5-MeO-DMT

5-MeO-DMT
INN: Mebufotenin
Clinical data
Other names5-Methoxy-N,N-dimethyltryptamine; 5-Methoxy-N,N-DMT; 5-MeO-DMT; 5-OMe-DMT; MDMT; O-Methylbufotenin; Mebufotenin; Methylbufotenin; N,N,O-Trimethylserotonin; CT-4334; BPL-002; BPL-003; LSR-1019
Routes of
administration		Inhalation, insufflation, sublingual, intramuscular, intravenous, oral (with an MAOITooltip monoamine oxidase inhibitor)[1][2][3]
Drug classSerotonergic psychedelic (hallucinogen)
ATC code
  • None
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • BR: Class F2 (Prohibited psychotropics)[4]
  • DE: Anlage I (Authorized scientific use only)
  • UK: Class A
  • US: Schedule I
  • Illegal in China, Sweden, Turkey
Pharmacokinetic data
BioavailabilityOral: inactive (without an MAOITooltip monoamine oxidase inhibitor) or weak[1][2]
MetabolismOxidative deamination (MAOTooltip monoamine oxidase), O-demethylation (CYP2D6)[2][1][5]
Metabolites
Onset of action
Elimination half-life
Duration of action
Identifiers
IUPAC name
  • 2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.012.558
Chemical and physical data
FormulaC13H18N2O
Molar mass218.300 g·mol−1
3D model (JSmol)
SMILES
  • COc2ccc1[nH]cc(CCN(C)C)c1c2
InChI
  • InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3 Y
  • Key:ZSTKHSQDNIGFLM-UHFFFAOYSA-N Y
  (verify)

5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine), also known as O-methylbufotenin or mebufotenin (INNTooltip International Nonproprietary Name), is a naturally occurring psychedelic of the tryptamine family.[6][1][5][2] It is found in a wide variety of plant species, and is also secreted by the glands of at least one toad species, the Colorado River toad.[6] It may occur naturally in humans as well.[6] Like its close relatives dimethyltryptamine (DMT) and bufotenin (5-HO-DMT), it has been used as an entheogen in South America.[6][8] Slang terms include five-methoxy, the power, bufo, and toad venom.[9] The drug has been described as the most powerful psychedelic[10][11] and, by journalist Michael Pollan, as the "Mount Everest of psychedelics".[11][12]

Adverse 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.[12] The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT1A and 5-HT2A receptors, among others.[1][5][13] However, 5-MeO-DMT differs from most other serotonergic psychedelics in having 100- to 1,000-fold higher affinity for the serotonin 5-HT1A receptor over the serotonin 5-HT2A receptor.[1][5][13] 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.[6][1][5] Nonetheless, 5-MeO-DMT reliably produces mystical experiences in most people who take it.[12] Like DMT, 5-MeO-DMT is only active non-orally and has a very rapid onset of action and short duration.[1][5] However, 5-MeO-DMT is 4- to 20-fold more potent than DMT in humans.[2][12]

5-MeO-DMT was first described by 1936, was first isolated from natural sources by 1959, and was first reported to be hallucinogenic by 1970.[11][6] The use of 5-MeO-DMT-containing toad venom was first described in 1984.[11][14] It is a controlled substance in some countries, for instance the United States, United Kingdom, Australia, and New Zealand.[6] The drug is used recreationally and several deaths have been reported in association with its use.[6][15] 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).[12][16] 5-MeO-DMT is being developed for potential use in medicine in the treatment of neuropsychiatric disorders such as depression.[17][6][1][5]

