4-AcO-DMT

Summary sheet: 4-AcO-DMT
4-AcO-DMT
4-AcO-DMT.svg
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
Class Membership
Psychoactive class Psychedelic
Chemical class Tryptamine
Routes of Administration

WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.



⇣ Oral
Dosage
Threshold 5 mg
Light 7.5 - 15 mg
Common 15 - 25 mg
Strong 25 - 45 mg
Heavy 45 mg +
Duration
Total 4 - 7 hours
Onset 15 - 40 minutes
Come up 30 - 75 minutes
Peak 2 - 3.5 hours
Offset 1 - 2 hours
After effects 4 - 48 hours



⇣ Insufflated
Dosage
Threshold 5 mg
Light 10 - 15 mg
Common 15 - 25 mg
Strong 25 - 50 mg
Heavy 50 mg +
Duration
Total 3 - 5 hours
Onset 5 - 25 minutes
Come up 30 - 60 minutes
Peak 1.5 - 2.5 hours
Offset 1 - 1.5 hours
After effects 2 hours






DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.

Interactions
Cannabis
Stimulants
Tramadol
Lithium

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 psychedelic substance of the 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-AcO-DMT was first synthesized in 1963 by Albert Hofmann and Franz Troxler as part of a chemical investigation into psilocin analogs.[1] 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.[2] Reports of recreational use began to surface shortly after its appearance on the online research chemical market in the 2010s.[citation needed]

Subjective effects include geometric visual effects, time distortion, 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".

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 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.

History and culture

 

This History and culture section is a stub.

As a result, it may contain incomplete or wrong information. You can help by expanding it.

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

Chemistry

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 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

Further information: 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 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.

Claims of subjective differences in effects between the acetylated and non-acetylated forms of psilocin vary:[3] 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

Users frequently describe 4-AcO-DMT as being extremely similar to psilocybin mushrooms. It is generally described as euphoric, gentle, warm, and colorful. Visuals are reported by some users to be brighter and more neon in a manner reminiscent of DMT. It is also reported to be less nauseating than psilocybin mushrooms, which may be due to the fact that it does not require digesting mushroom matter.

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.

Physical effects
 

    • 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.
    • Perception of bodily heaviness
    • 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 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 oftentimes 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 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 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 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.
    • 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 effect 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
 

Cognitive effects
 

Auditory effects
 

Multi-sensory effects
 

    • 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.
    • Dosage independent intensity[citation needed]

Transpersonal effects
 

Combination effects

  • 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.
  • Dissociatives - 4-AcO-DMT enhances the geometry, euphoria, dissociation and hallucinatory effects of all dissociatives, especially dissociative-induced holes, spaces, and voids. It may also significantly increase internal hallucinations, confusion, nausea, delusions and the chance of a psychotic reaction.
  • MDMA - 4-AcO-DMT strongly amplifies the visual, physical and cognitive effects of MDMA. The synergy between these substances is unpredictable, and it is best to start with lower doses than one would take for both substances individually. The toxicity risk 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 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

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

Additional experience reports can be found here:

Toxicity and harm potential

Further information: Research chemicals § Toxicity and harm potential, and Responsible use § Hallucinogens

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

Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

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.

  • Australia: 4-AcO-DMT can be considered an analog of psilocin, making it a Schedule 9 controlled substance in Australia under the Poisons Standard.[8] 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]
  • Brazil: 4-AcO-DMT is illegal to possess, produce, and sell as it is listed on Portaria SVS/MS nº 344.[9]
  • Germany: Because it is an ester of DMT, 4-AcO-DMT is controlled under Anlage I BtMG (Narcotics Act, Schedule I)[10] as of January 24, 1974.[11] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[12]
  • Italy: 4-AcO-DMT is illegal in Italy as it is an ester of an illegal substance.[citation needed]
  • Japan: 4-AcO-DMT is a controlled substance in Japan effective July 29th, 2015.[13]
  • Sweden: 4-AcO-DMT is a Schedule I controlled substance as of January 25, 2017[14]
  • Switzerland: 4-AcO-DMT could be considered an ester analog of Psilocin, which would make it illegal according to Buchstabe B.[15]
  • Turkey: 4-AcO-DMT is a classed as drug and is illegal to possess, produce, supply, or import.[16] [17]
  • United Kingdom: 4-AcO-DMT is a Class A drug in the UK as it is an ester of the Class A drug psilocin.[18]
  • 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

