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5-MeO-MiPT: Difference between revisions
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'''5-Methoxy-N-methyl-N-isopropyltryptamine''' (also known as '''5-MeO-MiPT''' and '''moxy''') is a lesser-known [[psychoactive class::psychedelic]] substance of the [[chemical class::tryptamine]] class. 5-MeO-MiPT is chemically related to tryptamines like [[5-MeO-DMT]] and [[5-MeO-DiPT]]. It produces its psychoactive effects through activity at [[serotonin]] [[receptors]] in the brain. | '''5-Methoxy-N-methyl-N-isopropyltryptamine''' (also known as '''5-MeO-MiPT''' and '''moxy''') is a lesser-known [[psychoactive class::psychedelic]] substance of the [[chemical class::tryptamine]] class. 5-MeO-MiPT is chemically related to tryptamines like [[5-MeO-DMT]] and [[5-MeO-DiPT]]. It produces its psychoactive effects through activity at [[serotonin]] [[receptors]] in the brain. | ||
The synthesis and pharmacology of 5-MeO-MiPT was first reported in 1985 by David Repke and Alexander Shulgin.<ref>Repke | The synthesis and pharmacology of 5-MeO-MiPT was first reported in 1985 by David Repke and Alexander Shulgin.<ref name="Repke1985">{{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> Its effects in humans was documented in Shulgin's book [[TiHKAL]] ("Tryptamines I Have Known and Loved"). | ||
Anecdotal reports describe 5-MeO-MiPT's effects as highly [[stimulating]] and mildly [[entactogenic]], lacking in typical psychedelic visual distortions. Many users report strong physical and tactile effects that serve to [[increased libido|enhance libido]] and sexual pleasure. An unpleasant "body load" is also often reported at common to high doses, marked by muscle tension and nausea. | Anecdotal reports describe 5-MeO-MiPT's effects as highly [[stimulating]] and mildly [[entactogenic]], lacking in typical psychedelic visual distortions. Many users report strong physical and tactile effects that serve to [[increased libido|enhance libido]] and sexual pleasure. An unpleasant "body load" is also often reported at common to high doses, marked by muscle tension and nausea. | ||
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5-MeO-MiPT, or 5-methoxy-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. 5-MeO-MiPT is substituted at R<sub>5</sub> of its indole heterocycle with a methoxy (MeO) functional group CH<sub>3</sub>O−; it also contains a methyl group and an isopropyl chain bound to the terminal amine R<sub>N</sub> of its tryptamine backbone (MiPT). | 5-MeO-MiPT, or 5-methoxy-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. 5-MeO-MiPT is substituted at R<sub>5</sub> of its indole heterocycle with a methoxy (MeO) functional group CH<sub>3</sub>O−; it also contains a methyl group and an isopropyl chain bound to the terminal amine R<sub>N</sub> of its tryptamine backbone (MiPT). | ||
5-MeO-MiPT is the N-substituted isopropyl homologue of [[5-MeO-DMT]].<ref> | 5-MeO-MiPT is the N-substituted isopropyl homologue of [[5-MeO-DMT]].<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/tihkal40.shtml|chapter=#40. 5-MeO-MiPT}}</ref> | ||
==Pharmacology== | ==Pharmacology== | ||
{{Further|Serotonergic psychedelic}} | {{Further|Serotonergic psychedelic}} | ||
