Mescaline

Base Information

• Chemical Name: Mescaline
• CAS No.: 54-04-6
• Molecular Formula: C11H17 N O3
• Molecular Weight: 211.261
• Hs Code.: 2922299090
• European Community (EC) Number: 200-190-7
• NSC Number: 30419
• UNII: RHO99102VC
• DSSTox Substance ID: DTXSID80202303
• Nikkaji Number: J4.150E
• Wikipedia: Mescaline
• Wikidata: Q193140
• Metabolomics Workbench ID: 51691
• ChEMBL ID: CHEMBL26687
• Mol file: 54-04-6.mol

Synonyms:3,4,5-Trimethoxyphenethylamine;Mescaline;Mezcalin;Peyote;Trimethoxyphenethylamine

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Chemical Property of Mescaline

Chemical Property:

• Vapor Pressure: 0.000293mmHg at 25°C
• Melting Point: 35-36°
• Refractive Index: 1.5718 (estimate)
• Boiling Point: 312.1°Cat760mmHg
• PKA: 9.57±0.10(Predicted)
• Flash Point: 145.8°C
• PSA: 53.71000
• Density: 1.067g/cm³
• LogP: 1.91390
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 211.12084340
• Heavy Atom Count: 15
• Complexity: 163

Purity/Quality:

Safty Information:

• Pictogram(s): Highly toxic by ingestion.
• Hazard Codes: Highly toxic by ingestion.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)CCN
• Recent ClinicalTrials: Role of the Serotonin 5-HT2A Receptor in Mescaline-induced Altered States of Consciousness
• Description: Mescaline is one of the main active ingredients in the peyote plant, Lophophora williamsii. It is also found in several other cacti including the South American Trichocereus otherwise known as the Peruvian torch species. Mescaline can also be synthesized in the laboratory. It is one of the oldest known hallucinogenic drugs. Ingestion of mescaline via use of the peyote cactus has been used in rituals by North American Indians dating back thousands of years. Ingestion of peyote was also common among the Aztec, Apache, and Pima Indians for religious, ceremonial, and medicinal purposes. Mescaline was isolated from peyote in 1896 by the chemist Hefter and in 1919, the chemical structure was confirmed by Spath. There are many analogs of mescaline with over 250 being prepared and self-tested by the chemist and pharmacologist, Alexander Shulgin (aka Sasha Shulgin). Mescaline became a Schedule I drug and was placed in Controlled Substances Act in 1970. Many of the related chemicals or analogs of mescaline were also placed in Schedule I of the Controlled Substances Act.
• Uses: Psychedelic Alkoloid Mescaline is used recreationally as a hallucinogenic drug and it is used in religious ceremonies for spiritual purposes by groups such as the Native American church. Mescaline is purported not to have any therapeutic benefits based on its Schedule I status. When used recreationally typical doses range from 300 to 500 mg orally.

Technology Process of Mescaline

There total 40 articles about Mescaline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

mescaline hydrochloride (832-92-8) → mescaline (54-04-6)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2013.03.077

Reference yield: 78.0%

1-(3,4,5-trimethoxyphenyl)-2-nitroethene (40663-31-8) → mescaline (54-04-6)

Guidance literature:

With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; for 6.5h; Inert atmosphere; Reflux;

DOI:10.1021/acs.joc.8b02888

Reference yield: 76.0%

2-(3,4,5-trimethoxyphenyl)acetamide (91248-14-5) → mescaline (54-04-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane; for 36h; Heating;

DOI:10.1002/(SICI)1099-1344(199801)41:1<53::AID-JLCR53>3.0.CO;2-K

upstream raw materials:

1-(3,4,5-trimethoxyphenyl)-2-nitroethene

2-(3,4,5-trimethoxyphenyl)acetonitrile

3,4,5-trimethoxy-β-nitrostyrene

2-(3,4,5-trimethoxyphenyl)acetamide

Downstream raw materials:

(3,4,5-trimethoxy-phenethyl)-carbamic acid ethyl ester

N-acetylmescaline

trimethyl-(3,4,5-trimethoxy-phenethyl)-ammonium; iodide

N-(3,4,5-trimethoxyphenethyl)-5-phenyl-4-hydroxypentanamide

Refernces

• 1、 M?der, Patrick,Bartholom?us, Ruben,Nicolussi, Simon,Baumann, Alice,Weis, Melanie,Chicca, Andrea,Rau, Mark,Sim?o, Ana Catarina,Gertsch, Jürg,Altmann, Karl-Heinz. "Synthesis and Biological Evaluation of Endocannabinoid Uptake Inhibitors Derived from WOBE437". supporting information. p. 145 - 154. Retrieved 2020/06/02.
• 2、 Fan, Tian-Yun,Yang, Yu-Xin,Zeng, Qing-Xuan,Wang, Xue-Lei,Wei, Wei,Guo, Xi-Xi,Zhao, Li-Ping,Song, Dan-Qing,Wang, Yan-Xiang,Wang, Li,Hong, Bin. "Structure–activity relationship and biological evaluation of berberine derivatives as PCSK9 down-regulating agents". . . Retrieved 2021/06/01.