4-AcO-DMT: Difference between revisions

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'''4-Acetoxy-N,N-dimethyltryptamine''' (also known as '''4-AcO-DMT''', '''4-~~Acetoxy~~-DMT''', '''O-~~Acetylpsilocin~~''', '''psilacetin''', and '''"synthetic mushrooms"''') is a novel lesser-known [[Psychoactive class::psychedelic]] substance of the [[Chemical class::tryptamine]] class. It is structurally related to [[psilocybin]] and [[psilocin]], the active ingredient in [[psilocybin mushrooms]] ("magic mushrooms"). 4-AcO-DMT is thought to produce its effects by binding to [[serotonin]] [[receptors]] in the brain; however, the precise mechanism is not known.

'''4-Acetoxy-''N'',''N''-dimethyltryptamine''' (also known as '''4-AcO-DMT''', '''4-acetoxy-DMT''', '''''O''-acetylpsilocin''', '''psilacetin''', and "'''synthetic mushrooms'''") is a novel lesser-known [[Psychoactive class::psychedelic]] substance of the [[Chemical class::tryptamine]] class. It is structurally related to [[psilocybin]] and [[psilocin]], the active ingredient in [[psilocybin mushrooms]] ("magic mushrooms"). 4-AcO-DMT is thought to produce its effects by binding to [[serotonin]] [[receptors]] in the brain; however, the precise mechanism is not known.

4-AcO-DMT was first synthesized in 1963 by [[wikipedia:Albert Hofmann|Albert Hofmann]] and Franz Troxler as part of a chemical investigation into psilocin analogs.<ref name="Patent">{{cite web|url=https://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=3075992&KC=&FT=E&locale=en_EP#|title=Bibliographic data: US3075992 (A) ― 1963-01-29|access-date=July 18, 2020|publisher=European Patent Office}}</ref> However, it was not tested for psychoactivity during this time. It is unknown when it was first explored in humans. A paper authored by [[David E. Nichols]] in 1999 proposed its potential use as an alternative to psilocybin for pharmacological research due to the lower cost of synthesis.<ref>{{cite journal|last1=Nichols|first1=D. E.|author-link1=David E. Nichols|last2=Frescas|first2=S.|date=June 1999|title=Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin|url=https://www.researchgate.net/profile/David_Nichols3/publication/244566641_Improvements_to_the_Synthesis_of_Psilocybin_and_a_Facile_Method_for_Preparing_the_O-Acetyl_Prodrug_of_Psilocin/links/542af96e0cf27e39fa917ae1/Improvements-to-the-Synthesis-of-Psilocybin-and-a-Facile-Method-for-Preparing-the-O-Acetyl-Prodrug-of-Psilocin.pdf|issn=0039-7881|eissn=1437-210X|journal=Synthesis|volume=1999|issue=6|pages=935-938}}</ref> Reports of recreational use began to surface shortly after its appearance on the online [[research chemical]] market in the 2010s.{{citation needed}}

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==Chemistry==

4-AcO-DMT~~, or 4-acetoxy-N,N-dimethyltryptamine,~~ is a synthetic member of organic compounds known as [[tryptamines]]. 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 a synthetic member of organic compounds known as [[tryptamines]]. 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.

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 {{SummarySheet}}
 {{SubstanceBox/4-AcO-DMT}}
-'''4-Acetoxy-N,N-dimethyltryptamine''' (also known as '''4-AcO-DMT''', '''4-Acetoxy-DMT''', '''O-Acetylpsilocin''', '''psilacetin''', and '''"synthetic mushrooms"''') is a novel lesser-known [[Psychoactive class::psychedelic]] substance of the [[Chemical class::tryptamine]] class. It is structurally related to [[psilocybin]] and [[psilocin]], the active ingredient in [[psilocybin mushrooms]] ("magic mushrooms"). 4-AcO-DMT is thought to produce its effects by binding to [[serotonin]] [[receptors]] in the brain; however, the precise mechanism is not known.
+'''4-Acetoxy-''N'',''N''-dimethyltryptamine''' (also known as '''4-AcO-DMT''', '''4-acetoxy-DMT''', '''''O''-acetylpsilocin''', '''psilacetin''', and "'''synthetic mushrooms'''") is a novel lesser-known [[Psychoactive class::psychedelic]] substance of the [[Chemical class::tryptamine]] class. It is structurally related to [[psilocybin]] and [[psilocin]], the active ingredient in [[psilocybin mushrooms]] ("magic mushrooms"). 4-AcO-DMT is thought to produce its effects by binding to [[serotonin]] [[receptors]] in the brain; however, the precise mechanism is not known.
 -AcO-DMT was first synthesized in 1963 by [[wikipedia:Albert Hofmann|Albert Hofmann]] and Franz Troxler as part of a chemical investigation into psilocin analogs.<ref name="Patent">{{cite web|url=https://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=3075992&KC=&FT=E&locale=en_EP#|title=Bibliographic data: US3075992 (A) ― 1963-01-29|access-date=July 18, 2020|publisher=European Patent Office}}</ref> However, it was not tested for psychoactivity during this time. It is unknown when it was first explored in humans. A paper authored by [[David E. Nichols]] in 1999 proposed its potential use as an alternative to psilocybin for pharmacological research due to the lower cost of synthesis.<ref>{{cite journal|last1=Nichols|first1=D. E.|author-link1=David E. Nichols|last2=Frescas|first2=S.|date=June 1999|title=Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin|url=https://www.researchgate.net/profile/David_Nichols3/publication/244566641_Improvements_to_the_Synthesis_of_Psilocybin_and_a_Facile_Method_for_Preparing_the_O-Acetyl_Prodrug_of_Psilocin/links/542af96e0cf27e39fa917ae1/Improvements-to-the-Synthesis-of-Psilocybin-and-a-Facile-Method-for-Preparing-the-O-Acetyl-Prodrug-of-Psilocin.pdf|issn=0039-7881|eissn=1437-210X|journal=Synthesis|volume=1999|issue=6|pages=935-938}}</ref> Reports of recreational use began to surface shortly after its appearance on the online [[research chemical]] market in the 2010s.{{citation needed}}
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 ==Chemistry==
--AcO-DMT, or 4-acetoxy-N,N-dimethyltryptamine, is a synthetic member of organic compounds known as [[tryptamines]]. Tryptamines share a core structure that consists of a bicylic indole heterocycle attached at R<sub>3</sub> to a terminal amino group via an ethyl side chain. 4-AcO-DMT is substituted at R<sub>4</sub> of its indole heterocycle with an acetoxy (-AcO) functional group CH<sub>3</sub>COO−. It also contains two methyl groups CH<sub>3</sub>- bound to the terminal amine R<sub>N</sub> of the ethyl side chain.
+-AcO-DMT is a synthetic member of organic compounds known as [[tryptamines]]. Tryptamines share a core structure that consists of a bicylic indole heterocycle attached at R<sub>3</sub> to a terminal amino group via an ethyl side chain. 4-AcO-DMT is substituted at R<sub>4</sub> of its indole heterocycle with an acetoxy (-AcO) functional group CH<sub>3</sub>COO−. It also contains two methyl groups CH<sub>3</sub>- bound to the terminal amine R<sub>N</sub> of the ethyl side chain.
 -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.