Compound: 5-Methoxy-N-methyltryptamine
SMILES: O(c1cc2c([N]C=C2CCNC)cc1)C
InChIKey: VLPMDCPQCJZBMV-UHFFFAOYSA-N
Synonyms: 5-Methoxy-N-methyltryptamine, 2009-03-2, 1H-Indole-3-ethanamine, 5-methoxy-N-methyl-, 2-(5-Methoxy-1H-indol-3-yl)-N-methylethanamine, N,O-dimethylserotonin, 5-methoxy-N-methyl-1H-indole-3-ethanamine, YBO217L5YV, 5-MEO-NMT, CHEBI:189635, DTXSID40173909, RefChem:103051, DTXCID3096400, n-methyl-5-methoxy-1h-indole-3-ethanamine, CHEMBL58579, INDOLE, 5-METHOXY-3-(2-METHYLAMINO)ETHYL-, N-METHYL-5-METHOXYTRYPTAMINE, 5-methoxy-3-(2-methylamino)ethylindole, 2-(5-Methoxy-1H-indol-3-yl)-N-methylethan-1-amine, Indole, 5-methoxy-3-[2-(methylamino)ethyl]-, INDOLE, 5-METHOXY-3-(2-(METHYLAMINO)ETHYL)-, BRN 0160626, UNII-YBO217L5YV, Oprea1_817351, SCHEMBL1130014, SCHEMBL29633095, CAA00903, BDBM50038691, STK365327, 5-Methoxy NMT, 2009-03-2, AKOS005443520, HY-W721249, PD150636, [2-(5-methoxyindol-3-yl)ethyl]methylamine, DB-199536, ST50451047, 2-(5-methoxy-1H-indol-3-yl)-ethyl-methyl-amine, 5-22-12-00025 (Beilstein Handbook Reference), [2-(5-Methoxy-1H-indol-3-yl)-ethyl]-methyl-amine, 2-(5-Methoxy-1H-indol-3-yl)-N-methylethanamine #, Q4639626, N,O-dimethylserotonin, 5-Methoxy-N-methyltryptamine, n-methyl-5-methoxy-1h-indole-3-ethanamine
Theoretical properties:
molecular_formula: C12H16N2O
molecular_weight: 204.27 g/mol
exact_mass: 204.126263138 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 4
heavy_atom_count: 15
topological_polar_surface_area: 37.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "N,O-dimethylserotonin is a tryptamine derivative hahing a methoxy group at position 5 of the indole portion and a methyl substituent on the side-chain nitrogen. It is functionally related to a serotonin.", "chebi": null, "chembl": null, "wikipedia": "5-MeO-DMT, also known as 5-methoxy-N,N-dimethyltryptamine, as well as O-methylbufotenin or mebufotenin, is an atypical psychedelic drug, entheogen, and alkaloid of the tryptamine and 5-methoxytryptamine families. It is found naturally in a wide variety of plant species, and is also secreted by the glands of at least one toad species, the Colorado River toad (Incilius alvarius, formerly Bufo alvarius). It may occur naturally in humans as well. Like its close relatives dimethyltryptamine (DMT) and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include five-methoxy, the power, bufo, and toad venom. The drug has been described as the most powerful psychedelic and, by journalist Michael Pollan, as the \"Mount Everest of psychedelics\".\nAdverse effects of 5-MeO-DMT include sickness, vomiting, headache, chest pressure, fatigue, anxiety, fear, terror, confusion, paranoia, crying, loss of awareness and motor control, and reactivations. The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT1A and 5-HT2A receptors, among others. However, 5-MeO-DMT differs from most other serotonergic psychedelics in having much greater activity at the serotonin 5-HT1A receptor in addition to the serotonin 5-HT2A receptor. In relation to this, 5-MeO-DMT has been described as an \"atypical\" psychedelic and as producing subjective effects notably distinct from those of DMT and other psychedelics, for instance having a relative lack of visual effects. Nonetheless, 5-MeO-DMT reliably produces mystical experiences in most people who take it. Like DMT, 5-MeO-DMT is only active non-orally and has a very rapid onset and short duration. However, 5-MeO-DMT is 4- to 20-fold more potent than DMT in humans.\n5-MeO-DMT was first described by 1936, was first isolated from natural sources by 1959, and was first reported to be hallucinogenic by 1970. The use of 5-MeO-DMT-containing toad venom was first described in 1984. It is a controlled substance in some countries, for instance the United States, United Kingdom, Australia, and New Zealand. The drug is used recreationally and several deaths have been reported in association with its use. Use of 5-MeO-DMT is rare compared with other psychedelics, with only 0.003% of the United States general population having reported taking it in 2019 (compared to 8.5% for psilocybin). 5-MeO-DMT is being developed for potential use in medicine in the treatment of neuropsychiatric disorders such as depression."}