4-AcO-DMT
| Summary sheet: 4-AcO-DMT |
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| Chemical Nomenclature | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Common names | 4-AcO-DMT, 4-Acetoxy-DMT, Psilacetin, O-Acetylpsilocin, "Synthetic shrooms" | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substitutive name | 4-Acetoxy-N,N-dimethyltryptamine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Systematic name | 3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl acetate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Psychoactive class | Psychedelic | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical class | Tryptamine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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4-Acetoxy-N,N-dimethyltryptamine (also known as 4-AcO-DMT, 4-Acetoxy-DMT, O-Acetylpsilocin, and Psilacetin) is a psychedelic substance of the tryptamine chemical class. Members of this group produce psilocin-like classical psychedelic effects when administered. It is structurally related to substituted tryptamines like 4-AcO-MET, 4-AcO-DET, and 4-AcO-MiPT.
4-AcO-DMT and several other esters of psilocin were originally patented on January 16, 1963 by Sandoz Ltd.[1][2] It had a limited history of use prior to its appearance online as a grey area research chemical. It has since gained a sizable cult following due to its reputation for producing traditional entheogenic effects despite having a purely synthetic origin.[citation needed]
The effects of 4-AcO-DMT are often compared to those of psychedelic tryptamines like psilocybin mushrooms and DMT. It is typically taken orally, less commonly via insufflation and rarely, via injection.[citation needed]
Notably, this compound has been proposed by psychedelics researcher David Nichols to be a potentially useful alternative to psilocybin for pharmacological research as both are thought to act as prodrugs for psilocin (4-HO-DMT), the primary active component of psilocybin mushrooms.[3] Its structural similarity to psilocybin is thought to account for the near identical effects they produce and they are often considered to be interchangeable.[citation needed]
Contents
Chemistry
4-Acetoxy-N,N-dimethyltryptamine, or 4-AcO-DMT, is a synthetic indole alkaloid molecule of the tryptamine chemical class. Tryptamines share a core structure comprising 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 RN of the ethyl side chain, meaning it contains the DMT molecule as its molecular backbone.
Structurally, 4-AcO-DMT is the acetate ester analog of psilocin (4-HO-DMT) and the N-substituted methyl homolog of 4-AcO-MET. It can be considered to be the O-acetylated form of psilocin, whereas psilocybin is the O-phosphorylated form.
Pharmacology
4-AcO-DMT's psychedelic effects are believed to come from its efficacy at the 5-HT2A receptor as a partial agonist. However, the role of these interactions and how they result in the psychedelic experience remains the subject of ongoing scientific investigation.
Pharmacokinetics
In the body, 4-AcO-DMT is thought to be deacetylated into psilocin during first pass metabolism, by the acidic conditions in the stomach, and it subsequently passes through the liver (this is made evident by the fact that 4-AcO-DMT is also active when injected). This has not been formally proven, however, and is based on reports that most users cannot identify the difference between these two compounds when ingested to the point that they are often considered as indistinguishable from each other in terms of their subjective effects.
There are, however, claims of subjective differences in effect between the acetylated and non-acetylated forms of psilocin.[4] Some users report that 4-AcO-DMT lasts slightly longer than psilocin while others report that it lasts for a considerably shorter time. Many users report less body load and nausea compared to psilocin. Some users find that the visual distortions produced by 4-AcO-DMT more closely resemble those produced by DMT than those produced by psilocybin mushrooms. These differences, if substantiated, may be due to unique effects produced by 4-AcO-DMT itself prior to deacetylation, to different pharmacokinetics (i.e. different rates of absorption and distribution), or both.
Subjective effects
The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects should be taken with a grain of salt and will rarely (if ever) occur all at once, but heavier doses will increase the chances and are more likely to induce a full range of effects. Likewise, adverse effects become much more likely on higher doses and may include serious injury or death.
Physical effects 
-
- 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.
- Spontaneous physical 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 physical and cognitive euphoria along with tranquility, a sense of lethargy or sedation, or total immobilization depending on the dose.
- Physical euphoria - This effect is not as reliably induceable for psychedelics like psilocin than it is with other substance classes like stimulants or entactogens, and can just as easily manifest as extreme physical discomfort without any apparent cause.
- 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.
- 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 mushrooms, perhaps owing to the fact that there is no fungal-matter the body has to digest when the isolated synthetic form is consumed.
- 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.
- 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.
- Muscle relaxation
- Excessive yawning - This effect seems to be uniquely pronounced among psilocin and related tryptamines. It can occur to a lesser degree on LSD and very rarely on psychedelic phenethylamines like mescaline. It typically occurs in conjunction with watery eyes.
- Watery eyes
- Olfactory hallucinations
- Pupil dilation
- Runny nose
- Salivation
- Teeth grinding - This component is considerably less intense when compared with substances like MDMA when it occurs.
- Seizure - This is likely a rare effect and is thought to primarily be a risk factor in those already predisposed to them, particularly while in physically taxing conditions such as being overheated, dehydrated, undernourished or fatigued. However, it should be noted that there are no documented cases of seizures occurring with this compound.[citation needed]
Visual effects 
-
Enhancements
Distortions
- Drifting (melting, flowing, breathing and morphing) - In comparison to other psychedelics, this effect can be described as highly detailed, realistic, slow and smooth in motion and static in appearance.
