4-AcO-DMT

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Summary sheet: 4-AcO-DMT
4-AcO-DMT
Molecular structure of Psilacetin
4-AcO-DMT.svg
Chemical Nomenclature
Common names 4-AcO-DMT, 4-Acetoxy-DMT, Psilacetin, O-Acetylpsilocin, "Shroom Powder"
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 - 10 mg
Light 10 - 20 mg
Common 20 - 30 mg
Strong 30 - 50 mg
Heavy 50 mg +
Duration
Total 4.5 - 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
Light 10 - 15 mg
Common 15 - 25 mg
Strong 25 - 40 mg
Heavy 40 mg +
Duration
Total 3 - 5 hours
Onset 5 - 25 minutes
Come up 30 - 60 minutes
Peak 1.5 - 2.5 hours
Offset 1 hours - 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.

4-Acetoxy-N,N-dimethyltryptamine (also known as 4-AcO-DMT, 4-Acetoxy-DMT, O-Acetylpsilocin, and Psilacetin) is a widely used synthetic psychedelic substance of the tryptamine chemical class that produces an array of "classical psychedelic" effects when administered. Its effects are often compared to those produced by entheogenic tryptamines like psilocybin mushrooms and DMT. It is typically taken orally, less commonly via insufflation and rarely, via injection.[citation needed]

This compound has been proposed by psychedelics researcher David Nichols to be a potentially useful alternative to psilocybin for pharmacological research as they are both believed to act as prodrugs for psilocin (4-HO-DMT), the primary active component of psilocybin mushrooms.[1] Its structural similarities to psilocin and psilocybin are thought to account for the near identical effects they produce and the three compounds are often considered to be interchangeable with each other.[citation needed]

Additionally, it is widely believed to have a similar if not near-identical toxicity profile as psilocybin itself, which makes it unusually physically benign and toxicologically predictable for a research chemical.

4-AcO-DMT and several other esters of psilocin were originally patented on January 16, 1963 by Sandoz Ltd. via Albert Hofmann & Franz Troxler.[2][3] Despite this, 4-AcO-DMT has a limited history of use prior to its release as a grey area compound on the online research chemical market, where it has over time gained a sizable cult following due to its reputation for producing classical entheogenic effects despite being a purely synthetic substance in origin.

After being exclusively distributed on the online grey-market for many years, 4-AcO-DMT has recently been documented being sold as "shroom pills" on the street (either in the form of pressed tablets or gel capsules).[citation needed]

Chemistry

A colour-coded visualization of 4-Acetoxy-N,N-dimethyltryptamine

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

Further information: Serotonergic psychedelic

Pharmacodynamics

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 has yet to be elucidated.

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 injury or death.

Physical effects
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Visual effects
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Cognitive effects
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Multi-sensory effects
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Transpersonal effects
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Experience reports

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

Additional experience reports can be found here:

Combinations

  • 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.

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, its close relationship with psilocin and psilocybin suggests that any would-be toxicity should be minimal.

Anecdotal evidence from people within the community who have taken 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

4-AcO-DMT is not habit-forming and the desire to use it can actually decrease with use. It is most often self-regulating.

Tolerance to the effects of 4-AcO-DMT is built almost immediately after ingestion. After that, it takes about 5-7 days for the tolerance to be reduced to half and 10-14 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

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This legality section is a stub.

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

  • International: The possession and sale of 4-AcO-DMT is currently unscheduled in most countries.
  • Belgium: The import of 4-AcO-DMT is illegal.
  • Brazil - Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.[6]
  • 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.
  • United Kingdom: 4-AcO-DMT is a Class A drug in the UK as it is an ester of the Class A drug psilocin.[7]
  • Italy: This drug is illegal as it is an ester of an illegal substance.
  • Sweden: 4-AcO-DMT was made illegal in Sweden on 25 January 2017.[citation needed]

See also

External links

References

  1. 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
  2. http://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US3075992
  3. http://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=3075992&KC=&FT=E&locale=en_EP
  4. http://www.erowid.org/experiences/subs/exp_4AcODMT.shtml
  5. 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
  6. http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
  7. Misuse of Drugs Act 1971 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I/paragraph/3