| Revision as of 18:32, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 476806082 of page 5-MeO-DMT for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 23:38, 22 December 2024 edit 風猷既頽 (talk | contribs)107 editsNo edit summaryTags: Visual edit Mobile edit Mobile web edit Advanced mobile edit |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{cs1 config|name-list-style=vanc}} |
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{{drugbox | verifiedrevid = 443355241 |
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{{Drugbox |
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| IUPAC_name = 2-(5-methoxy-1H-indol-3-yl)-''N,N''-dimethylethanamine |
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| Verifiedfields = verified |
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| Watchedfields = verified |
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| verifiedrevid = 477224937 |
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| drug_name = |
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| INN = Mebufotenin |
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| image = 5-MeO-DMT.svg |
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| image = 5-MeO-DMT.svg |
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| width = 160 |
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| width = 160 |
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| pregnancy_US = |
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| pregnancy_US = |
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| pregnancy_category = |
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| pregnancy_category = |
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| routes_of_administration = ], ], ], ], ], ] (with an {{Abbrlink|MAOI|monoamine oxidase inhibitor}})<ref name="ReckwegUthaugSzabo2022" /><ref name="ShenJiangWinter2010" /> |
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| legal_AU = |
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| class = ] (]) |
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<!-- Legal status --> |
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| legal_AU = S9 |
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| legal_BR = F2 |
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| legal_BR_comment = <ref>{{cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=] |language=pt-BR |publication-date=2023-07-25}}</ref> |
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| legal_CA = |
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| legal_CA = |
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| legal_UK = Class A |
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| legal_UK = Class A |
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| legal_US = |
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| legal_US = Schedule I |
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| legal_DE = Anlage I |
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| legal_status = Schedule I(]) |
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| legal_status = Illegal in China, Sweden, Turkey |
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| routes_of_administration = Smoked, Insufflated |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = ]: inactive (without an {{Abbrlink|MAOI|monoamine oxidase inhibitor}}) or weak<ref name="ReckwegUthaugSzabo2022" /><ref name="ShenJiangWinter2010" /> |
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| bioavailability = |
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| protein_bound = |
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| protein_bound = |
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| metabolism = ] ({{Abbrlink|MAO|monoamine oxidase}}), ''O''-demethylation (])<ref name="ShenJiangWinter2010" /><ref name="ReckwegUthaugSzabo2022" /><ref name="DourronNicholsSimonsson2023" /> |
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| metabolism = |
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| metabolites = * ]<ref name="ShenJiangWinter2010" /><ref name="DourronNicholsSimonsson2023" /> |
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| elimination_half-life = |
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| onset = * ]: seconds or 3–4{{nbsp}}min<ref name="ReckwegUthaugSzabo2022" /> |
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* ]: 3–4{{nbsp}}min<ref name="ShenJiangWinter2010" /> |
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* ]: 5–7{{nbsp}}min<ref name="ReckwegUthaugSzabo2022" /> |
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* ]: 1–6{{nbsp}}min<ref name="ReckwegUthaugSzabo2022" /> |
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| elimination_half-life = Minutes<ref name="DourronNicholsSimonsson2023" /> (12–19{{nbsp}}min in mice, 6–16{{nbsp}}min in rats)<ref name="ShenJiangWinter2010" /><ref name="ErmakovaDunbarRucker2022" /> |
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| duration_of_action = * ]: 10–30{{nbsp}}min<ref name="ReckwegUthaugSzabo2022" /><ref name="DourronNicholsSimonsson2023" /> |
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* ]: 45–70{{nbsp}}min<ref name="ReckwegUthaugSzabo2022" /><ref name="ShenJiangWinter2010" /> |
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* ]: ≤60{{nbsp}}min<ref name="ReckwegUthaugSzabo2022" /> |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = <!-- blanked - oldvalue: 1019-45-0 --> |
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| CAS_number = 1019-45-0 |
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| ATC_prefix = |
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| ATC_prefix = None |
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| ATC_suffix = |
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| ATC_suffix = |
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| PubChem = 1832 |
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| PubChem = 1832 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 1766 |
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| ChemSpiderID = 1766 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = X0MKX3GWU9 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C08309 |
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| KEGG = C08309 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 7257 |
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| ChEMBL = 7257 |
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| synonyms = 5-Methoxy-''N'',''N''-dimethyltryptamine; 5-Methoxy-''N'',''N''-DMT; ''O''-Methylbufotenin; Mebufotenin; Methylbufotenin; BPL-002; BPL-003; LSR-1019 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| IUPAC_name = 2-(5-Methoxy-1''H''-indol-3-yl)-''N'',''N''-dimethylethanamine |
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| C=13 | H=18 | N=2 | O=1 |
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| C = 13 | H = 18 | N = 2 | O = 1 |
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| molecular_weight = 218.298 g/mol |
