O-Acetylpsilocin: Difference between revisions

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+{{short description|Chemical compound}}
-{{Refimprove|date=March 2011}}
-{{Expert-subject|date=March 2011}}
+{{More citations needed|date=March 2011}}
 {{DISPLAYTITLE:''O''-Acetylpsilocin}}
+{{Infobox drug
-{{Drugbox
+| verifiedrevid = 447612407
-| Watchedfields = changed
+| drug_name = ''O''-Acetylpsilocin
-| verifiedrevid = 400333885
 | IUPAC_name = 3-[2-(Dimethylamino)ethyl]-1''H''-indol-4-yl acetate
 | image = O-Acetylpsilocin_chemical_structure.png
@@ Line 11: / Line 11: @@
 <!--Clinical data-->
 | tradename =
+| legal_AU = S9
-| legal_CA = notscheduled
+| legal_BR = F2
-| legal_US = notscheduled
+| legal_CA = Unscheduled
-| legal_status = May be considered Illegal in US if intended for human consumption (Analogue of Psilocin)
+| legal_DE = NpSG
+| legal_UK = Class A
+| legal_US = Unscheduled
 | routes_of_administration = Oral, IV, intranasal, rectal
 <!--Identifiers-->
+| CAS_number_Ref = {{cascite|correct|??}}
 | CAS_number = 92292-84-7
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 8BLF220HX1
 | ATC_prefix = none
 | PubChem = 15429212
@@ Line 25: / Line 31: @@
 <!--Chemical data-->
 | C=14 | H=18 | N=2 | O=2
+| smiles = CC(=O)Oc2cccc1[nH]cc(CCN(C)C)c12
-| molecular_weight = 246.3049 g/mol
-| smiles = CC(=O)Oc2cccc1ncc(CCN(C)C)c12
-| InChI = 1/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
-| InChIKey = RTLRUOSYLFOFHV-UHFFFAOYAA
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChI = 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
 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = RTLRUOSYLFOFHV-UHFFFAOYSA-N
+| synonyms = 4-Acetoxy-''N,N''-dimethyltryptamine, 3-(2'-dimethylaminoethyl)-4-acetoxy-indole<ref name="Esters of Indoles">{{ cite patent | country = US | number = 3075992 | status = patent | title = Esters of indoles | inventor = Hofmann A, Troxler F | assign1 = Sandoz Ltd. }}</ref>
 | melting_point = 172
 | melting_high = 173
 }}
+'''''O''-Acetylpsilocin''' (also known as '''psilacetin''', '''4-acetoxy-DMT''', '''4-AcO-DMT''', or '''synthetic shrooms''') is a semi-synthetic [[psychoactive drug]] that has been suggested by [[David E. Nichols|David Nichols]] to be a potentially useful alternative to psilocybin for pharmacological studies, as they are both believed to be [[prodrug]]s of [[psilocin]].<ref name="Nichols 1999 935–938">{{cite journal | vauthors = Nichols D, Fescas S |title=Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin |journal=Synthesis |volume=1999|year=1999 |issue= 6 |pages=935–938 |url=http://www.erowid.org/archive/rhodium/pdf/nichols/nichols-psilocin.pdf |access-date=17 January 2012 |url-status=live |archive-url= https://web.archive.org/web/20120217042615/http://www.erowid.org/archive/rhodium/pdf/nichols/nichols-psilocin.pdf |archive-date=17 February 2012 | doi=10.1055/s-1999-3490 |citeseerx=10.1.1.690.8071 |s2cid=32044725 }}</ref><ref>{{Cite web| vauthors = Bauer BE | date=2019-09-18|title=The State of the Art of Psilacetin (4-AcO-DMT)|url=https://psychedelicreview.com/the-state-of-the-art-of-psilacetin-4-aco-dmt/ |archive-url=|archive-date=|access-date=2021-02-13|website=Psychedelic Science Review|language=en-US}}</ref> However, some users report that ''O''-acetylpsilocin's subjective effects differ from those of psilocybin and psilocin.<ref name="erowid1">{{cite web|url=http://www.erowid.org/experiences/subs/exp_4AcODMT.shtml|title=4-AcO-DMT (also 4-acetoxy-N,N-dimethyltryptamine) : Erowid Exp: Main Index|website=www.erowid.org|url-status=live|archive-url=https://web.archive.org/web/20100728183810/http://www.erowid.org/experiences/subs/exp_4AcODMT.shtml|archive-date=2010-07-28}}</ref><ref>{{Cite web| vauthors = Janikian M |date=2020-05-26|title=The Complete Guide: 4-AcO-DMT a.k.a. Synthetic Shrooms|url=https://doubleblindmag.com/4-aco-dmt-or-synthetic-shrooms/ |website=DoubleBlind Mag|language=en-US}}</ref> Additionally, some users prefer 4-AcO-DMT to natural [[psilocybin mushroom]]s due to feeling fewer adverse side effects such as nausea and heavy body load, which are more frequently reported in experiences involving natural mushrooms.<ref>{{cite journal | vauthors = Palamar JJ, Acosta P | title = A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines | journal = Human Psychopharmacology | volume = 35 | issue = 1 | pages = e2719 | date = January 2020 | pmid = 31909513 | pmc = 6995261 | doi = 10.1002/hup.2719 }}</ref> It is the [[acetyl]]ated form of the [[psilocybin mushroom]] [[alkaloid]] [[psilocin]] and is a lower [[homologous series|homolog]] of [[4-Acetoxy-MET|4-AcO-MET]], [[4-Acetoxy-DET|4-AcO-DET]], [[4-AcO-MiPT]] and [[4-Acetoxy-DIPT|4-AcO-DiPT]].
