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{{SummarySheet}}
{{SummarySheet}}
{{SubstanceBox/4-AcO-DMT}}
{{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-Acetoxy-N,N-dimethyltryptamine''' (also known as '''4-AcO-DMT''', '''4-Acetoxy-DMT''', '''O-Acetylpsilocin''', and '''psilacetin''') is a novel [[Psychoactive class::psychedelic]] substance of the [[Chemical class::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.  
4-AcO-DMT was first synthesized in 1963 by [[wikipedia:Albert Hofmann|Albert Hofmann]] and Franz Troxler as part of a chemical investigation into psilocin analogs.<ref name="Patent">{{cite web|url=https://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=3075992&KC=&FT=E&locale=en_EP#|title=Bibliographic data: US3075992 (A) ― 1963-01-29|access-date=July 18, 2020|publisher=European Patent Office}}</ref> 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.<ref>{{cite journal|last1=Nichols|first1=D. E.|author-link1=David E. Nichols|last2=Frescas|first2=S.|date=June 1999|title=Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin|url=https://www.researchgate.net/profile/David_Nichols3/publication/244566641_Improvements_to_the_Synthesis_of_Psilocybin_and_a_Facile_Method_for_Preparing_the_O-Acetyl_Prodrug_of_Psilocin/links/542af96e0cf27e39fa917ae1/Improvements-to-the-Synthesis-of-Psilocybin-and-a-Facile-Method-for-Preparing-the-O-Acetyl-Prodrug-of-Psilocin.pdf|issn=0039-7881|eissn=1437-210X|journal=Synthesis|volume=1999|issue=6|pages=935-938}}</ref> Reports of recreational use began to surface shortly after its appearance on the online [[research chemical]] market in the 2010s.{{citation needed}}


The synthesis of 4-AcO-DMT was first reported in 1963 by [[wikipedia:Albert Hofmann|Albert Hofmann]] and Franz Troxler as part of an investigation into psilocin analogs.<ref>http://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US3075992</ref><ref>http://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=3075992&KC=&FT=E&locale=en_EP</ref> 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.<ref>Nichols, D. E., & Frescas, S. (1999). Improvements to the synthesis of psilocybin and a facile method for preparing the O-acetyl prodrug of psilocin. Synthesis, 1999(6), 935-938. </ref> Reports of recreational use began to surface shortly after its appearance on the online [[research chemical]] market in the 2010s.{{citation needed}}
[[Subjective effects]] include [[geometry|geometric visual effects]], [[time distortion]], [[introspection|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".


[[Subjective effects]] are reported to be nearly identical to those of [[psilocybin mushrooms]] and include [[geometry|geometric visual hallucinations]], [[time distortion]], [[introspection|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. Although its toxicity profile is believed to be near-identical with psilocybin mushrooms (see [[psilocybin mushrooms#Toxicity and harm potential|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.
 
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==
==History and culture==
{{historyStub}}
{{historyStub}}
4-AcO-DMT and several other esters of psilocin were patented on January 16, 1963 by Sandoz Ltd. via Albert Hofmann & Franz Troxler.<ref>US patent 3075992, Hofmann A, Troxler F, "Esters of indoles", assigned to Sandoz Ltd.</ref> However, its pharmacology and subjective effects were not investigated. It is unknown when 4-AcO-DMT's effect in humans were first explored.  
4-AcO-DMT and several other esters of psilocin were patented on January 16, 1963 by Sandoz Ltd. via Albert Hofmann & Franz Troxler.<ref name="Patent"></ref> However, its pharmacology and subjective effects were not investigated. It is unknown when 4-AcO-DMT's effects in humans were first explored.  