- Colour shifting
- Colour tinting
- Visual haze
- Diffraction
- Tracers
- After images
- Symmetrical texture repetition
- Perspective distortions
- Depth perception distortions
- Environmental orbism
- Scenery slicing
- Environmental geometry
Geometry
The visual geometry that is present throughout this experience 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 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 have a very "natural" feel to them and at higher dosages are significantly more likely to result in states of Level 8B visual geometry over Level 8A.
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:
- Transformations
- Machinescapes - This component 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.
- Internal hallucinations (autonomous entities; settings, sceneries, and landscapes; alterations in perspective and scenarios and plots) - This effect is very consistent in dark environments at appropriately high dosages. They can be comprehensively described through their 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.
- External hallucinations (autonomous entities; settings, sceneries, and landscapes; alterations in perspective and scenarios and plots)
Cognitive effects 
-
The cognitive effects of 4-AcO-DMT are described by many as extremely relaxing, profound and slow-paced in style when compared to other commonly used psychedelics such as LSD or 2C-B which tend to have a distinct energetic and stimulating push. It is also generally regarded as being notably more lucid than psilocybin mushrooms, which often leads users to report similarities between it and the DMT headspace, especially at higher doses. It contains a large number of both typical and unique psychedelic cognitive effects.
The most prominent of these effects generally include:
- Analysis enhancement - This effect is consistent in its manifestation with a tendency to be outrospective in nature, but may also manifest as introspection depending on one's set and setting.
- Novelty enhancement
- Immersion enhancement
- Creativity enhancement
- Conceptual thinking
- Personal bias suppression
- Multiple thought streams
- 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.
- Simultaneous emotions
- 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.
- 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.
- 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.
- Increased sense of humor
- Increased music appreciation
- Perceived exposure to inner mechanics of consciousness
- Cognitive euphoria
- Memory suppression
- Feelings of impending doom - This effect is usually only experienced during the come up phase but typically completely passes or subsides once the primary effects begin. It should be noted that this effect is relatively consistent and normal for psilocin and related tryptamines which is why a positive and well-informed mindset is key. Less regularly this aspect can also occur during the peak but will most often be met after with sensations of euphoria and rejuvenation.
- Catharsis - While this component can occur spontaneously on its own, it typically follows a particularly challenging phase of the experience, if not after the entire experience itself has ended.
- Rejuvenation - While this component can occur spontaneously on its own, it typically follows a particularly challenging phase of the experience, if not after the entire experience itself has ended.
- Thought connectivity
- Thought deceleration
- Thought organization
- Thought loops
- Time distortion
- Confusion
- Delusions
- Déjà vu
- Mindfulness
- 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.
- 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.
- Brain zaps - This effect is uncommon and believed to only occur in those who are predisposed to them. It is much less common and intense than it is with serotonin releasing agents such as MDMA.
Auditory effects 
Multi-sensory effects 
-
- 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.
- Dosage independent intensity[citation needed]
Transpersonal effects 
- It should be noted that these effects are the rarest and least reproducible those that can occur during a psychedelic experience. They are considered unique in that that simply taking more of the substance does not necessarily increase the chance they will occur, and are said to rely more on contextual factors such as the user's set and setting rather than the substance or dose itself. Their fullest manifestations are sometimes called "peak", "transcendent" or "transformative" experiences; however, they can still occur on a conceptual or cognitive level that can leave a lasting positive impact on the user.
Combinational effects
- Cannabis - When used in conjunction with cannabis, both the visual and cognitive effects of 4-AcO-DMT can be intensified and extended with extreme efficiency. This should be used with extreme caution, especially if one is not experienced with psychedelics. This interaction can also amplify the anxiety, confusion and psychotomimetic producing aspects of cannabis significantly. The THC and psilocybin synergy is unique in that the severity of its mind-altering qualities can greatly depend on when during the experience the cannabis is taken, as 4-AcO-DMT experiences are often considered to have less of a predictable continuity than many other commonly used psychedelics.
- Dissociatives - When used in combination with dissociatives, the geometry, euphoria, dissociation and hallucinatory effects are often greatly enhanced. Dissociative-induced holes, spaces, and voids while under the influence of psilocybin 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 - When used in conjunction with MDMA, the physical and cognitive effects of MDMA are amplified. The visual, physical and cognitive effects of the 4-AcO-DMT are also intensified, sometimes to the point of overwhelming euphoric bliss manifested through uniquely pleasurable body highs and headspaces, as well as fantastic colorful, intricate and majestic visuals. The synergy between these substances is unpredictable, and it is best to start with lower dosages than one would take for both substances individually. It should be noted that the potential toxic effects of this combination are, however, unknown.
- Alcohol - This interaction is not typically recommended 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, albeit on a more stressful manner on the body.
- Benzodiazepines - When used in combination with benzodiazepines, benzodiazepines can, depending on the dosage, 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 acquiring them for this purpose, however, due to the very high addiction potential associated with benzodiazepines.
