

4-Acetoxy-N,N-dimethyltryptamine (also known as 4-AcO-DMT, 4-Acetoxy-DMT, O-Acetylpsilocin, and psilacetin) is a novel psychedelic substance of the tryptamine class. It is a structural analog of psilocybin, the active ingredient in psilocybin mushrooms (magic mushrooms). Like psilocybin, it is thought to produce its effects primarily by binding to serotonin receptors in the brain; however, the precise mechanism is not fully understood.

The synthesis of 4-AcO-DMT was first reported in 1963 by Albert Hofmann and Franz Troxler as part of an investigation into psilocin analogs.[1] However, its pharmacology and subjective effects were not explored. A paper authored by David E. Nichols in 1999 proposed it as a potentially useful alternative to psilocybin for pharmacological research due to lower cost of synthesis.[2] Reports of recreational use began to surface shortly after its appearance on the online research chemical market in the 2010s.[citation needed]

Subjective effects are reported to be nearly identical to those of psilocybin mushrooms and include geometric visual hallucinations, time distortion, enhanced introspection, euphoria, and ego loss. 4-AcO-DMT is theorized to act as a prodrug to psilocin in a similar manner as 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.

Very little data exists on the pharmacology, metabolism, and toxicity of 4-AcO-DMT. While it is believed to have a favorable safety profile similar to that of psilocybin mushrooms (which are known to be physiologically non-toxic) there is currently no data to support this claim. It is highly advised to use harm reduction practices if using this substance.

History and culture

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4-AcO-DMT and several other esters of psilocin were patented on January 16, 1963 by Sandoz Ltd. via Albert Hofmann & Franz Troxler.[1] However, its pharmacology and subjective effects were not investigated. It is unknown when 4-AcO-DMT's effect in humans were first explored.

Chemistry

4-AcO-DMT, or 4-acetoxy-N,N-dimethyltryptamine, is a synthetic member of organic compounds known as tryptamines. Tryptamines share a core structure that consists of a bicylic indole heterocycle attached at R 3 to a terminal amino group via an ethyl side chain. 4-AcO-DMT is substituted at R 4 of its indole heterocycle with an acetoxy (-AcO) functional group CH 3 COO−. It also contains two methyl groups CH 3 - 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

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.

In the body, 4-AcO-DMT is suspected to be deacetylated into psilocin during first pass metabolism, by the acidic conditions in the stomach, and as it passes through the liver.

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.

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), a literature which relies on collected anecdotal reports and the personal experiences of PsychonautWiki contributors. As a result, they should be taken with a healthy amount of skepticism. It is worth noting that these effects will not necessarily occur in a consistent or reliable manner, although higher doses (common+) are more likely to induce the full spectrum of reported effects. Likewise, adverse effects become much more likely with higher doses and may include serious injury or death.

Combination effects

Cannabis - Cannabis intensifies the visual, sensory and cognitive effects of 4-AcO-DMT greatly. This should be used with extreme caution, especially if one is not experienced with psychedelics. This interaction can also amplify the anxiety, confusion and the psychosis risk of cannabis significantly.

- Cannabis intensifies the visual, sensory and cognitive effects of 4-AcO-DMT greatly. This should be used with extreme caution, especially if one is not experienced with psychedelics. This interaction can also amplify the anxiety, confusion and the psychosis risk of cannabis significantly. Dissociatives - 4-AcO-DMT enhances the the geometry, euphoria, dissociation and hallucinatory effects of dissociatives. Dissociative-induced holes, spaces, and voids while under the influence of 4-AcO-DMT can result in significantly more vivid visuals than dissociatives alone present, along with more intense internal hallucinations, confusion, nausea, delusions and chances of a psychotic reaction.

- 4-AcO-DMT enhances the the geometry, euphoria, dissociation and hallucinatory effects of dissociatives. Dissociative-induced holes, spaces, and voids while under the influence of 4-AcO-DMT can result in significantly more vivid visuals than dissociatives alone present, along with more intense internal hallucinations, confusion, nausea, delusions and chances 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 of this combination is unknown, although there is some evidence that suggests this may increase the the neurotoxic effects of MDMA. [3] [4] [5]

- 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 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 typically advised against due to alcohol’s ability to cause dehydration, nausea, and physical fatigue which can negatively affect the experience if taken in moderate to high doses. This combination is, however, considered to be reasonably safe in low doses and when used responsibly, this can often take the edge off the experience as well as dull its psychedelic effects in a fashion somewhat similar to benzodiazepines.