==Chemistry==
==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<sub>3</sub> to a terminal amino group via an ethyl side chain. 4-AcO-DMT is substituted at R<sub>4</sub> of its indole heterocycle with an acetoxy (-AcO) functional group CH<sub>3</sub>COO−. It also contains two methyl groups CH<sub>3</sub>- bound to the terminal amine R<sub>N</sub> of the ethyl side chain.  
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 R<sub>3</sub> to a terminal amino group via an ethyl side chain. 4-AcO-DMT is substituted at R<sub>4</sub> of its indole heterocycle with an acetoxy (-AcO) functional group CH<sub>3</sub>COO−. It also contains two methyl groups CH<sub>3</sub>- bound to the terminal amine R<sub>N</sub> 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.
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.
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==Pharmacology==
==Pharmacology==
{{Further|Serotonergic psychedelic}}
{{Further|Serotonergic psychedelic}}
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 [[Agonist#Agonists|partial agonist]] for the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]]. However, the role of these interactions and how they result in the [[psychedelic]] experience is the subject of ongoing scientific investigation.
The [[psychedelic]] effects of 4-AcO-DMT are believed to come from its activity as a [[Agonist#Agonists|partial agonist]] for the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> 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.
Claims of subjective differences in effects between the acetylated and non-acetylated forms of psilocin vary:<ref>"4-AcO-DMT (also 4-acetoxy-N,N-dimethyltryptamine) : Erowid Exp: Main Index". ''www.erowid.org''. Archived from the original on 2010-07-28.</ref> 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==
==Subjective effects==
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|{{effects/physical|
|{{effects/physical|


