Mall:SummarySheet Mall:SubstanceBox/4-AcO-DMT 4-Acetoxy-N,N-dimethyltryptamine (also known as 4-AcO-DMT, 4-acetoxy-DMT, O-acetylpsilocin, psilacetin, and "synthetic mushrooms") is a novel lesser-known Psychoactive class::psychedelic substance of the Chemical class::tryptamine class. It is structurally related to psilocybin and psilocin, the active ingredient in psilocybin mushrooms ("magic mushrooms"). 4-AcO-DMT is thought to produce its effects by binding to serotonin receptors in the brain; however, the precise mechanism is not known.

4-AcO-DMT was first synthesized in 1963 by Albert Hofmann and Franz Troxler as part of a chemical investigation into psilocin analogs. However, it was not tested for psychoactivity during this time. It is unknown when it was first explored in humans. A paper authored by David E. Nichols in 1999 proposed its potential use as an alternative to psilocybin for pharmacological research due to the lower cost of synthesis. Reports of recreational use began to surface shortly after its appearance on the online research chemical market in the 2010s.^{[källa behövs]}

Subjective effects include geometric visual effects, time distortion, enhanced introspection, euphoria, and ego loss. 4-AcO-DMT's effects are considered to be nearly identical to psilocybin, with some subtle differences. It has been theorized to act as a prodrug to psilocin in a manner similar to psilocybin, which may account for this similarity. 4-AcO-DMT's classical psychedelic effects and favorable tolerability profile has led it to become popular among novel psychoactive substance users who seek mystical or entheogenic experiences. It is occasionally sold in capsules or pressed pills and marketed as "synthetic shrooms".

Very little data exists on the pharmacology, metabolism, and toxicity of 4-AcO-DMT. Although its toxicity profile is believed to be near-identical with psilocybin mushrooms (see this section), which are known to be physiologically non-toxic, there is no hard data to support this claim. It is highly advised to use harm reduction practices if using this substance.

History and culture

Mall:HistoryStub 4-AcO-DMT and several other esters of psilocin were patented on January 16, 1963 by Sandoz Ltd. via Albert Hofmann & Franz Troxler. However, its pharmacology and subjective effects were not investigated. It is unknown when 4-AcO-DMT's effects in humans were first explored.

Chemistry

4-AcO-DMT is a synthetic member of organic compounds known as tryptamines. Tryptamines share a core structure that consists of a bicylic indole heterocycle attached at R₃ to a terminal amino group via an ethyl side chain. 4-AcO-DMT is substituted at R₄ of its indole heterocycle with an acetoxy (-AcO) functional group CH₃COO−. It also contains two methyl groups CH₃- bound to the terminal amine R_N of the ethyl side chain.

4-AcO-DMT is the acetate ester analog of psilocin (4-HO-DMT) and the N-substituted methyl homolog of 4-AcO-MET. It is the O-acetylated form of psilocin, whereas psilocybin is the O-phosphorylated form.

Pharmacology

Upon entering the body, O-acetylpsilocin, or 4-AcO-DMT, is deacetylated to psilocin by deacetylases/acetyltransferases during first-pass metabolism and during subsequent passes through the liver (evident as psilacetin is also active via parenteral routes of ingestion).

The psychedelic effects of 4-AcO-DMT are believed to come from its activity as a partial agonist for the 5-HT_2A receptor. However, the role of these interactions and how they result in the psychedelic experience is the subject of ongoing scientific investigation.

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

Subjective effects

Users frequently describe 4-AcO-DMT as being extremely similar to psilocybin mushrooms. It is generally described as euphoric, gentle, warm, and colorful. Visuals are reported by some users to be brighter and more neon in a manner reminiscent of DMT. It is also reported to be less nauseating than psilocybin mushrooms, which may be due to the fact that it does not require digesting mushroom matter.

Combination effects

• Cannabis - Cannabis is reported to strongly intensify the visual, sensory, and cognitive effects of 4-AcO-DMT. This combination should be used with extreme caution, as anecdotal reports suggest it increases the risk of experiencing a bad trip, characterized by anxiety, confusion, and psychosis.
• Dissociatives - 4-AcO-DMT enhances the geometry, euphoria, dissociation and hallucinatory effects of all dissociatives, especially dissociative-induced holes, spaces, and voids. It may also significantly increase internal hallucinations, confusion, nausea, delusions and the chance of a psychotic reaction.
• MDMA - 4-AcO-DMT strongly amplifies the visual, physical and cognitive effects of MDMA. The synergy between these substances is unpredictable, and it is best to start with lower doses than one would take for both substances individually. The toxicity risk of this combination is unknown, although there is some evidence that suggests this may increase the the neurotoxic effects of MDMA.
• Alcohol - This combination is not typically advised due to alcohol’s potential to produce dehydration, nausea, and physical fatigue, which can negatively affect the experience (for moderate to high doses). This combination is, however, considered to be reasonably safe in low doses and, when used responsibly, can often "take the edge off" the experience by dulling 4-AcO-DMT's psychedelic effects in a manner somewhat similar to benzodiazepines.
• Benzodiazepines - Depending on the dose, benzodiazepines can moderately to completely decrease the intensity of the cognitive, physical, and visual effects of a 4-AcO-DMT experience. They can be effective at mitigating bad trips by reducing excessive anxiety and hallucinations. Caution is advised when obtaining them for this purpose due to their high abuse potential.

