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5-MeO-DiPT: Difference between revisions

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{{Short description|Psychedelic tryptamine}}
{{DISPLAYTITLE:5-Methoxy-''N'',''N''-diisopropyltryptamine}}
{{Drugbox
| drug_name = 5-Methoxy-''N'',''N''-diisopropyltryptamine
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<!--Clinical data-->
| 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_UK = Class A
| legal_US = Schedule I
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01441
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C22724
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 133247
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}}
[[Image:5meodipt.jpg|thumb|right|5-MeO-DiPT tablets from [[Salem, Oregon|Salem]], [[Oregon]]]]
'''5-Methoxy-''N'',''N''-diisopropyltryptamine''' ('''5-MeO-DiPT''', sometimes called '''Foxyfoxy Methoxymethoxy''' or simply '''Foxyfoxy'''<ref>{{Citecite journal | doivauthors = 10.1016/j.bcp.2006.01.015Narimatsu 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 | pmiddisplay-authors = 165101266 | 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 = 1377–85|1377–1385 year = 2006| last1date = Narimatsu|April first1 =2006 Shizuo| last2pmid = Yonemoto| first2 =16510126 Rei| last3doi = Saito| first3 = Keita| last4 = Takaya| first4 = Kazuo| last5 = Kumamoto| first5 = Takuya| last6 = Ishikawa| first6 = Tsutomu| last7 = Asanuma| first7 = Masato| last8 = Funada| first8 = Masahiko| last9 = Kiryu| first9 = Kimio| last10 = Naito| first10 = Shinsaku| last11 = Yoshida| first11 = Yuzo| last12 = Yamamoto| first12 = Shigeo| last13 = Hanioka| first13 =10.1016/j.bcp.2006.01.015 Nobumitsu}}</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<sub>2A</sub> 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 =132–7 132–137 | 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<sub>1A</sub> receptor]].<ref>{{cite journal | vauthors = Ray TS | title = Psychedelics and the Humanhuman Receptoromereceptorome | journal = PLOS ONE | volume = 5 | issue = 2 | pages = e9019 | date = 2 February 2010 | pmcpmid = 281485420126400 |pmid pmc =20126400 2814854 | doi = 10.1371/journal.pone.0009019 | doi-access = free | bibcode = 2010PLoSO...5.9019R | doi-access = free }}</ref>
 
5-MeO-DiPT is [[Neurotoxin|neurotoxic]] in rats.<ref>{{Citecite journal |last1 vauthors = Noworyta-Sokołowska|first1=Karolina|last2= K, Kamińska|first2=Katarzyna|last3= K, Kreiner|first3=Grzegorz|last4= G, Rogóż|first4=Zofia|last5= Z, Gołembiowska K |first5=Krystyna|date=2016| 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|issn=1029-8428|pmc=5047954|pmid=27461536 }}</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 | authorvauthors = Baselt R. Baselt | 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>{{Citecite journal | doivauthors = 10.1016/j.forsciint.2005.11.026|Tanaka pmidE, =Kamata T, Katagi M, Tsuchihashi H, Honda K 16406422| title = A fatal poisoning with 5-methoxy-N,N-diisopropyltryptamine, Foxy | journal = Forensic Science International | volume = 163 | issue = 1–2 | pages = 152–4|152–154 year = 2006| last1date = Tanaka|November first1 =2006 Einosuke| last2pmid = Kamata| first2 =16406422 Tooru| last3doi = Katagi| first3 = Munehiro| last4 = Tsuchihashi| first4 = Hitoshi| last5 = Honda| first5 =10.1016/j.forsciint.2005.11.026 Katsuya}}</ref>
 
==Drug prohibition laws==
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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]]
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* [[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].
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[[Category:Neurotoxins]]
[[Category:Diisopropylamino compounds]]
[[Category:Methoxy compounds]]