-'''''O''-Acetylpsilocin''', 4'''-[[acetoxy]]-''N,N''-di[[methyl]][[tryptamine]]''', psilacetin, 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.<ref name="erowid1">http://www.erowid.org/experiences/subs/exp_4AcODMT.shtml</ref>  It is the [[acetyl]]ated form of the [[psychedelic]] [[mushroom]] [[alkaloid]] [[psilocin]], and is a lower [[homologous series|homologue]] of [[4-Acetoxy-DET|4-AcO-DET]], [[4-Acetoxy-MIPT|4-AcO-MiPT]] and [[4-Acetoxy-DIPT|4-AcO-DiPT]].
 == History ==
-''O''-Acetylpsilocin (Psilacetin) is a newer psychedelic with a limited history. It is theorized to be a [[prodrug]] for psilocin, as is psilocybin, which is naturally occurring in various mushrooms. Psilacetin is O-acetylated psilocin, whereas psilocybin is O-phosphorylated.
+''O''-Acetylpsilocin (psilacetin) and several other esters of psilocin were patented on January 16, 1963, by [[Sandoz]] Ltd via [[Albert Hofmann]] & Franz Troxler.<ref name="Esters of Indoles"/><ref>{{Cite patent | country = US | number = 3075992}}</ref> Despite this, psilacetin remains a psychedelic compound with a limited history of use. It is theorized to be a [[prodrug]] of psilocin, as is psilocybin, which occurs naturally in many species of psychedelic mushrooms. This is because the aromatic acetyl moiety on the 4th position of the indole ring system is subject to deacetylation in acidic conditions such as those found in the stomach.<ref>{{cite journal | vauthors = Staněk J, Černá MJ | title = Acidic deacetylation of sugar acetates. | journal = Tetrahedron Letters | date = January 1963 | volume = 4 | issue = 1 | pages = 35–7 | doi = 10.1016/S0040-4039(01)90572-6 }}</ref> Psilacetin is ''O''-acetylated psilocin, whereas psilocybin is ''O''-phosphorylated.
 == Chemistry ==
-''O''-Acetylpsilocin can be obtained by [[acetylation]] of psilocin under strongly [[acid]]ic or under [[Base (chemistry)|alkaline]] conditions.  It is a [[Chemical synthesis|synthetic]] compound. However, it is believed to be metabolized back into psilocin, which is [[Chemical synthesis|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 ''O''-acetylpsilocin 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.<ref>Like psilocybin, it is metabolically converted to psilocin and is therefore thought to be nearly identical to psilocybin in effects. erowid.org{{Verify credibility|date=February 2011}}</ref>
+''O''-Acetylpsilocin can be obtained by [[acetylation]] of psilocin under [[Base (chemistry)|alkaline]] or strongly [[acid]]ic conditions.  It is, therefore, a [[Organic compound#Synthetic compounds|synthetic]] compound. It is believed to be a [[prodrug]] of psilocin; however, speculation exists that psilacetin itself also may be psychoactive. ''O''-Acetylpsilocin is more resistant than psilocin to oxidation under basic conditions due to its acetoxy group. While ''O''-acetylpsilocin is not well researched (sometimes viewed negatively as a [[Designer drug|research chemical]], as opposed to psilocin and psilocybin), it is not as difficult as psilocybin to synthesize. Due to their similar proposed mechanisms of action, this factor may provide further support for the proposition that ''O''-acetylpsilocin might serve as an appropriate substitute for psilocybin in research of the application of psychedelic compounds in medicine.<ref name="Nichols 1999 935–938"/>
+Given enough time in unfavorable conditions ''O''-Acetylpsilocin can sometimes turn into a degraded form which is brown in color and can even progress into a brown/black goo of sorts. This is hypothesized to be a polymerization reaction and is said to have no effect on the potency of the drug. Preliminary [[Gas chromatography–mass spectrometry|GCMS]] analysis of the closely related homolog 4-Acetoxy-DET suggests that this degraded form of ''O''-Acetylpsilocin consists mainly of the hydroxy form of the parent molecule.<ref>{{cite web |title=Erowid 4-Acetoxy-DET Vaults : 4-Acetoxy-DET / Ethacetin Degradation |url=https://erowid.org/chemicals/4_acetoxy_det/4_acetoxy_det_article1.shtml |website=erowid.org |access-date=10 September 2023}}</ref>
 == Pharmacology ==
@@ Line 52: / Line 58: @@
 : ''See [[psilocin]] for more details.''