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| smiles = O(c1cc2c(cc1)ncc2CCN(C)C)C |
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| SMILES = COc2ccc1cc(CCN(C)C)c1c2 |
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| InChI = 1/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 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ZSTKHSQDNIGFLM-UHFFFAOYSA-N |
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| StdInChIKey = ZSTKHSQDNIGFLM-UHFFFAOYSA-N |
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| melting_point = |
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| melting_high = |
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}} |
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}} |
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'''5-MeO-DMT''' ('''5-methoxy-''N'',''N''-dimethyltryptamine'''), also known as '''''O''-methylbufotenin''' or '''mebufotenin''' ({{Abbrlink|INN|International Nonproprietary Name}}), is a ] ] of the ] family.<ref name="ErmakovaDunbarRucker2022">{{cite journal | vauthors = Ermakova AO, Dunbar F, Rucker J, Johnson MW | title = A narrative synthesis of research with 5-MeO-DMT | journal = J Psychopharmacol | volume = 36 | issue = 3 | pages = 273–294 | date = March 2022 | pmid = 34666554 | doi = 10.1177/02698811211050543 | pmc = 8902691 | url = }}</ref><ref name="ReckwegUthaugSzabo2022">{{cite journal | vauthors = Reckweg JT, Uthaug MV, Szabo A, Davis AK, Lancelotta R, Mason NL, Ramaekers JG | title = The clinical pharmacology and potential therapeutic applications of 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) | journal = J Neurochem | volume = 162 | issue = 1 | pages = 128–146 | date = July 2022 | pmid = 35149998 | pmc = 9314805 | doi = 10.1111/jnc.15587 | url = }}</ref><ref name="DourronNicholsSimonsson2023">{{cite journal | vauthors = Dourron HM, Nichols CD, Simonsson O, Bradley M, Carhart-Harris R, Hendricks PS | title = 5-MeO-DMT: An atypical psychedelic with unique pharmacology, phenomenology & risk? | journal = Psychopharmacology (Berl) | volume = | issue = | pages = | date = December 2023 | pmid = 38072874 | doi = 10.1007/s00213-023-06517-1 | url = }}</ref><ref name="ShenJiangWinter2010">{{cite journal | vauthors = Shen HW, Jiang XL, Winter JC, Yu AM | title = Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions | journal = Curr Drug Metab | volume = 11 | issue = 8 | pages = 659–666 | date = October 2010 | pmid = 20942780 | pmc = 3028383 | doi = 10.2174/138920010794233495 | url = }}</ref> It is found in a wide variety of plant species, and is also secreted by the glands of at least one toad species, the ].<ref name="ErmakovaDunbarRucker2022" /> It may occur naturally in humans as well.<ref name="ErmakovaDunbarRucker2022" /> Like its close relatives ] (DMT) and ] (5-HO-DMT), it has been used as an ] in ].<ref name="ErmakovaDunbarRucker2022" /><ref name="AraújoCarvalhoBastos2015">{{cite journal | vauthors = Araújo AM, Carvalho F, Bastos M, Guedes de Pinho P, Carvalho M | title = The hallucinogenic world of tryptamines: an updated review | journal = Archives of Toxicology | volume = 89 | issue = 8 | pages = 1151–1173 | date = August 2015 | pmid = 25877327 | doi = 10.1007/s00204-015-1513-x | bibcode = 2015ArTox..89.1151A | s2cid = 4825078 }}</ref> Slang terms include Five-methoxy, the power, bufo, and toad venom.<ref>{{cite web|url=https://thethirdwave.co/psychedelics/5-meo-dmt/|title=Ultimate Guide to 5-MeO-DMT - Experience, Benefits, & Side Effects|date=29 June 2020}}</ref> |
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The drug acts as a ] ], including of the ] ] and ]s among others.<ref name="ReckwegUthaugSzabo2022" /><ref name="DourronNicholsSimonsson2023" /><ref name="HolzeSinghLiechti2024">{{cite journal | vauthors = Holze F, Singh N, Liechti ME, D'Souza DC | title = Serotonergic Psychedelics: A Comparative Review of Efficacy, Safety, Pharmacokinetics, and Binding Profile | journal = Biol Psychiatry Cogn Neurosci Neuroimaging | volume = 9 | issue = 5 | pages = 472–489 | date = May 2024 | pmid = 38301886 | doi = 10.1016/j.bpsc.2024.01.007 | url = | doi-access = free }}</ref> However, 5-MeO-DMT differs from most other serotonergic psychedelics in having 100- to 1,000-fold higher ] for the serotonin 5-HT<sub>1A</sub> receptor over the serotonin 5-HT<sub>2A</sub> receptor.<ref name="ReckwegUthaugSzabo2022" /><ref name="DourronNicholsSimonsson2023" /><ref name="HolzeSinghLiechti2024" /> 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.<ref name="ErmakovaDunbarRucker2022" /><ref name="ReckwegUthaugSzabo2022" /><ref name="DourronNicholsSimonsson2023" /> Like DMT, 5-MeO-DMT has a very rapid ] and short ].<ref name="ReckwegUthaugSzabo2022" /><ref name="DourronNicholsSimonsson2023" /> However, 5-MeO-DMT is 4- to 10-fold more ] than DMT in humans.<ref name="ShenJiangWinter2010" /> |
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5-MeO-DMT was first ] in 1936 by ]<ref>Bulletin of Chemical Society of Japan, 11(3), 221-224</ref> (]), professor of ], and was first isolated from a natural source in 1959.<ref name="ErmakovaDunbarRucker2022" /> It is a ] in some countries, for instance the ], ], ], and ].<ref name="ErmakovaDunbarRucker2022" /> The drug is used ] and several deaths have been reported in association with its use.<ref name="ErmakovaDunbarRucker2022" /><ref name="MalacaLoFaroTamborra2020">{{cite journal | vauthors = Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA | title = Toxicology and Analysis of Psychoactive Tryptamines | journal = Int J Mol Sci | volume = 21 | issue = 23 | date = December 2020 | page = 9279 | pmid = 33291798 | pmc = 7730282 | doi = 10.3390/ijms21239279 | doi-access = free | url = }}</ref> 5-MeO-DMT is being developed for potential use in medicine in the treatment of ]s such as ].<ref name="ErmakovaDunbarRucker2022" /><ref name="ReckwegUthaugSzabo2022" /><ref name="DourronNicholsSimonsson2023" /> |
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==Chemistry== |
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5-MeO-DMT, also known as 5-methoxy-''N'',''N''-dimethyltryptamine, is a ] ]. It is the 5-] derivative of ] (DMT), the ''N'',''N''-] derivative of ] (5-MT; mexamine), and the ''O''-methylated derivative of ] (5-HO-DMT). |
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It has a relatively high experimental ] of 3.30.<ref name="ShenJiangWinter2010" /><ref name="McBride2000" /> |
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]s of 5-MeO-DMT include ], ], ], ], ], ], ], and ]. Other analogues include ] and ]. |
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==Effects== |
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When smoked, the duration of effects can be as little as ten minutes; when ], up to two hours. Effects vary and can range from radical perspective shifting and perception of new insights, euphoria, immersive experiences, ] and non-responsiveness, sensual/erotic enhancement, to dysphoria, fear, terror, panic, and ].<ref>{{cite web|url=https://erowid.org/chemicals/5meo_dmt/5meo_dmt_effects.shtml|publisher=Erowid.org|access-date=2021-07-30|title=5-MeO-DMT Effects by Erowid}}</ref>{{Better source needed|reason=Needed reliable source that binds WP:MEDRS |date=May 2023}} |
