O-Acetylpsilocin

O-Acetylpsilocin

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Systematic (IUPAC) name
3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl acetate
Clinical data
Routes of administration	Oral, IV, intranasal, rectal
Legal status
Legal status	CA: notscheduled US: notscheduled May be considered Illegal in US if intended for human consumption (Analogue of Psilocin)
Identifiers
CAS Number	92292-84-7
ATC code	none
Chemical data
Formula	C14H18N2O2
Molar mass	246.3049 g/mol[[]]
Physical data
Melting point	172 to 173 °C (342 to 343 °F)

O-Acetylpsilocin, 4-acetoxy-N,N-dimethyltryptamine, or 4-AcO-DMT is a research chemical, psychedelic drug and has been suggested to be a potentially useful alternative to psilocybin for pharmacological studies. It is the acetylated form of the psychedelic mushroom alkaloid psilocin, and is a lower homologue of 4-AcO-DET, 4-AcO-MiPT and 4-AcO-DiPT.

History

O-Acetylpsilocin (Psilacetin) is a newer psychedelic with a limited history. It is theorized to be a prodrug for psilocin, which is naturally occurring in various mushrooms.

Chemistry

O-Acetylpsilocin can be obtained by acetylation of psilocin under strongly acidic or under alkaline conditions. It is a synthetic compound. However, it is believed to be metabolized back into psilocin, which is natural and occurs in many mushrooms, most famously of the Psilocybe genus. O-Acetylpsilocin is more resistant than psilocin to oxidation under basic conditions due to its acetoxy group. While 4-AcO-DMT is fairly new and not well researched (making it a research chemical, and thus not as widely known as psilocin and psilocybin), O-Acetylpsilocin is not as difficult to produce as psilocybin, and may be of use in psychedelic research that specifically uses psilocin/psilocybin.

Pharmacology

See psilocin for more details.

In the body 4-acetylpsilocin is evidently rapidly deacetylated to psilocin by acetylases during first pass metabolism.

There are claims of subjective differences in effect between the acetylated and not acetylated forms of psilocin. Some users report that 4-AcO-DMT lasts slightly longer than psilocin; others report that it lasts for a considerably shorter time. Many users report less bodyload 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 psilocin.

Dosage

A dose of O-acetylpsilocin is 8 mg - 30 mg. These are slightly lower than that of the free phenol, psilocin. Some report very strong effects with 15 mg. The duration of 4-acetylpsilocin is usually between 3 and 6 hours. It is also somewhat more potent. A dose of 15 mg can produce a very profound experience, with effects such as ego loss, strong visuals (open and closed eye), and other effects similar to a high dose of psilocin. Comparison to 4-HO-DMT (Psilocin) dosage suggests that 4-AcO-DMT is somewhat more potent, and possibly more variable in terms of subjective susceptibility. 4-AcO-DMT seems to have a more steep dose-effect curve than Psilocin; therefore, caution should be taken, especially with higher doses. There is no known LD50, as there are no reported cases of fatal overdose and no known mechanism by which an excessive dose could be life-threatening.

Dosages vary depending on the type of salt. The hydrochloride has a lower molecular mass and is therefore more potent on a per weight basis; however, 4-AcO-DMT HCl is relatively unstable and will degrade quickly at room temperature. 4-AcO-DMT is now most commonly distributed as the fumaric acid salt (4-AcO-DMT fumarate). The fumarate is slightly less potent on a per weight basis but it is considerably more stable and will not degrade substantially at room temperature.

Effects

As with psilocybin, present in magic mushrooms, 4-Acetoxy-DMT is metabolized into psilocin. The effects of 4-Acetoxy-DMT are therefore very similar to the effects of psilocybin and psilocin. Users report dose-dependent colorful visual effects and a sense of physical energy or euphoria, sometimes accompanied by abstract, associative, "trippy" thought patterns, or derealization.

Several available reports of 4-Acetoxy-DMT compare it favorably to psilocybin, describing it as more euphoric, gentle, warm, and colorful. It has also been described as less jarring, and less likely to produce nausea. However, many of these comparisons are made with mushrooms, not pure psilocybin. In addition, it is unknown to what degree expectancy plays a role in shaping that experience. Onset # The onset appears to last 30-40 minutes, with peak effects beginning at around 2 hours. The onset has been characterized as smoother, gentler, and more pleasant than the onset of mushrooms. Duration # The primary effects of 4-Acetoxy-DMT seem to typically last 4-6 hours. They have been described as lasting from 3-4 hours (low oral doses) to 8-10 hours (moderate to strong oral doses). Visual Effects # Visuals Summary Needed.

Legal Status

4-AcO-DMT may possibly be considered an analogue of psilocin, which is a Schedule I drug under the Controlled Substances Act of the USA, if there is evidence that it was being used for human consumption.

See also

• 4-MeO-DMT
• Psilocybin
• Tryptamine
• Indole
• Psychedelic drug
• Psychoactive drug
• Manna
• Teonanacatl
• Ayahuasca
• Soma

External links

• Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin - A publication by David E. Nichols
• Erowid 4-Acetoxy-DMT Vault

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