- This combination is typically advised against due to alcohol’s ability to cause dehydration, nausea, and physical fatigue which can negatively affect the experience if taken in moderate to high doses. This combination is, however, considered to be reasonably safe in low doses and when used responsibly, this can often take the edge off the experience as well as dull its psychedelic effects in a fashion somewhat similar to benzodiazepines. Benzodiazepines - Depending on the dose, benzodiazepines can slightly to completely reduce the intensity of the cognitive, physical and visual effects of a 4-AcO-DMT experience. They can be very efficient at largely stopping or mitigating a bad trip at the cost of amnesia and reduced intensity. Caution is advised when obtaining them for this purpose due to their very high addiction and abuse potential.

Experience reports

Anecdotal reports which describe the effects of this compound within our experience index include:

Additional experience reports can be found here:

Toxicity and harm potential

The toxicity and long-term health effects of 4-AcO-DMT have not been studied and the exact 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 non-addictive with low potential for abuse.

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

Dangerous interactions

Although many psychoactive substances are reasonably safe to use on their own, they can quickly become dangerous or even life-threatening when combined with other substances. The list below includes some known dangerous combinations (although it cannot be guaranteed to include all of them). Independent research (e.g. Google, DuckDuckGo) should always be conducted to ensure that a combination of two or more substances is safe to consume. Some interactions listed have been sourced from TripSit.

Lithium - Lithium is commonly prescribed in the treatment of bipolar disorder. There is a large body of anecdotal evidence that suggests taking it with psychedelics significantly increases the risk of psychosis and seizures. As a result, this combination is strictly discouraged.

- Lithium is commonly prescribed in the treatment of bipolar disorder. There is a large body of anecdotal evidence that suggests taking it with psychedelics significantly increases the risk of psychosis and seizures. As a result, this combination is strictly discouraged. Cannabis - Cannabis has an unexpectedly strong and unpredictable synergy with the effects of psychedelics. Caution is advised with this combination as it can significantly increase the risk of adverse psychological reactions like anxiety, paranoia, panic attacks, and psychosis. Users are advised to start off with only a fraction of their normal cannabis dose and take long breaks between hits to avoid over intake.

- Cannabis has an unexpectedly strong and unpredictable synergy with the effects of psychedelics. Caution is advised with this combination as it can significantly increase the risk of adverse psychological reactions like anxiety, paranoia, panic attacks, and psychosis. Users are advised to start off with only a fraction of their normal cannabis dose and take long breaks between hits to avoid over intake. Stimulants ( Amphetamine, cocaine, methylphenidate , ...) - Stimulants affect many parts of the brain and alter dopaminergic function. Combined with psychedelics, stimulation can turn into severe anxiety, panic, thought loops, and paranoia. This interaction may result in an elevated risk of mania and psychosis. [ citation needed ]

( , ...) - Stimulants affect many parts of the brain and alter dopaminergic function. Combined with psychedelics, stimulation can turn into severe anxiety, panic, thought loops, and paranoia. This interaction may result in an elevated risk of mania and psychosis. Tramadol - Tramadol lowers the seizure threshold[6] and psychedelics may act as triggers for seizures in susceptible individuals.[ citation needed ]

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.

Belgium : 4-AcO-DMT is illegal to import in Belgium. [ citation needed ]

: 4-AcO-DMT is illegal to import in Belgium. Brazil : 4-AcO-DMT is illegal to possess, produce, and sell as it is listed on Portaria SVS/MS nº 344. [7]

: 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) [8] as of January 24, 1974. [9] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license. [10]

: 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. [ citation needed ]

: 4-AcO-DMT is illegal in Italy as it is an ester of an illegal substance. Sweden : 4-AcO-DMT was made illegal in Sweden on 25 January 2017. [ citation needed ]

: 4-AcO-DMT was made illegal in Sweden on 25 January 2017. Switzerland : 4-AcO-DMT could be considered an ester analog of Psilocin, which would make it illegal according to Buchstabe B. [11]

: 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. [12] [13]

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. [14]

: 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 unscheduled 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.[ citation needed ]

See also

Forum discussion

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