Mescaline

Mescaline
Clinical data
Other namesMescalin; Mezcalin; Mezcaline; 3,4,5-Trimethoxyphenethylamine; 3,4,5-TMPEA; TMPEA
AHFS/Drugs.commescaline
Routes of
administration
Oral, smoking, insufflation, intravenous[1][2]
Drug classSerotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
MetabolismOxidative deamination, N-acetylation, O-demethylation, conjugation, other pathways[4][5]
Metabolites• 3,4,5-Trimethoxyphenyl-acetaldehyde[4][1]
• 3,4,5-Trimethoxyphenylacetic acid[1]
• 3,4,5-Trimethoxyphenylethanol[5]
• Others[4][5][2]
Onset of actionOral: 0.5–3 hours[6][1][2]
Elimination half-life3.6 hours[6][7]
Duration of action≥10–12 hours[6][1][2]
ExcretionUrine (28–81% unchanged, 13–26% as TMPA)[1][4][5][2]
Identifiers
  • 2-(3,4,5-trimethoxyphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.174 Edit this at Wikidata
Chemical and physical data
FormulaC11H17NO3
Molar mass211.261 g·mol−1
3D model (JSmol)
Density1.067 g/cm3
Melting point35 to 36 °C (95 to 97 °F)
Boiling point180 °C (356 °F) at 12 mmHg
Solubility in watermoderately soluble in water mg/mL (20 °C)
  • O(c1cc(cc(OC)c1OC)CCN)C
  • 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 checkY
  • Key:RHCSKNNOAZULRK-UHFFFAOYSA-N checkY
  (verify)

Mescaline, also known as mescalin or mezcalin,[8] as well as 3,4,5-trimethoxyphenethylamine, is a naturally occurring psychedelic protoalkaloid of the substituted phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin.[4][1][6][5] It binds to and activates certain serotonin receptors in the brain, producing hallucinogenic effects.[1][6]

  1. ^ a b c d e f g h Vamvakopoulou IA, Narine KA, Campbell I, Dyck JR, Nutt DJ (January 2023). "Mescaline: The forgotten psychedelic". Neuropharmacology. 222: 109294. doi:10.1016/j.neuropharm.2022.109294. PMID 36252614.
  2. ^ a b c d e Cite error: The named reference Dinis-OliveiraPereiradaSilva2019 was invoked but never defined (see the help page).
  3. ^ Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
  4. ^ a b c d e Cassels BK, Sáez-Briones P (October 2018). "Dark Classics in Chemical Neuroscience: Mescaline". ACS Chem Neurosci. 9 (10): 2448–2458. doi:10.1021/acschemneuro.8b00215. PMID 29847089.
  5. ^ a b c d e Doesburg-van Kleffens M, Zimmermann-Klemd AM, Gründemann C (December 2023). "An Overview on the Hallucinogenic Peyote and Its Alkaloid Mescaline: The Importance of Context, Ceremony and Culture". Molecules. 28 (24): 7942. doi:10.3390/molecules28247942. PMC 10746114. PMID 38138432.
  6. ^ a b c d e Holze F, Singh N, Liechti ME, D'Souza DC (May 2024). "Serotonergic Psychedelics: A Comparative Review of Efficacy, Safety, Pharmacokinetics, and Binding Profile". Biol Psychiatry Cogn Neurosci Neuroimaging. 9 (5): 472–489. doi:10.1016/j.bpsc.2024.01.007. PMID 38301886.
  7. ^ Cite error: The named reference LeyHolzeArikci2023 was invoked but never defined (see the help page).
  8. ^ "Mescaline". PubChem. U.S. National Library of Medicine. Retrieved 22 October 2024.