Mescaline

Mescaline
Clinical data
Other names	Mescalin; Mezcalin; Mezcaline; 3,4,5-Trimethoxyphenethylamine; 3,4,5-TMPEA; TMPEA
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; UN: Psychotropic Schedule I;
Pharmacokinetic data
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: 0.5–3 hours
Elimination half-life	3.6 hours
Duration of action	≥10–12 hours
Excretion	Urine (28–81% unchanged, 13–26% as TMPA)
Identifiers
	IUPAC name 2-(3,4,5-trimethoxyphenyl)ethanamine;
CAS Number	54-04-6 ;
PubChem CID	4076;
ChemSpider	3934 ;
UNII	RHO99102VC;
KEGG	C06546 ;
ChEBI	CHEBI:28346 ;
ChEMBL	ChEMBL26687 ;
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 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]

^ ^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.
^ ^a ^b ^c ^d ^e Cite error: The named reference Dinis-OliveiraPereiradaSilva2019 was invoked but never defined (see the help page).
^ 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.
^ ^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.
^ ^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.
^ ^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.
^ Cite error: The named reference LeyHolzeArikci2023 was invoked but never defined (see the help page).
^ "Mescaline". PubChem. U.S. National Library of Medicine. Retrieved 22 October 2024.

[VamvakopoulouNarineCampbell2023-1] ^ ^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.

[Dinis-OliveiraPereiradaSilva2019-2] 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.

[CasselsSáez-Briones2018-4] 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.

[Doesburg-vanKleffensZimmermann-KlemdGründemann2023-5] 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.

[HolzeSinghLiechti2024-6] 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.

[LeyHolzeArikci2023-7] 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.

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