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Description

4-HO-MiPT Also known as:

  • 1H-Indol-4-ol, 3-[2-[methyl(1-methylethyl)amino]ethyl]-[ACD/Index Name]
  • 3-{2-[Isopropyl(methyl)amino]ethyl}-1H-indol-4-ol[German][ACD/IUPAC Name]
  • 3-{2-[Isopropyl(methyl)amino]ethyl}-1H-indol-4-ol[ACD/IUPAC Name]
  • 3-{2-[Isopropyl(méthyl)amino]éthyl}-1H-indol-4-ol[French][ACD/IUPAC Name]
  • 3-{2-[methyl(propan-2-yl)amino]ethyl}-1H-indol-4-ol
  • 4-HO-MiPT
  • 4-hydroxy-N,N-methyl-isopropyltryptamine
  • 4-HYDROXY-N-METHYL-N-ISOPROPYLTRYPTAMINE
  • 1-(2,3-Dimethyl-indol-1-yl)-3-methylamino-propan-2-ol
  • 3-(2-(Isopropyl(methyl)amino)ethyl)-1H-indol-4-ol
  • 3-(2-(methyl(propan-2-yl)amine)ethyl)-1 H-indol-4-ol[ACD/IUPAC Name]
  • 3-?[2-?[METHYL(1-?METHYLETHYL)AMINO]ETHYL]-?1H-?INDOL-?4-?OL
  • 3-[2-(Isopropyl-methyl-amino)-ethyl]-1H-indol-4-ol
  • 3-[2-[Methyl(1-methylethyl)amino]ethyl]-
  • 3-[2-[methyl(1-methylethyl)amino]ethyl]-1H-indol-4-ol
  • 3-[2-[methyl(propan-2-yl)amino]ethyl]-1H-indol-4-ol
  • 3-[2-[methyl(propan-2-yl)amino]ethyl]-1H-indol-4-ol fumarate
  • 4-hydroxy MiPT
  • 4-HYDROXY-N-ISOPROPYL-N-METHYLTRYPTAMINE
  • 4-hydroxy-N-isopropyl-N-methyltryptamine fumarate
  • '77872-43-6

A reasonably popular tryptamine deriviative and Psilocin analogue, first synthesised by Alexander Shulgin. It has been reported as having comparable effects to psychedelic mushrooms, though with a shorter duration.

Summary

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.

History

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.

Chemistry

4-HO-MiPT

4-HO-MiPT

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).

Common Name4-HYDROXY-N-METHYL-N-ISOPROPYLTRYPTAMINE
Systematic name4-HYDROXY-N-METHYL-N-ISOPROPYLTRYPTAMINE
FormulaC_{14}H_{20}N_{2}O
SMILESCC(C)N(C)CCc1c[nH]c2c1c(ccc2)O
Std. InChiInChI=1S/C14H20N2O/c1-10(2)16(3)8-7-11-9-15-12-5-4-6-13(17)14(11)12/h4-6,9-10,15,17H,7-8H2,1-3H3
Std. InChiKeyRXKGHZCQFXXWFQ-UHFFFAOYSA-N
Avg. Mass232.3214 Da
Molecular Weight232.3214
Monoisotopic Mass232.157562 Da
Nominal Mass232
ChemSpider ID8258221

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Dose Chart

Oral
Threshold5-10mg
Light10-15mg
Common15-20mg
Strong20-30mg
Heavy40mg+

Duration Chart

4-HO-MiPT Duration Data
Onset20-90 minutes
Duration3-6 hours
After-effects1-8 hours

Auditory Effects

Psychological Effects

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:

Pharmacological Effects

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.

Physical Effects

  • 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.

Sensory Effects

  • 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.

Subjective Effects

Disclaimer: The effects listed below are cited from the Subjective Effect Index (SEI), which relies on assorted 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 on higher doses and may include serious injury or death.

Visual Effects

Enhancements

Distortions

Geometry

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.

Hallucinatory states

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:

Legal Status

  • 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 and trading is punishable. Possession is illegal but not penalized.
  • 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.
  • 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.
  • Sources

    References

    1. 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
    2. http://isomerdesign.com/PiHKAL/read.php?domain=tk&id=22 | 4-HO-MiPT (TiHKAL / Isomer Design)
    3. 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
    4. 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
    5. http://isomerdesign.com/PiHKAL/read.php?domain=tk&id=22
    6. 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. :10.1007/BF03161089.  1556-9039.
    7. List of controlled substances: Portaria SVS/MS nº 344 (Portuguese) | http://portal.anvisa.gov.br/lista-de-substancias-sujeitas-a-controle-especial
    8. "Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes" (PDF) (in German). Bundesanzeiger Verlag. Retrieved December 10, 2019.
    9. "Anlage NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
    10. "§ 4 NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
    11. "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).
    12. http://www.notisum.se/rnp/sls/sfs/20050733.pdf
    13. 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

    Information made possible with:

    1. PsychonautWiki is a community-driven online encyclopedia that aims to document the field of psychonautics in a comprehensive, scientifically-grounded manner.
    2. Erowid is a non-profit educational & harm-reduction resource with 60 thousand pages of online information about psychoactive drugs
    3. PubChem National Center for Bio Informatics
    4. Chemspider is a free chemical structure database providing fast access to over 34 million structures, properties and associated information.
    5. Wikipedia

    Additional APIs were used to construct this information. Thanks to ChemSpider, NCBI, PubChem etc.

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