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MiPLA: Difference between revisions
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'''N-Methyl-N-isopropyllysergamide''' (also known as '''methylisopropyllysergamide''', '''Lamide''' and '''MiPLA''') is a lesser-known novel [[psychoactive class::psychedelic]] substance of the [[chemical class::lysergamide]] class. MiPLA is structurally related to [[LSD]] and likely has a similar mechanism of action, working primarily by binding to the [[serotonin]]-2A [[receptor]] in the brain.{{citation needed}} | '''N-Methyl-N-isopropyllysergamide''' (also known as '''methylisopropyllysergamide''', '''Lamide''' and '''MiPLA''') is a lesser-known novel [[psychoactive class::psychedelic]] substance of the [[chemical class::lysergamide]] class. MiPLA is structurally related to [[LSD]] and likely has a similar mechanism of action, working primarily by binding to the [[serotonin]]-2A [[receptor]] in the brain.{{citation needed}} | ||
MiPLA was first discovered by Albert Hoffman as a part of the original structure-activity research for [[LSD]].{{citation needed}} It has recently been researched in greater detail by by a team led by David E. Nichols at Purdue University.{{citation needed}} MiPLA and its effects are also mentioned in Alexander Shulgin's "Pharmacology Notes #9" and "Pharmacology Notes C".<ref>https://erowid.org/library/books_online/shulgin_labbooks/shulgin_pharmacology_notebook9_searchable.pdf</ref><ref>https://erowid.org/library/books_online/shulgin_labbooks/shulgin_pharmacology_notebookc_searchable.pdf</ref> According to Shulgin, human subjects administered MiPLA at doses of 180–300 μg experienced LSD-like psychedelic effects, making it about two- to threefold less potent than LSD.<ref>Halberstadt | MiPLA was first discovered by Albert Hoffman as a part of the original structure-activity research for [[LSD]].{{citation needed}} It has recently been researched in greater detail by by a team led by David E. Nichols at Purdue University.{{citation needed}} MiPLA and its effects are also mentioned in Alexander Shulgin's "Pharmacology Notes #9" and "Pharmacology Notes C".<ref>{{cite book|author=Alexander Shulgin|author-link=Alexander Shulgin|title=Pharmacology Notes IX (The Shulgin Lab Books)|publisher=Erowid|url=https://erowid.org/library/books_online/shulgin_labbooks/shulgin_pharmacology_notebook9_searchable.pdf}}</ref><ref>{{cite book|author=Alexander Shulgin|author-link=Alexander Shulgin|title=Pharmacology Notes C (The Shulgin Lab Books)|publisher=Erowid|url=https://erowid.org/library/books_online/shulgin_labbooks/shulgin_pharmacology_notebookc_searchable.pdf}}</ref> According to Shulgin, human subjects administered MiPLA at doses of 180–300 μg experienced LSD-like psychedelic effects, making it about two- to threefold less potent than LSD.<ref>{{cite journal|last1=Halberstadt|first1=A. L.|last2=Klein|first2=L. M.|last3=Chatha|first3=M.|last4=Valenzuela|first4=L. B.|last5=Stratford|first5=A.|last6=Wallach|first6=Jason|last7=Nichols|first7=D. E.|author-link7=David E. Nichols|last8=Brandt|first8=S. D.|title=Pharmacological characterization of the LSD analog ''N''-ethyl-''N''-cyclopropyl lysergamide (ECPLA)|journal=Psychopharmacology|year=2018|volume=236|pages=799–808|doi=10.1007/s00213-018-5055-9|issn=0033-3158|eissn=1432-2072|oclc=2409222}}</ref> | ||
User reports describe the effects of MiPLA as similar to those of LSD but with some notable differences. It has been described as more mentally and physically oriented than LSD but with a less introspective headspace, accompanied by subtle visuals. It also has a notably shorter duration at around 6 hours and is generally described as less anxiety-provoking than LSD and other lysergamides. | User reports describe the effects of MiPLA as similar to those of LSD but with some notable differences. It has been described as more mentally and physically oriented than LSD but with a less introspective headspace, accompanied by subtle visuals. It also has a notably shorter duration at around 6 hours and is generally described as less anxiety-provoking than LSD and other lysergamides. | ||
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The chemical name of MiPLA is methylisopropyllysergamide. MiPLA belongs to a class of organic compounds known as lysergamides, which are a subclass of ergolines (derivatives of the alkaloids found in the ergot fungus). The most prominent member of the lysergamides is [[LSD]], lysergic acid diethylamide. | The chemical name of MiPLA is methylisopropyllysergamide. MiPLA belongs to a class of organic compounds known as lysergamides, which are a subclass of ergolines (derivatives of the alkaloids found in the ergot fungus). The most prominent member of the lysergamides is [[LSD]], lysergic acid diethylamide. | ||
