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

{{Short description|Psychedelic tryptamine}}

| drug_name = 5-Methoxy-''N'',''N''-diisopropyltryptamine

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477225221

| tradename =

| 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_DE = Anlage I, In general

/ Unscheduled unless that it was for human consumption.

/ Illegal in Sweden, Denmark, Greece, Japan, Singapore and China.

| excretion =

| CAS_number_Ref = {{cascite|changed|CAS}}

| CAS_number = 4021-34-5

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C22724

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 12D06G8W8E

| C=17 | H=26 | N=2 | O=1

| smiles = CC(C)N(C(C)C)CCC1=C[NH]C(C=C2)=C1C=C2OC

[[Image:5meodipt.jpg|thumb|right|5-MeO-DiPT tablets from [[Salem, Oregon|Salem]], [[Oregon]]]]

'''5-Methoxy-''N'',''N''-diisopropyltryptamine''' ('''5-MeO-DiPT''', sometimes called '''foxy methoxy''' or simply '''foxy'''<ref>{{cite journal | vauthors = Narimatsu S, Yonemoto R, Saito K, Takaya K, Kumamoto T, Ishikawa T, Asanuma M, Funada M, Kiryu K, Naito S, Yoshida Y, Yamamoto S, Hanioka N | display-authors = 6 | title = Oxidative metabolism of 5-methoxy-N,N-diisopropyltryptamine (Foxy) by human liver microsomes and recombinant cytochrome P450 enzymes | journal = Biochemical Pharmacology | volume = 71 | issue = 9 | pages = 1377–1385 | date = April 2006 | pmid = 16510126 | doi = 10.1016/j.bcp.2006.01.015 }}</ref>) is a [[psychedelic drug|psychedelic]] tryptamine and the [[methoxy group|methoxy]] [[derivative (chemistry)|derivative]] of [[diisopropyltryptamine]] (DiPT).

==Pharmacology==

The mechanism that produces the purported hallucinogenic and entheogenic effects of 5-MeO-DiPT is thought to result primarily from [[5-HT2A receptor|5-HT_2A receptor]] [[agonist|agonism]], although additional mechanisms of action such as [[monoamine oxidase inhibitor|monoamine oxidase inhibition]] (MAOI) may be involved also.<ref name="pmid17223101">{{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> The strongest receptor binding affinity for 5-MeO-DiPT is at the [[5-HT1A receptor|5-HT_1A receptor]].<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>

5-MeO-DiPT is [[Neurotoxin|neurotoxic]] in rats.<ref>{{cite journal | vauthors = Noworyta-Sokołowska K, Kamińska K, Kreiner G, Rogóż Z, Gołembiowska K | title = Neurotoxic Effects of 5-MeO-DIPT: A Psychoactive Tryptamine Derivative in Rats | journal = Neurotoxicity Research | volume = 30 | issue = 4 | pages = 606–619 | date = November 2016 | pmid = 27461536 | pmc = 5047954 | doi = 10.1007/s12640-016-9654-0 }}</ref>

==Overdose==

Excessive doses have caused clinical intoxication, characterized by nausea, vomiting, agitation, hypotension, mydriasis, tachycardia and hallucinations, in a number of young adults. A number of these overdoses are attributed to the drug’s extended onset of action, where first time users, who were unfamiliar with the drug, administered a second dose after initially feeling no effects. [[Rhabdomyolysis]] and renal failure occurred in one young man and another one died 3–4 hours after an apparent rectal overdose.<ref>{{cite book | vauthors = Baselt R | title = Disposition of Toxic Drugs and Chemicals in Man | edition = 8th | publisher = Biomedical Publications | location = Foster City, CA | date = 2008 | pages = 975–976}}</ref> At least one death has been attributed to consumption of 5-MeO-DiPT.<ref>{{cite journal | vauthors = Tanaka E, Kamata T, Katagi M, Tsuchihashi H, Honda K | title = A fatal poisoning with 5-methoxy-N,N-diisopropyltryptamine, Foxy | journal = Forensic Science International | volume = 163 | issue = 1–2 | pages = 152–154 | date = November 2006 | pmid = 16406422 | doi = 10.1016/j.forsciint.2005.11.026 }}</ref>

==Drug prohibition laws==

{{More citations needed|section|date=June 2019|small=y}}

===China===

As of October 2015 5-MeO-DiPT 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=zh | 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>

===Denmark===

Illegal since February 2004.

===Germany===

Illegal since September 1999.

===Greece===

Illegal since February 2003.

===Japan===

Illegal since April 2005.

===Singapore===

Illegal since early 2006.

===Sweden===

[[Riksdag|''Sveriges riksdags'']] health ministry [[:sv:Statens folkhälsoinstitut|''Statens folkhälsoinstitut'']] classified 5-MeO-DiPT 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'') as of Oct 1, 2004, in their regulation '''SFS 2004:696''' listed as '''5-metoxi-N,N-diisopropyltryptamin (5-MeO-DIPT)''', making it illegal to sell or possess.<ref>{{cite web |url=http://www.notisum.se/rnp/sls/sfs/20040696.pdf |title=notisum.se |access-date=2013-09-06 |url-status=live |archive-url=https://web.archive.org/web/20130929063316/http://www.notisum.se/rnp/sls/sfs/20040696.pdf |archive-date=2013-09-29 }}</ref>

===United States===

On April 4, 2003, the [[United States]] [[Drug Enforcement Administration|DEA]] added both 5-MeO-DiPT and [[Alpha-Methyltryptamine|alpha-methyltryptamine]] (AMT) to Schedule I of the [[Controlled Substances Act]] under "emergency scheduling" procedures. The drugs were officially placed into Schedule I on September 29, 2004. Prior to its prohibition in the U.S., 5-MeO-DiPT was sold online alongside psychoactive analogues such as [[Diisopropyltryptamine|DiPT]], and [[Dipropyltryptamine|DPT]], neither of which have yet been expressly outlawed.

== See also ==

* [[5-MeO-DiBF]]

* [[5-MeO-DMT]]

* [[5-MeO-DPT]]

* [[5-MeO-AMT]]

* [[5-MeO-MiPT]]

* [[Dimethyltryptamine|DMT]]

* [[Dipropyltryptamine|DPT]]

* [[Alphamethyltryptamine|AMT]]

* [[Diisopropyltryptamine|DIPT]]

* [[N-Methyl-N-isopropyltryptamine|MIPT]]

== References ==

{{Reflist}}

== External links ==

* [http://www.deadiversion.usdoj.gov/fed_regs/rules/2004/fr0929.htm Official Ruling Placing 5-MeO-DIPT into Schedule I]

* [http://www.erowid.org/chemicals/5meo_dipt/5meo_dipt.shtml Erowid information on 5-MeO-DIPT].

* [https://isomerdesign.com/PiHKAL/read.php?domain=tk&id=37 5-MeO-DIPT entry in TiHKAL • info]

{{Hallucinogenic tryptamines}}

{{Serotonin receptor modulators}}

{{Sigma receptor modulators}}

{{Tryptamines}}

{{DEFAULTSORT:Methoxy-N N-diisopropyltryptamine 5-}}

[[Category:Designer drugs]]

[[Category:Phenol ethers]]

[[Category:Psychedelic tryptamines]]

[[Category:Serotonin receptor agonists]]

[[Category:Neurotoxins]]

[[Category:Diisopropylamino compounds]]

[[Category:Methoxy compounds]]