MiPLA: Difference between revisions
>Unity Grammatics |
>Graham wiki ref formatting |
||
(13 intermediate revisions by 6 users not shown) | |||
Line 1: | Line 1: | ||
{{SummarySheet}} | |||
{{SubstanceBox/MiPLA}} | {{SubstanceBox/MiPLA}} | ||
'''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>{{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. | |||
Very little data exists about the pharmacological properties, metabolism, and toxicity of MiPLA. It is highly advised to use harm reduction practices when using this substance. | |||
Very little data exists about the pharmacological properties, metabolism, and toxicity of | |||
==Chemistry== | ==Chemistry== | ||
The chemical name of | 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 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 | 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== | ||
As with its structurally related lysergamides, | As with its structurally related lysergamides, MiPLA principally acts as a 5-HT2A partial agonist, through which it exerts its psychedelic effects. However, the role of these interactions and how they result in the psychedelic experience is unclear. | ||
Owing to similarities in chemical structure, | Owing to similarities in chemical structure, MiPLA and LSD have highly similar binding profiles at monoamine receptors (i.e. [[serotonin]], [[dopamine]], and [[norepinephrine]]).{{citation needed}} | ||
One study found | One study found MiPLA to fully substitute for LSD in rats, with about half the potency of the training drug.{{citation needed}} | ||
==Subjective effects== | ==Subjective effects== | ||
{{EffectStub}} | {{EffectStub}} | ||
MiPLA is commonly reported to be significantly shorter in its duration and less uncomfortable in both its [[Uncomfortable_physical_effects|negative physical side effects]] and general [[anxiety]]. | |||
{{Preamble/SubjectiveEffects}} | {{Preamble/SubjectiveEffects}} | ||
Line 32: | Line 32: | ||
|{{effects/physical| | |{{effects/physical| | ||
*'''[[Effect::Stimulation]]''' - Similar to LSD, | *'''[[Effect::Stimulation]]''' - Similar to LSD, MiPLA is considered to be primarily stimulating in nature. This is in distinction to other, more commonly used psychedelics such as [[psilocybin]] which are more consistent in producing [[sedation]] and [[muscle relaxation|relaxedness]]. | ||
*'''[[Effect::Spontaneous bodily sensations]]''' - The "body high" of | *'''[[Effect::Spontaneous bodily sensations]]''' - The "body high" of MiPLA can be described as proportionally intense in comparison to its accompanying visual and cognitive effects. It behaves as a pleasurable, fast-moving, sharp and location specific tingling sensation. For some, it is manifested spontaneously at different unpredictable points throughout the experience, but for most it maintains a steady presence that rises with the onset and hits its limit once the peak has been reached. In comparison to LSD, MiPLA is a little less sharp in the tingling sensations it produces as but is otherwise essentially indistinguishable. | ||
*'''[[Effect::Physical euphoria]]''' - Physical euphoria on | *'''[[Effect::Physical euphoria]]''' - Physical euphoria on MiPLA is not as consistent as it is with substances like [[stimulants]] or [[entactogens]], and can just as easily manifest as physical discomfort without any apparent reason. | ||
*'''[[Effect::Changes in felt bodily form]]''' - This effect is often accompanied by a sense of warmth or [[Unity and interconnectedness#Unity between the self and specific external systems|unity]] and usually occurs during and up to the peak of the experience or directly afterward. Users can feel as if they are physically part of or conjoined with other objects. This is usually reported as feeling comfortable and peaceful in its sensations. | *'''[[Effect::Changes in felt bodily form]]''' - This effect is often accompanied by a sense of warmth or [[Unity and interconnectedness#Unity between the self and specific external systems|unity]] and usually occurs during and up to the peak of the experience or directly afterward. Users can feel as if they are physically part of or conjoined with other objects. This is usually reported as feeling comfortable and peaceful in its sensations. | ||
*'''[[Effect::Tactile enhancement]]''' - Feelings of enhanced tactile sensations are consistently present at moderate levels throughout most | *'''[[Effect::Tactile enhancement]]''' - Feelings of enhanced tactile sensations are consistently present at moderate levels throughout most MiPLA trips. | ||
