Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 5-MeO-DMT: Difference between pages

{{short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477224937

| IUPAC_name = 2-(5-Methoxy-1''H''-indol-3-yl)-''N'',''N''-dimethylethanamine

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU = S9

| legal_BR = F2

| 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=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>

| legal_CA =

| legal_US = Schedule I

| legal_DE = Anlage I

| legal_status = Illegal in China, Sweden, Turkey

| routes_of_administration = Smoked, Insufflated, Oral (with a [[MAOI]])

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 1019-45-0

| ATC_prefix =

| ATC_suffix =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = X0MKX3GWU9

| C=13 | H=18 | N=2 | O=1

| smiles = COc2ccc1[nH]cc(CCN(C)C)c1c2

| melting_point =

| melting_high =

[[File:Bufo alvarius1.jpg|thumb|Colorado River toad]]

'''5-MeO-DMT''' ('''5-methoxy-''N'',''N''-dimethyltryptamine''') or '''O-methyl-bufotenin''' is a [[psychedelic drug|psychedelic]] of the [[Substituted tryptamine|tryptamine]] class. It is found in a wide variety of plant species, and also is secreted by the glands of at least one toad species, the [[Colorado River toad]]. Like its close relatives [[Dimethyltryptamine|DMT]] and [[bufotenin]] (5-HO-DMT), it has been used as an [[entheogen]] in [[South America]].<ref>{{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 | 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>

==Chemistry==

5-MeO-DMT was first [[Organic synthesis|synthesized]] in 1936, and in 1959 it was isolated as one of the [[Psychoactive drug|psychoactive]] ingredients of ''[[Anadenanthera peregrina]]'' [[seed]]s used in preparing [[Anadenanthera peregrina|Yopo]] snuff. It was once believed to be a major component of the [[neuropsychopharmacology|psychoactive effects]] of the snuff, although this has recently been shown to be unlikely, due to the limited or sometimes even non-existent quantity contained within the seeds, which instead achieve their psychoactivity from the ''O''-[[Demethylation|demethylated]] [[metabolite]] of 5-MeO-DMT, [[bufotenin]].<ref>{{cite journal | vauthors = Ott J | title = Pharmañopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine | journal = Journal of Psychoactive Drugs | volume = 33 | issue = 3 | pages = 273–281 | date = July–September 2001 | pmid = 11718320 | doi = 10.1080/02791072.2001.10400574 | s2cid = 5877023 }}</ref><ref name=Shen/> It is [[metabolism|metabolized]] mainly by [[CYP2D6]].<ref name=Shen>{{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 = Current Drug Metabolism | volume = 11 | issue = 8 | pages = 659–666 | date = October 2010 | pmid = 20942780 | pmc = 3028383 | doi = 10.2174/138920010794233495 }}</ref>

==Effects==

When smoked, the duration of effects can be as little as ten minutes; when [[Insufflation (medicine)|insufflated]], up to two hours. Effects vary and can range from radical perspective shifting and perception of new insights, euphoria, immersive experiences, [[Dissociation (psychology)|dissociation]] and non-responsiveness, sensual/erotic enhancement, to dysphoria, fear, terror, panic, and [[ego death]].<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}}

==Uses==

It has anti-anxiety and anti-depressant 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>

===Religious use===<!-- [[Church of the Tree of Life]] redirects here -->

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 [[sacrament]]. 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 [[parsley]] was probably one of the two most common forms of [[route of administration|ingestion]] in the [[United States]].<ref name="Erowid"/>{{Unreliable source?|date=October 2023}}

==Pharmacology==

5-MeO-DMT is a [[Methoxylation|methoxylated]] [[derivative (chemistry)|derivative]] of [[Dimethyltryptamine|DMT]]. While most common psychedelics are believed to primarily elicit psychological effects through [[agonist|agonism]] of serotonin 5-HT_2A receptors, 5-MeO-DMT shows 1000-fold greater [[Affinity (pharmacology)|affinity]] for [[5-HT1A receptor|5-HT_1A]] over [[5-HT2A receptor|5-HT_2A]];<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 [[5-HT1A receptor|5-HT_1A]] 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_1A selective antagonist [[WAY-100635]] while 5-HT_2A selective antagonist [[volinanserin]] 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 [[mechanism of action|mechanisms of action]] such as [[reuptake inhibitor|inhibition]] of [[monoamine]] [[reuptake]] 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 [[satisfaction with life]], and easing of [[anxiety]], [[Mood disorder#Depressive disorders|depression]], and [[post-traumatic stress disorder]] (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 [[neurogenesis]] 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>

==Clinical development==

5-MeO-DMT is being developed and evaluated for potential therapeutic effects in patients with [[Treatment-resistant depression|Treatment-Resistant Depression]] (TRD).<ref>{{cite web|url=https://www.ghres.com/|title=Home &#124; GH Research|website=GH Research Limited}}</ref> [[Biopharmaceutical]] 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>

Beckley Psytech in collaboration with King's College London research 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> 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>

