4-AcO-DMT

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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 Common Heavy
5 - 7.5 - 15 - 25 - 45 mg
Light Strong
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 Common Heavy
5 - 10 - 15 - 25 - 50 mg
Light Strong
Threshold 5 mg
Light 10 - 15
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 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 novel psychedelic substance of the tryptamine class. 4-AcO-DMT is chemically similar to psilocybin, the active constituent of psilocybin mushrooms (magic mushrooms). It belongs to a group known as the substituted tryptamines, which act by modifying the activity of the serotonin system in the brain.

The synthesis of 4-AcO-DMT was first reported in 1963 by Albert Hofmann and Franz Troxler.[1][2] However, further studies were not 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.

User reports indicate that the subjective effects of 4-AcO-DMT are extremely similar to those of psilocybin mushrooms. 4-AcO-DMT is theorized to act as a prodrug to psilocin like psilocybin, which may account for this similarity. Notable effects include geometric visual hallucinations, time distortion, enhanced introspection, and ego loss. Its classical psychedelic effects and favorable tolerability has led it to become popular among novel psychoactive substance users, particularly those seeking 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.

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, 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 is the O-acetylated form of psilocin, whereas psilocybin is the O-phosphorylated form.

Pharmacology

Further information: Serotonergic psychedelic

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.

There are, however, claims of subjective differences 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 or to different pharmacokinetics (i.e. different rates of absorption and distribution)

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
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Visual effects
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Cognitive effects
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Multi-sensory effects
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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 the neurotoxic effects of MDMA may become amplified.[5][6][7]
  • 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:


Additional experience reports can be found here:

Toxicity and harm potential

The toxicity and long-term health effects of 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 short history of human usage. It is assumed to have a similar safety profile as psilocybin mushrooms due to similarities in chemical structure, although there is currently no evidence to support this.

Anecdotal evidence 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 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[8] and psychedelics may act as triggers for seizures in susceptible persons.[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 in Belgium.[citation needed]
  • Brazil: Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.[9]
  • 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.[10]
  • 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.[11]
  • 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

  1. http://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US3075992
  2. http://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=3075992&KC=&FT=E&locale=en_EP
  3. 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.
  4. http://www.erowid.org/experiences/subs/exp_4AcODMT.shtml
  5. 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
  6. 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
  7. Ecstasy induces apoptosis via 5-HT(2A)-receptor stimulation in cortical neurons. | https://www.ncbi.nlm.nih.gov/pubmed/17572501
  8. 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
  9. http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
  10. BtMG Anlage I | https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html
  11. Misuse of Drugs Act 1971 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I/paragraph/3