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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

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

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.

    Data is constantly updated so please check back later to see if there is any more available information on this substance.