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4-HO-MiPT: Difference between revisions
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'''4-Hydroxy-N-methyl-N-isopropyltryptamine''' (also known as '''4-HO-MiPT''', and '''Miprocin''') is a novel [[psychoactive class::psychedelic]] substance of the [[chemical class::tryptamine]] class that produces [[psilocybin|psilocybin-like]] psychedelic effects when [[routes of administration|administered]]. It is part of a series of psychedelic [[tryptamines|substituted tryptamines]] such as [[4-AcO-DMT]], [[4-HO-MET]], [[4-HO-DiPT]] that are considered to produce variations of the core psychedelic effects typified by [[psilocin]]. | '''4-Hydroxy-N-methyl-N-isopropyltryptamine''' (also known as '''4-HO-MiPT''', and '''Miprocin''') is a novel [[psychoactive class::psychedelic]] substance of the [[chemical class::tryptamine]] class that produces [[psilocybin|psilocybin-like]] psychedelic effects when [[routes of administration|administered]]. It is part of a series of psychedelic [[tryptamines|substituted tryptamines]] such as [[4-AcO-DMT]], [[4-HO-MET]], [[4-HO-DiPT]] that are considered to produce variations of the core psychedelic effects typified by [[psilocin]]. | ||
This substance is relatively uncommon and has only a short history of human use. [[Alexander Shulgin]] evaluated its activity in humans in 1979, describing a trial of 12mg as a richly insightful and highly erotic experience.<ref>Shulgin | This substance is relatively uncommon and has only a short history of human use. [[Alexander Shulgin]] evaluated its activity in humans in 1979, describing a trial of 12mg as a richly insightful and highly erotic experience.<ref>{{cite book|author=Alexander Shulgin|author-link=Alexander Shulgin|title=Pharmacology Notes II (The Shulgin Lab Books)|publisher=Erowid|url=https://erowid.org/library/books_online/shulgin_labbooks/shulgin_pharmacology_notebook9_searchable.pdf|page=312|place=Lafayette, CA|year=1980}}</ref> | ||
A description of 4-HO-MiPT is included in Shulgin's 1997 book [[TiHKAL]].<ref> | A description of 4-HO-MiPT is included in Shulgin's 1997 book [[TiHKAL]].<ref name="TiHKAL">{{cite book|title=TiHKAL: The Continuation|title-link=TiHKAL|last1=Shulgin|first1=Alexander|last2=Shulgin|first2=Ann|author-link1=Alexander Shulgin|year=1997|publisher=Transform Press|location=United States|isbn=0-9630096-9-9|oclc=38503252|chapter-url=https://erowid.org/library/books_online/tihkal/tihkal22.shtml|chapter=#22. 4-HO-MiPT}}</ref> Shulgin's trials and other anecdotal reports suggest that 4-HO-MiPT is similar in activity to [[psilocin]], the active component in [[psilocybin mushrooms]]. | ||
Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-HO-MiPT in humans. As with [[psilocin]], there have been no reported deaths from 4-HO-MiPT use despite the existence of reports of people taking doses which far exceeds the active dose. This suggests that it is well-tolerated physiologically.{{citation needed}} | Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-HO-MiPT in humans. As with [[psilocin]], there have been no reported deaths from 4-HO-MiPT use despite the existence of reports of people taking doses which far exceeds the active dose. This suggests that it is well-tolerated physiologically.{{citation needed}} | ||
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==History and culture== | ==History and culture== | ||
{{historyStub}} | {{historyStub}} | ||