*'''[[Effect::Temperature regulation suppression]]'''{{citation needed}} | *'''[[Effect::Temperature regulation suppression]]'''{{citation needed}} | ||
*'''[[Effect::Increased bodily temperature]]'''{{citation needed}} | *'''[[Effect::Increased bodily temperature]]'''{{citation needed}} | ||
Line 74: | Line 74: | ||
====[[Geometry]]==== | ====[[Geometry]]==== | ||
The [[visual geometry]] evoked by | The [[visual geometry]] evoked by MiPLA can be described as more similar in appearance to that of [[LSD]], [[2C-B]] or [[4-HO-MET]] than [[psilocin]], [[LSA]] or [[DMT]]. It can be comprehensively described through its [[Visual_effects:_Geometry#Variations|variations]] as primarily intricate in complexity, algorithmic in form, unstructured in organization, brightly lit, colourful and cartoonish in scheme, organic in feel, flat in shading, soft in its edges, large in size, slow in speed, smooth in motion, either angular or round in its corners, non-immersive in-depth and consistent in intensity. At higher dosages, it consistently results in states of [[Effect::Level 8B]] visual geometry over [[Level 8A]]. | ||
In comparison to LSD specifically, | In comparison to LSD specifically, MiPLA's geometry tends to be more rounded in its corners, slightly softer in its edges, warmer in hue, and slightly less intricate in its form. Aside from this, it is otherwise identical in its appearance. | ||
====Hallucinatory states==== | ====Hallucinatory states==== | ||
MiPLA is capable of producing a full range of low and high level hallucinatory states in a fashion that is a less consistent and reproducible than that of many other commonly used psychedelics such as [[psilocin]] or [[DMT]] but considerably more likely to when compared to that of [[LSD]]. This can feel similar to the hallucinations which occur with [[4-AcO-DMT]] but tends to occur almost exclusively at [[heavy|heavier]] [[dosage|doses]]. Some of these effects include: | |||
*'''[[Effect::Machinescapes]]''' | *'''[[Effect::Machinescapes]]''' | ||
Line 119: | Line 119: | ||
}} | }} | ||
{{effects/transpersonal| | {{effects/transpersonal| | ||
Reports indicate that the transpersonal effects of | Reports indicate that the transpersonal effects of MiPLA are comparatively weaker than those of LSD and other lysergamides, as well as classical psychedelics such as [[psilocybin mushrooms]] or [[mescaline]]. | ||
*'''[[Effect::Existential self-realization]]''' | *'''[[Effect::Existential self-realization]]''' | ||
Line 128: | Line 128: | ||
===Experience reports=== | ===Experience reports=== | ||
Anecdotal reports which describe the effects of this compound within our [[experience index]] include: | Anecdotal reports which describe the effects of this compound within our [[experience index]] include: | ||
{{#ask: [[Category: | {{#ask: [[Category:MiPLA]][[Category:Experience]]|format=ul|Columns=1}} | ||
Additional experience reports can be found here: | Additional experience reports can be found here: | ||
* [https://erowid.org/experiences/subs/exp_MIPLA.shtml Erowid Experience Vaults: | |||
*[https://erowid.org/experiences/subs/exp_MIPLA.shtml Erowid Experience Vaults: MiPLA] | |||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}} | {{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}} | ||
The toxicity and long-term health effects of recreational | The toxicity and long-term health effects of recreational MiPLA use has not been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because MiPLA is a [[research chemical]] with very little history of human usage. | ||
The current body of anecdotal reports suggests that there are no negative health effects attributed to simply trying the substance by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption. | The current body of anecdotal reports suggests that there are no negative health effects attributed to simply trying the substance by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption. | ||
However, as is the case for LSD, it is possible that | However, as is the case for LSD, it is possible that MiPLA can act as a potential trigger for those with underlying psychiatric conditions. Those with a personal or family history of mental illness are generally advised not to use this substance, particularly outside of a supervised medical setting. | ||
It is strongly recommended that one uses [[responsible drug use|harm reduction practices]] when using this substance. | It is strongly recommended that one uses [[responsible drug use|harm reduction practices]] when using this substance. | ||
