4-HO-MiPT

Last updated

4-HO-MiPT
4-HO-MiPT.svg
4-HO-MiPT-3d-sticks.png
Clinical data
Other names4-OH-MiPT; 4-Hydroxy-N-methyl-N-isopropyltryptamine; Miprocin
Routes of
administration 		Oral [1]
Drug class Non-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • BR: Class F2 (Prohibited psychotropics) [2]
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US:Unscheduled
Pharmacokinetic data
Onset of action 10–20 minutes [1] [3]
Duration of action 4–6 hours [1]
Identifiers
  • 3-{2-[methyl(propan-2-yl)amino]ethyl}-1H-indol-4-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C14H20N2O
Molar mass 232.327 g·mol−1
3D model (JSmol)
Melting point 123 to 125 °C (253 to 257 °F)
  • CN(C(C)C)CCC2=CNC1=CC=CC(O)=C12
  • InChI=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 Yes check.svgY
  • Key:RXKGHZCQFXXWFQ-UHFFFAOYSA-N Yes check.svgY
   (verify)

4-HO-MiPT, also known as 4-hydroxy-N-methyl-N-isopropyltryptamine or as miprocin, is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). [1] [3] [4] It appears to be similar to psilocin in terms of onset, duration, and effects, but may be around twice as potent in comparison and hence is used at lower doses. [1] [3] [4] The drug is taken orally. [1] [3] [4]

Contents

The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor among others. [3] [5] It is closely related structurally to MiPT, 4-HO-DiPT, and psilocin (4-HO-DMT). [1]

4-HO-MiPT was first described in the literature by David Repke and colleagues in 1981. [6] [7] [3] [8] Its effects in humans were subsequently described by Repke and Alexander Shulgin in 1985 [4] and 1997. [1] [3]

Use and effects

According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) and other publications, 4-HO-MiPT has a dose range of 12 to 25 mg, an onset of action of 10 to 20 minutes, peak effects occurring after 40 to 45 minutes, and a duration of 4 to 6 hours. [1] [3] [4] [9] It has an estimated typical dose of 18.5 mg. [9] The drug has been described as at least twice as potent as psilocin (4-HO-DMT) at comparable doses, with 20 mg 4-HO-MiPT being subjectively stronger than 50 mg psilocin in one individual. [1] [3] However, in another person, the effects of 4-AcO-MiPT (a prodrug of 4-HO-MiPT) at a dose of 30 mg were described as considerably more modest. [1]

The effects of 4-HO-MiPT have been reported to include closed-eye visuals, vivid mental imagery, few psychedelic visuals, wave-form visuals, intense color alterations, multiple images of the same object with intense colored halos, illusory alteration of the size and distance of objects, heightening of senses, intensification and enhanced discrimination of sounds, increased sense of bodily processes such as blood flow and muscles, synesthesia of sound and sight, intense alteration in sense of time and distance, feelings of drifting in and out of the body, flight of ideas, philosophical thinking, euphoria, enhanced music appreciation, enhanced eroticism, and facilitation of love, insights, fantasy, introspection, and discovery. [1] [3] [4] Other effects included intoxication, sedation, feeling drunk, relaxation, some initial anxiety, easy to difficult verbal communication, easy distraction and annoyance by external stimuli such as light, appetite loss, and insomnia. [1] [3] [4] Physical effects of the drug have been reported to include twitching, muscle sensations, motor incoordination, slight lightheadedness, mild vertigo, jaw clenching, and body tremors. [1] [4]

Interactions

Pharmacology

Pharmacodynamics

4-HO-MiPT activities
TargetAffinity (Ki, nM)
5-HT2A 5.2 (EC50 Tooltip half-maximal effective concentration)
100% (Emax Tooltip maximal efficacy)
5-HT2B 10.3 (EC50)
49% (Emax)
5-HT2C 166 (EC50)
76% (Emax)
Notes: The smaller the value, the more avidly 4-HO-MiPT interacts with the site. Sources: [5]

4-HO-MiPT acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. [3] [5] It was a potent full agonist of the serotonin 5-HT2A receptor, a moderate-efficacy partial agonist of the serotonin 5-HT2B receptor, and a high-efficacy partial agonist of the serotonin 5-HT2C receptor. [5] However, 4-HO-MiPT showed much greater and about 30-fold selectivity for activation of the serotonin 5-HT2A receptor relative to the serotonin 5-HT2C receptor. [5] Other serotonin receptors, such as the serotonin 5-HT1A receptor, were not assessed. [5] The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. [9] [5]

Chemistry

4-HO-MiPT, also known as , is a synthetic derivative of the substituted tryptamine and 4-hydroxytryptamine families. [1] It is the 4-hydroxy analogue of N-methyl-N-isopropyltryptamine (MiPT) and the N-isopropyl homologue of psilocin (4-HO-DMT). [1]

Properties

4-HO-MiPT appears to be a relatively unstable compound, discoloring quickly if not kept in an inert atmosphere and in a freezer. [1] [3] The drug and its prodrug analogue 4-AcO-MiPT have been used as the free base, hydrochloride salt, and fumarate salt. [1] [6] [7]

Crystal structure

In August 2019, Chadeayne et al. solved the crystal structure of 4-HO-MiPT fumarate. [3] [6] Its systematic name is [2-(4-hydroxy-1H-indol-3-yl)ethyl](methyl)propan-2-ylazanium 3-carboxyprop-2-enoate monohydrate. [6] The salt consists of a protonated tryptammonium cation and a 3-carboxyacrylate (hydrogen fumarate) anion in the asymmetric unit along with a water molecule of crystallization. [6]

