4-AcO-DMT
| Summary sheet: 4-AcO-DMT |
| 4-AcO-DMT | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Chemical Nomenclature | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Common names | 4-AcO-DMT, 4-Acetoxy-DMT, Psilacetin, O-Acetylpsilocin, "Synthetic mushrooms" | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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 novel psychedelic substance of the tryptamine class. 4-AcO-DMT is chemically similar to psilocybin, the active ingredient in psilocybin mushrooms (magic mushrooms). It belongs to a group known as the substituted tryptamines which produce their effects through action at serotonin receptors in the brain.
The synthesis of 4-AcO-DMT was first reported in 1963 by Albert Hofmann and Franz Troxler.[1][2] However, its properties were not examined and no further studies were carried out. A 1999 paper by David E. Nichols suggested it as a useful alternative to psilocybin for pharmacological research.[3] Reports of human use began to surface following its appearance on the online research chemical market in the 2010s.
Users report that the subjective effects of 4-AcO-DMT are extremely similar to those of psilocybin mushrooms. Like psilocybin, 4-AcO-DMT is theorized to act as a prodrug to psilocin, which may account for this similarity. Typical effects include geometric visual hallucinations, time distortion, enhanced introspection, and ego loss. 4-AcO-DMT's classical psychedelic effects and favorable tolerability profile has led it to become popular among novel psychoactive substance users, particularly those seeking mystical or entheogenic experiences.
Very little data exists on the pharmacology, metabolism, and toxicity of 4-AcO-DMT. Like other psychedelics, it is assumed to be non-toxic and non-addictive (although there is no evidence to support this). It is highly advised to use harm reduction practices if using this substance.
Contents
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 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.
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-HT2A 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.
The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. These 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 of inducing 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.
- Perception of bodily heaviness
- 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 physical and cognitive euphoria along with tranquility, a sense of lethargy or sedation, or total immobilization depending on the dose.
- 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 itchy or even ticklish against the skin.
- 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.
- Changes in felt gravity
- 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
- Frequent urination
- Gustatory enhancement
- Olfactory enhancement
- Olfactory hallucination
- Pupil dilation
- Runny nose
- Increased salivation
- Teeth grinding - This component is considerably less intense when compared with substances like MDMA when it occurs.
- Brain zaps - This effect is uncommon and thought to only occur in those who are predisposed to them. It is much less prevalent and intense than those that occur with serotonin releasing agents such as MDMA.
- Seizure[citation needed] - This is a rarely observed 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.
Visual effects 
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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 patterning
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 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 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 hallucination (autonomous entities; settings, sceneries, and landscapes; perspective hallucinations 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 hallucination (autonomous entities; settings, sceneries, and landscapes; perspective hallucinations and scenarios and plots) - These are more common within dark environments and 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.
Cognitive effects 
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The cognitive effects and general head space of 4-AcO-DMT are commonly described as extremely relaxing, profound and slow-paced in style when compared to other commonly used psychedelics, such as LSD or 2C-B, which have a distinct energetic and stimulating push. It is also generally regarded as being notably more lucid than psilocybin mushrooms.
- 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
- 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
- Rejuvenation - While this component can occur spontaneously at any point, it typically follows a difficult phase of the experience, if not the entire experience itself.
- Thought connectivity
- Thought deceleration
- Thought organization
- Thought loops
- Time distortion
- Confusion
- Delusion
- 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.
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]
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 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 - 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.[4][5][6]
- 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.
- 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.
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:170mg 4-AcO-DMT - Recklessness rewarded
- 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: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 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 safe to use on their own, they can become dangerous or even life-threatening when taken with other substances. The list below contains some potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses but still increase the possibility of injury of death. Independent research should always be conducted to ensure that a combination of two or more substances is safe before consumption.
- Lithium - Lithium is commonly used as treatment for bipolar disorder. It is known to dangerously amplify the intensity of psychedelics and has been strongly linked to psychosis and seizures.
- Stimulants - Stimulants affect many parts of the brain. Combined with psychedelics, stimulation can turn into uncontrollable anxiety, panic, thought loops and paranoia. This interaction results in an elevated risk of psychosis.[citation needed]
- Tramadol - Tramadol lowers the seizure threshold[7] and psychedelics may act as triggers for seizures in susceptible individuals.[citation needed]
Legal status
The possession and sale of 4-AcO-DMT is currently unscheduled in most countries.
- 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.[8]
- 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.[9]
- 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]
- United Kingdom: 4-AcO-DMT is a Class A drug in the UK as it is an ester of the Class A drug psilocin.[10]
- 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
External links
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
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
- ↑ 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.
- ↑ 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
- ↑ 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
- ↑ Ecstasy induces apoptosis via 5-HT(2A)-receptor stimulation in cortical neurons. | https://www.ncbi.nlm.nih.gov/pubmed/17572501
- ↑ 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