===Overdose=== | ===Overdose=== | ||
The LD<sub>50</sub> of | The LD<sub>50</sub> of MiPLA is unknown. Adverse psychological reactions may be more likely to occur at higher doses. Some of these include [[anxiety]], [[delusions]], [[panic attacks]] and (more rarely) [[seizures]]. Medical attention is usually only needed in the case of severe psychotic episodes or “fake acid” (a counterfeit substance such as [[25x-NBOMe]] or [[DOx]]). Administration of [[benzodiazepines]] or [[antipsychotics]] can help to relieve the negative psychological effects of MiPLA. | ||
===Dependence and abuse potential=== | ===Dependence and abuse potential=== | ||
Like other [[serotonergic psychedelics]], | Like other [[serotonergic psychedelics]], MiPLA is believed to have a [[Addiction potential::low potential for abuse and dependence]]. This is owing to its structural and pharmacological similarities with [[LSD]]. See [[LSD#Dependence and abuse|this section]] to learn more about the dependence and abuse potential of LSD. It should be noted that all claims related to the abuse potential of MiPLA are preliminary and based on anecdotal (as opposed to clinical) evidence and should be interpreted with caution. | ||
As with LSD, tolerance to the effects of | As with LSD, tolerance to the effects of MiPLA forms [[Time to full tolerance::almost immediately after ingestion]]. After that, it is assumed to take about [[Time to half tolerance::5-7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::14 days]] to be return to baseline (in the absence of further consumption). | ||
Due to its activity at the 5-HT<sub>2A</sub> receptor, | Due to its activity at the 5-HT<sub>2A</sub> receptor, MiPLA produces cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of MiPLA all psychedelics will have a reduced effect. | ||
===Dangerous interactions=== | ===Dangerous interactions=== | ||
{{DangerousInteractions/Intro}} | {{DangerousInteractions/Intro}} | ||
{{DangerousInteractions/Psychedelics}} | |||
==Legal status== | ==Legal status== | ||
{{legalStub}} | {{legalStub}} | ||
MiPLA is not scheduled under the UN Convention on Psychotropic Substances. It is considered to exist in a legal grey area throughout most of the world, meaning that it might not be specifically illegal but individuals may still be charged for its possession under certain circumstances such as under analogue laws and with the intent to sell or consume. | |||
*'''Austria | |||
*'''United States | *'''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}} | |||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Research chemical]] | *[[Research chemical]] | ||
Line 174: | Line 176: | ||
==External links== | ==External links== | ||
* [https://en.wikipedia.org/wiki/Methylisopropyllysergamide | |||
* [https://isomerdesign.com/PiHKAL/explore.php?domain=tk&id=5327 | *[https://en.wikipedia.org/wiki/Methylisopropyllysergamide MiPLA (Wikipedia)] | ||
*[https://isomerdesign.com/PiHKAL/explore.php?domain=tk&id=5327 MiPLA (TiHKAL / Isomer Design)] | |||
===Discussion=== | ===Discussion=== | ||
* [http://www.bluelight.org/vb/threads/784440-The-Small-amp-Handy- | |||
*[http://www.bluelight.org/vb/threads/784440-The-Small-amp-Handy-MiPLA-(Methylisopropyllysergamide)-Thread The Small & Handy MiPLA Thread (Bluelight)] | |||
==Literature== | ==Literature== | ||
* Halberstadt, A. L., Klein, L. M., Chatha, M., Valenzuela, L. B., Stratford, A., Wallach, J., ... & Brandt, S. D. (2018). Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA). Psychopharmacology, 1-10. http://dx.doi.org/10.1007/s00213-018-5055-9 | |||
* [https://heffter.org/docs/hrireview/02/chap6.pdf Nichols, D. E. (2001). LSD and its lysergamide cousins. The Heffter Review of Psychedelic Research. Santa Fe, New Mexico: Heffter Research Institute, 80-87.] | *Halberstadt, A. L., Klein, L. M., Chatha, M., Valenzuela, L. B., Stratford, A., Wallach, J., ... & Brandt, S. D. (2018). Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA). Psychopharmacology, 1-10. http://dx.doi.org/10.1007/s00213-018-5055-9 | ||
*[https://heffter.org/docs/hrireview/02/chap6.pdf Nichols, D. E. (2001). LSD and its lysergamide cousins. The Heffter Review of Psychedelic Research. Santa Fe, New Mexico: Heffter Research Institute, 80-87.] | |||
==References== | ==References== | ||
<references /> | <references /> | ||
[[Category:Substance]] | |||
[[Category:Psychoactive substance]] | |||
[[Category:Hallucinogen]] | |||
[[Category:Psychedelic]] | |||
[[Category:Lysergamide]] | |||
[[Category:Research chemical]] | |||
{{#set:Featured=true}} |