''O''-Acetylpsilocin (also known as psilacetin, 4-acetoxy-DMT, 4-AcO-DMT, or synthetic shrooms) is a semi-synthetic

psychoactive drug A psychoactive drug, psychopharmaceutical, psychoactive agent or psychotropic drug is a chemical substance, that changes functions of the nervous system, and results in alterations in perception, mood, consciousness, cognition or behavior. ...

that has been suggested by David Nichols to be a potentially useful alternative to psilocybin for pharmacological studies, as they are both believed to be

prodrug A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug ...

s of

psilocin Psilocin (also known as 4-HO-DMT, 4-hydroxy DMT, psilocine, psilocyn, or psilotsin) is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated counte ...

. However, some users report that ''O''-acetylpsilocin's subjective effects differ from those of psilocybin and psilocin. Additionally, some users prefer 4-AcO-DMT to natural

psilocybin 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'', ''Pan ...

due to feeling fewer adverse side effects such as nausea and heavy body load, which are more frequently reported in experiences involving natural mushrooms. It is the

acetyl In organic chemistry, acetyl is a functional group with the chemical formula and the structure . It is sometimes represented by the symbol Ac (not to be confused with the element actinium). In IUPAC nomenclature, acetyl is called ethanoyl, ...

ated form of the

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

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

and is a lower

homolog In biology, homology is similarity due to shared ancestry between a pair of structures or genes in different taxa. A common example of homologous structures is the forelimbs of vertebrates, where the wings of bats and birds, the arms of prima ...

of 4-AcO-MET,

4-AcO-DET 4-Acetoxy-DET (4-Acetoxy-''N'',''N''-diethyltryptamine), also known as ethacetin, ethylacybin or 4-AcO-DET, is a psychedelic tryptamine. It was first synthesized in 1958 by Albert Hofmann in the Sandoz lab.

, 4-AcO-MiPT and 4-AcO-DiPT.

History

''O''-Acetylpsilocin (psilacetin) and several other esters of psilocin were patented on January 16, 1963 by

Sandoz Novartis AG is a Swiss-American multinational pharmaceutical corporation based in Basel, Switzerland and Cambridge, Massachusetts, United States (global research).name="novartis.com">https://www.novartis.com/research-development/research-loc ...

Ltd via

Albert Hofmann Albert Hofmann (11 January 1906 – 29 April 2008) was a Swiss chemist known for being the first to synthesize, ingest, and learn of the psychedelic effects of lysergic acid diethylamide (LSD). Hofmann's team also isolated, named and synthesiz ...

& Franz Troxler. Despite this, psilacetin remains a psychedelic compound with a limited history of use. It is theorized to be a

of psilocin, as is psilocybin, which occurs naturally in many species of hallucinogenic mushrooms. This is because the aromatic acetyl moiety on the 4th position of the indole ring system is subject to deacetylation in acidic conditions such as those found in the stomach. Psilacetin is ''O''-acetylated psilocin, whereas psilocybin is ''O''-phosphorylated.

Chemistry

''O''-Acetylpsilocin can be obtained by

acetylation : In organic chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed ''acetate esters'' or simply '' acetates''. Deacetylation is the oppo ...

of psilocin under

alkaline In chemistry, an alkali (; from ar, القلوي, al-qaly, lit=ashes of the saltwort) is a base (chemistry), basic, ionic compound, ionic salt (chemistry), salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as ...

or strongly

acid In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...

ic conditions. It is, therefore, a

semi-synthetic Semisynthesis, or partial chemical synthesis, is a type of chemical synthesis that uses chemical compounds isolated from natural sources (such as microbial cell cultures or plant material) as the starting materials to produce novel compounds with ...

compound. It is believed to be a

of psilocin; however, speculation exists that psilacetin itself also may be psychoactive. ''O''-Acetylpsilocin is more resistant than psilocin to oxidation under basic conditions due to its acetoxy group. While ''O''-acetylpsilocin is not well researched (sometimes viewed negatively as a

research chemical Research chemicals are chemical substances used by scientists for medical and scientific research purposes. One characteristic of a research chemical is that it is for laboratory research use only; a research chemical is not intended for human o ...

