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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 novel [[psychoactive class::psychedelic]] substance of the [[chemical class::lysergamide]] class. MiPLA is chemically similar to LSD and has a similar mechanism of action, working primarily by stimulating [[serotonin]] [[receptors]] in the brain.
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>
MiPLA was first discovered by Albert Hoffman as a part of the original structure-activity research into LSD. It has recently been researched in greater detail by by the team led by David E. Nichols at Purdue University. MiPLA and its effects are also mentioned in Alexander Shulgin's Pharmacology notes #9 and Pharmacology notes C,
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 with major differences. It is thought to be 1/3rd as potent as [[LSD]] itself, with an active dose reported at between 100-200 micrograms. It is often described as being more mentally and physically oriented but with a less introspective headspace and subtle, albeit pronounced visuals. It also has a notably shorter duration at 4-6 hours and is generally described as less anxiety-provoking than 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 MiPLA. While it is often characterized by users as being generally more recreational and non-threatening compared to [[LSD]], it is highly advised to approach this highly potent [[hallucinogenic]] substance with the proper amount of precaution and [[harm reduction practices]] if using it.
==Chemistry==
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.
==Chemistry==
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, or methylisopropyllysergamide, is a semi-synthetic alkaloid belonging to the lysergamide chemical class. MiPLA is a structural analogue of
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, 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, MiPLA and LSD have highly similar binding profiles at monoamine receptors (i.e. [[serotonin]], [[dopamine]], and [[norepinephrine]]).{{citation needed}}
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}}
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]].
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]].
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|{{effects/physical|
|{{effects/physical|
*'''[[Effect::Stimulation]]''' - In terms of its effects on the physical energy levels of the user, MiPLA is regarded as being able primarily stimulating in nature in the same vein as LSD. 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::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 MiPLA can be described as proportionally intense in comparison to its accompanying visual and cognitive effects. It behaves as a euphoric, 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, it is a little less sharp in the tingling sensations it produces as but is otherwise essentially indistinguishable.
*'''[[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::Perception of bodily lightness]]''' - This component typically accompanies any feelings of [[stimulation]] that this compound can produce.
*'''[[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::Physical euphoria]]''' - It should be noted that this effect is not as reliably induceable 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 MiPLA trips. If [[Effect::8A Geometry|level 8A geometry]] is reached, an intense sensation of suddenly becoming aware of and being able to feel every single nerve ending across a person's entire body all at once becomes consistently present.
*'''[[Effect::Tactile enhancement]]''' - Feelings of enhanced tactile sensations are consistently present at moderate levels throughout most MiPLA trips.
*'''[[Effect::Temperature regulation suppression]]''' - This component can occur with the use of any lysergamide or psychedelic, but reports suggest it may be pronounced in MiPLA. It is highly advised that users of this compound, especially at heavier doses, monitor their bodily temperature and use techniques like hot showers or cold packs to regulate their core and brain temperature throughout the experience, and to generally always maintain proximity to a climate-controlled environment.
*'''[[Effect::Nausea]]''' - Mild nausea is occasionally reported when this substance is consumed in moderate to high dosages, usually during the peak, and either passes soon after the user has vomited or gradually fades by itself as the peak sets in.
*'''[[Effect::Nausea]]'''
*'''[[Effect::Stamina enhancement]]''' - This is generally mild in comparison to traditional [[stimulants]].
*'''[[Effect::Stamina enhancement]]''' - Generally mild in comparison to traditional [[stimulants]].
*'''[[Effect::Seizure]]''' - The possibility of seizures is extrapolated from the seizures that have been reported following the use of [[LSD]]. They are thought to mainly be a risk in those who are genetically predisposed to them, particularly while accompanied by physically taxing conditions such as dehydration, fatigue or undernourishment.
*'''[[Effect::Seizure]]'''{{citation needed}} - The possibility of seizures is extrapolated from the seizures that have been reported following the use of [[LSD]]. They are thought to mainly be a risk in those who are genetically predisposed to them, particularly while accompanied by physically taxing conditions such as dehydration, fatigue or undernourishment.