-In the body O-acetylpsilocin is evidently rapidly deacetylated to psilocin by [[deacetylase]]s during [[first pass effect|first pass metabolism]]{{Citation needed|date=November 2010}} and during subsequent passes through the liver (evident as psilacetin is also active via parenteral routes of ingestion).
+In the body ''O''-acetylpsilocin is [[Deacetylation|deacetylated]] to psilocin by [[Histone deacetylase|deacetylases]]/[[acetyltransferase]]s during [[first pass effect|first pass metabolism]]{{Citation needed|date=November 2010}} and during subsequent passes through the liver (evident as psilacetin is also active via parenteral routes of ingestion).
-There are claims of subjective differences in effect between the acetylated and not acetylated forms of psilocin.<ref name="erowid1"/> Some users report that ''O''-acetylpsilocin lasts slightly longer than psilocin; 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 ''O''-acetylpsilocin more closely resemble those produced by [[dimethyltryptamine|DMT]] than those produced by psilocin. These differences could be possible if psilacetin is active itself and not merely as a prodrug. Many users, however, can not tell the difference between these two compounds when ingested.
+Claims of subjective differences in effects between the acetylated and non-acetylated forms of psilocin vary:<ref name="erowid1"/> some users report that ''O''-acetylpsilocin lasts slightly longer, whilst others report that it lasts for a considerably shorter time.  Many users report less [[body load]] and nausea compared with psilocin.  Some users find that the visual effects produced by ''O''-acetylpsilocin more closely resemble those produced by [[dimethyltryptamine|DMT]] than those produced by psilocin or psilocybin. These differences could be possible if psilacetin is psychoactive in itself and not merely as a prodrug. Despite this, there have been no controlled clinical studies to distinguish among the phenomenological effects of psilacetin, psilocin, and psilocybin.
+[[File:4-AcO-DMT 1g.png|thumbnail|4-AcO-DMT shown in powder form]]
-== Dosage ==
+== Legality ==
-A dose of ''O''-acetylpsilocin is 8&nbsp;mg - 30&nbsp;mg.  These are slightly lower than that of the free [[phenol]], psilocin.  Some report very strong effects with 15&nbsp;mg. A dose of 15&nbsp;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 psilocin dosage suggests that ''O''-acetylpsilocin is somewhat more potent, and possibly more variable in terms of subjective susceptibility. ''O''-Acetylpsilocin 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.
+{{more citations needed|date=March 2011}}
+===Australia===
-Dosages vary slightly depending on the type of [[salt (chemistry)|salt]]. The [[hydrochloride]] has a higher molecular mass and is therefore less potent on a per weight basis than its freebase form; however, freebase ''O''-acetylpsilocin is relatively unstable and will degrade quickly at room temperature. ''O''-Acetylpsilocin is now most commonly distributed as the fumaric acid salt (''O''-acetylpsilocin fumarate). The fumarate is even less potent on a per weight basis, but is also considerably more stable and will not degrade substantially at room temperature. The ratio of hydrochloride to fumarate is approximately .93:1.
