Mescaline

Details

• Internal ID: ee520216-5706-47a7-a461-f9dfa1912297
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenethylamines
• IUPAC Name: 2-(3,4,5-trimethoxyphenyl)ethanamine
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)CCN
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)CCN
• 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
• InChI Key: RHCSKNNOAZULRK-UHFFFAOYSA-N
• Popularity: 2,844 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₇NO₃
• Molecular Weight: 211.26 g/mol
• Exact Mass: 211.12084340 g/mol
• Topological Polar Surface Area (TPSA): 53.70 Ų
• XlogP: 0.70

Synonyms

• Mescalin
• Tmpea
• 3,4,5-Trimethoxyphenethylamine
• Mezcaline
• 54-04-6
• 2-(3,4,5-Trimethoxyphenyl)ethanamine
• 3,4,5-Trimethoxybenzeneethanamine
• 3,4,5-Trimethoxyphenylethylamine
• mescalina
• mezcalina
• Meskalin
• Mezcalin
• Benzeneethanamine, 3,4,5-trimethoxy-
• Mescalin [German]
• Phenethylamine, 3,4,5-trimethoxy-
• NSC 30419
• Trimethoxyphenethylamine
• Mescline
• Mezcline
• Ethane, 1-amino-2-(3,4,5-trimethoxyphenyl)-
• 2-(3,4,5-trimethoxy-phenyl)-ethylamine
• EINECS 200-190-7
• UNII-RHO99102VC
• NSC-30419
• BRN 1374088
• RHO99102VC
• CHEBI:28346
• HSDB 7503
• 1-amino-2-(3,4,5-trimethoxyphenyl)ethane
• CHEMBL26687
• DEA No. 7381
• DTXSID80202303
• 2-(3,4,5-Trimethoxyphenyl)ethylamine
• MESCALINE (MART.)
• MESCALINE [MART.]
• Peyote
• NCGC00247674-01
• 3,4,5-trimethoxyphenethyl-amine
• M (PSYCHEDELIC)
• MESCALINE [MI]
• MESCALINE [HSDB]
• D0L8MR
• Constituent of Peyote cacti
• MESCALINE [WHO-DD]
• 3,5-Trimethoxyphenethylamine
• Oprea1_166025
• SCHEMBL34190
• DivK1c_000984
• 3,4,5-trimethoxyphenethylamin
• 3,5-Trimethoxyphenylethylamine
• Constituent of "Peyote" cacti
• DEA No. 7381(ChemID)
• Ethane,4,5-trimethoxyphenyl)-
• 3,4,5-trimethoxy-phenethylamine
• KBio1_000984
• DTXCID40124794
• NINDS_000984
• Benzeneethanamine,4,5-trimethoxy-
• WLN: Z2R CO1 DO1 EO1
• 3,4,5-Trimethoxy-b-phenethylamine
• NSC30419
• BDBM50059891
• (3,4,5-trimethoxy)-benzylmethylamine
• AKOS000277426
• SB37575
• IDI1_000984
• 2-(3,4,5-trimethoxyphenyl)-ethyl-amine
• 2-(3,4,5-Trimethoxyphenyl)ethanamine #
• 3,4,5-Trimethoxyphenylethylamine(ChemID)
• 3,4,5-TRIMETHYOXYBENZENEETHANAMINE
• LS-103730
• Phenethylamine, 3,4,5-trimethoxy- (8CI)
• Benzeneethanamine, 3,4,5-trimethoxy- (9CI)
• C06546
• Q193140
• J-505719
• Ethane, 1-amino-2-(3,4,5-trimethoxyphenyl)-(ChemID)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	551 nM	Ki	PMID: 9301661
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	795.1 nM	Ki	PMID: 9301661
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	302.8 nM	Ki	PMID: 9301661

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.51%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.81%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.36%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.84%	91.11%
CHEMBL4581	P52732	Kinesin-like protein 1	89.12%	93.18%
CHEMBL1255126	O15151	Protein Mdm4	86.26%	90.20%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.06%	90.24%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.64%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.27%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.99%	96.00%
CHEMBL2885	P07451	Carbonic anhydrase III	81.06%	87.45%

Plants that contains it

• Aconitum carmichaelii
• Austrocylindropuntia cylindrica
• Cylindropuntia imbricata
• Gymnocalycium bodenbenderianum
• Gymnocalycium gibbosum
• Gymnocalycium monvillei
• Lophophora diffusa
• Lophophora williamsii
• Myristica fragrans
• Opuntia humifusa
• Pereskia aculeata
• Senegalia berlandieri
• Stenocereus treleasei
• Turbinicarpus pseudopectinatus
• Vachellia rigidula

Cross-Links

• PubChem: 4076
• NPASS: NPC105513
• ChEMBL: CHEMBL26687
• LOTUS: LTS0076396
• wikiData: Q193140