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The subjective effects of 5-MeO-DMT are described as distinct from those of DMT and other psychedelics.<ref name="DourronNicholsSimonsson2023" /><ref name="ErmakovaDunbarRucker2022" /> Whereas DMT is described as producing more "information-rich" experiences, with "rich sensory phenomenology", visuals, and experiences of encountering entities and visiting other worlds, 5-MeO-DMT is described as having a relative lack of visual effects, producing a sense of "nothingness", and causing experiences that are said to be "content-free" and sometimes known as "whiteouts".<ref name="DourronNicholsSimonsson2023" /><ref name="ErmakovaDunbarRucker2022" /> These experiences have been described as "beyond ordinary human comprehension", with a subjective impression of a void or ] of the experience.<ref name="DourronNicholsSimonsson2023" /><ref name="ErmakovaDunbarRucker2022" /> In spite of this however, some have described the experiences as ]ic, ], and ]ful, whereas others have described them as terror or "information overwhelm".<ref name="DourronNicholsSimonsson2023" /> As with DMT and other psychedelics, the experiences with 5-MeO-DMT are often described as overwhelming, profound, spiritual, religious, and/or mystical.<ref name="DourronNicholsSimonsson2023" /><ref name="ErmakovaDunbarRucker2022" /> |
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The experiences of 5-MeO-DMT have been related to the experience of ]s.<ref name="DourronNicholsSimonsson2023" /> |
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==Uses== |
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Preliminary clinical findings suggest that 5-MeO-DMT might have ] and ] effects.<ref>{{cite journal | vauthors = Davis AK, So S, Lancelotta R, Barsuglia JP, Griffiths RR | title = 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) used in a naturalistic group setting is associated with unintended improvements in depression and anxiety | journal = The American Journal of Drug and Alcohol Abuse | volume = 45 | issue = 2 | pages = 161–169 | date = March 2019 | pmid = 30822141 | pmc = 6430661 | doi = 10.1080/00952990.2018.1545024 }}</ref><ref>{{cite journal | vauthors = Davis AK, Barsuglia JP, Lancelotta R, Grant RM, Renn E | title = The epidemiology of 5-methoxy- N, N-dimethyltryptamine (5-MeO-DMT) use: Benefits, consequences, patterns of use, subjective effects, and reasons for consumption | journal = Journal of Psychopharmacology | volume = 32 | issue = 7 | pages = 779–792 | date = July 2018 | pmid = 29708042 | pmc = 6248886 | doi = 10.1177/0269881118769063 }}</ref> |
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===Religious use===<!-- ] redirects here --> |
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The Church of the Tree of Life, founded in California in 1971 by John Mann but now defunct, declared the use of 5-MeO-DMT to be a ]. From approximately 1971 to the late 1980s, 5-MeO-DMT was discreetly available to its members.<ref>{{cite book |title=The Book of Sacraments: Ritual Use of Magical Plants | vauthors = Mann J, Gottlieb A |publisher=Ronin Publishing |year=2015 |orig-year=First published 1970|isbn=978-1-57951-210-1|contribution=back cover}}</ref><ref name="Erowid">{{cite web |url=https://www.erowid.org/chemicals/5meo_dmt/5meo_dmt_timeline.php |title=5-MeO-DMT Timeline |work=Erowid}}</ref> Between 1970 and 1990, smoking of 5-MeO-DMT on ] was probably one of the two most common forms of ] in the ].<ref name="Erowid"/>{{Unreliable source?|date=October 2023}} |
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==Pharmacology== |
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===Pharmacodynamics=== |
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{| class="wikitable floatright" style="font-size:small;" |
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|+ {{Nowrap|Activities of 5-MeO-DMT}} |
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! ] !! ] (K<sub>i</sub>, nM) |
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| ] || 1.9–28 (K<sub>i</sub>)<br />3.92–1,060 ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}})<br />68–98% ({{Abbrlink|E<sub>max</sub>|maximal efficacy}}) |
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|- |
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| ] || 14–351 (K<sub>i</sub>)<br />1.53 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />78% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) |
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|- |
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| ] || 2.3–20 (K<sub>i</sub>)<br />37 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />98% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) |
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|- |
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| ] || 360–528 (K<sub>i</sub>)<br />92–160 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />119% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) |
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|- |
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| ] || 37 (K<sub>i</sub>)<br />14 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />93% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) |
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|- |
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| ] || 15–2,011 (K<sub>i</sub>)<br />1.80–3.87 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />82–101% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) |
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|- |
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| ] || 36–3,884 (K<sub>i</sub>)<br />5.87 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />73% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) |
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|- |
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| ] || 42–538 (K<sub>i</sub>)<br />31 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />84% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) |
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|- |
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| ] || >10,000 |
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|- |
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| ] || >10,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) |
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| ] || 277–505 (K<sub>i</sub>)<br />110 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />107% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) |
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|- |
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| ] || 6.5–78 (K<sub>i</sub>)<br />0.24 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />125% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) |