, as opposed to psilocin and psilocybin), it is not as difficult as psilocybin to synthesize. Due to their similar proposed mechanisms of action, this factor may provide further support for the proposition that ''O''-acetylpsilocin might serve as an appropriate substitute for psilocybin in research of the application of psychedelic compounds in medicine.

Pharmacology

: ''See

for more details.'' In the body ''O''-acetylpsilocin is deacetylated to psilocin by deacetylases/

acetyltransferase Acetyltransferase (or transacetylase) is a type of transferase enzyme that transfers an acetyl group. Examples include: * Histone acetyltransferases including CBP histone acetyltransferase * Choline acetyltransferase * Chloramphenicol acetyltransf ...

s during

first pass metabolism The first pass effect (also known as first-pass metabolism or presystemic metabolism) is a phenomenon of drug metabolism whereby the concentration of a drug, specifically when administered orally, is greatly reduced before it reaches the system ...

and during subsequent passes through the liver (evident as psilacetin is also active via parenteral routes of ingestion). Claims of subjective differences in effects between the acetylated and non-acetylated forms of psilocin vary: some users report that ''O''-acetylpsilocin lasts slightly longer, whilst others report that it lasts for a considerably shorter time. Many users report less

body load Body load is the specific physical or tactile sensations brought on by psychoactive drugs, especially psychedelics. Generally, body load is an unpleasant physical sensation that is difficult to describe objectively either in terms of other sensation ...

and nausea compared with psilocin. Some users find that the visual effects produced by ''O''-acetylpsilocin more closely resemble those produced by

DMT ''N'',''N''-Dimethyltryptamine (DMT or ''N'',''N''-DMT, SPL026) is a substituted tryptamine that occurs in many plants and animals, including human beings, and which is both a derivative and a structural analog of tryptamine. It is used as a ...

than those produced by psilocin or psilocybin. These differences could be possible if psilacetin is psychoactive in itself and not merely as a prodrug. Despite this, there have been no controlled clinical studies to distinguish among the phenomenological effects of psilacetin, psilocin, and psilocybin. 4-AcO-DMT 1g

Legality

Australia

''O''-Acetylpsilocin can be considered an analog of

making it a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015). A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.

United States

''O''-Acetylpsilocin is ambiguously legal for use as a lab reagent or research chemical; however, it is an acetate ester of psilocin, meaning it would be considered Schedule I under the

Federal Analogue 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 ...

if sold for human consumption.

United Kingdom

''O''-Acetylpsilocin, being an ester of psilocin, is a

Class A drug These drugs are known in the UK as ''controlled drugs'', because this is the term by which the act itself refers to them. In more general terms, however, many of these drugs are also controlled by the Medicines Act 1968, there are many other dru ...

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 Nation ...

Italy

''O''-Acetylpsilocin is illegal in Italy as it is an

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

of a prohibited substance.

Sweden

The Riksdag added 4-AcO-DMT to Narcotic Drugs Punishments Act under ''swedish schedule I'' (''"substances, plant materials and fungi which normally do not have medical use"'' ) as of January 25, 2017, published by Medical Products Agency (MPA) in regulation ''HSLF-FS 2017:1'' listed as 4-acetoxi-N,N-dimetyltryptamin.

Israel

''O''-Acetylpsilocin is technically illegal in Israel as of being a derivative of DMT

References

External links

4-AcO-DMT information at IsomerDesign.com

Erowid 4-Acetoxy-DMT Vault

"Esters of Indoles" US Patent # 3,075,992
- Awarded to

Ltd. (via

& Franz Troxler) on January 29, 1963. {{DEFAULTSORT:Acetylpsilocin, ''O''- Tryptamine alkaloids Mycotoxins Psychedelic tryptamines Entheogens Serotonin receptor agonists Acetate esters Prodrugs Designer drugs Dimethylamino compounds