Synthesis

The chemical synthesis of 4-HO-MiPT has been described. [1] [8]

History

4-HO-MiPT was first described in the scientific literature by David Repke and colleagues in 1981. [6] [7] [3] [8] Its effects in humans were described by Repke and Alexander Shulgin and colleagues in 1985. [6] [7] [4] The pharmacology of 4-HO-MiPT at serotonin receptors was described by Dennis McKenna and Repke and colleagues in 1990. [6] [10] The effects of 4-HO-MiPT in humans were described in greater detail by Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved). [1] [3]

Society and culture

Russia

4-HO-MiPT is in Schedule 1 in Russia as an analog of 4-hydroxytryptamine.[ citation needed ]

Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 4-HO-MiPT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of 1 November 2005, in regulation SFS 2005:733 listed as "4-hydroxi-N,N-metylisopropyltryptamin (4-HO-MIPT)", making it illegal to sell or possess. [11]

United Kingdom

The substance could also be considered illegal in the United Kingdom under the Misuse of Drugs Act 1971.[ citation needed ]

United States

4-HO-MiPT is an unscheduled drug in the United States. However, it is arguably an analog of psilocin, which could lead to prosecution under the Federal Analog Act.[ citation needed ]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252. http://www.erowid.org/library/books_online/tihkal/tihkal22.shtml
  2. ↑ Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
  3. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 Bauer BE (6 January 2020). "4-HO-MiPT". Psychedelic Science Review. Retrieved 9 October 2025.
  4. 1 2 3 4 5 6 7 8 9 Repke DB, Grotjahn DB, Shulgin AT (July 1985). "Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents". J Med Chem. 28 (7): 892–896. doi:10.1021/jm00145a007. PMID   4009612.
  5. 1 2 3 4 5 6 7 Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, et al. (April 2021). "Investigation of the Structure-Activity Relationships of Psilocybin Analogues" (PDF). ACS Pharmacology & Translational Science. 4 (2): 533–542. doi:10.1021/acsptsci.0c00176. PMC   8033608 . PMID   33860183.
  6. 1 2 3 4 5 6 7 8 Chadeayne AR, Pham DN, Golen JA, Manke DR (September 2019). "The fumarate salts of the N-isopropyl-N-methyl derivatives of DMT and psilocin". Acta Crystallogr E Crystallogr Commun. 75 (Pt 9): 1316–1320. doi:10.1107/S2056989019011253. PMC   6727059 . PMID   31523457. The synthesis of N-methyl-N-isopropyltryptamine (MiPT) was reported in 1981 (Repke et al., 1981). In 1985, Repke and co-workers reported that of the compounds in the series of N,N-dialkyl-4-hydroxytryptamines, the N-methyl-N-isopropyl derivative (4-HO-MiPT) is the most potent based upon qualitative effects on humans (Repke et al., 1985). Later quantitative studies showed the N-methyl-N-isopropyl derivatives of DMT and psilocin to be more potent as seratonin-1A, 2A and 2B receptors compared to the analogous dimethyl compounds (McKenna et al., 1990).
  7. 1 2 3 4 Chadeayne AR, Pham DN, Golen JA, Manke DR (April 2020). "Bis(4-hy-droxy-N-isopropyl-N-methyl-trypt-ammo-nium) fumarate: a new crystalline form of miprocin". Acta Crystallogr E Crystallogr Commun. 76 (Pt 4): 514–517. doi:10.1107/S2056989020002923. PMC   7133045 . PMID   32280495. 4-Hydroxy-N-methyl-N-isopropyltryptamine (4-HOMiPT), aka 'miprocin', is a psilocybin analogue. Its synthesis was first reported in 1981 by Repke and co-workers (Repke et al., 1981); its psychedelic effects were later described in collaboration with Alexander Shulgin (Repke et al., 1985). Miprocin is reported to produce an experience that is both relaxing, stoning and mildly sedating with a marked physical stimulation that distinguishes it from related substances such as psilocybin mushrooms. In a report last year, we presented the first structure of 4-HO-MiPT (Chadeayne, Pham et al., 2019a), which crystallizes as the hydrofumarate monohydrate. Herein we report the reaction of this salt with lead(II) acetate to generate the 4-hydroxy-N-isopropyl-N-methyltryptaminium/fumarate compound in a 2:1 ratio. The solid state structure of the new salt is presented here.
  8. 1 2 3 Repke DB, Ferguson WJ, Bates DK (1981). "Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols". Journal of Heterocyclic Chemistry. 18 (1): 175–179. doi:10.1002/jhet.5570180131. ISSN   0022-152X.
  9. 1 2 3 Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC   9191653 . PMID   31917152. Table 4 Human potency data for selected hallucinogens. [...]
  10. ↑ McKenna DJ, Repke DB, Lo L, Peroutka SJ (March 1990). "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes". Neuropharmacology. 29 (3): 193–198. doi:10.1016/0028-3908(90)90001-8. PMID   2139186.
  11. ↑ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor" [Regulation amending the Ordinance (1999: 58) on Prohibition against certain dangerous goods](PDF). Swedish Code of Statutes (in Swedish). 6 October 2005. Archived from the original (PDF) on 26 June 2021. Retrieved 6 September 2013.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.