The first synthesis of 4-HO-MiPT was published in 1981 by a team of chemists led by David Repke.<ref>Repke | The first synthesis of 4-HO-MiPT was published in 1981 by a team of chemists led by David Repke.<ref>{{cite journal|last1=Repke|first1=D. B.|last2=Ferguson|first2=W. J.|last3=Bates|first3=D. K.|title=Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols|journal=Journal of Heterocyclic Chemistry|issn=0022-152X|oclc=1783072|year=1981|volume=18|issue=1|pages=175–179|doi=10.1002/jhet.5570180131|}}</ref> Repke and Shulgin later collaborated on a paper evaluating the effects of different oxygen substituents on the MiPT structure, describing 4-HO-MiPT as the most interesting of the series and the only one to possess classical hallucinogen effects.<ref>{{cite journal|last1=Repke|first1=D. B.|last2=Grotjahn|first2=D. B.|last3=Shulgin|first3=A. T.|author-link3=Alexander Shulgin|title=Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents|journal=Journal of Medicinal Chemistry|year=1985|volume=28|issue=7|pages=892–896|doi=10.1021/jm00145a007|pmid=4009612|issn=0022-2623|eissn=1520-4804|oclc=39480771}}</ref> | ||
==Chemistry== | ==Chemistry== | ||
[[File:Tryptamine1.png|thumb|235px|right|Generic structure of a tryptamine molecule.]] | [[File:Tryptamine1.png|thumb|235px|right|Generic structure of a tryptamine molecule.]] | ||
4-HO-MiPT or 4-hydroxy-N-methyl-N-isopropyltryptamine is a synthetic indole alkaloid molecule of the [[tryptamine]] class. Tryptamines share a core structure comprised of a bicylic indole heterocycle attached at R<sub>3</sub> to an amino group via an ethyl side chain. 4-HO-MiPT is substituted at R<sub>4</sub> of its indole heterocycle with a hydroxyl (HO) functional group OH-. It also contains a methyl group and an isopropyl chain bound to the terminal amine R<sub>N</sub> of its tryptamine backbone (MiPT). 4-HO-MiPT is the N-substituted isopropyl homologue of [[4-HO-DMT]] (''Psilocin'').<ref> | 4-HO-MiPT or 4-hydroxy-N-methyl-N-isopropyltryptamine is a synthetic indole alkaloid molecule of the [[tryptamine]] class. Tryptamines share a core structure comprised of a bicylic indole heterocycle attached at R<sub>3</sub> to an amino group via an ethyl side chain. 4-HO-MiPT is substituted at R<sub>4</sub> of its indole heterocycle with a hydroxyl (HO) functional group OH-. It also contains a methyl group and an isopropyl chain bound to the terminal amine R<sub>N</sub> of its tryptamine backbone (MiPT). 4-HO-MiPT is the N-substituted isopropyl homologue of [[4-HO-DMT]] (''Psilocin'').<ref name="TiHKAL"></ref> | ||
==Pharmacology== | ==Pharmacology== | ||
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==Legal status== | ==Legal status== | ||
{{legalStub}} | {{legalStub}} | ||
*'''Brazil''': As of August 21, 2018, 4-HO-MiPT has been added to Portaria SVS/MS nº 344. Possession, distribution and use of this substance is now considered illegal.<ref> | *'''Brazil''': As of August 21, 2018, 4-HO-MiPT has been added to Portaria SVS/MS nº 344. Possession, distribution and use of this substance is now considered illegal.<ref>{{cite web|url=http://portal.anvisa.gov.br/lista-de-substancias-sujeitas-a-controle-especial|title=Lista de substâncias sujeitas a controle especial no Brasil|access-date=August 27, 2020|publisher=Agência Nacional de Vigilância Sanitária (ANVISA) [Brazilian Health Regulatory Agency]|language=pt}}</ref> | ||
*'''Germany''': 4-HO-MiPT is controlled under the NpSG (New Psychoactive Substances Act) as of July 18, 2019.<ref>{{cite web|url= | *'''Germany''': 4-HO-MiPT is controlled under the NpSG<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> (''New Psychoactive Substances Act'') as of July 18, 2019.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl119s1083.pdf|title=Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes|publisher=Bundesanzeiger Verlag|work=Bundesgesetzblatt Jahrgang 2019 Teil I Nr. 27|pages=1083-1094|publication-date=July 17, 2019|language=de|issn=0341-1095}}</ref> Production and import with the aim to place it on the market, administration to another person, placing it on the market and trading is punishable. Possession is illegal but not punishable.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__3.html|title=§ 3 NpSG|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> The legislator considers it possible that orders of 4-AcO-MET are punishable as an incitement to place it on the market.<ref>{{cite web|url=http://dip21.bundestag.de/dip21/btd/18/085/1808579.pdf|title=Gesetzentwurf der Bundesregierung: Entwurf eines Gesetzes zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|page=20|date=May 30, 2016|id=Drucksache 18/8579|publisher=Deutscher Bundestag|language=de}}</ref> | ||