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| ] || 3.9–30 (K<sub>i</sub>)<br />65.7 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />107% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) |
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| ] || 210 (K<sub>i</sub>)<br />257 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) |
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| ] || 16 (K<sub>i</sub>)<br /> 112 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) |
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| ] || 4,373–>10,000 |
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| ] || 2,188–>10,000 |
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| ] || {{Abbr|ND|No data}} |
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| ] || 938–1,890 |
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| ] || 430–2,640 |
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| ] || 206–508 |
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| ] || >10,000 |
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| ] || 2,679–>10,000 |
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| ] || >10,000 |
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| ] || 80–>10,000 |
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| ] || 3,562–>10,000 |
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| ] || 498–>10,000 |
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| ] || 3,120–>10,000 |
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|- |
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| ] || >10,000 |
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| ] || 7,580 |
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|- |
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| ]–] || >10,000 |
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|- |
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| ]–] || >10,000 |
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|- |
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| ] || >10,000 |
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|- |
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| ] || >10,000 |
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| {{Abbrlink|SERT|Serotonin transporter}} || 2,032–3,603 (K<sub>i</sub>)<br />2,184 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />>10,000 ({{Abbr|EC<sub>50</sub>|Half-maximal effective concentration}}) |
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| {{Abbrlink|NET|Norepinephrine transporter}} || 2,859–>10,000 (K<sub>i</sub>)<br />>10,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />>10,000 ({{Abbr|EC<sub>50</sub>|Half-maximal effective concentration}}) |
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|- |
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| {{Abbrlink|DAT|Dopamine transporter}} || >10,000 (K<sub>i</sub>)<br />>10,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />>10,000 ({{Abbr|EC<sub>50</sub>|Half-maximal effective concentration}}) |
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|- class="sortbottom" |
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| colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' The smaller the value, the more avidly the drug binds to the site. Proteins are mostly but not exclusively human. '''Refs:''' <ref name="ErmakovaDunbarRucker2022" /><ref name="HolzeSinghLiechti2024" /><ref name="Ray2010">{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | pages = e9019 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | doi-access = free | bibcode = 2010PLoSO...5.9019R | url = }}</ref><ref name="CameronTombariLu2021">{{cite journal | vauthors = Cameron LP, Tombari RJ, Lu J, Pell AJ, Hurley ZQ, Ehinger Y, Vargas MV, McCarroll MN, Taylor JC, Myers-Turnbull D, Liu T, Yaghoobi B, Laskowski LJ, Anderson EI, Zhang G, Viswanathan J, Brown BM, Tjia M, Dunlap LE, Rabow ZT, Fiehn O, Wulff H, McCorvy JD, Lein PJ, Kokel D, Ron D, Peters J, Zuo Y, Olson DE | title = A non-hallucinogenic psychedelic analogue with therapeutic potential | journal = Nature | volume = 589 | issue = 7842 | pages = 474–479 | date = January 2021 | pmid = 33299186 | pmc = 7874389 | doi = 10.1038/s41586-020-3008-z | bibcode = 2021Natur.589..474C | url = }}</ref><ref name="HalberstadtNicholsGeyer2012">{{cite journal | vauthors = Halberstadt AL, Nichols DE, Geyer MA | title = Behavioral effects of α,α,β,β-tetradeutero-5-MeO-DMT in rats: comparison with 5-MeO-DMT administered in combination with a monoamine oxidase inhibitor | journal = Psychopharmacology (Berl) | volume = 221 | issue = 4 | pages = 709–718 | date = June 2012 | pmid = 22222861 | pmc = 3796951 | doi = 10.1007/s00213-011-2616-6 | url = }}</ref><ref name="delaFuenteRevengaFernández-SáezHerrera-Arozamena2015">{{cite journal | vauthors = de la Fuente Revenga M, Fernández-Sáez N, Herrera-Arozamena C, Morales-García JA, Alonso-Gil S, Pérez-Castillo A, Caignard DH, Rivara S, Rodríguez-Franco MI | title = Novel N-Acetyl Bioisosteres of Melatonin: Melatonergic Receptor Pharmacology, Physicochemical Studies, and Phenotypic Assessment of Their Neurogenic Potential | journal = J Med Chem | volume = 58 | issue = 12 | pages = 4998–5014 | date = June 2015 | pmid = 26023814 | doi = 10.1021/acs.jmedchem.5b00245 | url = }}</ref><ref name="BloughLandavazoDecker2014" /><ref name="JayakodiarachchiMaurerSchultz2024" /><ref name="PDSPKiDatabase">{{cite web | title=PDSP Database | website=UNC | url=https://pdsp.unc.edu/databases/pdsp.php?testDDRadio=testDDRadio&testLigandDD=1287&kiAllRadio=all&doQuery=Submit+Query | language=zu | access-date=27 November 2024}}</ref><ref name="BindingDB">{{cite web | last=Liu | first=Tiqing | title=BindingDB BDBM30707 2-(5-methoxy-1H-indol-3-yl)-N,N-dimethyl-ethanamine::2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine::2-(5-methoxy-1H-indol-3-yl)ethyl-dimethyl-amine::3-(2-DIMETHYLAMINOETHYL)-5-METHOXYINDOLE::CHEMBL7257::MLS000069438::Methoxydimethyltryptamines::SMR000059066::US20240166618, Compound 5-MeO-DMT::WO2023019367, Compound 5-MeO-DMT::cid_1832 | website=BindingDB | url=https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=30707 | access-date=27 November 2024}}</ref> |