5-MeO-MiPT's [[psychedelic]] effects are believed to come from its efficacy at the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] as a [[Agonist#Agonists|partial agonist | 5-MeO-MiPT's [[psychedelic]] effects are believed to come from its efficacy at the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] as a [[Agonist#Agonists|partial agonist]<ref name="pmid17223101">{{cite journal|title=The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain|pmid=17223101|volume=559|issue=2–3|year=2007|pages=132-137|first1=F.|last1=Nagai|first2=R.|last2=Nonaka|first3=K.|last3=Satoh|first4=H.|last4=Kamimura|journal=European Journal of Pharmacology|issn=0014-2999|eissn=1879-0712|oclc=01568459|doi=10.1016/j.ejphar.2006.11.075}}</ref><ref name="Repke1985"/> and additional mechanisms of action such as the inhibition of [[MAOI|MAO]] (i.e. digestive enzymes in the stomach) have also been speculated upon, though this has yet to be demonstrated scientifically. | ||
==Subjective effects== | ==Subjective effects== | ||
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{{DangerousInteractions/5-MeO-xxT}} | {{DangerousInteractions/5-MeO-xxT}} | ||
There are no known deaths from 5-MeO-MiPT but, as a [[monoamine]] [[reuptake inhibitor]] (MRI)<ref | There are no known deaths from 5-MeO-MiPT but, as a [[monoamine]] [[reuptake inhibitor]] (MRI)<ref name="pmid17223101"/>, injury could occur when excessive doses are taken or when it is taken with drugs such as [[MAOIs]], [[RIMA]]s, [[stimulant]]s and any substance which act as a [[releasing agent]] or [[reuptake inhibitor]] of [[neurotransmitters]] such as [[serotonin]] and [[dopamine]].<ref>{{cite journal|title=Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity|url=https://bjanaesthesia.org/article/S0007-0912(17)34956-5/fulltext|doi=10.1093/bja/aei210|last=Gillman|first=P. K.|journal=British Journal of Anaesthesia|volume=95|issue=4|year=2005|pages=434–441|issn=0007-0912|eissn=1471-6771|oclc=01537271}}</ref> | ||
==Legal status== | ==Legal status== | ||
*'''Brazil''': 5-MeO-MiPT is illegal to produce, sell, or possess as it is listed on Portaria SVS/MS nº 344.<ref>{{cite web|url=http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7|title=RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016|publication-date=December 5, 2016|publisher=Agência Nacional de Vigilância Sanitária (ANVISA) [Brazilian Health Regulatory Agency (ANVISA)]|language=pt}}</ref> | |||
*'''Brazil''': 5-MeO-MiPT is illegal to produce, sell, or possess as it is listed on Portaria SVS/MS nº 344.<ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref> | *'''China''': 5-MeO-MiPT is controlled as a Category I psychotropic substance and is illegal to sell, buy, import, export, and manufacture.<ref>{{cite web|title=Erowid China Psychoactive Law Update: September 2015|url=https://www.erowid.org/psychoactives/law/countries/china/china_law_2015_09_27_list_of_newly_controlled_chemicals.pdf|access-date=September 29, 2020|publisher=Erowid}}</ref> | ||
*'''China''': 5-MeO-MiPT is controlled as a Category I psychotropic substance and is illegal to sell, buy, import, export, and manufacture.<ref>Erowid China Psychoactive Law Update: September 2015 | https://www.erowid.org/psychoactives/law/countries/china/china_law_2015_09_27_list_of_newly_controlled_chemicals.pdf</ref> | *'''Finland''': 5-MeO-MiPT was banned in Finland in December 2014.<ref>{{cite web|title=1130/2014: Valtioneuvoston asetus: kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista|publication-date=December 19, 2014|url=https://www.erowid.org/psychoactives/law/countries/finland/finland_law1_2014.pdf|work=Suomen Säädöskokoelma|language=fi}}</ref> | ||
*'''Finland''': 5-MeO-MiPT was banned in Finland in December 2014.<ref> | *'''Germany''': 5-MeO-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-HO-MiPT 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> | ||
*'''Germany''': 5-MeO-MiPT is controlled under the NpSG (New Psychoactive Substances Act) as of July 18, 2019.<ref>{{cite web|url= | |||
