4-HO-MiPT

4-HO-MiPT
Clinical data
Other names	4-hydroxy-N-methyl-N-isopropyl tryptamine
Routes of; administration	Oral, intranasal, rectal, IV, IM
ATC code	None;
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); DE: NpSG (Industrial and scientific use only); UK: Class A; US: Unscheduled;
Identifiers
	IUPAC name 3-{2-[methyl(propan-2-yl)amino]ethyl}-1H-indol-4-ol;
CAS Number	77872-43-6 ;
PubChem CID	10082683;
ChemSpider	8258221 ;
UNII	4GAJ9OJ8YZ;
ChEMBL	ChEMBL171419 ;
CompTox Dashboard (EPA)	DTXSID30228492 ;
Chemical and physical data
Formula	C14H20N2O
Molar mass	232.327 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	123 to 125 °C (253 to 257 °F)
	SMILES CN(C(C)C)CCC2=CNC1=CC=CC(O)=C12;
	InChI 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 ; Key:RXKGHZCQFXXWFQ-UHFFFAOYSA-N ;
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4-HO-MiPT (miprocin, 4-hydroxy-N-methyl-N-isopropyltryptamine) is a synthetic substituted aromatic compound and a lesser-known psychedelic tryptamine. It is thought to be a serotonergic psychedelic, similar to magic mushrooms, LSD and mescaline.^[2] Its molecular structure and pharmacological effects somewhat resemble those of the tryptamine psilocin, which is the primary psychoactive chemical in magic mushrooms.

History

4-HO-MiPT was presumably first synthesized by Alexander Shulgin. Its synthesis is described in his book TiHKAL along with reports by people who had ingested the compound. Shulgin's trials and other anecdotal information suggest that 4-HO-MiPT is a synthetic psychedelic similar in activity to psilocin. It is relatively uncommon and has only a short history of human use.

Chemistry

Miprocin is the 4-hydroxyl analog of the chemical N-methyl-N-isopropyltryptamine as well as the isopropyl homolog and possible structural analog of psilocin.

In August 2019, Chadeayne et al. solved the crystal structure of 4-HO-MiPT fumarate.^[3] Its systematic name is [2-(4-hydroxy-1Hindol-3-yl)ethyl](methyl)propan-2-ylazanium 3-carboxyprop-2-enoate monohydrate. 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.

Pharmacology

4-HO-MiPT is thought to be a serotonergic psychedelic.^[2] Like other serotonergic psychedelics, its method of action is believed to result from its partial agonism of 5-HT_2A and 5-HT_1A serotonin receptors.^[2]

Toxicity

Very little is known about the toxicity of 4-HO-MiPT. Its chemical structure and pharmacological activity are very similar to psilocin, a compound which is not associated with compulsive use or physical dependence. However, because very little research has been done on 4-HO-MiPT, it cannot be definitively concluded that its pharmacological actions in the human body do not differ from those of psilocin. To date, there have been no reported deaths from 4-HO-MiPT.^{[citation needed]}

Duration

Onset of action is 15 to 45 minutes and has a duration of 4 to 6 hours, depending on dose. The duration of action is one half-hour to two hours when injected IV.^{[citation needed]}

Drug prohibition laws

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.^[4]

United Kingdom

The substance could also be considered illegal in the UK under the Misuse of Drugs Act 1971.

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.

Russia

4-HO-MiPT is in Schedule 1 in Russia as an analog of 4-hydroxytryptamine.

References

^ 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.
^ ^a ^b ^c "4-HO-MiPT". Psychedelic Science Review. 6 January 2020. Retrieved 5 July 2022.
^ Chadeayne AR, Pham DN, Golen JA, Manke DR (September 2019). "N-methyl derivatives of DMT and psilocin". Acta Crystallographica Section E. 75 (Pt 9): 1316–1320. doi:10.1107/S2056989019011253. PMC 6727059. PMID 31523457.
^ "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.

External links

[1] 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.

[:0-2] "4-HO-MiPT". Psychedelic Science Review. 6 January 2020. Retrieved 5 July 2022.

[3] Chadeayne AR, Pham DN, Golen JA, Manke DR (September 2019). "N-methyl derivatives of DMT and psilocin". Acta Crystallographica Section E. 75 (Pt 9): 1316–1320. doi:10.1107/S2056989019011253. PMC 6727059. PMID 31523457.

[4] "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.

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