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5-MeO-DMT is a ] ] of ] (DMT). While most common psychedelics are believed to primarily elicit psychological effects through ] of serotonin 5-HT<sub>2A</sub> receptors, 5-MeO-DMT shows 1,000-fold greater ] for ] over ];<ref>{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | pages = e9019 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | doi-access = free | bibcode = 2010PLoSO...5.9019R }}</ref> In line with its affinity for ] receptors, 5-MeO-DMT is extremely potent at suppressing the firing of dorsal raphe 5-HT neurons.<ref>{{cite journal | vauthors = Rogawski MA, Aghajanian GK | title = Serotonin autoreceptors on dorsal raphe neurons: structure-activity relationships of tryptamine analogs | journal = J Neurosci | volume = 1 | issue = 10 | pages = 1148–1154 | date = October 1981 | doi = 10.1523/JNEUROSCI.01-10-01148.1981 | pmid = 6793698 | pmc = 6564212 }}</ref> Further, its activity in rats was attenuated with the 5-HT<sub>1A</sub> selective antagonist ] while 5-HT<sub>2A</sub> selective antagonist ] failed to demonstrate any change.<ref>{{cite journal | vauthors = Krebs-Thomson K, Ruiz EM, Masten V, Buell M, Geyer MA | title = The roles of 5-HT1A and 5-HT2 receptors in the effects of 5-MeO-DMT on locomotor activity and prepulse inhibition in rats | journal = Psychopharmacology | volume = 189 | issue = 3 | pages = 319–329 | date = December 2006 | pmid = 17013638 | doi = 10.1007/s00213-006-0566-1 | s2cid = 23396616 }}</ref> Additional ] such as ] of ] ] may be involved.<ref>{{cite journal | vauthors = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = European Journal of Pharmacology | volume = 559 | issue = 2–3 | pages = 132–137 | date = March 2007 | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 }}</ref> A 2019 European study with 42 volunteers showed that a single inhalation produced sustained enhancement of ], and easing of ], ], and ] (PTSD).<ref name=pmid30982127>{{cite journal | vauthors = Uthaug MV, Lancelotta R, van Oorsouw K, Kuypers KP, Mason N, Rak J, Šuláková A, Jurok R, Maryška M, Kuchař M, Páleníček T, Riba J, Ramaekers JG | display-authors = 6 | title = A single inhalation of vapor from dried toad secretion containing 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) in a naturalistic setting is related to sustained enhancement of satisfaction with life, mindfulness-related capacities, and a decrement of psychopathological symptoms | journal = Psychopharmacology | volume = 236 | issue = 9 | pages = 2653–2666 | date = September 2019 | pmid = 30982127 | pmc = 6695371 | doi = 10.1007/s00213-019-05236-w | doi-access = free }}</ref> A 2018 study demonstrated that a single dose of 5-MeO-DMT induced ] in mice.<ref>{{cite journal | vauthors = Lima da Cruz RV, Moulin TC, Petiz LL, Leão RN | title = A Single Dose of 5-MeO-DMT Stimulates Cell Proliferation, Neuronal Survivability, Morphological and Functional Changes in Adult Mice Ventral Dentate Gyrus | journal = Frontiers in Molecular Neuroscience | volume = 11 | pages = 312 | date = 2018 | pmid = 30233313 | pmc = 6131656 | doi = 10.3389/fnmol.2018.00312 | doi-access = free }}</ref> |
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Similarly to other serotonergic psychedelics, 5-MeO-DMT is a ] ], including of the serotonin 5-HT<sub>1A</sub>, 5-HT<sub>2A</sub>, ], and ]s, among others.<ref name="ReckwegUthaugSzabo2022" /><ref name="DourronNicholsSimonsson2023" /><ref name="JayakodiarachchiMaurerSchultz2024">{{cite journal | vauthors = Jayakodiarachchi N, Maurer MA, Schultz DC, Dodd CJ, Thompson Gray A, Cho HP, Boutaud O, Jones CK, Lindsley CW, Bender AM | title = Evaluation of the Indazole Analogs of 5-MeO-DMT and Related Tryptamines as Serotonin Receptor 2 Agonists | journal = ACS Med Chem Lett | volume = 15 | issue = 2 | pages = 302–309 | date = February 2024 | pmid = 38352850 | pmc = 10860182 | doi = 10.1021/acsmedchemlett.3c00566 | url = }}</ref><ref name="BloughLandavazoDecker2014" /> It is 4- to 10-fold more ] as a hallucinogen than DMT in humans.<ref name="ShenJiangWinter2010" /> In contrast to most serotonergic psychedelics however, it is has been said that it is unclear that the hallucinogenic effects of 5-MeO-DMT are principally mediated by activation of the ] ].<ref name="DourronNicholsSimonsson2023" /> In any case, 5-MeO-DMT does still activate the serotonin 5-HT<sub>2A</sub> receptor and does still produce psychedelic effects.<ref name="DourronNicholsSimonsson2023" /> It has been proposed that 5-MeO-DMT be considered an "atypical" psychedelic.<ref name="DourronNicholsSimonsson2023" /> This relates to the fact that 5-MeO-DMT has 100- to 1,000-fold ] for the serotonin ] over the serotonin 5-HT<sub>2A</sub> receptor and that the actions of 5-MeO-DMT appear to be primarily mediated by serotonin 5-HT<sub>1A</sub> receptor activation.<ref name="ReckwegUthaugSzabo2022" /><ref name="DourronNicholsSimonsson2023" /><ref name="ShenJiangWinter2010" /><ref name="HolzeSinghLiechti2024" /> For example, the ] of drugs substituting for 5-MeO-DMT in ] assays is well-correlated with their serotonin 5-HT<sub>1A</sub> receptor ], and the ] effects of 5-MeO-DMT are attenuated by serotonin 5-HT<sub>1A</sub> receptor ]s.<ref name="ShenJiangWinter2010" /> However, there is partial ] of 5-MeO-DMT to the selective serotonin ] agonist ] in animals.<ref name="ShenJiangWinter2010" /> In accordance with the preceding findings, 5-MeO-DMT is reported to produce notably distinct subjective effects compared DMT and other psychedelics in humans.<ref name="DourronNicholsSimonsson2023" /> |
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Although 5-MeO-DMT shows dramatically higher affinity for the serotonin 5-HT<sub>1A</sub> receptor than for the serotonin 5-HT<sub>2A</sub> receptor, the situation appears to be very different in terms of its actual activational potencies at these receptors.<ref name="CummingScheideggerDornbierer2021">{{cite journal | vauthors = Cumming P, Scheidegger M, Dornbierer D, Palner M, Quednow BB, Martin-Soelch C | title = Molecular and Functional Imaging Studies of Psychedelic Drug Action in Animals and Humans | journal = Molecules | volume = 26 | issue = 9 | date = April 2021 | page = 2451 | pmid = 33922330 | pmc = 8122807 | doi = 10.3390/molecules26092451 | doi-access = free | url = }}</ref><ref name="BloughLandavazoDecker2014" /><ref name="CameronTombariLu2021" /> Its {{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}} values have been found to be 1.80 to 3.87{{nbsp}}nM at the serotonin 5-HT<sub>2A</sub> receptor and 3.92 to 1,060{{nbsp}}nM at the serotonin 5-HT<sub>1A</sub> receptor.<ref name="CummingScheideggerDornbierer2021" /><ref name="BloughLandavazoDecker2014" /><ref name="CameronTombariLu2021" /><ref name="BindingDB" /> For comparison, the {{Abbr|EC<sub>50</sub>|half-maximal effective concentration}} values of DMT were found to be 38.3{{nbsp}}nM at the serotonin 5-HT<sub>2A</sub> receptor and >10,000{{nbsp}}nM at the serotonin 5-HT<sub>1A</sub> receptor in one of the same studies.<ref name="CummingScheideggerDornbierer2021" /><ref name="BloughLandavazoDecker2014" /> Hence, 5-MeO-DMT appears to be similarly potent or as much as 200-fold more potent as an agonist of the serotonin 5-HT<sub>2A</sub> receptor than of the serotonin 5-HT<sub>1A</sub> receptor.<ref name="CummingScheideggerDornbierer2021" /><ref name="BloughLandavazoDecker2014" /><ref name="CameronTombariLu2021" /> In addition, 5-MeO-DMT is 10-fold more potent than DMT as an agonist of the serotonin 5-HT<sub>2A</sub> receptor.<ref name="CummingScheideggerDornbierer2021" /><ref name="BloughLandavazoDecker2014" /> |