*'''[[Effect::Sedation]]''' - 4-AcO-DMT is considered by most to be relaxing, stoning and mildly sedating. This sense of sedation is often accompanied by compulsive yawning.
*'''[[Effect::Sedation]]''' - 4-AcO-DMT is typically reported to be relaxing, stoning, and mildly sedating. This sense of sedation is often accompanied by [[excessive yawning]] and watery eyes.
*'''[[Effect::Perception of bodily heaviness]]'''
*'''[[Effect::Perception of bodily heaviness]]'''
*'''[[Effect::Spontaneous bodily sensations]]''' - The general "body high" of 4-AcO-DMT can be described as a pleasurable, warm, soft and all-encompassing tingling sensation. This maintains a consistent presence that steadily rises with the onset and hits its limit once the peak has been reached. Once the peak of the experience or sensation is reached it can produce feelings of pronounced [[euphoria|physical and cognitive euphoria]] along with tranquility, a sense of lethargy or sedation, or total immobilization depending on the dose.  
*'''[[Effect::Spontaneous bodily sensations]]''' - The general "body high" of 4-AcO-DMT can be described as pleasurable, warm, soft, and all-encompassing tingling sensation. This maintains a consistent presence that steadily rises with the onset and hits its limit once the peak has been reached. Once the peak of the experience or sensation is reached it can produce feelings of pronounced [[euphoria|physical and cognitive euphoria]] along with tranquility, a sense of lethargy or sedation, or total immobilization depending on the dose.  
*'''[[Effect::Tactile enhancement]]''' - This effect is less prominent than with that of [[LSD]] or [[2C-B]] but is still present and unique in its character. It is repeatedly described as feeling very primitive in its nature often times with the small hairs on the user's arms or legs feeling slightly [[itchiness|itchy]] or even ticklish against the skin.
*'''[[Effect::Tactile enhancement]]''' - This effect is less prominent than with that of [[LSD]] or [[2C-B]] but is still present and unique in its character. It is repeatedly described as feeling very primitive in its nature oftentimes with the small hairs on the user's arms or legs feeling slightly [[itchiness|itchy]] or even ticklish against the skin.
*'''[[Effect::Changes in felt bodily form]]''' - This effect is often accompanied by a sense of warmth and usually occurs around or directly after the peak of the experience. Users can feel as if they are physically part of or conjoined with other objects in a seamless continuity. This is usually reported as feeling comfortable, tranquil and mindful, though it can also manifest in the form of bodily tension.
*'''[[Effect::Changes in felt bodily form]]''' - This effect is often accompanied by a sense of warmth and usually occurs around or directly after the peak of the experience. Users can feel as if they are physically part of or conjoined with other objects in a seamless continuity. This is usually reported as feeling comfortable, tranquil, and mindful, though it can also manifest in the form of bodily tension.
*'''[[Effect::Changes in felt gravity]]'''
*'''[[Effect::Changes in felt gravity]]'''
*'''[[Effect::Nausea]]''' - This effect can be greatly lessened or even completely avoided if the individual has an empty stomach prior to ingestion. It is sometimes recommended that one either refrain from eating for approximately 6 to 8 hours before-hand, or to eat a light meal 3 to 4 hours before if the user is feeling physically fatigued and undernourished. The nausea produced by 4-AcO-DMT is generally considered to be much less prominent than it is with [[Psilocybin#Psilocybin-containing mushrooms|psilocybin mushrooms]], perhaps owing to the fact that there is no fungal-matter the body has to digest when the isolated synthetic form is consumed.  