}}
}}
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|{{effects/cognitive|
|{{effects/cognitive|
In comparison to other psychedelics such as [[psilocin]], [[LSA]] and [[ayahuasca]], MiPLA is significantly more stimulating and fast-paced in terms of the specific style of thought stream which it produces and contains a large number of potential effects associated with both psychedelic tryptamines and phenethylamines. In comparison to [[LSD]], it is often reported to be less [[anxiety]]-provoking and generally more emotionally comfortable and forgiving.
The most prominent of these cognitive effects generally include:
*'''[[Effect::Analysis enhancement]]''' - This effect is consistent in its manifestation and [[outrospection]] dominant.
*'''[[Effect::Analysis enhancement]]''' - This effect is consistent in its manifestation and [[outrospection]] dominant.
*'''[[Effect::Conceptual thinking]]'''
*'''[[Effect::Conceptual thinking]]'''
*'''[[Effect::Cognitive euphoria]]''' - This component is, generally speaking less consistent and pronounced than it is with substances like [[psilocybin]] and [[MDMA]]. The mental euphoria experienced on MiPLA is usually simply due to an enhancement of the user’s current psychological and emotional state coupled with its more regularly occurring effect, [[physical euphoria]].
*'''[[Effect::Cognitive euphoria]]'''
*'''[[Effect::Novelty enhancement]]'''
*'''[[Effect::Novelty enhancement]]'''
*'''[[Effect::Immersion enhancement]]'''
*'''[[Effect::Immersion enhancement]]'''
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{{effects/transpersonal|
{{effects/transpersonal|
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]]'''
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}}
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===Combination effects===
*'''[[Alcohol]]''' - Alcohol's central depressant effects can counteract some of the anxiety and bodily tension produced by MiPLA. However, alcohol can cause [[dehydration]], [[nausea]] and [[physical fatigue]] which can negatively impact the tone of the trip. Users are advised to pace themselves and drink a portion of their usual amount.
*'''[[Benzodiazepines]]''' - Benzodiazepines are highly effective at reducing the intensity of MiPLA's effects through the general suppression of brain activity.
*'''[[Cannabis]]''' - Cannabis strongly intensifies the sensory and cognitive effects of MiPLA. Extreme caution is advised when using this combination as it can significantly increase the chances of a negative psychological reaction like [[anxiety]], [[confusion]] and [[psychosis]]. Users are advised to start off with only a fraction of their usual cannabis dose and take long breaks between hits to avoid over intake.
*'''[[Dissociatives]]''' - MiPLA enhances the cognitive, visual and general hallucinatory effects of dissociatives. Dissociative-induced [[Visual_disconnection#Holes.2C_spaces_and_voids|holes, spaces, and voids]] and [[internal hallucinations]] become more vivid and intense on MiPLA. These effects correspond with an increased risk of [[confusion]], [[delusions]], and [[psychosis]].
*'''[[MDMA]]''' - MiPLA and MDMA are highly synergistic and mutually enhance each other's physical, cognitive, and visual effects. The synergy between these substances is unpredictable so it is advised to start with markedly lower doses than one would take for each individually. There is some evidence that suggests that co-administration of LSD with MDMA increases the neurotoxicity of the latter,<ref>Armstrong, B. D., Paik, E., Chhith, S., Lelievre, V., Waschek, J. A., & Howard, S. G. (2004). Potentiation of (DL)‐3, 4‐methylenedioxymethamphetamine (MDMA)‐induced toxicity by the serotonin 2A receptor partial agonist d‐lysergic acid diethylamide (MiPLA), and the protection of same by the serotonin 2A/2C receptor antagonist MDL 11,939. Neuroscience Research Communications, 35(2), 83-95. https://doi.org/10.1002/nrc.20023</ref><ref>Potentiation of MDMA-induced dopamine release and serotonin neurotoxicity by 5-HT2 receptor agonists | https://indiana.pure.elsevier.com/en/publications/potentiation-of-34-methylenedioxymethamphetamine-induced-dopamine</ref><ref>Ecstasy induces apoptosis via 5-HT(2A)-receptor stimulation in cortical neurons. | https://www.ncbi.nlm.nih.gov/pubmed/17572501</ref> and this may extend to MiPLA.
