|Summary sheet: 4-HO-MiPT|
|Common names||4-HO-MiPT, Miprocin|
|Systematic name||3-(2-[Isopropyl (methyl) amino]ethyl)-1H-indol-4-ol|
|Routes of Administration|
4-Hydroxy-N-methyl-N-isopropyltryptamine (also known as 4-HO-MiPT, and Miprocin) is a novel psychedelic substance of the tryptamine class that produces psilocybin-like psychedelic effects when administered. It is part of a series of psychedelic substituted tryptamines such as 4-AcO-DMT, 4-HO-MET, 4-HO-DiPT that are considered to produce variations of the core psychedelic effects typified by psilocin.
This substance is relatively uncommon and has only a short history of human use. Alexander Shulgin evaluated its activity in humans in 1979, describing a trial of 12mg as a richly insightful and highly erotic experience. A description of 4-HO-MiPT is included in Shulgin's 1997 book TiHKAL. Shulgin's trials and other anecdotal reports suggest that 4-HO-MiPT is similar in activity to psilocin, the active component in psilocybin mushrooms.
Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-HO-MiPT in humans. As with psilocin, there have been no reported deaths from 4-HO-MiPT use despite the existence of reports of people taking doses which far exceeds the active dose. This suggests that it is well-tolerated physiologically.
- 1 History and culture
- 2 Chemistry
- 3 Pharmacology
- 4 Subjective effects
- 5 Toxicity and harm potential
- 6 Legal status
- 7 See also
- 8 External links
- 9 References
History and culture
This History and culture section is a stub.
As a result, it may contain incomplete or wrong information. You can help by expanding it.
The first synthesis of 4-HO-MiPT was published in 1981 by a team of chemists led by David Repke. Repke and Shulgin later collaborated on a paper evaluating the effects of different oxygen substituents on the MiPT structure, describing 4-HO-MiPT as the most interesting of the series and the only one to possess classical hallucinogen effects.
4-HO-MiPT or 4-hydroxy-N-methyl-N-isopropyltryptamine is a synthetic indole alkaloid molecule of the tryptamine class. Tryptamines share a core structure comprised of a bicylic indole heterocycle attached at R3 to an amino group via an ethyl side chain. 4-HO-MiPT is substituted at R4 of its indole heterocycle with a hydroxyl (HO) functional group OH-. It also contains a methyl group and an isopropyl chain bound to the terminal amine RN of its tryptamine backbone (MiPT). 4-HO-MiPT is the N-substituted isopropyl homologue of 4-HO-DMT (Psilocin).
4-HO-MiPT's psychedelic effects are believed to come from its efficacy at the 5-HT2A receptor as a partial agonist. However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.
Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), a literature which relies on collected anecdotal reports and the personal experiences of PsychonautWiki contributors. As a result, they should be taken with a healthy amount of skepticism. It is worth noting that these effects will not necessarily occur in a consistent or reliable manner, although higher doses (common+) are more likely to induce the full spectrum of reported effects. Likewise, adverse effects become much more likely with higher doses and may include serious injury or death.
- Sedation & Stimulation - 4-HO-MiPT is considered have the paradoxical property of both being relaxing, stoning and mildly sedating with a marked sense of physical stimulation that distinguishes it from related substances like psilocybin mushrooms or 4-AcO-DMT.
- Spontaneous physical sensations - The "body high" of 4-HO-MiPT can be described as a pleasurable, warm, soft, and all-encompassing tingling sensation. This maintains a consistent presence that steadily rises following the onset and hits its limit once the peak has been reached.
- Changes in felt bodily form - This effect is often accompanied by a sense of warmth or psychophysical unity and usually occurs around or directly after the peak of the experience. Users can feel as if they are physically part of or conjoined with other objects in a seamless continuity. This is usually reported as feeling comfortable, tranquil and mindful, though it can also manifest in the form of bodily tension.
- Changes in felt gravity
- Nausea - This effect can be greatly lessened or even completely avoided if the individual has an empty stomach prior to ingestion. It is sometimes recommended that one either refrain from eating for approximately 6 to 8 hours before-hand, or to eat a light meal 3 to 4 hours before if the user is feeling physically fatigued and undernourished. The nausea produced by 4-HO-MiPT is generally considered to be much less prominent than it is with psilocybin mushrooms, perhaps owing to the fact that there is no fungal-matter the body has to digest when the isolated synthetic form is consumed.
- Temperature regulation suppression - 4-HO-MiPT can cause fluctuates in the user's internal sense of temperature, which can manifest as sudden bouts of uncomfortable coldness or warmth, which is why a climate-controllable environment is strongly recommended in terms of a proper setting for a trip.
- Muscle contractions - The muscle contractions that can occasionally be produced by 4-HO-MiPT tend to be transient and benign feeling in nature, compared to many other tryptamines, phenethylamines and lysergamides.
- Olfactory hallucination
- Frequent urination
- Pupil dilation
- Increased salivation
- Excessive yawning - This effect seems to be uniquely pronounced among psilocin and related tryptamines. It can occur to a lesser degree on LSD and very rarely on psychedelic phenethylamines like mescaline. It typically occurs in conjunction with watery eyes.
