MiPLA: Difference between revisions

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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 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>Huang X, Marona-Lewicka D, Pfaff RC, Nichols ~~DE (March 1994~~)~~. "~~Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives~~". ''Pharmacology Biochemistry and Behavior''. '''~~47~~''' (~~3): ~~667–73~~. doi:10.1016/0091-3057(94)90172-4~~. <nowiki>PMID 8208787</nowiki>.~~</ref> while all other dialkyl analogues tested (dimethyl, dipropyl, methylethyl etc.) are only around 1/10 as potent as LSD,<ref>Hofmann A ~~(June 1959~~)~~. "~~Psychotomimetic drugs; chemical and pharmacological aspects~~" (PDF). ''Acta Physiologica et Pharmacologica Neerlandica''. '''~~8~~''': 240–58. <nowiki>PMID 13852489</nowiki>.~~</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>~~US patent 2997470,~~ Pioch RP, "Lysergic ~~Acid Amides", published 1956-03-05, issued 1961-08-22~~</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>Nichols ~~DE (2001~~)~~. "LSD and its lysergamide cousins" (PDF~~)~~. ''~~The Heffter Review of Psychedelic Research''. Santa Fe, New Mexico: Heffter Research Institute~~. '''~~2~~'''~~: ~~80–7~~.</ref>

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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 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>Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE (March 1994). "Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives". ''Pharmacology Biochemistry and Behavior''. '''47''' (3): 667–73. doi:10.1016/0091-3057(94)90172-4. <nowiki>PMID 8208787</nowiki>.</ref> while all other dialkyl analogues tested (dimethyl, dipropyl, methylethyl etc.) are only around 1/10 as potent as LSD,<ref>Hofmann A (June 1959). "Psychotomimetic drugs; chemical and pharmacological aspects" (PDF). ''Acta Physiologica et Pharmacologica Neerlandica''. '''8''': 240–58. <nowiki>PMID 13852489</nowiki>.</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>US patent 2997470, Pioch RP, "Lysergic Acid Amides", published 1956-03-05, issued 1961-08-22</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>Nichols DE (2001). "LSD and its lysergamide cousins" (PDF). ''The Heffter Review of Psychedelic Research''. Santa Fe, New Mexico: Heffter Research Institute. '''2''': 80–7.</ref>
+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==