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Besides the serotonin receptors, 5-MeO-DMT is an ] of the ] ] and ]s.<ref name="delaFuenteRevengaFernández-SáezHerrera-Arozamena2015" /><ref name="BindingDB" /><ref name="PDSPKiDatabase" /> Unlike DMT, 5-MeO-DMT is not a ] or agonist of the ]s.<ref name="ErmakovaDunbarRucker2022" /><ref name="BindingDB" /><ref name="PDSPKiDatabase" /> In contrast to certain other tryptamines, 5-MeO-DMT is inactive as a ], including of ], ], and ].<ref name="BloughLandavazoDecker2014" /> However, it is a weak ], with an {{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}} value of 2,184{{nbsp}}nM.<ref name="BloughLandavazoDecker2014" /> Conversely, it is inactive as a ] and ] ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}} = >10,000{{nbsp}}nM).<ref name="BloughLandavazoDecker2014" /> |
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Similarly to DMT, but in contrast to most other psychedelics, like LSD and psilocybin,<ref name="Halberstadt2015">{{cite journal | vauthors = Halberstadt AL | title = Recent advances in the neuropsychopharmacology of serotonergic hallucinogens | journal = Behav Brain Res | volume = 277 | issue = | pages = 99–120 | date = January 2015 | pmid = 25036425 | doi = 10.1016/j.bbr.2014.07.016 | pmc = 4642895 | url = }}</ref><ref name="JiménezBouso2022">{{cite journal | vauthors = Jiménez JH, Bouso JC | title = Significance of mammalian N, N-dimethyltryptamine (DMT): A 60-year-old debate | journal = J Psychopharmacol | volume = 36 | issue = 8 | pages = 905–919 | date = August 2022 | pmid = 35695604 | doi = 10.1177/02698811221104054 | url = }}</ref> there appears to be very little development of ] with 5-MeO-DMT.<ref name="ErmakovaDunbarRucker2022" /><ref name="BloughLandavazoDecker2014">{{cite journal | vauthors = Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB | title = Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes | journal = Psychopharmacology (Berl) | volume = 231 | issue = 21 | pages = 4135–4144 | date = October 2014 | pmid = 24800892 | pmc = 4194234 | doi = 10.1007/s00213-014-3557-7 | url = }}</ref><ref name="ReckwegUthaugSzabo2022" /><ref name="DourronNicholsSimonsson2023" /> In fact, there may even be ] to the effects of 5-MeO-DMT.<ref name="DourronNicholsSimonsson2023" /> The lack of tolerance development with 5-MeO-DMT may be due to ] of the serotonin 5-HT<sub>2A</sub> receptor.<ref name="ErmakovaDunbarRucker2022" /> More specifically, 5-MeO-DMT activates the ] ] of the serotonin 5-HT<sub>2A</sub> receptor with much less ] in recruiting ].<ref name="ErmakovaDunbarRucker2022" /><ref name="BloughLandavazoDecker2014" /> Activation of β-arrestin2 is linked to ] and ].<ref name="JiménezBouso2022" /><ref name="BarksdaleDossFonzo2024">{{cite journal | vauthors = Barksdale BR, Doss MK, Fonzo GA, Nemeroff CB | title = The mechanistic divide in psychedelic neuroscience: An unbridgeable gap? | journal = Neurotherapeutics | volume = 21 | issue = 2 | pages = e00322 | date = March 2024 | pmid = 38278658 | doi = 10.1016/j.neurot.2024.e00322 | pmc = 10963929 | url = }}</ref><ref name="WallachCaoCalkins2023">{{cite journal | vauthors = Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD | title = Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential | journal = Nat Commun | volume = 14 | issue = 1 | pages = 8221 | date = December 2023 | pmid = 38102107 | doi = 10.1038/s41467-023-44016-1 | pmc = 10724237 | url = }}</ref> |
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===Pharmacokinetics=== |
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5-MeO-DMT is ] and is thought to easily cross the ].<ref name="ShenJiangWinter2010" /> Accordingly, 5-MeO-DMT readily accumulates in the brain in animals with levels higher than in blood.<ref name="ShenJiangWinter2010" /> This is in notable contrast to ] (5-HO-DMT or ''N'',''N''-dimethylserotonin) and ] (5-HT), which are ] and ].<ref name="ShenJiangWinter2010" /><ref name="PlazasFaraone2023">{{cite journal | vauthors = Plazas E, Faraone N | title = Indole Alkaloids from Psychoactive Mushrooms: Chemical and Pharmacological Potential as Psychotherapeutic Agents | journal = Biomedicines | volume = 11 | issue = 2 | date = February 2023 | page = 461 | pmid = 36830997 | pmc = 9953455 | doi = 10.3390/biomedicines11020461 | doi-access = free | url = }}</ref><ref name="McBride2000">{{cite journal | vauthors = McBride MC | title = Bufotenine: toward an understanding of possible psychoactive mechanisms | journal = J Psychoactive Drugs | volume = 32 | issue = 3 | pages = 321–331 | date = 2000 | pmid = 11061684 | doi = 10.1080/02791072.2000.10400456 | url = }}</ref> |
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Bufotenin is an ] of 5-MeO-DMT, formed by ''O''-] by ] ].<ref name="ShenJiangWinter2010" /> Bufotenin notably has much higher ] for the serotonin 5-HT<sub>2A</sub> receptor than 5-MeO-DMT itself.<ref name="ShenJiangWinter2010" /> However, bufotenin does not seem to be extensively produced from 5-MeO-DMT in the brain.<ref name="ShenJiangWinter2010" /> In addition, peripherally formed bufotenin may not be able to exert significant central effects due to its limited ability to cross into the brain.<ref name="ShenJiangWinter2010" /> Hence, the involvement of bufotenin in the psychoactive effects of 5-MeO-DMT is uncertain.<ref name="ShenJiangWinter2010" /> |
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The ] of 5-MeO-DMT can be dramatically reduced and its levels markedly augmented and prolonged by ]s (MAOIs).<ref name="ShenJiangWinter2010" /> In addition, MAOIs allow 5-MeO-DMT to become ] in humans.<ref name="ShenJiangWinter2010" /> Combination of 5-MeO-DMT with MAOIs has sometimes resulted in ] and death in humans.<ref name="ShenJiangWinter2010" /> |
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==Sources== |
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In addition to naturally-occurring sources, 5-MeO-DMT can be produced synthetically.<ref>{{cite journal | vauthors = Sherwood AM, Claveau R, Lancelotta R, Kaylo KW, Lenoch K | title = Synthesis and Characterization of 5-MeO-DMT Succinate for Clinical Use | journal = ACS Omega | volume = 5 | issue = 49 | pages = 32067–32075 | date = December 2020 | pmid = 33344861 | pmc = 7745443 | doi = 10.1021/acsomega.0c05099 }}</ref><ref>{{cite web | vauthors = Carpenter DE |date=2021-02-02 |title=Psychedelic Toads Pushed To The Limit, Conservationists Urge Synthetic 5-MeO-DMT Option |url=https://www.forbes.com/sites/davidcarpenter/2021/02/02/psychedelic-toads-pushed-to-the-limit-conservationists-urge-synthetic-5-meo-dmt-option/ |access-date=2021-02-04 |website=Forbes |language=en}}</ref> |
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{| class="wikitable sortable" |
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|+ Plant sources |
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! Family !! Plants |
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| ] || '']'',<ref>{{cite journal | vauthors = Uthaug MV, Lancelotta R, Szabo A, Davis AK, Riba J, Ramaekers JG | title = Prospective examination of synthetic 5-methoxy-N,N-dimethyltryptamine inhalation: effects on salivary IL-6, cortisol levels, affect, and non-judgment | journal = Psychopharmacology | volume = 237 | issue = 3 | pages = 773–785 | date = March 2020 | pmid = 31822925 | pmc = 7036074 | doi = 10.1007/s00213-019-05414-w }}</ref> '']'',<ref name="bluezoo_tryptamines">{{cite web |url=http://bluezoo.org/tryptamines/plants.html|title=tryptamines: fungi |website=bluezoo.org}}</ref> '']''<ref name="erowid_tryptamines">{{cite web |url=https://www.erowid.org/psychoactives/faqs/faqs_tryptamine.shtml |title=Erowid Psychoactive Vaults: Tryptamine FAQ |website=www.erowid.org}}</ref><!-- is melicope from rutaceae or rubiaceae? --> |
