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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''', and '''psilacetin''') is a novel [[Psychoactive class::psychedelic]] substance of the [[Chemical class::tryptamine]] class. 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. | '''4-Acetoxy-N,N-dimethyltryptamine''' (also known as '''4-AcO-DMT''', '''4-Acetoxy-DMT''', '''O-Acetylpsilocin''', and '''psilacetin''') is a novel [[Psychoactive class::psychedelic]] substance of the [[Chemical class::tryptamine]] class. 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 [[wikipedia:Albert Hofmann|Albert Hofmann]] and Franz Troxler as part of an investigation into psilocin analogs.<ref> | The synthesis of 4-AcO-DMT was first reported in 1963 by [[wikipedia:Albert Hofmann|Albert Hofmann]] and Franz Troxler as part of an 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, 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.<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}} | ||
[[Subjective effects]] are reported to be nearly identical to those of [[psilocybin mushrooms]] and include [[geometry|geometric visual hallucinations]], [[time distortion]], [[introspection|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. | [[Subjective effects]] are reported to be nearly identical to those of [[psilocybin mushrooms]] and include [[geometry|geometric visual hallucinations]], [[time distortion]], [[introspection|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. | ||
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==History and culture== | ==History and culture== | ||
{{historyStub}} | {{historyStub}} | ||
4-AcO-DMT and several other esters of psilocin were patented on January 16, 1963 by Sandoz Ltd. via Albert Hofmann & Franz Troxler.<ref | 4-AcO-DMT and several other esters of psilocin were patented on January 16, 1963 by Sandoz Ltd. via Albert Hofmann & Franz Troxler.<ref name="Patent"></ref> However, its pharmacology and subjective effects were not investigated. It is unknown when 4-AcO-DMT's effect in humans were first explored. | ||
==Chemistry== | ==Chemistry== | ||
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*'''[[Cannabis]]''' - Cannabis intensifies the visual, sensory and cognitive effects of 4-AcO-DMT greatly. This should be used with extreme caution, especially if one is not experienced with psychedelics. This interaction can also amplify the [[anxiety]], [[confusion]] and the [[psychosis]] risk of cannabis significantly. | *'''[[Cannabis]]''' - Cannabis intensifies the visual, sensory and cognitive effects of 4-AcO-DMT greatly. This should be used with extreme caution, especially if one is not experienced with psychedelics. This interaction can also amplify the [[anxiety]], [[confusion]] and the [[psychosis]] risk of cannabis significantly. | ||
*'''[[Dissociatives]]''' - 4-AcO-DMT enhances the the geometry, euphoria, dissociation and hallucinatory effects of dissociatives. Dissociative-induced [[Visual_disconnection#Holes.2C_spaces_and_voids|holes, spaces, and voids]] while under the influence of 4-AcO-DMT can result in significantly more vivid visuals than dissociatives alone present, along with more intense [[internal hallucinations]], [[confusion]], [[nausea]], [[delusions]] and chances of a [[psychosis|psychotic reaction]]. | *'''[[Dissociatives]]''' - 4-AcO-DMT enhances the the geometry, euphoria, dissociation and hallucinatory effects of dissociatives. Dissociative-induced [[Visual_disconnection#Holes.2C_spaces_and_voids|holes, spaces, and voids]] while under the influence of 4-AcO-DMT can result in significantly more vivid visuals than dissociatives alone present, along with more intense [[internal hallucinations]], [[confusion]], [[nausea]], [[delusions]] and chances of a [[psychosis|psychotic reaction]]. | ||
*'''[[MDMA]]''' - 4-AcO-DMT strongly amplifies the visual, physical and cognitive effects of [[MDMA]]. The synergy between these substances is unpredictable, and it is best to start with lower doses than one would take for both substances individually. The toxicity of this combination is unknown, although there is some evidence that suggests this may increase the the neurotoxic effects of MDMA.<ref>Armstrong | *'''[[MDMA]]''' - 4-AcO-DMT strongly amplifies the visual, physical and cognitive effects of [[MDMA]]. The synergy between these substances is unpredictable, and it is best to start with lower doses than one would take for both substances individually. The toxicity of this combination is unknown, although there is some evidence that suggests this may increase the the neurotoxic effects of MDMA.<ref>{{cite journal|last1=Armstrong|first1=B. D.|last2=Paik|first2=E.|last3=Chhith|first3=S.|last4=Lelievre|first4=V.|last5=Waschek|first5=J. A.|last6=Howard|first6=S. G.|date=October 26, 2004|title=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|journal=Neuroscience Research Communications|volume=35|issue=2|pages=83-95|doi=10.1002/nrc.20023|eissn=1520-6769}}</ref><ref>{{cite journal|last1=Gudelsky|first1=G. A.|last2=Yamamoto|first2=B. K.|last3=Nash|first3=F.|pages=325-330|volume=264|issue=3|journal=European Journal of Pharmacology|date=November 3, 1994|doi=10.1016/0014-2999(94)90669-6|issn=0014-2999|eissn=1879-0712|oclc=01568459|title=Potentiation of 3,4-methylenedioxymethamphetamine-induced dopamine release and serotonin neurotoxicity by 5-HT<sub>2</sub> receptor agonists}}</ref><ref>{{cite journal|pmid=17572501|doi=10.1016/j.neuro.2007.04.005|journal=NeuroToxicology|issn=0161-813X|oclc=47153737|title=Ecstasy induces apoptosis via 5-HT<sub>2A</sub>-receptor stimulation in cortical neurons|first1=J. P.|last1=Capela|first2=E.|last2=Fernandes|first3=F.|last3=Remião|first4=M. L.|last4=Bastos|first5=A.|last5=Meisel|first6=F.|last6=Carvalhoa|volume=28|issue=4|date=July 2007|pages=868-875}}</ref> | ||