  1. ^ a b c d e f g h i j k l m n o Reckweg JT, Uthaug MV, Szabo A, Davis AK, Lancelotta R, Mason NL, et al. (July 2022). "The clinical pharmacology and potential therapeutic applications of 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT)". J Neurochem. 162 (1): 128–146. doi:10.1111/jnc.15587. PMC 9314805. PMID 35149998.
  2. ^ a b c d e f g h i Shen HW, Jiang XL, Winter JC, Yu AM (October 2010). "Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions". Curr Drug Metab. 11 (8): 659–666. doi:10.2174/138920010794233495. PMC 3028383. PMID 20942780.
  3. ^ Cite error: The named reference TiHKAL was invoked but never defined (see the help page).
  4. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  5. ^ a b c d e f g h i j Dourron HM, Nichols CD, Simonsson O, Bradley M, Carhart-Harris R, Hendricks PS (December 2023). "5-MeO-DMT: An atypical psychedelic with unique pharmacology, phenomenology & risk?". Psychopharmacology (Berl). 242 (7): 1457–1479. doi:10.1007/s00213-023-06517-1. PMID 38072874.
  6. ^ a b c d e f g h i j Ermakova AO, Dunbar F, Rucker J, Johnson MW (March 2022). "A narrative synthesis of research with 5-MeO-DMT". J Psychopharmacol. 36 (3): 273–294. doi:10.1177/02698811211050543. PMC 8902691. PMID 34666554.
  7. ^ Bistue Millón MB, Noguera L, Bruno D, Vita L, Zanino M, Kassuha DE, et al. (July 2025). "Safety and tolerability of multiple sublingual microdoses of 5-MeO-DMT in adults with moderate symptoms of depression and/or anxiety: a randomized, double-blind, placebo-controlled study". Neuropsychopharmacology. doi:10.1038/s41386-025-02167-3. PMID 40659913.
  8. ^ Araújo AM, Carvalho F, Bastos M, Guedes de Pinho P, Carvalho M (August 2015). "The hallucinogenic world of tryptamines: an updated review". Archives of Toxicology. 89 (8): 1151–1173. Bibcode:2015ArTox..89.1151A. doi:10.1007/s00204-015-1513-x. PMID 25877327. S2CID 4825078.
  9. ^ "Ultimate Guide to 5-MeO-DMT - Experience, Benefits, & Side Effects". 29 June 2020.
  10. ^ Linden J, Robin D (2023). "Other psychedelics". Psychedelics as Psychiatric Medications. Oxford University PressOxford. p. 95–C8P41. doi:10.1093/med/9780192863607.003.0008. ISBN 978-0-19-286360-7. We complete this chapter by paying some attention to what many feel is the most interesting and most powerful psychedelic of them all. It gives us great pleasure to introduce 5-methoxy-N, N-DMT (5-MeO), aka the 'God Molecule'. 5-MeO is an extremely powerful, naturally occurring, psychedelic tryptamine [...]
  11. ^ a b c d Cite error: The named reference Delgrasso2024 was invoked but never defined (see the help page).
  12. ^ a b c d e Hayes C (14 April 2025). "A Toad Less Traveled: Should 5-MeO-DMT Have a Role in Treating Depression?". Psychedelic Medicine. doi:10.1089/psymed.2024.0049. ISSN 2831-4425. Retrieved 6 May 2025.
  13. ^ a b Holze F, Singh N, Liechti ME, D'Souza DC (May 2024). "Serotonergic Psychedelics: A Comparative Review of Efficacy, Safety, Pharmacokinetics, and Binding Profile". Biol Psychiatry Cogn Neurosci Neuroimaging. 9 (5): 472–489. doi:10.1016/j.bpsc.2024.01.007. PMID 38301886.
  14. ^ Cite error: The named reference WeilDavis1994 was invoked but never defined (see the help page).
  15. ^ Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA (December 2020). "Toxicology and Analysis of Psychoactive Tryptamines". Int J Mol Sci. 21 (23): 9279. doi:10.3390/ijms21239279. PMC 7730282. PMID 33291798.
  16. ^ Sexton JD, Nichols CD, Hendricks PS (2019). "Population Survey Data Informing the Therapeutic Potential of Classic and Novel Phenethylamine, Tryptamine, and Lysergamide Psychedelics". Front Psychiatry. 10: 896. doi:10.3389/fpsyt.2019.00896. PMC 7026018. PMID 32116806.
  17. ^ Hayes C (14 April 2025). "A Toad Less Traveled: Should 5-MeO-DMT Have a Role in Treating Depression?". Psychedelic Medicine. doi:10.1089/psymed.2024.0049. ISSN 2831-4425. Retrieved 6 May 2025.
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