Experience reports

Anecdotal reports which describe the effects of this compound within our experience index include: {{#ask: |format=ul|Columns=2}} Additional experience reports can be found here:

• Erowid Experience Vaults: 4-AcO-DMT

Toxicity and harm potential

Mall:Further The toxicity and long-term health effects of 4-AcO-DMT have not been studied and the exact Toxicity::toxic dose is unknown. This is because 4-AcO-DMT is a research chemical with a very short history of human usage. 4-AcO-DMT is assumed to have a similar safety profile as psilocybin mushrooms due to their similar chemical structures, although there is currently no data to support this.

Anecdotal evidence suggests that there are no negative health effects attributed to simply trying 4-AcO-DMT by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

It is strongly recommended that one use harm reduction practices when using this substance.

Dependence and abuse potential

Like other psychedelics, 4-AcO-DMT is considered to be Addiction potential::non-addictive with low potential for abuse.

Tolerance to the effects of 4-AcO-DMT is built Time to full tolerance::almost immediately after ingestion. After that, it takes about Time to zero tolerance::7 days for tolerance to return to baseline (in the absence of further consumption). 4-AcO-DMT produces cross-tolerance with [[Cross-tolerance::all psychedelics]], meaning that after the consumption of 4-AcO-DMT all psychedelics will have a reduced effect.

Legal status

4-AcO-DMT is not listed under any international drug schedules such as the UN Convention on Psychotropic Substances. As a result, it exists in a legal grey area in many countries, meaning that while it is not specifically illegal, individuals may still be charged for its possession under certain circumstances such as under analogue laws and with the intent to sell or consume.

• Australia: 4-AcO-DMT can be considered an analog of psilocin, making it a Schedule 9 controlled substance in Australia under the Poisons Standard. 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.
• Belgium: 4-AcO-DMT is illegal to import in Belgium.^{[källa behövs]}
• Brazil: 4-AcO-DMT is illegal to possess, produce, and sell as it is listed on Portaria SVS/MS nº 344.
• Germany: Because it is an ester of DMT, 4-AcO-DMT is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of January 24, 1974. It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.
• Italy: 4-AcO-DMT is illegal in Italy as it is an ester of an illegal substance.^{[källa behövs]}
• Japan: 4-AcO-DMT is a controlled substance in Japan effective July 29th, 2015.
• Sweden: 4-AcO-DMT is a Schedule I controlled substance as of January 25, 2017
• Switzerland: 4-AcO-DMT could be considered an ester analog of Psilocin, which would make it illegal according to Buchstabe B.
• Turkey: 4-AcO-DMT is a classed as drug and is illegal to possess, produce, supply, or import.
• United Kingdom: 4-AcO-DMT is a Class A drug in the UK as it is an ester of the Class A drug psilocin.
• United States: 4-AcO-DMT is not scheduled in the United States. It may be considered an analogue of psilocin, a Schedule I drug under the Controlled Substances Act, which means the sale for human consumption or the use for non-medical or research purposes could be prosecuted as crimes under the Federal Analogue Act.^{[källa behövs]}

See also

• Responsible use
• Psychedelic
• Tryptamine
• Psilocybin mushrooms
• DMT

External links

• O-Acetylpsilocin (Wikipedia)
• 4-AcO-DMT (Erowid Vault)
• 4-AcO-DMT (Isomer Design)

Forum discussion

• The Big and Dandy 4-AcO-DMT Thread (Bluelight)

Literature

• Vargas‐Perez, H., Grieder, T. E., Ting‐A‐Kee, R., Maal‐Bared, G., Chwalek, M., & van der Kooy, D. (2017). A single administration of the hallucinogen, 4‐acetoxy‐dimethyltryptamine, prevents the shift to a drug‐dependent state and the expression of withdrawal aversions in rodents. European Journal of Neuroscience, 45(11), 1410-1417. https://doi.org/10.1111/ejn.13572

References

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