*'''[[Effect::Nausea]]''' - This effect can be greatly lessened or even completely avoided if the individual has an empty stomach prior to ingestion. It is sometimes recommended that one either refrain from eating for approximately 6 to 8 hours beforehand or to eat a light meal 3 to 4 hours before if the user is feeling physically fatigued and undernourished. The nausea produced by 4-AcO-DMT is generally considered to be much less prominent than it is with [[Psilocybin#Psilocybin-containing mushrooms|psilocybin mushrooms]], perhaps owing to the fact that there is no fungal-matter the body has to digest when the isolated synthetic form is consumed.  
*'''[[Effect::Temperature regulation suppression]]''' - 4-AcO-DMT can cause fluctuates in the user's internal sense of temperature, which can manifest as sudden bouts of uncomfortable coldness or warmth, which is why a climate-controllable environment is strongly recommended.
*'''[[Effect::Temperature regulation suppression]]''' - 4-AcO-DMT can cause fluctuations in the user's internal sense of temperature, which can manifest as sudden bouts of uncomfortable coldness or warmth, which is why a climate-controllable environment is strongly recommended.
*'''[[Effect::Muscle contractions]]''' - The muscle contractions that can occur on 4-AcO-DMT tend to be transient and benign feeling in nature, compared to many other [[tryptamines]], [[phenethylamines]] and [[lysergamides]].
*'''[[Effect::Muscle contractions]]''' - The muscle contractions that can occur on 4-AcO-DMT tend to be transient and benign feeling in nature, compared to many other [[tryptamines]], [[phenethylamines]] and [[lysergamides]].
*'''[[Effect::Muscle relaxation]]'''
*'''[[Effect::Muscle relaxation]]'''
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====[[Effect::Geometry]]====
====[[Effect::Geometry]]====
The visual geometry of 4-AcO-DMT can be described as more similar in appearance to that of [[psilocin]], low-medium dose [[DMT]], and [[ayahuasca]] as opposed to [[LSD]] or [[2C-B]]. It can be comprehensively described through its [[Visual_effects:_Geometry#Variations|variations]] as intricate in complexity, abstract in form, organic in style, structured in organization, brightly lit and multicoloured in scheme, glossy in shading, soft in edges, large in size, slow in speed, smooth in motion, rounded in corners, non-immersive in-depth and consistent in intensity. They can be described as having a "natural" feel and, at higher doses, are significantly more likely to result in states of [[Effect::Level 8B]] visual geometry over [[Level 8A]].
The visual geometry of 4-AcO-DMT can be described as more similar in appearance to that of [[psilocin]], low-medium dose [[DMT]], and [[ayahuasca]] as opposed to [[LSD]] or [[2C-B]]. It can be comprehensively described through its [[Visual_effects:_Geometry#Variations|variations]] as intricate in complexity, abstract in form, organic in style, structured in organization, brightly lit and multicolored in scheme, glossy in shading, soft in edges, large in size, slow in speed, smooth in motion, rounded in corners, non-immersive in-depth and consistent in intensity. They can be described as having a "natural" feel and, at higher doses, are significantly more likely to result in states of [[Effect::Level 8B]] visual geometry over [[Level 8A]].


