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