Compound: 4-d Mescaline
SMILES: O(c1c(OC)cc(CCN)cc1OC)C([2H])([2H])[2H]
InChIKey: RHCSKNNOAZULRK-HPRDVNIFSA-N
Synonyms: 4-d Mescaline, 4-D (psychedelic), Mescaline, 4-trideuteromethoxy, 46N9S93HNE, UNII-46N9S93HNE, 3,5-Methoxy-4-trideuteromethoxyphenethylamine, 1020518-87-9, 1-(3,5-Dimethoxy-4-(2H3)methoxyphenyl)propan-2-amine, 4-D, SCHEMBL31079671
Theoretical properties:
molecular_formula: C11H17NO3
molecular_weight: 214.28 g/mol
exact_mass: 214.13967364 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: 3
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": null, "chebi": "A primary ammonium ion that is the conjugate acid of mescaline resulting from the protonation of the primary amino group; Major microspecies at pH 7.3.", "chembl": null, "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"}