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4-HO-MiPT Also known as:
- 1H-Indol-4-ol, 3-[2
-[methyl(1-methylet[ACD/Index Name] hyl)amino]ethyl]-
hyl)amino]ethyl}-1H[German][ACD/IUPAC Name] -indol-4-ol
hyl)amino]ethyl}-1H[ACD/IUPAC Name] -indol-4-ol
hyl)amino]éthyl}-1H[French][ACD/IUPAC Name] -indol-4-ol
-2-yl)amine)ethyl)-[ACD/IUPAC Name] 1 H-indol-4-ol
ETHYLETHYL)AMINO]ET HYL]-?1H-?INDOL-?4- ?OL
-2-yl)amino]ethyl]- 1H-indol-4-ol fumar ate
- 4-hydroxy MiPT
yl-N-methyltryptami ne fumarate
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.
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.
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.
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).
|Avg. Mass||232.3214 Da|
|Monoisotopic Mass||232.157562 Da|
|4-HO-MiPT Duration Data|
- 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
- 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.
- List of controlled substances: Portaria SVS/MS nº 344 (Portuguese) | http://portal.anvisa.gov.br/lista-de-substancias-sujeitas-a-controle-especial
- "Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes" (PDF) (in German). Bundesanzeiger Verlag. Retrieved December 10, 2019.
- "Anlage NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
- "§ 4 NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
- "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).
- 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
- 1717 CheMall HE050097
- 1717 CheMall HE103448
- A&J Pharmtech AJ-83383
- ABI Chemicals AC2A05W8Q
- AK Scientific 9657AE
- AKos AKOS022182928
- Ark Pharm, Inc. AK-77115
- Aurora Fine Chemicals A06.998.030
- Aurora Fine Chemicals K05.595.152
- BGS International BG04556304
- Biosynth Carbosynth FH24436
- BLDpharm BD221974
- Cayman Chemical 11552
- Cayman Chemical 11552.0
- Cayman Chemical CM246846
- ChEMBL CHEMBL171419
- Chembo Pharma KB-72570
- Chemenu CM246846
- ChemIDplus 77872436
- EPA DSSTox DTXCID50150983
- Erowid 4-HO-MiPT
- FDA UNII - NLM 4GAJ9OJ8YZ
- Finetech Industry FT-0669668
- Journal of Heterocyclic Chemistry 19810175_15A
- LabNetwork LN01293210
- MuseChem R012879
- MuseChem R012880
- PubChem 10082683
- Syntharise Chemical SRISEC020
- Thomson Pharma 00533248
- VulcanChem VC059921
- VulcanChem VC059923
- Wikidata Q162772
- Wikipedia 4-HO-MiPT
Information made possible with:
- PsychonautWiki is a community-driven online encyclopedia that aims to document the field of psychonautics in a comprehensive, scientifically-grounded manner.
- Erowid is a non-profit educational & harm-reduction resource with 60 thousand pages of online information about psychoactive drugs
- PubChem National Center for Bio Informatics
- Chemspider is a free chemical structure database providing fast access to over 34 million structures, properties and associated information.
Additional APIs were used to construct this information. Thanks to ChemSpider, NCBI, PubChem etc.
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