====Hallucinatory states====
====Hallucinatory states====
4-AcO-DMT produces a full range of high level hallucinatory states in a fashion that is more consistent and reproducible than that of many other commonly used [[psychedelics]]. These effects generally include:
4-AcO-DMT produces a full range of high-level hallucinatory states in a fashion that is more consistent and reproducible than that of many other commonly used [[psychedelics]]. These effects generally include:


*'''[[Effect::Transformations]]'''
*'''[[Effect::Transformations]]'''
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*'''[[Effect::Personal bias suppression]]'''
*'''[[Effect::Personal bias suppression]]'''
*'''[[Effect::Multiple thought streams]]'''
*'''[[Effect::Multiple thought streams]]'''
*'''[[Effect::Emotion enhancement]]''' - This effect can be described as being more prominent, consistent and profound when compared to other traditional psychedelics such as [[mescaline]] or [[LSD]]. This can lead to strong feelings of compassion, urgency and even completely sporadic moments of intense emotional significance that can also be periodically affected by [[enhancement and suppression cycles]]. Many reports suggest, however, that that the experience is not as consistently emotionally-charged as that produced by consuming [[psilocybin mushrooms]].
*'''[[Effect::Emotion enhancement]]''' - This effect can be described as being more prominent, consistent and profound when compared to other traditional psychedelics such as [[mescaline]] or [[LSD]]. This can lead to strong feelings of compassion, urgency and even completely sporadic moments of intense emotional significance that can also be periodically affected by [[enhancement and suppression cycles]].  
*'''[[Effect::Simultaneous emotions]]'''
*'''[[Effect::Simultaneous emotions]]'''
*'''[[Effect::Empathy, affection, and sociability enhancement]]''' - This effect differs from [[MDMA]] and other [[entactogens]] in that it isn't as central to the experience, feels less forced and more natural and is experienced at a less consistent rate. While the substance consistently produces heightened empathy and affection, sociability enhancement in particular only occurs rarely if at all due to the language and memory suppressing cognitive effects that accompany the experience.
*'''[[Effect::Empathy, affection, and sociability enhancement]]''' - This effect differs from [[MDMA]] and other [[entactogens]] in that it isn't as central to the experience, feels less forced and more natural and is experienced at a less consistent rate. While the substance consistently produces heightened empathy and affection, sociability enhancement in particular only occurs rarely if at all due to the language and memory suppressing cognitive effects that accompany the experience.
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}}
}}
===Combination effects===
===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.
 
*'''[[Dissociatives]]''' - 4-AcO-DMT enhances the the geometry, euphoria, dissociation and hallucinatory effects of dissociatives. Dissociative-induced [[Visual_disconnection#Holes.2C_spaces_and_voids|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 [[psychosis|psychotic reaction]].
*'''[[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]].
*'''[[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.<ref>Armstrong, B. D., Paik, E., Chhith, S., Lelievre, V., Waschek, J. A., & Howard, S. G. (2004). Potentiation of (DL)‐3, 4‐methylenedioxymethamphetamine (MDMA)‐induced toxicity by the serotonin 2A receptior partial agonist d‐lysergic acid diethylamide (LSD), and the protection of same by the serotonin 2A/2C receptor antagonist MDL 11,939. Neuroscience Research Communications, 35(2), 83-95. https://doi.org/10.1002/nrc.20023</ref><ref>Potentiation of MDMA-induced dopamine release and serotonin neurotoxicity by 5-HT2 receptor agonists | https://indiana.pure.elsevier.com/en/publications/potentiation-of-34-methylenedioxymethamphetamine-induced-dopamine</ref><ref>Ecstasy induces apoptosis via 5-HT(2A)-receptor stimulation in cortical neurons. | https://www.ncbi.nlm.nih.gov/pubmed/17572501</ref>
*'''[[Dissociatives]]''' - 4-AcO-DMT enhances the geometry, euphoria, dissociation and hallucinatory effects of all dissociatives, especially dissociative-induced [[Visual_disconnection#Holes.2C_spaces_and_voids|holes, spaces, and voids]]. It may also significantly increase [[internal hallucinations]], [[confusion]], [[nausea]], [[delusions]] and the chance of a [[psychosis|psychotic reaction]].
*'''[[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.
*'''[[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.<ref>{{cite journal|last1=Armstrong|first1=B. D.|last2=Paik|first2=E.|last3=Chhith|first3=S.|last4=Lelievre|first4=V.|last5=Waschek|first5=J. A.|last6=Howard|first6=S. G.|date=October 26, 2004|title=Potentiation of (DL)‐3, 4‐methylenedioxymethamphetamine (MDMA)‐induced toxicity by the serotonin 2A receptior partial agonist d‐lysergic acid diethylamide (LSD), and the protection of same by the serotonin 2A/2C receptor antagonist MDL 11,939|journal=Neuroscience Research Communications|volume=35|issue=2|pages=83-95|doi=10.1002/nrc.20023|eissn=1520-6769}}</ref><ref>{{cite journal|last1=Gudelsky|first1=G. A.|last2=Yamamoto|first2=B. K.|last3=Nash|first3=F.|pages=325-330|volume=264|issue=3|journal=European Journal of Pharmacology|date=November 3, 1994|doi=10.1016/0014-2999(94)90669-6|issn=0014-2999|eissn=1879-0712|oclc=01568459|title=Potentiation of 3,4-methylenedioxymethamphetamine-induced dopamine release and serotonin neurotoxicity by 5-HT<sub>2</sub> receptor agonists}}</ref><ref>{{cite journal|pmid=17572501|doi=10.1016/j.neuro.2007.04.005|journal=NeuroToxicology|issn=0161-813X|oclc=47153737|title=Ecstasy induces apoptosis via 5-HT<sub>2A</sub>-receptor stimulation in cortical neurons|first1=J. P.|last1=Capela|first2=E.|last2=Fernandes|first3=F.|last3=Remião|first4=M. L.|last4=Bastos|first5=A.|last5=Meisel|first6=F.|last6=Carvalhoa|volume=28|issue=4|date=July 2007|pages=868-875}}</ref>
*'''[[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.
*'''[[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===
===Experience reports===
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{{#ask: [[Category:4-AcO-DMT]][[Category:Experience]]|format=ul|Columns=2}}
{{#ask: [[Category:4-AcO-DMT]][[Category:Experience]]|format=ul|Columns=2}}
Additional experience reports can be found here:
Additional experience reports can be found here:
* [https://www.erowid.org/experiences/subs/exp_4AcODMT.shtml Erowid Experience Vaults: 4-AcO-DMT]
 