*'''[[Alcohol]]''' - This combination is typically advised against due to alcohol’s ability to cause [[dehydration]], [[nausea]], and [[physical fatigue]] which can negatively affect the experience if taken in moderate to high doses. This combination is, however, considered to be reasonably safe in low doses and when used responsibly, this can often take the edge off the experience as well as dull its psychedelic effects in a fashion somewhat similar to benzodiazepines. | *'''[[Alcohol]]''' - This combination is typically advised against due to alcohol’s ability to cause [[dehydration]], [[nausea]], and [[physical fatigue]] which can negatively affect the experience if taken in moderate to high doses. This combination is, however, considered to be reasonably safe in low doses and when used responsibly, this can often take the edge off the experience as well as dull its psychedelic effects in a fashion somewhat similar to benzodiazepines. | ||
*'''[[Benzodiazepines]]''' - Depending on the dose, benzodiazepines can slightly to completely reduce the intensity of the cognitive, physical and visual effects of a 4-AcO-DMT experience. They can be very efficient at largely stopping or mitigating a [[bad trip]] at the cost of amnesia and reduced intensity. Caution is advised when obtaining them for this purpose due to their very high addiction and abuse potential. | *'''[[Benzodiazepines]]''' - Depending on the dose, benzodiazepines can slightly to completely reduce the intensity of the cognitive, physical and visual effects of a 4-AcO-DMT experience. They can be very efficient at largely stopping or mitigating a [[bad trip]] at the cost of amnesia and reduced intensity. Caution is advised when obtaining them for this purpose due to their very high addiction and abuse potential. | ||
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*'''Belgium''': 4-AcO-DMT is illegal to import in Belgium.{{citation needed}} | *'''Belgium''': 4-AcO-DMT is illegal to import in Belgium.{{citation needed}} | ||
*'''Brazil''': 4-AcO-DMT is illegal to possess, produce, and sell as it is listed on Portaria SVS/MS nº 344.<ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref> | *'''Brazil''': 4-AcO-DMT is illegal to possess, produce, and sell as it is listed on Portaria SVS/MS nº 344.<ref>{{cite web|url=http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7|title=RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016|publication-date=December 5, 2016|publisher=Agência Nacional de Vigilância Sanitária (ANVISA) [Brazilian Health Regulatory Agency (ANVISA)]|language=pt}}</ref> | ||
*'''Germany''': Because it is an ester of DMT, 4-AcO-DMT is controlled under Anlage I BtMG (Narcotics Act, Schedule I) | *'''Germany''': Because it is an ester of DMT, 4-AcO-DMT is controlled under Anlage I BtMG (Narcotics Act, Schedule I)<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Betäubungsmittelgesetz (BtMG) Anlage I|trans-title=Narcotics Act (BtMG) Schedule I|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> as of January 24, 1974.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl174s0097.pdf|work=Bundesgesetzblatt Jahrgang 1974 Teil I Nr. 6|pages=97-98|publication-date=January 23, 1974|date=January 17, 1974|eissn=0344-7634|title=Sechste Verordnung über die den Betäubungsmitteln gleichgestellten Stoffe|publisher=Bundesanzeiger Verlag|language=de}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=Betäubungsmittelgesetz (BtMG) § 29|trans-title=Narcotics Act (BtMG) § 29|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> | ||
*'''Italy''': 4-AcO-DMT is illegal in Italy as it is an ester of an illegal substance.{{citation needed}} | *'''Italy''': 4-AcO-DMT is illegal in Italy as it is an ester of an illegal substance.{{citation needed}} | ||
*'''Sweden''': 4-AcO-DMT was made illegal in Sweden on 25 January 2017.{{citation needed}} | *'''Sweden''': 4-AcO-DMT was made illegal in Sweden on 25 January 2017.{{citation needed}} | ||
*'''Switzerland''': 4-AcO-DMT could be considered an ester analog of Psilocin, which would make it illegal according to Buchstabe B.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | *'''Switzerland''': 4-AcO-DMT could be considered an ester analog of Psilocin, which would make it illegal according to Buchstabe B.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | ||
*'''United Kingdom''': 4-AcO-DMT is a Class A drug in the UK as it is an ester of the Class A drug psilocin.<ref> | *'''United Kingdom''': 4-AcO-DMT is a Class A drug in the UK as it is an ester of the Class A drug psilocin.<ref>{{cite web|title=Part I: Class A Drugs|url=http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I|work="Misuse of Drugs Act 1971"|access-date=January 7, 2020|publisher=UK Government}}</ref> | ||
*'''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.{{citation needed}} | *'''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.{{citation needed}} | ||