- Watery eyes
- Teeth grinding - This component is considerably less intense when compared with that of substances like MDMA when it does happen to occur, but happens more readily than with related substances like psilocin or psilocybin, perhaps owing to the greater degree of stimulation it produces.
- Seizure - This is a likely a rare effect but may occur for those who are predisposed to them, especially while in physically taxing conditions such as being dehydrated, fatigued, undernourished, or overheated. However it should be noted that there are no documented cases of seizures occurring with this compound.
- Drifting (melting, breathing, morphing and flowing)
- Colour shifting
- Depth perception distortions
- Perspective distortions
- Symmetrical texture repetition
- After images
- Brightness alteration
The visual geometry that may be experienced can be described as more similar in appearance to that of psilocin, ayahuasca and 2C-E than LSD or 2C-B. It can be comprehensively described through its variations as intricate in complexity, abstract in form, organic in style, structured in organization, brightly lit and multicoloured in scheme, glossy in shading, soft in edges, large in size, slow in speed, smooth in motion, rounded in corners, non-immersive in depth and consistent in intensity. The visuals have a very "natural" feel to them and at higher dosages are significantly more likely to result in states of level 8B visual geometry over level 8A.
4-HO-MiPT and its various other forms produce a full range of high level hallucinatory states in a fashion that is more consistent and reproducible than that of many other commonly used psychedelics. These effects generally 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 almost exclusively 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) - These are more common within dark environments and 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 almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.
The cognitive effects of 4-HO-MiPT are described by many as extremely relaxing, profound and stoning in style when compared to other commonly used psychedelics such as LSD or 2C-B which tend to be energetic and stimulating. It contains a large number of typical and unique psychedelic cognitive effects.
The most prominent of these typical effects generally include:
- Analysis enhancement
- Conceptual thinking
- Autonomous voice communication
- Déjà vu
- Emotion enhancement
- Enhancement and suppression cycles - This can be described as constant waves of extremely stimulated and profound thinking which are spontaneously surpassed in a cyclic fashion by waves of general thought suppression and mental intoxication. These two states seem to switch between each other in a consistent loop once every 20 - 60 minutes.
- Cognitive euphoria
- Increased libido
- Immersion enhancement
- Novelty enhancement
- Creativity enhancement
- Feelings of impending doom
- Increased sense of humor
- Increased music appreciation
- Memory suppression
- Personal bias suppression
- Thought connectivity
- Thought loops
- Time distortion
- Synaesthesia - In its fullest manifestation, this is a very rare and non-reproducible effect. Increasing the dosage can increase the likelihood of this occurring, but seems to only be a prominent part of the experience among those who are already predisposed to synaesthetic states.
- It should be noted that these effects are reported to occur less reliably and impactfully than with the closely related psilocin or psilocybin, and generally require heavier doses to potentially induce. They are listed below as follows:
- Cannabis - Cannabis majorly amplifies the sensory and cognitive effects of 4-HO-MiPT. This should be used with extreme caution, especially if one is not experienced with psychedelics. This interaction can also amplify the anxiety, confusion and delusion producing aspects of cannabis significantly. Those who choose to use this combination are advised to start off with only a fraction of their usual cannabis dose, and slow down the pace of their normal intake considerably.
- Dissociatives - Dissociatives can enhance the geometry, euphoria, dissociation and hallucinatory effects of 4-HO-MiPT. Dissociative-induced holes, spaces, and voids while under the influence of psilocybin can result in significantly more vivid visuals than dissociatives alone, along with more intense internal hallucinations, confusion, nausea, delusions and chances of a psychotic reaction.
- Benzodiazepines - Depending on the dosage, benzodiazepines can slightly to completely reduce the intensity of the cognitive, physical and visual effects of a miprocin trip. They can be very efficient at largely stopping or mitigating a bad trip at the cost of amnesia and reduced trip intensity. Caution is advised when acquiring them for this purpose, however, due to the very high addiction potential that benzodiazepines possess.
- Psychedelics - When used in combination with other psychedelics, the physical, cognitive and visual effects of each substance intensify and synergize strongly with each other. The synergy between those substances is unpredictable, and for this reason, is generally not advised. If choosing to combine psychedelics, it is recommended to start with lower dosages than one would take for either substance individually.
There are currently anecdotal reports which describe the effects of this compound within our experience index.
- Experience:30mg 4-HO-MiPT - Positively groovy
- Experience:4-HO-MiPT (~10mg) - Very Promising Material
- Experience:4-HO-MiPT / A care free psychedelic getaway
- Experience:4-HO-MiPT/ Treating lifelong insomnia
Additional experience reports can be found here:
Toxicity and harm potential
This toxicity and harm potential section is a stub.
As such, it may contain incomplete or even dangerously wrong information. You can help by expanding or correcting it.
The toxicity and long-term health effects of recreational 4-HO-MiPT use do not seem to have been studied in any scientific context and the exact toxic dose is unknown. This is because 4-HO-MiPT is a research chemical with very little history of human usage.