===Experience reports===
===Experience reports===
There are currently {{#ask:[[Category:MiPLA]][[Category:Experience]] | format=count}} anecdotal reports which describe the effects of this compound within our [[experience index]].
Anecdotal reports which describe the effects of this compound within our [[experience index]] include:
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 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 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.
As with other psychedelic substances, there are relatively few physical side effects that have been reported associated with acute MiPLA exposure. Although no formal studies have been conducted, it is likely that as with [[LSD]] itself, MiPLA is able to be considered non-addictive, with an [[Toxicity::extremely low toxicity]] relative to dose.<ref>Passie, T., Halpern, J. H., Stichtenoth, D. O., Emrich, H. M., & Hintzen, A. (2008). [http://www.maps.org/w3pb/new/2008/2008_Passie_23067_1.pdf The Pharmacology of Lysergic Acid Diethylamide: A Review], 14, 295–314. https://doi.org/10.1111/j.1755-5949.2008.00059.x</ref> It is also likely that as with LSD, there are little to no negative physical, cognitive, psychiatric or other toxic consequences associated with acute MiPLA exposure.
However, as with LSD and psychedelics in general, 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.
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.
===Tolerance and addiction potential===
===Overdose===
Although no formal studies have been conducted, it is not unreasonable to assume that as with LSD itself, MiPLA is [[Addiction potential::not habit-forming]] and that the desire to use it can actually decrease with use.
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.
Tolerance to the effects of MiPLA are built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes 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 back at baseline (in the absence of further consumption). MiPLA presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the use of MiPLA all psychedelics will have a reduced effect.
===Dependence and abuse potential===
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.
Owing to its activity at the 5-HT<sub>2A</sub> receptor, MiPLA presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of MiPLA all psychedelics will have a reduced effect.
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).
===Overdose===
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.
The LD<sub>50</sub> of MiPLA is unknown. Adverse psychological reactions are common especially at higher dosages. Some of these include [[anxiety]], [[delusions]], [[panic attacks]] and more rarely [[seizures]]. Medical attention is usually only needed if suspected of severe psychotic episodes or “fake acid” (such as [[25i-NBOMe]] or [[DOB]]). Administration of [[benzodiazepines]] or [[antipsychotics]] can help to relieve the negative cognitive effects of MiPLA.
===Dangerous interactions===
===Dangerous interactions===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Psychedelics}}
==Legal status==
{{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''': 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}}
*'''[[Tramadol]]''' - Tramadol lowers the seizure threshold<ref>Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., & Abdollahi, M. (2009). Dose-independent occurrence of seizure with tramadol. Journal of medical toxicology, 5(2), 63-67. doi:10.1007/BF03161089</ref> and [[psychedelics]] may act as triggers for seizures, particularly in those who are predisposed to them.{{citation needed}}
==See also==
*'''[[Stimulants]]''' - Stimulants affect many parts of the brain. Combined with psychedelics, stimulation can turn into uncontrollable [[anxiety]], [[Panic attacks|panic]], [[thought loops]] and [[paranoia]]. This interaction may cause elevated risk of psychosis.{{citation needed}}
*'''[https://en.wikipedia.org/wiki/Lithium_(medication) Lithium]''' - Lithium is often used as treatment for bipolar disorder. It may possibly cause elevated risk of seizures and psychosis due to its [[Glutamate|glutaminergic]] and [[GABA|GABAergic]] effects.{{citation needed}}
*[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
==Further reading==
*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.]
*[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.]
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.
DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.
N-Methyl-N-isopropyllysergamide (also known as methylisopropyllysergamide, Lamide and MiPLA) is a lesser-known novel psychedelic substance of the 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".[1][2] 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.[3]
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.
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 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,[4] while all other dialkyl analogues tested (dimethyl, dipropyl, methylethyl etc.) are only around 1/10 as potent as LSD,[5] 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,[6] 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.[7]
Pharmacology
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.
MiPLA is commonly reported to be significantly shorter in its duration and less uncomfortable in both its negative physical side effects and general anxiety.
Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWikicontributors. As a result, they should be viewed with a healthy degree of skepticism.
It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.
Physical effects
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 relaxedness.
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.
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.