*'''Japan''': 5-MeO-MiPT is controlled as a "Designated Substance" (Shitei-Yakubutsu) by the Pharmaceutical Affairs Law, making it illegal to possess or sell.{{citation needed}} | *'''Japan''': 5-MeO-MiPT is controlled as a "Designated Substance" (Shitei-Yakubutsu) by the Pharmaceutical Affairs Law, making it illegal to possess or sell.{{citation needed}} | ||
*'''Latvia''': 5-MeO-MiPT is a Schedule I drug in Latvia.<ref> | *'''Latvia''': 5-MeO-MiPT is a Schedule I drug in Latvia.<ref>{{cite web|url=http://likumi.lv/doc.php?id=121086|title=Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem|publisher=VSIA Latvijas Vēstnesis|access-date=January 1, 2020|publication-date=November 10, 2005|language=lv}}</ref> | ||
*'''New Zealand''': 5-MeO-MiPT is an analogue of DMT which makes it a Class C controlled drug in New Zealand.<ref>http://www.legislation.govt.nz/act/public/1975/0116/latest/whole.html#DLM436576</ref> | *'''New Zealand''': 5-MeO-MiPT is an analogue of DMT which makes it a Class C controlled drug in New Zealand.<ref>{{cite web|url=http://www.legislation.govt.nz/act/public/1975/0116/latest/whole.html#DLM436576|title=Schedule 1: Class A controlled drugs|access-date=September 19, 2020|work=Misuse of Drugs Act 1975|publisher=Parliamentary Counsel Office (PCO)}}</ref> | ||
*'''Romania''': 5-MeO-MiPT and other derivatives are illegal in Romania, as of January 2011.{{citation needed}} | *'''Romania''': 5-MeO-MiPT and other derivatives are illegal in Romania, as of January 2011.{{citation needed}} | ||
*'''Switzerland''': 5-MeO-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''': 5-MeO-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''': 5-MeO-MiPT is a Class A drug in the UK as it is an ether of the drug 5-HO-MiPT | *'''United Kingdom''': 5-MeO-MiPT is a Class A drug in the UK as it is an ether of the drug 5-HO-MiPT, which is a Class A drug 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''': 5-MeO-MiPT is unscheduled in the United States. It may be considered an analogue of [[5-MeO-DiPT]], 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''': 5-MeO-MiPT is unscheduled in the United States. It may be considered an analogue of [[5-MeO-DiPT]], 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}} | ||
**'''Florida''': 5-MeO-MiPT is a Schedule I drug in Florida.<ref>The 2015 Florida Statutes | **'''Florida''': 5-MeO-MiPT is a Schedule I drug in Florida.<ref>{{cite web|title=The 2015 Florida Statutes - Chapter 893|url=http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html|publisher=The Florida Legislature|access-date=July 18, 2020}}</ref> | ||
**'''Louisiana''': 5-MeO-MiPT is a Schedule I drug (as of June 2013).<ref>5-MeO- | **'''Louisiana''': 5-MeO-MiPT is a Schedule I drug (as of June 2013).<ref>{{cite web|title=5-MeO-MIPT: Legal Status|publisher=Erowid|url=https://www.erowid.org/chemicals/5meo_mipt/5meo_mipt_law.shtml|date=July 7, 2005|access-date=September 29, 2020}}</ref> | ||
**'''Minnesota''': Minnesota banned a series of drugs including 5-MeO-MiPT.<ref> | **'''Minnesota''': Minnesota banned a series of drugs including 5-MeO-MiPT.<ref>{{cite web|title=2019 Minnesota Statutes|publisher=Office of the Revisor of Statutes|year=2019|access-date=September 29, 2020|url=https://www.revisor.mn.gov/statutes/?id=152.02}}</ref> | ||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Psychedelics]] | *[[Psychedelics]] | ||
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==External links== | ==External links== | ||
*[https://en.wikipedia.org/wiki/5-MeO-MiPT 5-MeO-MiPT (Wikipedia)] | *[https://en.wikipedia.org/wiki/5-MeO-MiPT 5-MeO-MiPT (Wikipedia)] | ||
*[https://erowid.org/chemicals/5meo_mipt/5meo_mipt.shtml 5-MeO-MiPT (Erowid Vault)] | *[https://erowid.org/chemicals/5meo_mipt/5meo_mipt.shtml 5-MeO-MiPT (Erowid Vault)] | ||