Compound: mescaline
SMILES: O(c1c(OC)cc(CCN)cc1OC)C
InChIKey: RHCSKNNOAZULRK-UHFFFAOYSA-N
Synonyms: mescaline, Mescalin, 3,4,5-Trimethoxyphenethylamine, Mezcaline, 54-04-6, 2-(3,4,5-Trimethoxyphenyl)ethanamine, 3,4,5-Trimethoxybenzeneethanamine, 3,4,5-Trimethoxyphenylethylamine, Benzeneethanamine, 3,4,5-trimethoxy-, NSC-30419, RHO99102VC, CHEBI:28346, DTXSID80202303, RefChem:6005, DTXCID40124794, 200-190-7, Trimethoxyphenethylamine, Tmpea, Mezcalin, mescalina, mezcalina, Meskalin, 2-(3,4,5-trimethoxy-phenyl)-ethylamine, Mescline, Mezcline, 2-(3,4,5-Trimethoxyphenyl)ethylamine, Phenethylamine, 3,4,5-trimethoxy-, NSC 30419, Ethane, 1-amino-2-(3,4,5-trimethoxyphenyl)-, M (PSYCHEDELIC), CHEMBL26687, 1-amino-2-(3,4,5-trimethoxyphenyl)ethane, 3,4,5-trimethoxy-phenylethylamine, A1AFW, Mescalin [German], NCGC00247674-01, EINECS 200-190-7, BRN 1374088, UNII-RHO99102VC, DEA No. 7381, 3,4,5-trimethoxyphenethyl-amine, HSDB 7503, MESCALINE [MI], 2-(3,4,5-Trimethoxyphenyl)ethan-1-amine, MESCALINE [HSDB], MESCALINE [MART.], Constituent of Peyote cacti, MESCALINE [WHO-DD], 3,5-Trimethoxyphenethylamine, Epitope ID:2278946, Oprea1_166025, SCHEMBL34190, DivK1c_000984, 3,5-Trimethoxyphenylethylamine, Ethane,4,5-trimethoxyphenyl)-, SCHEMBL28007519, 3,4,5-trimethoxy-phenethylamine, GTPL13139, KBio1_000984, NINDS_000984, Benzeneethanamine,4,5-trimethoxy-, WLN: Z2R CO1 DO1 EO1, 3,4,5-Trimethoxy-b-phenethylamine, NSC30419, BDBM50059891, MFCD00128240, (3,4,5-trimethoxy)-benzylmethylamine, AKOS000277426, FT55211, SB37575, IDI1_000984, 2-(3,4,5-trimethoxyphenyl)-ethyl-amine, 2-(3,4,5-Trimethoxyphenyl)ethanamine #, Phenethylamine, 3,4,5-trimethoxy- (8CI), NS00005689, Benzeneethanamine, 3,4,5-trimethoxy- (9CI), C06546, Q193140
Theoretical properties:
molecular_formula: C11H17NO3
molecular_weight: 211.26 g/mol
exact_mass: 211.12084340 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 5
heavy_atom_count: 15
topological_polar_surface_area: 53.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals. ...  Takes up CO2 from the air and forms crystalline carbonate
color: Crystals. ...  Takes up CO2 from the air and forms crystalline carbonate
boiling_point: 180 °C at 12 mm Hg
melting_point: 35-36 °C
solubility: Moderately soluble in water; soluble in chloroform, benzene. Practically insoluble in ether, petroleum ether.
Descriptions:
{"pubchem": "Mescaline is a phenethylamine alkaloid that is phenethylamine substituted at positions 3, 4 and 5 by methoxy groups. It has a role as a hallucinogen and a plant metabolite. It is a phenethylamine alkaloid, a primary amino compound and a member of methoxybenzenes. It is a conjugate base of a mescalinium.", "chebi": "A phenethylamine alkaloid that is phenethylamine substituted at positions 3, 4 and 5 by methoxy groups.", "chembl": "MESCALINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 1.0.", "wikipedia": "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).\nMescaline is used recreationally, spiritually, and medically, with psychedelic effects occurring at doses from 100 to 1,000 mg and it can be used 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 0.9 hours and a duration that increases with dose, ranging from about 6 to 14 hours. Ketanserin blocks mescaline\u2019s psychoactive effects, and while it's unclear if mescaline is metabolized by monoamine oxidase enzymes, preliminary evidence suggests harmala alkaloids may potentiate effects.\nMescaline primarily acts as a partial agonist at serotonin 5-HT2A receptors, with varying affinity and efficacy across multiple serotonin, adrenergic, dopamine, histamine, muscarinic, and trace amine receptors. It is a relatively hydrophilic psychedelic compound structurally related to dopamine, first synthesized in 1919, with numerous synthetic methods and potent analogues developed since. Mescaline occurs naturally in various cacti species, with concentrations varying widely, and is biosynthesized in plants from phenylalanine via biochemical pathways likely linked to stress responses.\nThe practice of ingesting mescaline-containing cacti extracts dates back over 6,000 years. \nPeyote cacti were studied scientifically in the 19th and 20th centuries, culminating in the isolation of mescaline as the primary psychoactive compound in cacti, legal recognition of religious use, and ongoing exploration of the therapeutic potential of mescaline analogues. Mescaline and the cacti that produce it are largely illegal worldwide, though exceptions exist for religious, scientific, or ornamental use, and the compound has influenced many notable cultural figures. Very few studies concerning mescaline's activity and potential therapeutic effects in people have been conducted since the early 1970s.\n\n"}