Psychedelic Research Chemicals or RC Chems are new synthetic substances which are structurally similar to the original drug, while being functional analogs. Data on their effects limited due as they’re fairly new and do not have a lot of human consumption history.

Psychedelics are substances (natural or laboratory made) which cause profound changes in a one’s perceptions of reality. While under the influence of hallucinogens, users might hallcuniate visually and auditorily.

This is a commonly used substance with well known effects, but that does not guarantee the substance will be safe. The safety profile has been established based on usage data commonly reported by others.

Disclaimer: Psychedelic drugs offer some of the most powerful and intense psychological experiences. Additionally these substances are illegal in many places. We understand that even though these substances are illegal, their use occurs frequently. We do not condone breaking of the law. By providing accurate information about these substances, we encourage the user to make responsible decisions and practice harm reduction.

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Description

4-AcO-DMT Also known as:

  • 1H-Indol-4-ol, 3-[2-(dimethylamino)ethyl]-, acetate (ester)[ACD/Index Name]
  • 3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl acetate[ACD/IUPAC Name]
  • 3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl-acetat[German][ACD/IUPAC Name]
  • 4-acetoxy-N,N-dimethyltryptamine
  • 4-AcO-DMT
  • 8BLF220HX1
  • Acétate de 3-[2-(diméthylamino)éthyl]-1H-indol-4-yle[French][ACD/IUPAC Name]
  • [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] acetate
  • 3-(2-(Diethylamino)ethyl)-1H-indol-4-yl acetate
  • 3-(2-(dimethylamine)ethyl)-1H-indol-4-yl-acetate[ACD/IUPAC Name]
  • 3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl acetate fumarate salt
  • 4-Acetoxy-N,N-dimethyltryptamine free base
  • 4-acetoxy-N,N-dimethyltryptamine fumarate
  • 4-Acetoxy-N,N-dimethyltryptamine, free base
  • '92292-84-7
  • A-0279
  • MFCD04279029[MDL number]
  • MFCD04972029
  • UNII:8BLF220HX1
  • 3-(2-(Dimethylamino)ethyl)-1H-indol-4-yl acetate
  • 3-(2-(Dimethylamino)ethyl)-1H-indol-4-ylacetate

A prodrug for Psilocin with extremely similar effects as Mushrooms.

Summary

It is a structural analog of psilocybin, the active ingredient in psilocybin mushrooms (magic mushrooms). Like psilocybin, it is thought to produce its effects primarily by binding to serotonin receptors in the brain; however, the precise mechanism is not fully understood. The synthesis of 4-AcO-DMT was first reported in 1963 by and Franz Troxler as part of an investigation into psilocin analogs.

However, its pharmacology and subjective effects were not explored. A paper authored by David E. Nichols in 1999 proposed it as a potentially useful alternative to psilocybin for pharmacological research due to lower cost of synthesis.

Reports of recreational use began to surface shortly after its appearance on the online research chemical market in the 2010s. Subjective effects are reported to be nearly identical to those of psilocybin mushrooms and include geometric visual hallucinations, time distortion, enhanced introspection, euphoria, and ego loss. 4-AcO-DMT is theorized to act as a prodrug to psilocin in a similar manner as 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. Very little data exists on the pharmacology, metabolism, and toxicity of 4-AcO-DMT. While it is believed to have a favorable safety profile similar to that of psilocybin mushrooms (which are known to be physiologically non-toxic) there is currently no data to support this claim.

It is highly advised to use harm reduction practices if using this substance.

History

4-AcO-DMT and several other esters of psilocin were patented on January 16, 1963 by Sandoz Ltd. via Albert Hofmann & Franz Troxler. However, its pharmacology and subjective effects were not investigated.

It is unknown when 4-AcO-DMT’s effect in humans were first explored.

Chemistry

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.

Common NameO-Acetylpsilocin
Systematic nameO-Acetylpsilocin
FormulaC_{14}H_{18}N_{2}O_{2}
SMILESCC(=O)Oc1cccc2c1c(c[nH]2)CCN(C)C
Std. InChiInChI=1S/C14H18N2O2/c1-10(17)18-13-6-4-5-12-14(13)11(9-15-12)7-8-16(2)3/h4-6,9,15H,7-8H2,1-3H3
Std. InChiKeyRTLRUOSYLFOFHV-UHFFFAOYSA-N
Avg. Mass246.3049 Da
Molecular Weight246.3049
Monoisotopic Mass246.136826 Da
Nominal Mass246
ChemSpider ID21106357

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Dose Chart

Oral
Light5-10mg
Common10-25mg
Heavy25-40mg

Duration Chart

4-AcO-DMT Duration Data
Onset20-90 minutes
Duration4-8 hours
After-effects1-12 hours

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.

  • Belgium: 4-AcO-DMT is illegal to import in Belgium.

  • Brazil: 4-AcO-DMT is illegal to possess, produce, and sell as it is listed on Portaria SVS/MS nº 344.
  • Germany: Because it is an ester of DMT, 4-AcO-DMT is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of January 24, 1974. It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.
  • Italy: 4-AcO-DMT is illegal in Italy as it is an ester of an illegal substance.
  • Sweden: 4-AcO-DMT was made illegal in Sweden on 25 January 2017.
  • United Kingdom: 4-AcO-DMT is a Class A drug in the UK as it is an ester of the Class A drug psilocin.
  • 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.

    • Sources

    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. US patent 3075992, Hofmann A, Troxler F, "Esters of indoles", assigned to Sandoz Ltd.
    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. :10.1007/BF03161089.  1556-9039.
    9. http://portal.anvisa.gov.br/documents/10181/3115436/(1)RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
    10. "Sechste Verordnung über die den Betäubungsmitteln gleichgestellten Stoffe" (in German). Bundesanzeiger Verlag. Retrieved December 10, 2019.
    11. "Anlage I BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
    12. "§ 29 BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
    13. Misuse of Drugs Act 1971 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I/paragraph/3

    Information made possible with:

    1. PsychonautWiki is a community-driven online encyclopedia that aims to document the field of psychonautics in a comprehensive, scientifically-grounded manner.
    2. Erowid is a non-profit educational & harm-reduction resource with 60 thousand pages of online information about psychoactive drugs
    3. PubChem National Center for Bio Informatics
    4. Chemspider is a free chemical structure database providing fast access to over 34 million structures, properties and associated information.
    5. Wikipedia

    Additional APIs were used to construct this information. Thanks to ChemSpider, NCBI, PubChem etc.

    Data is constantly updated so please check back later to see if there is any more available information on this substance.