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|-6 |
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| ] || '']'',<ref name="trout_notes">{{cite web |url=https://troutsnotes.com/pdf/SomeSimpleTryptamines_2ndEd_2007_with_addendum.pdf |title= Some simple tryptomines |website=troutsnotes.com |access-date=2020-07-04}}</ref> '']'',<ref name="trout_notes" /> '']'',<ref name="trout_notes" /> '']'',<ref name="trout_notes" /> '']'',<ref name="erowid_tryptamines" /><ref name="bluezoo_tryptamines" /> ],<ref name="trout_notes" /> '']'',<ref name="bluezoo_tryptamines" /><ref name="erowid_tryptamines" /> '']''<ref name="bluezoo_tryptamines" /><ref name="erowid_tryptamines" /> |
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|- |
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| ] || '']''<ref name="trout_notes" /> |
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|- |
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| ] || '']''<ref name="forensic_chemistry" /> |
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|- |
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| ] || '']'',<ref name="bluezoo_tryptamines" /> '']''<ref name="bluezoo_tryptamines" /> |
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|- |
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| ] || '']'',<ref name="bluezoo_tryptamines" /> '']'',<ref name="bluezoo_tryptamines" /> '']'',<ref name="forensic_chemistry" /> '']'',<ref name="bluezoo_tryptamines"/> '']'',<ref name="forensic_chemistry" /> '']'',<ref name="forensic_chemistry" /> '']'',<ref name="forensic_chemistry" /> '']'',<ref name="forensic_chemistry" /> '']''<ref name="forensic_chemistry" /> |
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] |
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{| class="wikitable sortable" |
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|+ Animal Sources |
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|- |
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! Family !! Animals |
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|- |
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| ] || ] (''Incilius alvarius'')<ref>{{cite web |url=https://www.forbes.com/sites/davidcarpenter/2020/02/02/5-meo-dmt-the-20-minute-psychoactive-toad-experience-thats-transforming-lives/ |title=5-MeO-DMT: The 20-Minute Psychoactive Toad Experience That's Transforming Lives | vauthors = Carpenter DE |website=Forbes}}</ref><ref name=pmid30982127/><ref name="erowid_tryptamines" /> |
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The ] is a noted animal source of 5-MeO-DMT. First described in 1983 by Ken Nelson (writing under the pseudonym of Albert Most), smoking the ] secretions of the animal produces a powerful and short-lived ].<ref>{{cite web | vauthors = Nelson K |others= Illustrated by Gail Patterson |title=Bufo alvarius: The Psychedelic Toad of the Sonoran Desert |url=https://www.erowid.org/archive/sonoran_desert_toad/almost.htm |access-date=October 20, 2023 |website=]}}</ref> The smoking of ''I. alvarius'' secretions should not be confused with the urban legend of ].<ref>{{cite web | vauthors = Shulgin A, Shulgin A |title=Tryptamines I Have Known And Loved: The Continuation |url=https://erowid.org/library/books_online/tihkal/tihkal38.shtml |access-date=October 20, 2023 |website=]}}</ref> Since 1983, the animal has since became a popular source of 5-MeO-DMT for recreational or ].<ref>{{cite news | vauthors = Romero S |date=2022-03-20 |title=Demand for This Toad's Psychedelic Toxin Is Booming. Some Warn That's Bad for the Toad. |language=en-US |work=The New York Times |url=https://www.nytimes.com/2022/03/20/us/toad-venom-psychedelic.html |access-date=2023-10-20 |issn=0362-4331}}</ref> Unfortunately, this increased demand and use of the toads as a source of 5-MeO-DMT has put strain on their populations.<ref>{{cite web |date=2023-07-12 |title=The Sonoran Desert toad can get you high. Poachers have taken notice. |url=https://www.nationalgeographic.com/animals/article/sonoran-desert-toad-dmt-psychedelic-movement |archive-url=https://web.archive.org/web/20230712175204/https://www.nationalgeographic.com/animals/article/sonoran-desert-toad-dmt-psychedelic-movement |url-status=dead |archive-date=July 12, 2023 |access-date=2023-10-20 |website=Animals |language=en}}</ref> Concerned with the ecological impacts of the growing use of ''I. alvarius'' secretions as a source of 5-MeO-DMT, Ken Nelson would later advocate for the use of synthetic 5-MeO-DMT and conservation of the Colorado River Toad.<ref>{{cite book | vauthors = Morris H |date=2021-02-02 | chapter = Preface | edition = 2021 | title = Bufo alvarius: The Psychedelic Toad of the Sonoran Desert | chapter-url= https://www.psychedelictoadofthesonorandesert.com/preface |url-status=live |archive-url= https://web.archive.org/web/20210202114012/https://www.psychedelictoadofthesonorandesert.com/preface|archive-date= 2021-02-02|access-date=2023-10-20 }}</ref> |
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{| class="wikitable sortable" |
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|+ Fungal Sources |
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|- |
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! Family !! Fungi |
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|- |
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| ] || '']'',<ref name="forensic_chemistry">{{cite book | vauthors = Khan JI, Kennedy TJ, Christian JR DR |title= Basic Principles of Forensic Chemistry |date=2011 |publisher=Springer Science & Business Media |isbn=978-1-934115-06-0 |pages=195 |url=https://books.google.com/books?id=9qrXBjRF388C&pg=PA195 }}</ref> '']''<ref name="forensic_chemistry" /> |
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==Legal status== |
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=== Australia === |
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As a ] of ''N'',''N''-dimethyltryptamine (DMT), 5-MeO-DMT is a ] prohibited substance under the ].<ref>{{cite web |title=Poisons Standard July 2016 |date=24 June 2016 |url=https://www.legislation.gov.au/Details/F2016L01071 |publisher=Federal Register of Legislation}}</ref> |
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=== Canada === |
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5-MeO-DMT is legal for personal use and possession in Canada,<ref>{{cite web |title=Is 5-MeO-DMT (Bufo) Legal in Canada? Understanding 5-MeO-DMT Laws and Regulations |url=https://www.psychedeliclaw.ca/5meodmt-bufotenin |access-date=2023-11-28 |website=PsychedelicLaw.ca |language=en-US}}</ref> though sale, distribution, and other activities involving the substance are illegal under Canadian federal law. |
