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.

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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

4-AcO-DMT

4-AcO-DMT

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

Auditory Effects

Psychological Effects

The cognitive effects and general head space of 4-AcO-DMT are commonly described as extremely relaxing, profound and slow-paced in style when compared to other commonly used psychedelics, such as LSD or 2C-B, which have a distinct energetic and stimulating push. It is also generally regarded as being notably more lucid than psilocybin mushrooms.

Pharmacological Effects

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.

Physical Effects

  • Sedation - 4-AcO-DMT is considered by most to be relaxing, stoning and mildly sedating. This sense of sedation is often accompanied by compulsive yawning.
  • Perception of bodily heaviness
  • Spontaneous bodily sensations - The general "body high" of 4-AcO-DMT can be described as a 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 often times 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 before-hand, 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 fluctuates 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 - 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.

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

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.

Visual Effects

Enhancements

Distortions

Geometry

The visual geometry of 4-AcO-DMT can be described as more similar in appearance to that of psilocin, low-medium dose DMT, and ayahuasca as opposed to LSD or 2C-B. It can be comprehensively described through its variations as intricate in complexity, abstract in form, organic in style, structured in organization, brightly lit and multicoloured in scheme, glossy in shading, soft in edges, large in size, slow in speed, smooth in motion, rounded in corners, non-immersive in-depth and consistent in intensity. They can be described as having a "natural" feel and, at higher doses, are significantly more likely to result in states of Level 8B visual geometry over Level 8A.

Hallucinatory states

4-AcO-DMT produces a full range of high level hallucinatory states in a fashion that is more consistent and reproducible than that of many other commonly used psychedelics. These effects generally include:

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

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