4-HO-MiPT

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.[1] Its molecular structure and pharmacological effects somewhat resemble those of the tryptamine psilocin, which is the primary psychoactive chemical in magic mushrooms.

"Miprocin" redirects here. Not to be confused with Mupirocin.

4-HO-MiPT
Clinical data
Other names4-hydroxy-N-methyl-N-isopropyl tryptamine
Routes of
administration		Oral, intranasal, rectal, IV, IM
ATC code
  • None
Legal status
Legal status
  • 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
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H20N2O
Molar mass232.327 g·mol−1
3D model (JSmol)
Melting point123 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 Y
  • Key:RXKGHZCQFXXWFQ-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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 4-HO-DMT.

In August 2019, Chadeayne et al. solved the crystal structure of 4-HO-MiPT fumarate.[2] 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.[1] Like other serotonergic psychedelics, its method of action is believed to result from its partial agonism of 5-HT2A and 5-HT1A serotonin receptors.[1]

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 isn't 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.

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.

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.[3]

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.

See also

References
  1. "4-HO-MiPT". Psychedelic Science Review. 6 January 2020. Retrieved 5 July 2022.
  2. 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.
  3. "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.
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