4-AcO-DMT: Difference between revisions

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==Chemistry==
==Chemistry==
4-AcO-DMT, or 4-acetoxy-N,N-dimethyltryptamine, is a synthetic indole [[alkaloid]] molecule of the [[tryptamine]] chemical class. Tryptamines share a core structure comprising a bicylic indole heterocycle attached at R<sub>3</sub> to a terminal amino group via an ethyl side chain.
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 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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====[[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 dosages 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 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]].


====Hallucinatory states====
====Hallucinatory states====
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*'''[[Effect::Transformations]]'''
*'''[[Effect::Transformations]]'''
*'''[[Effect::Machinescapes]]''' - This effect is a rare effect that typically only occurs at very strong to heavy doses, and not as consistently as with notably visual psychedelics like [[DMT]], [[ETH-LAD]], and [[2C-P]], and atypical psychedelics like [[salvia]].
*'''[[Effect::Machinescapes]]''' - This effect is a rare effect that typically only occurs at very strong to heavy doses, and not as consistently as with notably visual psychedelics like [[DMT]], [[ETH-LAD]], and [[2C-P]], and atypical psychedelics like [[salvia]].
*'''[[Effect::Internal hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'') - This effect is very consistent in dark environments at appropriately high dosages. They can be comprehensively described through their [[Visual_effects:_Internal_hallucinations#Variations|variations]] as lucid in believability, interactive in style, new experiences in content, autonomous in controllability, [[Geometry|geometry]]-based in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.
*'''[[Effect::Internal hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'') - This effect is very consistent in dark environments at appropriately high doses. They can be comprehensively described through their [[Visual_effects:_Internal_hallucinations#Variations|variations]] as lucid in believability, interactive in style, new experiences in content, autonomous in controllability, [[Geometry|geometry]]-based in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.
*'''[[Effect::External hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'') - These are more common within dark environments and can be comprehensively described through their [[External_hallucinations#Variations|variations]] as lucid in believability, interactive in style, new experiences in content, autonomous in controllability, geometry-based in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.
*'''[[Effect::External hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'') - These are more common within dark environments and can be comprehensively described through their [[External_hallucinations#Variations|variations]] as lucid in believability, interactive in style, new experiences in content, autonomous in controllability, geometry-based in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.


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*'''[[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.
*'''[[Effect::Language suppression]]''' - This effect can be described as a perceived inability or general unwillingness to talk aloud despite feeling perfectly capable of formulating coherent thoughts within one's internal narrative. It is much more common among inexperienced users.
*'''[[Effect::Language suppression]]''' - This effect can be described as a perceived inability or general unwillingness to talk aloud despite feeling perfectly capable of formulating coherent thoughts within one's internal narrative. It is much more common among inexperienced users.
*'''[[Effect::Enhancement and suppression cycles]]''' - This can be described as constant waves of extremely stimulated and profound thinking which are spontaneously surpassed in a cyclic fashion by waves of general thought suppression and mental intoxication. These two states seem to switch between each other in a consistent loop once every 20 to 60 minutes when it does occur.
*'''[[Effect::Enhancement and suppression cycles]]''' - This can be described as constant waves of extremely stimulated and profound thinking which are spontaneously surpassed in a cyclic fashion by waves of general thought suppression and mental intoxication. These two states seem to switch between each other in a consistent loop once every 20 to 60 minutes when present.
*'''[[Effect::Increased sense of humor]]'''
*'''[[Effect::Increased sense of humor]]'''
**'''[[Effect::Laughter fits]]'''
**'''[[Effect::Laughter fits]]'''
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*'''[[Effect::Déjà vu]]'''
*'''[[Effect::Déjà vu]]'''
*'''[[Effect::Mindfulness]]'''
*'''[[Effect::Mindfulness]]'''
*'''[[Effect::Ego replacement]]''' - Although this effect is rare and more likely to occur with certain psychedelics like [[DMT]] or [[ayahuasca]], it can still occur spontaneously, typically with higher dosages.
*'''[[Effect::Ego replacement]]''' - Although this effect is rare and more likely to occur with certain psychedelics like [[DMT]] or [[ayahuasca]], it can still occur spontaneously, typically with higher doses.
*'''[[Effect::Personality regression]]''' - While this effect is not typically observed, it can still spontaneously manifest and is thought to depend primarily on the user's [[set and setting]].
*'''[[Effect::Personality regression]]''' - While this effect is not typically observed, it can still spontaneously manifest and is thought to depend primarily on the user's [[set and setting]].


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{{effects/multisensory|
{{effects/multisensory|


*'''[[Effect::Synaesthesia]]''' - In its fullest manifestation, this is a very rare and non-reproducible effect. Increasing the dosage can increase the likelihood of this occurring, but seems to only be a prominent part of the experience among those who are already predisposed to synaesthetic states.
*'''[[Effect::Synaesthesia]]''' - In its fullest manifestation, this is a very rare and non-reproducible effect. Increasing the dose can increase the likelihood of this occurring, but seems to only be a prominent part of the experience among those who are already predisposed to synaesthetic states.
*'''[[Effect::Dosage independent intensity]]'''{{citation needed}}
*'''[[Effect::Dosage independent intensity]]'''{{citation needed}}


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*'''[[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]]''' - 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]].
*'''[[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]].
*'''[[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 dosages 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>
*'''[[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>
*'''[[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 dosages. 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.
*'''[[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.
*'''[[Benzodiazepines]]''' - Depending on the dosage, 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.
*'''[[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===
===Experience reports===
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*[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)]
===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)]


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[[Category:Tryptamine]]
[[Category:Tryptamine]]
[[Category:Research chemical]]
[[Category:Research chemical]]
{{#set:Featured=true
|RN1=CH₃
|RN2=CH₃
|Rα=
|R4=O-C(=O)-CH₃
|R5=
}}
{{#set:Featured=true}}