TMPEA, 3,4,5-trimethoxyphenylethylamine, 3,4,5-trimethoxyphenethylamine, 1-amino-2-(3,4,5-trimethoxyphenyl)ethane, 3,4,5-trimethoxybenzeneethanamine
Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a naturally occurring classical psychedelic protoalkaloid of the substituted phenethylamine class, found in cacti like peyote (Lophophora williamsii) and San Pedro (certain species of the genus Echinopsis).
Key facts
- Drug.UNII
- RHO99102VC
- Drug.KEGG
- C06546
- Drug.ChEBI
- 28346
- Drug.ChEMBL
- 26687
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 477169864
- Drug.image
- Mescaline Structural Formulae bondline.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 225px
- Drug.image2
- Mescaline-3D-xray-ballstick.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 165px
- Drug.pregnancy_US
- C
- Drug.class
- Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
- Drug.routes_of_administration
- Oral, smoking, insufflation, intravenous
- Drug.ATC_prefix
- None
- Drug.legal_AU
- Schedule 9
- Drug.legal_BR
- F2
via Wikipedia infobox
Chemical data
- Formula
- C11H17NO3
- Molecular weight
- 211.26 g/mol
- IUPAC name
- 2-(3,4,5-trimethoxyphenyl)ethanamine
- SMILES
- COC1=CC(=CC(=C1OC)OC)CCN
- InChIKey
- RHCSKNNOAZULRK-UHFFFAOYSA-N
- XLogP
- 0.7
- Polar surface area
- 53.7 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 211.121
Show 3 more facts
- Commons category
- Mescaline
- chemical formula
- C₁₁H₁₇NO₃
- canonical SMILES
- COC1=CC(=CC(=C1OC)OC)CCN
Sources (6)
via Wikidata · CC0
~35 min read
Article
32 sectionsContents
- Use and effects
- Contraindications
- Adverse effects
- Tolerance
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Absorption
- Distribution
- Metabolism
- Elimination
- Chemistry
- Properties
- Synthesis
- Analogues
- Natural occurrence
- Biosynthesis
- History
- Society and culture
- Legal status
- United States
- United Kingdom
- Australia
- Other countries
- Notable individuals
- Research
- See also
- References
- Further reading
- External links
Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a naturally occurring classical psychedelic protoalkaloid of the substituted phenethylamine class, found in cacti like peyote (Lophophora williamsii) and San Pedro (certain species of the genus Echinopsis).
Mescaline is taken orally and is used recreationally, spiritually, and medically, with psychedelic effects occurring at doses from 100 to 1,000mg and it can be consumed in pure crystalline form or via the crude extract of mescaline-containing cacti. Mescaline induces a psychedelic experience characterized by vivid visual patterns, altered perception of time and self, synesthesia, and spiritual effects, with an onset of 0.5 to 0.9hours and a duration that increases with dose, ranging from about 6 to 14hours. Ketanserin blocks mescaline’s psychoactive effects, and while it's unclear if mescaline is metabolized by monoamine oxidase enzymes, preliminary evidence suggests harmala alkaloids may potentiate effects.