==Sources==

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>

{| class="wikitable sortable"

|+ Plant sources

|-

! Family !! Plants

|-

| [[Rutaceae]] || ''[[Dictyoloma incanescens]]'',<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> ''[[Limonia acidissima]]'',<ref name="bluezoo_tryptamines">{{cite web |url=http://bluezoo.org/tryptamines/plants.html|title=tryptamines: fungi |website=bluezoo.org}}</ref> ''[[Melicope leptococca]]''<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? -->

|-6

| [[Fabaceae]] || ''[[Anadenanthera peregrina]]'',<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> ''[[Acacia auriculiformis]]'',<ref name="trout_notes" /> ''[[Acacia victoriae]]'',<ref name="trout_notes" /> ''[[Desmodium gangeticum]]'',<ref name="trout_notes" /> ''[[Lespedeza bicolor]]'',<ref name="erowid_tryptamines" /><ref name="bluezoo_tryptamines" /> [[Mimosa pudica]],<ref name="trout_notes" /> ''[[Mucuna pruriens]]'',<ref name="bluezoo_tryptamines" /><ref name="erowid_tryptamines" /> ''[[Phyllodium pulchellum]]''<ref name="bluezoo_tryptamines" /><ref name="erowid_tryptamines" />

|-

| [[Poaceae]] || ''[[Phalaris tuberosa]]''<ref name="trout_notes" />

|-

| [[Malpighiaceae]] || ''[[Diplopterys cabrerana]]''<ref name="forensic_chemistry" />

|-

| [[Cactaceae]] || ''[[Echinocereus salm-dyckianus]]'',<ref name="bluezoo_tryptamines" /> ''[[Echinocereus triglochidiatus]]''<ref name="bluezoo_tryptamines" />

|-

| [[Myristicaceae]] || ''[[Horsfieldia superba]]'',<ref name="bluezoo_tryptamines" /> ''[[Iryanthera macrophylla]]'',<ref name="bluezoo_tryptamines" /> ''[[Osteophloeum platyspermum]]'',<ref name="forensic_chemistry" /> ''[[Virola theiodora]]'',<ref name="bluezoo_tryptamines"/> ''[[Virola calophylla|V. calophylla]]'',<ref name="forensic_chemistry" /> ''[[Virola multinervia|V. multinervia]]'',<ref name="forensic_chemistry" /> ''[[Virola peruviana|V. peruviana]]'',<ref name="forensic_chemistry" /> ''[[Virola rufula|V. rufula]]'',<ref name="forensic_chemistry" /> ''[[Virola venosa|V. venosa]]''<ref name="forensic_chemistry" />

|}

{| class="wikitable sortable"

|+ Animal Sources

|-

! Family !! Animals

|-

| [[Bufonidae]] || [[Colorado River toad]] (''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" />

|}

The [[Colorado River toad]] 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 [[Parotoid gland|parotoid]] secretions of the animal produces a powerful and short-lived [[psychedelic experience]].<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=[[Erowid]]}}</ref> The smoking of ''I. alvarius'' secretions should not be confused with the urban legend of [[toad licking]].<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=[[Erowid]]}}</ref> Since 1983, the animal has since became a popular source of 5-MeO-DMT for recreational or [[Entheogen|spiritual purposes]].<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>

{| class="wikitable sortable"

|+ Fungal Sources

|-

! Family !! Fungi

|-

| [[Amanitaceae]] || ''[[Amanita citrina]]'',<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> ''[[Amanita porphyria]]''<ref name="forensic_chemistry" />

|}

==Legal status==

=== Australia ===

As a [[structural analog]] of ''N'',''N''-dimethyltryptamine (DMT), 5-MeO-DMT is a [[Standard for the Uniform Scheduling of Medicines and Poisons#Schedule 9: prohibited substance|Schedule 9]] prohibited substance under the [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard]].<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>

=== Canada ===

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.

=== China ===

As of October 2015, 5-MeO-DMT is a [[controlled substance]] in [[China]].<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>

===Germany===

As of 2001 5-MeO-DMT is listed as a controlled substance. Attachement I BtMG. BGBl. I 2001, 1180 - 1186;

===Sweden===

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 [[:sv:Lagen om förbud mot vissa hälsofarliga varor|''Lagen om förbud mot vissa hälsofarliga varor'']] (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>

===Turkey===

5-MeO-DMT has been controlled in [[Turkey]] 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>

===United States===

5-MeO-DMT was made a [[List of Schedule I drugs (US)|Schedule I]] [[Controlled Substances Act|controlled substance]] 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>

== See also ==

* [[4-MeO-DMT]]

* [[5-MeO-AMT]]

* [[5-MeO-DIPT]]

* [[5-EtO-DMT]]

* [[5-MeO-MET]]

* [[5-Methoxytryptamine]]

* [[Dimemebfe]]

* [[EMDT]]

* [[Hamilton's Pharmacopeia]]

* [[List of entheogens]]

* [[Psychoplastogen]]

== References ==

{{Reflist|30em}}

== External links ==

* [https://www.erowid.org/chemicals/5meo_dmt/5meo_dmt.shtml Erowid's 5-MeO-DMT Vault]

* [https://isomerdesign.com/PiHKAL/read.php?domain=tk&id=38 5-MeO-DMT Entry in TiHKAL • info]

{{Hallucinogens}}

{{Serotonin receptor modulators}}

{{Sigma receptor modulators}}

{{Tryptamines}}

{{DEFAULTSORT:MeO-DMT, 5-}}

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[[Category:Psychedelic tryptamines]]

[[Category:Tryptamine alkaloids]]

[[Category:Indole ethers at the benzene ring]]

[[Category:Serotonin receptor agonists]]

[[Category:Psychedelic drugs]]

[[Category:Designer drugs]]

[[Category:Dimethylamino compounds]]