*[https://www.erowid.org/experiences/subs/exp_4AcODMT.shtml Erowid Experience Vaults: 4-AcO-DMT]


==Toxicity and harm potential==
==Toxicity and harm potential==
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==Legal status==
==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.  
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.<ref name="Poisons Standard">{{cite web |title = Poisons Standard | date = October 2020| work = Federal Register of Legislation | publisher = Australian Government | url = https://www.legislation.gov.au/Details/F2020L01255|access-date=October 23, 2020}}</ref> 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.{{citation needed}}
*'''Belgium''': 4-AcO-DMT is illegal to import in Belgium.{{citation needed}}
*'''Brazil''': 4-AcO-DMT is illegal to possess, produce, and sell as it is listed on Portaria SVS/MS nº 344.<ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref>
*'''Brazil''': 4-AcO-DMT is illegal to possess, produce, and sell as it is listed on Portaria SVS/MS nº 344.<ref>{{cite web|url=http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7|title=RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016|publication-date=December 5, 2016|publisher=Agência Nacional de Vigilância Sanitária (ANVISA) [Brazilian Health Regulatory Agency (ANVISA)]|language=pt}}</ref>
*'''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.<ref>{{cite web|url=https://www.eve-rave.net/abfahrer/download.sp?id=2460|title=Sechste Verordnung über die den Betäubungsmitteln gleichgestellten Stoffe|publisher=Bundesanzeiger Verlag|access-date=December 10, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Anlage I BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 10, 2019|language=de}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=§ 29 BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 10, 2019|language=de}}</ref>
*'''Germany''': Because it is an ester of DMT, 4-AcO-DMT is controlled under Anlage I BtMG (Narcotics Act, Schedule I)<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Betäubungsmittelgesetz (BtMG) Anlage I|trans-title=Narcotics Act (BtMG) Schedule I|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> as of January 24, 1974.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl174s0097.pdf|work=Bundesgesetzblatt Jahrgang 1974 Teil I Nr. 6|pages=97-98|publication-date=January 23, 1974|date=January 17, 1974|eissn=0344-7634|title=Sechste Verordnung über die den Betäubungsmitteln gleichgestellten Stoffe|publisher=Bundesanzeiger Verlag|language=de}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=Betäubungsmittelgesetz (BtMG) § 29|trans-title=Narcotics Act (BtMG) § 29|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref>
*'''Italy''': 4-AcO-DMT is illegal in Italy as it is an ester of an illegal substance.{{citation needed}}
*'''Italy''': 4-AcO-DMT is illegal in Italy as it is an ester of an illegal substance.{{citation needed}}
*'''Sweden''': 4-AcO-DMT was made illegal in Sweden on 25 January 2017.{{citation needed}}
*'''Japan''': 4-AcO-DMT is a controlled substance in Japan effective July 29th, 2015.<ref>{{cite web|url=https://www.mhlw.go.jp/stf/houdou/0000092698.html|title=危険ドラッグの成分４物質を新たに指定薬物に指定|publisher=厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)]|access-date=May 2, 2022|language=ja}}</ref>
*'''United Kingdom''': 4-AcO-DMT is a Class A drug in the UK as it is an ester of the Class A drug psilocin.<ref>Misuse of Drugs Act 1971 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I/paragraph/3</ref>
*'''Sweden''': 4-AcO-DMT is a Schedule I controlled substance as of January 25, 2017<ref>{{cite web |url=https://lakemedelsverket.se/upload/lvfs/HSLF-FS_2017_1.pdf |title=Gemensamma författningssamlingen avseende hälso- och sjukvård, socialtjänst, läkemedel, folkhälsa m.m.|issn=2002-1054|archive-url=https://web.archive.org/web/20171031012708/https://lakemedelsverket.se/upload/lvfs/HSLF-FS_2017_1.pdf |archive-date=October 31, 2017|id=HSLF-FS 2017:1|date=January 10, 2017|publication-date=January 16, 2017|publisher=Läkemedelsverket [Medical Products Agency]}}</ref>
*'''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}}
*'''Switzerland''': 4-AcO-DMT could be considered an ester analog of Psilocin, which would make it illegal according to Buchstabe B.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''Turkey:''' 4-AcO-DMT is a classed as drug and is illegal to possess, produce, supply, or import.<ref name="Bakanlar Kurulu Kararı - Karar Sayısı : 2013/5742">https://resmigazete.gov.tr/eskiler/2014/01/20140125-3.htm</ref> <ref name="List of illegal substances for law"> https://resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf</ref>
*'''United Kingdom''': 4-AcO-DMT is a Class A drug in the UK as it is an ester of the Class A drug psilocin.<ref>{{cite web|title=Part I: Class A Drugs|url=http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I|work="Misuse of Drugs Act 1971"|access-date=January 7, 2020|publisher=UK Government}}</ref>
*'''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.{{citation needed}}


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Psychedelic]]
*[[Psychedelic]]
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==External links==
==External links==
*[https://en.wikipedia.org/wiki/O-Acetylpsilocin O-Acetylpsilocin (Wikipedia)]
*[https://en.wikipedia.org/wiki/O-Acetylpsilocin O-Acetylpsilocin (Wikipedia)]
*[https://erowid.org/chemicals/4_acetoxy_dmt/4_acetoxy_dmt.shtml 4-AcO-DMT (Erowid Vault)]
*[https://erowid.org/chemicals/4_acetoxy_dmt/4_acetoxy_dmt.shtml 4-AcO-DMT (Erowid Vault)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=5370 4-AcO-DMT (Isomer Design)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=5370 4-AcO-DMT (Isomer Design)]
===Forum discussion===
===Forum discussion===
*[http://www.bluelight.org/vb/threads/262868-The-Big-and-Dandy-4-AcO-DMT-Thread The Big and Dandy 4-AcO-DMT Thread (Bluelight)]
*[http://www.bluelight.org/vb/threads/262868-The-Big-and-Dandy-4-AcO-DMT-Thread The Big and Dandy 4-AcO-DMT Thread (Bluelight)]


==Literature==
==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
*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==
==References==
<references/>
<references />


[[Category:Substance]]
[[Category:Substance]]
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[[Category:Tryptamine]]
[[Category:Tryptamine]]
[[Category:Research chemical]]
[[Category:Research chemical]]
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