+''O''-Acetylpsilocin can be considered an analog of [[psilocin]] making it a Schedule 9 prohibited substance in Australia under the [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard]] (October 2015).<ref name="Poisons Standard">{{cite web | title = Poisons Standard October 2015 | url=https://www.comlaw.gov.au/Details/F2015L01534 |access-date=2016-01-06 |url-status=live |archive-url=https://web.archive.org/web/20160119074606/https://www.comlaw.gov.au/Details/F2015L01534/ |archive-date=2016-01-19 | publisher = Australian Government | work = Federal Register of Legislation }}</ref> A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.<ref name="Poisons Standard" />
-{| class="wikitable"
-|-
-! ''O''-Acetylpsilocin Fumarate !! Oral Dose
-|-
-| Threshold || 4&nbsp;mg-7&nbsp;mg
-|-
-| Light || 8&nbsp;mg-12&nbsp;mg
-|-
-| Common || 13&nbsp;mg-17&nbsp;mg
-|-
-| Strong || 18&nbsp;mg-23&nbsp;mg
-|-
-| Heavy || 24&nbsp;mg+
-|}
+===United States===
-These above doses are taken from the site erowid.org, which advises potential users of this chemical as a psychedelic drug: "Please note that the above doses should only be used as a general outline. This chemical is still relatively new, with a short history of human use. Every individual reacts differently to every chemical."{{dubious|date=April 2011}}
+''O''-Acetylpsilocin is ambiguously legal for use as a lab reagent or research chemical; however, it is an acetate ester of psilocin, meaning it would be considered akin to a Schedule I Controlled Substance under the [[Federal Analogue Act]] if sold for human consumption.
-== Effects ==
+===United Kingdom===
+''O''-Acetylpsilocin, being an ester of psilocin, is a [[Class A drug]] in the UK under the [[Misuse of Drugs Act 1971]].<ref>{{Cite act
-''O''-Acetylpsilocin is theorized to be metabolized into psilocin, as such is the case with psilocybin, however reports indicate that ''O''-acetylpsilocin may be active on its own. The effects of ''O''-acetylpsilocin are therefore somewhat 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.  Other users have reported effects closer to those of an oral DMT experience.
+| url=http://www.legislation.gov.uk/ukpga/1971/38/schedule/2
+| date=1971
+| title=[[Misuse of Drugs Act 1971]]
+| article=2 Part I
+| article-type=Schedule
+}}</ref>
+===Czech Republic===
-Several available reports of ''O''-acetylpsilocin 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, and it has been noted by users that ''O''-acetylpsilocin is a somewhat sedating psychedelic. 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.
+''O''-Acetylpsilocin is prohibited in Czech republic except strictly limited research and therapeutical purposes.<ref name="463/2013">{{cite web | title = Government regulation of the list of the addictive substances | url=https://www.zakonyprolidi.cz/cs/2013-463#p1-1-d | publisher = Czech Government | work = Federal Register of Legislation }}</ref>
+===Italy===
-There are several drugs that can decrease or even block the subjective effects of psychedelics, such as psilacetin/psilocybin/psilocin, 2C-x compounds, and other tryptamine and phenylethylamine based drugs that act via agonism of the 5-HT2A receptor. These include SSRI's (fluoxetine (Prozac), fluvoxamine (Luvox), paroxetine (Paxil), and drugs that block the 5-HT2A receptor such as trazodone (Desyrel), and atypical anti-psychotics including risperidone (Risperdal), olanzapine (Zyprexa), et al. Several days of abstinence from these drugs will allow clearance of 5-HT2A drugs, and up to a week may be required after stopping SSRI's to allow serotonin receptors to resensitize, and up-regulate after being suppressed by the increased serotonin levels that result from SSRI use. Of course, discontinuing these drugs may allow for the re-emergence of symtpoms of the conditions for which they were taken (if being used medically), as well as produce withdrawal/discontinuation effects, depending on the drug, dose, and duration of use.
+''O''-Acetylpsilocin is illegal in Italy as it is an [[ester]] of a prohibited substance.
-== Onset ==
+===Sweden===
-The onset appears to last 20–40 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.
+[[Riksdag|The Riksdag]] added 4-AcO-DMT to [[:sv:Narkotikastrafflagen|Narcotic Drugs Punishments Act]] under ''swedish schedule I'' (''"substances, plant materials and fungi which normally do not have medical use"'' ) as of January 25, 2017, published by [[Medical Products Agency (Sweden)|Medical Products Agency (MPA)]] in regulation ''HSLF-FS 2017:1'' listed as '''4-acetoxi-N,N-dimetyltryptamin'''.<ref>{{cite web |url=https://lakemedelsverket.se/upload/lvfs/HSLF-FS_2017_1.pdf |title= Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika | trans-title = Regulations on changes in the Swedish Medicines Agency's regulations (LVFS 2011:10) on lists of narcotics | language = sv |access-date=2017-04-21 |url-status=live |archive-url=https://web.archive.org/web/20171031012708/https://lakemedelsverket.se/upload/lvfs/HSLF-FS_2017_1.pdf |archive-date=2017-10-31 }}</ref>
-== Duration ==
+===Israel===
+''O''-Acetylpsilocin is technically illegal in Israel as of being a derivative of DMT.