Anecdotal evidence from those have tried 4-HO-MiPT suggests that there are no negative health effects attributed to simply trying the drug 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.
It is strongly recommended that one use harm reduction practices when using this substance.
Tolerance and addiction potential
4-HO-MiPT is not habit-forming and the desire to use it can actually decrease with use. It is most often self-regulating.
Tolerance to the effects of 4-HO-MiPT are built almost immediately after ingestion. After that, it takes about 3 days for the tolerance to be reduced to half and 7 days to be back at baseline (in the absence of further consumption). 4-HO-MiPT presents cross-tolerance with all psychedelics, meaning that after the consumption of 4-HO-MiPT all psychedelics will have a reduced effect.
Although many psychoactive substances are reasonably safe to use on their own, they can quickly become dangerous or even life-threatening when combined with other substances. The list below includes some known dangerous combinations (although it cannot be 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 interactions listed have been sourced from TripSit.
- Lithium - Lithium is commonly prescribed in 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 has an unexpectedly strong and unpredictable synergy with the effects of psychedelics. 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 over intake.
- Stimulants (Amphetamine, cocaine, methylphenidate, ...) - Stimulants affect many parts of the brain and alter dopaminergic function. Combined with psychedelics, stimulation can turn into severe anxiety, panic, thought loops, and paranoia. This interaction may result in an elevated risk of mania and psychosis.
- Tramadol - Tramadol lowers the seizure threshold and psychedelics may act as triggers for 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.
- Brazil: As of August 21, 2018, 4-HO-MiPT has been added to Portaria SVS/MS nº 344. Possession, distribution and use of this substance is now considered illegal.
- Germany: 4-HO-MiPT 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, placing it on the market and trading is punishable. Possession is illegal but not punishable. The legislator considers it possible that orders of 4-HO-MiPT are punishable as an incitement to place it on the market.
- Poland: 4-HO-MiPT is a NPS class drug in Poland, making it illegal to possess or distribute.
- Sweden: 4-HO-MiPT is classified as a health hazard under the act Lagen om förbud mot vissa hälsofarliga varor (translated as the "Act on the Prohibition of Certain Goods Dangerous to Health") as of November 1, 2005, making it illegal to sell or possess.
- Switzerland: 4-HO-MiPT is a controlled substance specifically named under Verzeichnis E.
- United Kingdom: 4-HO-MiPT is a Class A drug in the United Kingdom as a result of the tryptamine catch-all clause.
- United States: 4-HO-MiPT is unscheduled in the United States. It may be considered an analogue of psilocin (4-HO-DMT) which is a Schedule I drug under the Controlled Substances Act. As such, the sale for human consumption or the use for illicit non-medical or industrial intents and purposes could be prosecuted as crimes under the Federal Analogue Act.
- Alexander Shulgin (1980). Pharmacology Notes II (The Shulgin Lab Books) (PDF). Lafayette, CA: Erowid. p. 312.
- Shulgin, Alexander; Shulgin, Ann (1997). "#22. 4-HO-MiPT". TiHKAL: The Continuation. United States: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
- Repke, D. B.; Ferguson, W. J.; Bates, D. K. (1981). "Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols". Journal of Heterocyclic Chemistry. 18 (1): 175–179. doi:10.1002/jhet.5570180131. ISSN 0022-152X. OCLC 1783072.
- Repke, D. B.; Grotjahn, D. B.; Shulgin, A. T. (1985). "Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents". Journal of Medicinal Chemistry. 28 (7): 892–896. doi:10.1021/jm00145a007. eISSN 1520-4804. ISSN 0022-2623. OCLC 39480771. PMID 4009612.
- 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.
- "Lista de substâncias sujeitas a controle especial no Brasil" (in Portuguese). Agência Nacional de Vigilância Sanitária (ANVISA) [Brazilian Health Regulatory Agency]. Retrieved August 27, 2020.
- "Anlage NpSG" (in German). Bundesamt für Justiz [Federal Office of Justice]. 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. ISSN 0341-1095.
- "§ 4 NpSG" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019.
- "§ 3 NpSG" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019.
- "Gesetzentwurf der Bundesregierung: Entwurf eines Gesetzes zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe" (PDF) (in German). Deutscher Bundestag. May 30, 2016. p. 20. Drucksache 18/8579.
- "Rozporządzenie Ministra zdrowia z dnia 21 sierpnia 2019 r. zmieniające rozporządzenie w sprawie wykazu substancji psychotropowych, środków odurzających oraz nowych substancji psychoaktywnych" (PDF) (in Polish). Sejm Rzeczypospolitej Polskiej [Sejm of the Republic of Poland]. August 21, 2019.
- "Svensk författningssamling Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor" (PDF) (in Swedish) (published October 18, 2005). October 6, 2005. SFS 2005:733.
- "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020.
- "Schedule 2: Part I: Class A Drugs". "Misuse of Drugs Act 1971". UK Government. Retrieved August 20, 2020.