External links

Forum discussion

Literature

  • Vargas‐Perez, H., Grieder, T. E., Ting‐A‐Kee, R., Maal‐Bared, G., Chwalek, M., & van der Kooy, D. (2017). A single administration of the hallucinogen, 4‐acetoxy‐dimethyltryptamine, prevents the shift to a drug‐dependent state and the expression of withdrawal aversions in rodents. European Journal of Neuroscience, 45(11), 1410-1417. https://doi.org/10.1111/ejn.13572

References

  1. ↑ 1.0 1.1 "Bibliographic data: US3075992 (A) ― 1963-01-29". European Patent Office. Retrieved July 18, 2020. 
  2. ↑ Nichols, D. E.; Frescas, S. (June 1999). "Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin" (PDF). Synthesis. 1999 (6): 935–938. eISSN 1437-210X. ISSN 0039-7881. 
  3. ↑ "4-AcO-DMT (also 4-acetoxy-N,N-dimethyltryptamine) : Erowid Exp: Main Index". www.erowid.org. Archived from the original on 2010-07-28.
  4. ↑ Armstrong, B. D.; Paik, E.; Chhith, S.; Lelievre, V.; Waschek, J. A.; Howard, S. G. (October 26, 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. doi:10.1002/nrc.20023. eISSN 1520-6769. 
  5. ↑ Gudelsky, G. A.; Yamamoto, B. K.; Nash, F. (November 3, 1994). "Potentiation of 3,4-methylenedioxymethamphetamine-induced dopamine release and serotonin neurotoxicity by 5-HT2 receptor agonists". European Journal of Pharmacology. 264 (3): 325–330. doi:10.1016/0014-2999(94)90669-6. eISSN 1879-0712. ISSN 0014-2999. OCLC 01568459. 
  6. ↑ Capela, J. P.; Fernandes, E.; Remião, F.; Bastos, M. L.; Meisel, A.; Carvalhoa, F. (July 2007). "Ecstasy induces apoptosis via 5-HT2A-receptor stimulation in cortical neurons". NeuroToxicology. 28 (4): 868–875. doi:10.1016/j.neuro.2007.04.005. ISSN 0161-813X. OCLC 47153737. PMID 17572501. 
  7. ↑ 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. ISSN 1556-9039. 
  8. ↑ "Poisons Standard". Federal Register of Legislation. Australian Government. October 2020. Retrieved October 23, 2020. 
  9. ↑ "RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016" (in Portuguese). Agência Nacional de Vigilância Sanitária (ANVISA) [Brazilian Health Regulatory Agency (ANVISA)]. December 5, 2016. 
  10. ↑ "Betäubungsmittelgesetz (BtMG) Anlage I" [Narcotics Act (BtMG) Schedule I] (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019. 
  11. ↑ "Sechste Verordnung über die den Betäubungsmitteln gleichgestellten Stoffe" (PDF). Bundesgesetzblatt Jahrgang 1974 Teil I Nr. 6 (in German). Bundesanzeiger Verlag (published January 23, 1974). January 17, 1974. pp. 97–98. eISSN 0344-7634. 
  12. ↑ "Betäubungsmittelgesetz (BtMG) § 29" [Narcotics Act (BtMG) § 29] (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019. 
  13. ↑ "危険ドラッグの成分４物質を新たに指定薬物に指定" (in Japanese). 厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)]. Retrieved May 2, 2022. 
  14. ↑ "Gemensamma författningssamlingen avseende hälso- och sjukvård, socialtjänst, läkemedel, folkhälsa m.m" (PDF). Läkemedelsverket [Medical Products Agency] (published January 16, 2017). January 10, 2017. ISSN 2002-1054. HSLF-FS 2017:1. Archived from the original (PDF) on October 31, 2017. 
  15. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020. 
  16. ↑ https://resmigazete.gov.tr/eskiler/2014/01/20140125-3.htm
  17. ↑ https://resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf
  18. ↑ "Part I: Class A Drugs". "Misuse of Drugs Act 1971". UK Government. Retrieved January 7, 2020. 


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