-The primary effects of ''O''-acetylpsilocin 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 are described to start near the 2 hour mark, lasting up to 5 hours.
-The visuals are quite mild at average doses, with mental effects dominating primarily. With closed eyes a person may perceive patterns, colors, and strange, sometimes intense subconscious awareness (perceived in a visual way). Open eyed visuals are fleeting and consist of slight movement, especially peripherally, and increased color intensity. At higher doses, full hallucinations are not uncommonly reported, but not consistent. Above 25 mg the visuals are reported to gain intensity and can include very complex geometric and dynamic patterns, "melting" of objects and loss of object comprehension (as if one was just born and seeing objects for the first time).
-== Legal status ==
-{{Unreferenced section|date=March 2011}}
--AcO-DMT is unscheduled in the United States. It may be considered an [[Analog (chemistry)|analog]] of psilocin, which is a [[Controlled Substances Act#Schedule I controlled substances|Schedule I]] drug under the [[Controlled Substances Act]] of the [[USA]], and as such sale for human consumption or possession to ingest or use for illicit non-medical or industrial intents and purposes could be prosecuted as crimes under the Federal Analog Act.
-''O''-Acetylpsilocin could also be considered illegal in the UK under the [[Misuse of Drugs Act 1971]].  [[Ester]] derivatives of prohibited substances also hold criminal penalties. ''O''-Acetylpsilocin is an ester of psilocin, to which it metabolizes.  This means that it potentially carries the same penalty as any Class A drug, such as [[heroin]] or [[cocaine]], though the drug is still being sold over the internet in the UK as an alternative to wild mushrooms.
 == See also ==
+* [[4-AcO-DPT]]
 * [[4-MeO-DMT]]
+* [[4-PrO-DMT]]
+* [[ALD-52]]
+* [[Ayahuasca]]
 * [[Psilocybin]]
+* [[Psilocybin mushroom]]
+* [[Psychedelic drug]]
+* [[Serotonergic psychedelic]]
 * [[Tryptamine]]
-* [[Indole]]
-* [[Psychedelic drug]]
-* [[Psychoactive drug]]
-* [[Manna]]
-* [[Teonanacatl]]
-* [[Ayahuasca]]
-* [[Soma]]
 == References ==
@@ Line 120: / Line 113: @@
 == External links ==
+* [http://isomerdesign.com/PiHKAL/explore.php?domain=pk&id=5370 4-AcO-DMT information at IsomerDesign.com]
-* [http://www.erowid.org/references/refs_view.php?ID=6535/ Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the ''O''-Acetyl Prodrug of Psilocin] - A publication by [[David E. Nichols]]
-* [http://www.erowid.org/chemicals/4_acetoxy_dmt/4_acetoxy_dmt.shtml Erowid 4-Acetoxy-DMT Vault]
+* [https://www.erowid.org/chemicals/4_acetoxy_dmt/4_acetoxy_dmt.shtml Erowid 4-Acetoxy-DMT Vault]
+* [https://www.erowid.org/archive/rhodium/pdf/psilocin.esters.pdf "Esters of Indoles" US Patent # 3,075,992] - Awarded to [[Sandoz]] Ltd. (via [[Albert Hofmann]] & Franz Troxler) on January 29, 1963.
 {{Tryptamines}}
+{{Hallucinogenic tryptamines}}
+{{Serotonergics}}
 {{DEFAULTSORT:Acetylpsilocin, ''O''-}}
-[[Category:Alkaloids]]
+[[Category:Tryptamine alkaloids]]
+[[Category:Mycotoxins]]
 [[Category:Psychedelic tryptamines]]
+[[Category:Entheogens]]
+[[Category:Serotonin receptor agonists]]
 [[Category:Acetate esters]]
+[[Category:Prodrugs]]
+[[Category:Designer drugs]]
-[[de:Psilocin]]
+[[Category:Dimethylamino compounds]]
-[[es:Psilocina]]
-[[it:Psilocina]]
-[[pl:4-AcO-DMT]]
-[[fi:O-Asetyylipsilosiini]]
-[[sv:Psilocin]]