|Summary sheet: 4-HO-MiPT|
|Molecular structure of 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 synthetic psychedelic substance of the tryptamine chemical class that produces effects similar to psilocin (the active component in psilocybin mushrooms) 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.
Today, 4-HO-MiPT is either used recreationally or as an entheogenic substance and is typically distributed as a grey-area research chemical by online vendors. After some time spent exclusively on the online market, there is evidence that suggests it is becoming increasingly popular on the streets, where prefilled capsules containing it have been found being sold as "shroom pills".
- 1 History and culture
- 2 Chemistry
- 3 Pharmacology
- 4 Subjective effects
- 5 Toxicity and harm potential
- 6 Legality
- 7 See also
- 8 External links
- 9 References
History and culture
This History and Culture section is a stub.
As such, 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.
The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects should be taken with a grain of salt and will rarely (if ever) occur all at once, but heavier doses will increase the chances and are more likely to induce a full range of effects. Likewise, adverse effects become much more likely on higher doses and may include serious injury or death.
- 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
- Sedation and Stimulation - In terms of its effects on the physical energy levels of the user, 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.
- 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 hallucinations
- Pupil dilation
- 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 very rare effect but is thought to be able to occur in 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 is present throughout this trip 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 hallucinations (autonomous entities; settings, sceneries, and landscapes; alterations in perspective 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.
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.
- Increased libido
- Immersion enhancement
- Novelty enhancement
- 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:
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 / A care free psychedelic getaway
Additional experience reports can be found here:
Toxicity and harm potential
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 people within the community who 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.
This legality section is a stub.
As such, it may contain incomplete or wrong information. You can help by expanding it.
- 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.
- 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.
- Shulgin, Alexander. "Pharmacology Lab Notes #2". Lafayette, CA. (1976-1980). p312 (Erowid.org) | https://erowid.org/library/books_online/shulgin_labbooks/shulgin_labbook2_searchable.pdf
- http://isomerdesign.com/PiHKAL/read.php?domain=tk&id=22 | 4-HO-MiPT (TiHKAL / Isomer Design)
- Repke, DB; Ferguson, WJ; Bates, DK. Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols. J. Heterocycl. Chem., 1 Jan 1981, 18 (1), 175–179. 368 kB. http://dx.doi.org/10.1002/jhet.5570180131 | http://onlinelibrary.wiley.com/doi/10.1002/jhet.5570180131/abstract
- Repke, DB; Grotjahn, DB; Shulgin, AT. Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents. J. Med. Chem., 1 Jan 1985, 28 (7), 892–896. 711 kB. http://dx.doi.org/10.1021/jm00145a007 | http://pubs.acs.org/doi/abs/10.1021/jm00145a007
- Misuse of Drugs Act 1971 (Legislation.gov.uk) |http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I#reference-M_F_c7632653-ddad-4420-f307-e3da1e36d30e