MiPLA is a structural isomer of LSD. Like LSD, the chemical structure of MiPLA is based on the lysergic acid amide structural skeleton. However, whereas LSD has two ethyl groups bound to the amide nitrogen, MiPLA is substituted with a methyl and isopropyl group. | MiPLA is a structural isomer of LSD. Like LSD, the chemical structure of MiPLA is based on the lysergic acid amide structural skeleton. However, whereas LSD has two ethyl groups bound to the amide nitrogen, MiPLA is substituted with a methyl and isopropyl group. MiPLA is a chiral compound with two stereocenters at R<sub>5</sub> and R<sub>8</sub>. The differences in psychoactivity between the stereoisomers have not yet been investigated. | ||
MIPLA and its ethylisopropyl homologue are the only simple N,N-dialkyl lysergamides that approach the potency of LSD itself, being around 1/3-1/2 the potency of LSD,<ref>{{cite journal | vauthors=((Huang, X.)), ((Marona-Lewicka, D.)), ((Pfaff, R. C.)), ((Nichols, D. E.)) | journal=Pharmacology Biochemistry and Behavior | title=Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives | volume=47 | issue=3 | pages=667–673 | date= March 1994 | url=https://linkinghub.elsevier.com/retrieve/pii/0091305794901724 | issn=00913057 | doi=10.1016/0091-3057(94)90172-4}}</ref> while all other dialkyl analogues tested (dimethyl, dipropyl, methylethyl etc.) are only around 1/10 as potent as LSD,<ref>{{cite journal | vauthors=((Hofmann, A.)) | journal=Acta Physiologica Et Pharmacologica Neerlandica | title=Psychotomimetic drugs; chemical and pharmacological aspects | volume=8 | pages=240–258 | date= June 1959 | issn=0001-6748}}</ref> although some N-monoalkyl lysergamides such as the ''sec''-butyl and ''t''-butyl derivatives were also found to show an activity profile and potency comparable to LSD,<ref>{{Citation | vauthors=((Pioch, R. P.)) | title=Lysergic acid amides | url=https://patents.google.com/patent/US2997470A/en}}</ref> and the mono-isopropyl derivative is only slightly weaker than MIPLA. Apart from its lower potency, the hallucinogenic effects of methylisopropyllysergamide are similar to those of LSD itself, and the main use for this drug has been in studies of the binding site at the 5-HT<sub>2A</sub> receptor through which LSD exerts most of its pharmacological effects.<ref>{{cite journal | vauthors=((Nichols, D. E.)) | journal=The Heffter Review of Psychedelic Research. Santa Fe, New Mexico: Heffter Research Institute | title=LSD and its lysergamide cousins | volume=2 | pages=80–87 | date= 2001 | url=http://www.thevespiary.org/rhodium/Rhodium/pdf/nichols/nichols-lsd.lysergamide.cousins.pdf}}</ref> | |||
==Pharmacology== | ==Pharmacology== | ||
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Additional experience reports can be found here: | Additional experience reports can be found here: | ||
*[https://erowid.org/experiences/subs/ | *[https://erowid.org/experiences/subs/exp_MIPLA.shtml Erowid Experience Vaults: MiPLA] | ||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
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*'''Austria''': MiPLA is technically not illegal but it may fall in the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich) as an analogue of LSD. {{citation needed}} | *'''Austria''': MiPLA is technically not illegal but it may fall in the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich) as an analogue of LSD. {{citation needed}} | ||
*'''Germany''': MiPLA is controlled under the NpSG (New Psychoactive Substances Act) | *'''Germany''': MiPLA is controlled under the NpSG (''New Psychoactive Substances Act'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]|access-date=December 10, 2019|language=de}}</ref> 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|access-date=January 1, 2020|language=de}}</ref> Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]|access-date=December 10, 2019|language=de}}</ref> | ||
*'''Switzerland''': MiPLA can be considered a controlled substance as a defined derivative of Lysergic Acid under Verzeichnis E point 263. It is legal when used for scientific or industrial use.<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 States''': MiPLA is not scheduled but may be considered to be an analogue of LSD, which would make it illegal to possess for human consumption under the Federal Analogue Act.{{citation needed}} | *'''United States''': MiPLA is not scheduled but may be considered to be an analogue of LSD, which would make it illegal to possess for human consumption under the Federal Analogue Act.{{citation needed}} | ||
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==References== | ==References== | ||
<references /> | <references /> | ||
[[Category:Substance]] | |||
[[Category:Psychoactive substance]] | [[Category:Psychoactive substance]] | ||
[[Category:Hallucinogen]] | [[Category:Hallucinogen]] | ||
[[Category:Psychedelic]] | [[Category:Psychedelic]] | ||
[[Category:Lysergamide]] | [[Category:Lysergamide]] | ||
[[Category:Research chemical]] | |||
{{#set:Featured=true}} | {{#set:Featured=true}} | ||