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=== China === |
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As of October 2015, 5-MeO-DMT is a ] in ].<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref> |
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===Germany=== |
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As of 2001 5-MeO-DMT is listed as a controlled substance. Attachement I BtMG. BGBl. I 2001, 1180 - 1186; |
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===Sweden=== |
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The Swedish government classified 5-MeO-DMT, listed as 5-metoxi-N,N-dimetyltryptamin (5-MeO-DMT) in their regulation SFS 2004:696, as "health hazard" under the act ] (translated ''Act on the Prohibition of Certain Goods Dangerous to Health'') in October 2004, making it illegal to sell or possess.<ref>{{cite web | url=https://www.notisum.se/rnp/sls/sfs/20040696.pdf | title=Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor | work=Svensk författningssamling | date=7 September 2004 | language=sv}}</ref> |
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===Turkey=== |
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5-MeO-DMT has been controlled in ] since December 2013.<ref>{{cite web | url=http://www.resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf | title=Turkish Law | work=Resmi Gazete | date=16 December 2013}}</ref> |
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===United States=== |
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5-MeO-DMT was made a ] ] in January 2011.<ref>{{cite journal | author = Drug Enforcement Administration (DEA), Department of Justice | title = Schedules of controlled substances: placement of 5-methoxy-N,N-dimethyltryptamine into Schedule I of the Controlled Substances Act. Final rule | journal = Federal Register | volume = 75 | issue = 243 | pages = 79296–79300 | date = December 2010 | pmid = 21171485 | url = https://www.gpo.gov/fdsys/pkg/FR-2010-12-20/pdf/2010-31854.pdf }}</ref> |
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==Research== |
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5-MeO-DMT is being developed and evaluated for potential therapeutic effects in patients with ] (TRD).<ref>{{cite web|url=https://www.ghres.com/|title=Home | GH Research|website=GH Research Limited}}</ref> ] company GH Research has sponsored a completed phase 1 study in healthy volunteers<ref>{{cite journal | vauthors = Reckweg J, Mason NL, van Leeuwen C, Toennes SW, Terwey TH, Ramaekers JG | title = A Phase 1, Dose-Ranging Study to Assess Safety and Psychoactive Effects of a Vaporized 5-Methoxy-N, N-Dimethyltryptamine Formulation (GH001) in Healthy Volunteers | journal = Frontiers in Pharmacology | volume = 12 | pages = 760671 | date = 2021 | pmid = 34912222 | pmc = 8667866 | doi = 10.3389/fphar.2021.760671 | doi-access = free }}</ref> and phase 1/2 study in TRD patients where 87.5% of patients with TRD were brought into remission on day 7 in the phase 2 part of the study.<ref>{{cite press release | author = GH Research PLC |date=2021-12-06 |title=GH Research Announces Successful Outcome of the Phase 2 part of its Phase 1/2 Clinical Trial of GH001 in Treatment-Resistant Depression |url=https://www.globenewswire.com/en/news-release/2021/12/06/2346425/0/en/GH-Research-Announces-Successful-Outcome-of-the-Phase-2-part-of-its-Phase-1-2-Clinical-Trial-of-GH001-in-Treatment-Resistant-Depression.html |access-date=2022-10-07 |website=GlobeNewswire News Room |language=en}}</ref> GH Research is currently planning a phase 2b study in TRD patients and have received approval for studies in patients with bipolar II disorder and a current depressive episode and patients with postpartum depression.<ref>{{cite press release | author =GH Research PLC|date=2022-08-23 |title=GH Research Reports Second Quarter 2022 Financial Results and Provides Business Updates |url=https://www.globenewswire.com/en/news-release/2022/08/23/2502831/0/en/GH-Research-Reports-Second-Quarter-2022-Financial-Results-and-Provides-Business-Updates.html |access-date=2022-10-07 |website=GlobeNewswire News Room |language=en}}</ref> |
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Beckley Psytech in collaboration with King's College London is evaluating the safety and tolerability of intranasal 5-MeO-DMT in healthy subjects, in a phase 1 study.<ref>{{cite web | vauthors = Carpenter DE |date=2022-02-16 |title=More Companies Embrace 5-MeO-DMT to Create Therapies |url=https://www.lucid.news/companies-embrace-5-meo-dmt-therapies/ |access-date=2022-03-06 |website=Lucid News |language=en-US}}</ref><ref>{{Cite press release |last=Atai |first=Life Sciences |date=2024-03-27 |title=atai Life Sciences Announces Positive Initial Results from Beckley Psytech's Phase 2a Open Label Study of BPL-003 (Intranasal 5-MeO-DMT) in Treatment Resistant Depression |url=https://www.globenewswire.com/news-release/2024/03/27/2853041/0/en/atai-Life-Sciences-Announces-Positive-Initial-Results-from-Beckley-Psytech-s-Phase-2a-Open-Label-Study-of-BPL-003-Intranasal-5-MeO-DMT-in-Treatment-Resistant-Depression.html |access-date=2024-10-06 |website=GlobeNewswire News Room |language=en}}</ref> Beckley Psytech CEO Cosmo Feilding-Mellen sees a potential in the short-acting nature of 5-MeO-DMT compared to psilocybin: "Requiring one or two therapists to sit in a room with a single patient for the entire duration of an MDMA or psilocybin experience, which is essentially a whole working day, is probably going to be very resource-intensive and expensive. There is already a global shortage of psychotherapists, and this poses a potential bottleneck to patient access in the future."<ref>{{cite news | vauthors = Siebert A |title=Could 5-MeO-DMT Allow For More Affordable Psychedelic-Assisted Therapy? Beckley Psytech Thinks So |url=https://www.forbes.com/sites/amandasiebert/2022/02/28/could-5-meo-dmt-allow-for-more-affordable-psychedelic-assisted-therapy--beckley-psytech-thinks-so/ |access-date=2022-03-06 |website=Forbes |language=en}}</ref> |
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== See also == |
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* ] |
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* ] |
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* ] |
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== References == |
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{{Reflist|30em}} |
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== External links == |
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{{Hallucinogens}} |
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{{Serotonin receptor modulators}} |
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{{Melatonin receptor modulators}} |
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{{Tryptamines}} |
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{{DEFAULTSORT:MeO-DMT, 5-}} |
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