4-HO-MiPT (miprocin, 4-hydroxy-''N''-methyl-''N''-isopropyltryptamine) is a

synthetic Synthetic things are composed of multiple parts, often with the implication that they are artificial. In particular, 'synthetic' may refer to: Science * Synthetic chemical or compound, produced by the process of chemical synthesis * Synthetic ...

substituted A substitution reaction (also known as single displacement reaction or single substitution reaction) is a chemical reaction during which one functional group in a chemical compound is replaced by another functional group. Substitution reactions ar ...

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

compound and a lesser-known

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science o ...

tryptamine Tryptamine is an indolamine metabolite of the essential amino acid, tryptophan. The chemical structure is defined by an indole ─ a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the f ...

. It is thought to be a

serotonergic psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science of ...

, similar to

magic mushrooms Psilocybin mushrooms, commonly known as magic mushrooms, are a polyphyletic informal group of fungi that contain psilocybin which turns into psilocin upon ingestion. Biological genera containing psilocybin mushrooms include ''Psilocybe'', ...

, LSD and

mescaline Mescaline or mescalin (3,4,5-trimethoxyphenethylamine) is a naturally occurring psychedelic protoalkaloid of the substituted phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin. Biological ...

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

History

4-HO-MiPT was presumably first synthesized by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymetha ...

. 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 In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydrox ...

analog of the chemical ''N''-methyl-''N''-isopropyltryptamine as well as the isopropyl homolog and possible

structural analog A structural analog (analogue in modern traditional English; Commonwealth English), also known as a chemical analog or simply an analog, is a compound having a structure similar to that of another compound, but differing from it in respect to a c ...

of 4-HO-DMT. In August 2019, Chadeayne et al. solved the crystal structure of 4-HO-MiPT fumarate. Its systematic name is -(4-hydroxy-1Hindol-3-yl)ethylmethyl)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 Serotonergic () or serotoninergic () means "pertaining to or affecting serotonin". Serotonin is a neurotransmitter. A synapse is serotonergic if it uses serotonin as its neurotransmitter. A serotonergic neuron ''produces'' serotonin. A substance is ...

. 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 receptor 5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in the central and peripheral nervous systems. They mediate both excitatory and inhibitory ne ...

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.

United Kingdom

The substance could also be considered illegal in the UK under the

Misuse of Drugs Act 1971 The Misuse of Drugs Act 1971 is an Act of the Parliament of the United Kingdom. It represents action in line with treaty commitments under the Single Convention on Narcotic Drugs, the Convention on Psychotropic Substances, and the United Nati ...

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 The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed in ...

Russia

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

References

External links

Erowid 4-HO-MiPT Vault

4-HO-MIPT entry in TiHKAL

4-HO-MIPT entry in TiHKAL • info
{{DEFAULTSORT:4-Ho-Mipt Designer drugs Entheogens Phenols Psychedelic tryptamines Serotonin receptor agonists Isopropyl compounds