4-AcO-DMT

From PsychonautWiki
(Redirected from 4-aco-DMT)
Jump to: navigation, search
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 shrooms"
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
7.5 - 7.5 - 15 - 25 - 45 mg
Light Strong
Threshold 7.5 mg
Light 7.5 - 15 mg
Common 15 - 25 mg
Strong 25 - 45 mg
Heavy 45 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
Threshold Common Heavy
- 10 - 15 - 25 - 40 mg
Light Strong
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 lesser-known psychedelic substance of the tryptamine class that produces psilocin-like psychedelic effects when administered. It belongs to a group known as the substituted tryptamines, which includes chemically related compounds such as 4-AcO-MET, 4-AcO-DET, and 4-AcO-MiPT.

4-AcO-DMT and several other esters of psilocin were originally patented in 1963 by Sandoz Ltd.[1][2] However, its use in humans remained limited prior to appearing online as a grey area research chemical in the 2000s. It has since gained a cult following due to its reputation for inducing traditional entheogenic effects despite being purely synthetic in origin.[citation needed]

The effects of 4-AcO-DMT are often described as virtually indistinguishable from those of psilocybin mushrooms and psilocin. This can be attributed to similarities in their chemical structures. Notably, 4-AcO-DMT has been proposed by psychedelics researcher David E. Nichols to be a potentially useful alternative to psilocybin for pharmacological research as they are noth thought to act as prodrugs for psilocin (4-HO-DMT), the primary active component of psilocybin mushrooms.[3]

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

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 is the subject of ongoing scientific investigation.

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
Child.svg

Visual effects
Eye.svg

Cognitive effects
User.svg

Multi-sensory effects
Gears.svg

Combinational effects

  • Cannabis - When combined with cannabis, both the visual and cognitive effects of 4-AcO-DMT intensify 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 - 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 euphoria. 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, 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:


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 brief history of human usage. However, it is generally assumed to have a similar safety profile as psilocybin mushrooms due to their similarity in chemical structure.

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 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 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 (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

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. 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
  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