MiPLA: Difference between revisions

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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.

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 R5 and R8. The differences in psychoactivity between the stereoisomers have not yet been investigated.

~~MiPLA is a chiral compound with two stereocenters at~~ R<~~sub~~>5</~~sub~~> and R8. 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-HT2A 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==

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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}}

*'''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}}

@@ Line 12: / Line 12: @@
 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 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==
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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}}
 *'''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}}