- Psychedelics - When used in combination with other psychedelics, each substance's physical, cognitive and visual effects intensify and synergize strongly. The synergy between those substances is unpredictable, and for this reason, generally not advised. If choosing to combine psychedelics, it is recommended to start with significantly lower dosages than one would take for either substance individually.
Experience reports
Anecdotal reports which describe the effects of this compound within our experience index include:
- Experience:100mg 4-AcO-DMT (insufflated) - Went deep in a dark house
- Experience:20mg (insufflated) - Four years of sustained unity during everyday sober living
- Experience:20mg (insufflated) - I was overcome with feelings about my family
- Experience:20mg (insufflated) - permanent all-encompassing states of unity and interconnectedness
- Experience:20mg - A profound sense of oneness
- Experience:20mg - High Weight, No Effects
- Experience:20mg - I looked up and saw an angry god-like figure made of clouds glaring down at me
- Experience:20mg - Relationship problems
- Experience:25mg (insufflated) - Simultaneously amazing and horrible
- Experience:25mg - A labyrinth of organs and a storybook walk
- Experience:25mg 4-AcO-DMT (insufflated) - An interesting night of television
- Experience:26mg - I begged the shroom aliens to kill me
- Experience:26mg - Stage 3 Trip
- Experience:35mg 4-AcO-DMT (rectal) - Colorful Bliss of Ice Cream
- Experience:4-AcO-DMT -- Recklessness rewarded
- Experience:40 mg - A relaxing morning in the park
- Experience:40mg + Syrian Rue (unknown dosage) - My one bad trip
- Experience:40mg + Syrian rue (3g) - My triumphant return
- Experience:40mg - Brothermind and the Forest's Hand
- Experience:45mg 2cc & 45mg 4-aco-dmt - Ego death and loneliness
- Experience:50mg - How's the short-term memory?
- Experience:60mg 4-AcO-DMT + Syrian rue (3g) - Surrender
- Experience:60mg 4-AcO-DMT Nonstop Quasi-Orgasmic Objectless Euphoria
- Experience:70 mg - Overcoming personal problems
- Experience:A combination of 25mg 4-AcO-DMT and unknown amount of 6-APB (benzofury)
Additional experience reports can be found here:
Toxicity and harm potential
The toxicity and long-term health effects of recreational 4-AcO-DMT has not been studied in any scientific context and the exact toxic dose is unknown. This is because 4-AcO-DMT is a research chemical with a very brief history of human usage. However, it is assumed to have a similar toxicity profile as psilocybin due to their structural similarity.
Anecdotal reports from those who have tried 4-AcO-DMT suggests that there are no negative health effects attributed to simply trying the substance 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.
Tolerance and addiction potential
Although no formal studies have been conducted, it is believed that 4-AcO-DMT is not habit-forming and the desire to use it can actually decrease with use.
Tolerance to the effects of 4-AcO-DMT is built almost immediately after ingestion. After that, it takes about 3 days for the tolerance to be reduced to half and 7 days to be back at baseline (in the absence of further consumption). 4-AcO-DMT presents 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 safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.
- Lithium - Lithium is often used as treatment for bipolar disorder. It can dangerously amplify the intensity of psychedelics and has been strongly linked with psychosis and seizures. The causes are poorly understood, but it may be due to its glutaminergic and GABAergic properties.[citation needed]
- Stimulants - Stimulants affect many parts of the brain. Combined with psychedelics, stimulation can turn into uncontrollable anxiety, panic, thought loops and paranoia. This interaction may cause elevated risk of psychosis.[citation needed]
- Tramadol - Tramadol lowers the seizure threshold[5] and psychedelics may act as triggers for seizures, particularly in those who are predisposed to them.[citation needed]
Legal status
The possession and sale of 4-AcO-DMT is currently unscheduled in most countries.
- Belgium: The import of 4-AcO-DMT is illegal.[citation needed]
- Brazil: Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.[6]
- Germany: 4-AcO-DMT is not explicitly mentioned in the BtMG. However, as it is an ester of psilocin, it is illegal to possess, produce and sell.[7]
- Italy: This drug is illegal 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]
- United Kingdom: 4-AcO-DMT is a Class A drug in the UK as it is an ester of the Class A drug psilocin.[8]
- United States: 4-AcO-DMT is unscheduled in the United States. It may be considered an analogue of psilocin (which is 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
External links
Discussion
References
- ↑ http://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US3075992
- ↑ http://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=3075992&KC=&FT=E&locale=en_EP
- ↑ Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin | http://www.erowid.org/archive/rhodium/pdf/nichols/nichols-psilocin.pdf
- ↑ http://www.erowid.org/experiences/subs/exp_4AcODMT.shtml
- ↑ Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., & Abdollahi, M. (2009). Dose-independent occurrence of seizure with tramadol. Journal of medical toxicology, 5(2), 63-67. doi:10.1007/BF03161089
- ↑ http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
- ↑ BtMG Anlage I | https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html
- ↑ Misuse of Drugs Act 1971 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I/paragraph/3