|Summary sheet: MiPLA|
|Common names||MiPLA, Lamide|
|Routes of Administration|
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.
MiPLA was first discovered by Albert Hoffman as a part of the original structure-activity research for LSD. It has recently been researched in greater detail by by a 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". 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.
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, while all other dialkyl analogues tested (dimethyl, dipropyl, methylethyl etc.) are only around 1/10 as potent as LSD, 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, 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.
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.
One study found MiPLA to fully substitute for LSD in rats, with about half the potency of the training drug.
|This subjective effects section is a stub.|
As such, it is still in progress and may contain incomplete or wrong information.
You can help by expanding or correcting it.
Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), a research literature based on collected anecdotal reports and the personal experiences of PsychonautWiki contributors. As a result, they should be regarded with a healthy degree of skepticism. It is worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce a full spectrum of effects. Likewise, adverse effects become much more likely with higher doses and may include addiction, serious injury, or death ☠.
- 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.
- Temperature regulation suppression
- Increased bodily temperature
- Stamina enhancement - Generally mild in comparison to traditional stimulants.
- Bodily control enhancement
- Appetite suppression
- Difficulty urinating
- Increased blood pressure
- Increased heart rate
- Increased perspiration
- Muscle contractions
- Muscle spasms
- Increased libido
- Excessive yawning - This effect is significantly less pronounced than it is with psilocybin and its related compounds, the four-position substituted tryptamines.
- Pupil dilation
- Increased salivation
- 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.
- 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.
- After images
- Colour shifting
- Depth perception distortions
- Scenery slicing
- Symmetrical texture repetition
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.
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 heavier doses. 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.
- External hallucination (autonomous entities; settings, sceneries, and landscapes; perspective hallucinations and scenarios and plots)
- Analysis enhancement - This effect is consistent in its manifestation and outrospection dominant.
- Conceptual thinking
- Cognitive euphoria
- Novelty enhancement
- Immersion enhancement
- Focus enhancement - This effect is experienced exclusively on low or threshold dosages and feels less forced than it does with stimulants.
- Immersion enhancement
- Motivation enhancement
- Emotion enhancement
- Increased music appreciation
- Increased sense of humor
- Memory suppression
- Time distortion
- Déjà vu
- Thought acceleration
- Thought loops
Anecdotal reports which describe the effects of this compound within our experience index include:
Additional experience reports can be found here:
Toxicity and harm potential
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.
It is strongly recommended that one uses harm reduction practices when using this substance.
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 all psychedelics, meaning that after the consumption of MiPLA all psychedelics will have a reduced effect.
Although many psychoactive substances are reasonably safe to use on their own, they can suddenly become dangerous or even life-threatening when combined with other substances. The following list includes some known dangerous combinations (although it is not guaranteed to include all of them). Independent research (e.g. Google, DuckDuckGo) should always be conducted to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.
- 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.
- Cannabis - 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.
- Stimulants - Stimulants like amphetamine, cocaine or methylphenidate affect many parts of the brain and alter dopaminergic function. This combination can increase the risk of anxiety, paranoia, panic attacks, and thought loops. This interaction may also result in an elevated risk of mania and psychosis.
- Tramadol - Tramadol is well-documented to lower the seizure threshold and psychedelics may act to trigger seizures in susceptible individuals.
This legality section is a stub.
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.
- Germany: MiPLA is controlled under the NpSG (New Psychoactive Substances Act) as of July 18, 2019. 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.
- 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.
- 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.
- 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
- Nichols, D. E. (2001). LSD and its lysergamide cousins. The Heffter Review of Psychedelic Research. Santa Fe, New Mexico: Heffter Research Institute, 80-87.
- Alexander Shulgin. Pharmacology Notes IX (The Shulgin Lab Books) (PDF). Erowid.
- Alexander Shulgin. Pharmacology Notes C (The Shulgin Lab Books) (PDF). Erowid.
- 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. eISSN 1432-2072. ISSN 0033-3158. OCLC 2409222.
- 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. PMID 8208787.
- Hofmann A (June 1959). "Psychotomimetic drugs; chemical and pharmacological aspects" (PDF). Acta Physiologica et Pharmacologica Neerlandica. 8: 240–58. PMID 13852489.
- US patent 2997470, Pioch RP, "Lysergic Acid Amides", published 1956-03-05, issued 1961-08-22
- 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.
- 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. ISSN 1556-9039.
- "Anlage NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. Retrieved December 10, 2019.
- "Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes" (PDF). Bundesgesetzblatt Jahrgang 2019 Teil I Nr. 27 (in German). Bundesanzeiger Verlag. July 17, 2019. pp. 1083–1094. Retrieved January 1, 2020.
- "§ 4 NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. Retrieved December 10, 2019.
- "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020.