*'''Poland''': 4-HO-MiPT is a NPS class drug in Poland, making it illegal to possess or distribute.<ref>{{cite web|title=Rozporządzenie Ministra zdrowia z dnia 21 sierpnia 2019 r. zmieniające rozporządzenie w sprawie wykazu substancji psychotropowych, środków odurzających oraz nowych substancji psychoaktywnych|url=http://prawo.sejm.gov.pl/isap.nsf/download.xsp/WDU20190001745/O/D20191745.pdf|language=pl}}</ref> | *'''Poland''': 4-HO-MiPT is a NPS class drug in Poland, making it illegal to possess or distribute.<ref>{{cite web|title=Rozporządzenie Ministra zdrowia z dnia 21 sierpnia 2019 r. zmieniające rozporządzenie w sprawie wykazu substancji psychotropowych, środków odurzających oraz nowych substancji psychoaktywnych|url=http://prawo.sejm.gov.pl/isap.nsf/download.xsp/WDU20190001745/O/D20191745.pdf|language=pl|date=August 21, 2019|publisher=Sejm Rzeczypospolitej Polskiej [Sejm of the Republic of Poland]}}</ref> | ||
*'''Sweden''': 4-HO-MiPT is classified as a health hazard under the act ''Lagen om förbud mot vissa hälsofarliga varor'' (translated as the "Act on the Prohibition of Certain Goods Dangerous to Health") as of November 1, 2005, making it illegal to sell or possess.<ref>http://www.notisum.se/rnp/sls/sfs/20050733.pdf</ref> | *'''Sweden''': 4-HO-MiPT is classified as a health hazard under the act ''Lagen om förbud mot vissa hälsofarliga varor'' (translated as the "Act on the Prohibition of Certain Goods Dangerous to Health") as of November 1, 2005, making it illegal to sell or possess.<ref>{{cite web|title=Svensk författningssamling Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor|url=http://www.notisum.se/rnp/sls/sfs/20050733.pdf|id=SFS 2005:733|language=sv|date=October 6, 2005|publication-date=October 18, 2005|}}</ref> | ||
*'''Switzerland''': 4-HO-MiPT is a controlled substance specifically named under Verzeichnis E.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | *'''Switzerland''': 4-HO-MiPT is a controlled substance specifically named under Verzeichnis E.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | ||
*'''United Kingdom''': 4-HO-MiPT is a Class A drug in the United Kingdom as a result of the tryptamine catch-all clause.<ref> | *'''United Kingdom''': 4-HO-MiPT is a Class A drug in the United Kingdom as a result of the tryptamine catch-all clause.<ref>{{cite web|title=Schedule 2: Part I: Class A Drugs|url=http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I|work="Misuse of Drugs Act 1971"|access-date=August 20, 2020|publisher=UK Government}}</ref> | ||
*'''United States''': 4-HO-MiPT is unscheduled in the United States. It may be considered an analogue of [[psilocin]] (''4-HO-DMT'') which is a Schedule I drug under the Controlled Substances Act. As such, the sale for human consumption or the use for illicit non-medical or industrial intents and purposes could be prosecuted as crimes under the Federal Analogue Act.{{citation needed}} | *'''United States''': 4-HO-MiPT is unscheduled in the United States. It may be considered an analogue of [[psilocin]] (''4-HO-DMT'') which is a Schedule I drug under the Controlled Substances Act. As such, the sale for human consumption or the use for illicit non-medical or industrial intents and purposes could be prosecuted as crimes under the Federal Analogue Act.{{citation needed}} | ||