Changes in felt bodily form - This effect is often accompanied by a sense of warmth or 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.
Tactile enhancement - Feelings of enhanced tactile sensations are consistently present at moderate levels throughout most MiPLA trips.
Seizure[citation needed] - The possibility of seizures is extrapolated from the seizures that have been reported following the use of LSD. They are thought to mainly be a risk in those who are genetically predisposed to them, particularly while accompanied by physically taxing conditions such as dehydration, fatigue or undernourishment.
Drifting(melting, breathing, morphing and flowing) - In comparison to other psychedelics, this effect can be described as highly detailed yet cartoon-like in appearance. The distortions are slow and smooth in motion and fleeting in their appearance. This is nearly identical in appearance to the visual drifting which occurs under the influence of LSD.
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 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 Level 8B visual geometry over Level 8A.
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
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 heavierdoses. Some of these effects include:
Internal hallucination (autonomous entities; settings, sceneries, and landscapes; perspective hallucinations and scenarios and plots) - This effect is very consistent in dark environments at appropriately high dosages. They can be comprehensively described through their variations as lucid in believability, interactive in style, new experiences in content, autonomous in controllability, geometry-based in style and occasionally of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.
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.
The toxicity and long-term health effects of recreational MiPLA use has not been studied in any scientific context and the exact 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). 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 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.
The LD50 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
Like other serotonergic psychedelics, MiPLA is believed to have a low potential for abuse and dependence. This is owing to its structural and pharmacological similarities with LSD. See 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 MiPLA forms almost immediately after ingestion. After that, it is assumed to take about 5-7 days for the tolerance to be reduced to half and 14 days to be return to baseline (in the absence of further consumption).
Due to its activity at the 5-HT2A receptor, MiPLA produces cross-tolerance with [[Cross-tolerance::all psychedelics]], meaning that after the consumption of MiPLA all psychedelics will have a reduced effect.
Dangerous interactions
Warning:Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).
Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.
[[Wikipedia:Lithium_(medication)|DangerousInteraction::Lithium]] - Lithium is commonly prescribed for the treatment of bipolar disorder. There is a large body of anecdotal evidence that suggests taking it with psychedelics significantly increases the risk of psychosis and seizures. As a result, this combination is strictly discouraged.
"[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Cannabis may have an unexpectedly strong and unpredictable synergy with the effects of MiPLA. Caution is advised with this combination as it can significantly increase the risk of adverse psychological reactions like anxiety, paranoia, panic attacks, and psychosis. Users are advised to start off with only a fraction of their normal cannabis dose and take long breaks between hits to avoid unintentional overdose.
"[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Tramadol is well-documented to lower the seizure threshold[8] and psychedelics may act to trigger seizures in susceptible individuals.[citation needed]
As such, it may contain incomplete or wrong information. You can help by expanding it.
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: 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)[9] as of July 18, 2019.[10] 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.[11]
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.[12]
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]
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
↑Halberstadt, A. L.; Klein, L. M.; Chatha, M.; Valenzuela, L. B.; Stratford, A.; Wallach, Jason; Nichols, D. E.; Brandt, S. D. (2018). "Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA)". Psychopharmacology. 236: 799–808. doi:10.1007/s00213-018-5055-9. eISSN1432-2072. ISSN0033-3158. OCLC2409222.
↑Hofmann, A. (June 1959). "Psychotomimetic drugs; chemical and pharmacological aspects". Acta Physiologica Et Pharmacologica Neerlandica. 8: 240–258. ISSN0001-6748.
↑Nichols, D. E. (2001). "LSD and its lysergamide cousins"(PDF). The Heffter Review of Psychedelic Research. Santa Fe, New Mexico: Heffter Research Institute. 2: 80–87.
↑Talaie, H.; Panahandeh, R.; Fayaznouri, M. R.; Asadi, Z.; Abdollahi, M. (2009). "Dose-independent occurrence of seizure with tramadol". Journal of Medical Toxicology. 5 (2): 63–67. doi:10.1007/BF03161089. ISSN1556-9039.
↑"Anlage NpSG" (in Deutsch). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. Retrieved December 10, 2019.
↑"§ 4 NpSG" (in Deutsch). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. Retrieved December 10, 2019.
