APICA: Difference between revisions

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'''2NE1''' ('''APICA''', '''JWH-018 adamantyl ~~carboxamide''', '''N-(1-adamantyl)-1-pentyl-1H-indole-3-~~carboxamide''') is a ~~drug that acts~~ as a potent [[agonist]] for the CB1 and CB2 [[cannabinoid]] [[receptor]]s<ref>Samuel D. Banister, Jordyn Stuart, Richard C. Kevin, Amelia Edington, Mitchell Longworth, Shane M. Wilkinson, Corinne Beinat, Alexandra S. Buchanan, David E. Hibbs, Michelle Glass, Mark Connor, Iain S. McGregor, and Michael Kassiou. "Effects of Bioisosteric Fluorine in Synthetic Cannabinoid Designer Drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135" Chemical Neuroscience. 2015;6(8);1445-1458;doi:10.1021/acschemneuro.5b00107 (Pubmed / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/25921407</ref> ~~which produces~~ subjective effects somewhat similar to that of [[cannabis]] with a short duration and an emphasis on intense physical sensations. The name 2NE1 appears to be a reference to the South Korean all-girl KPop group with that name.<ref>2NE1 (Wikipedia) | https://en.wikipedia.org/wiki/2NE1</ref> Its metabolism has been described in the scientific literature.<ref>Tim Sobolevsky, Ilya Prasolov and Grigory Rodchenkov. "Study on the phase I metabolism of novel synthetic cannabinoids, APICA and its fluorinated analogue". Drug Testing and Analysis. 2015;7(2);131-142;doi:10.1002/dta.1756 (Pubmed / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/25428705</ref>. It was first identified in Japan as a constituent of a brown powder sold in late 2011 under the name "Fragrance Powder" as a mixture with its [[indazole]] analogue AKB48<ref>Nahoko Uchiyama, Maiko Kawamura, Ruri Kikura-Hanajiri, Yukihiro Goda. "Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide(APINACA), and detection of five synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB-13 (CRA-13), and AM-1248, as designer drugs in illegal products" Forensic Toxicol (2012) 30: 114-125;doi:10.1007/s11419-012-0136-7 (SpringerLink) | http://link.springer.com/article/10.1007/s11419-012-0136-7</ref> and has been available for sale as a grey area [[research chemical]] through online vendors.

'''2NE1''' (also known as '''APICA''' or '''JWH-018 adamantyl carboxamide''') is a novel synthetic designer [[psychoactive class::cannabinoid]]. It has been shown to act as a potent [[agonist]] for the CB1 and CB2 [[cannabinoid]] [[receptor]]s<ref>Samuel D. Banister, Jordyn Stuart, Richard C. Kevin, Amelia Edington, Mitchell Longworth, Shane M. Wilkinson, Corinne Beinat, Alexandra S. Buchanan, David E. Hibbs, Michelle Glass, Mark Connor, Iain S. McGregor, and Michael Kassiou. "Effects of Bioisosteric Fluorine in Synthetic Cannabinoid Designer Drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135" Chemical Neuroscience. 2015;6(8);1445-1458;doi:10.1021/acschemneuro.5b00107 (Pubmed / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/25921407</ref> and has been reported to produce subjective effects somewhat similar to that of [[cannabis]], albeit with a short duration and an emphasis on intense physical sensations.

Cannabinoids are commonly smoked or vaporized to achieve a quick [[onset]] of effects and rapid [[offset]]. 2NE1 is [[oral]]ly active when dissolved in a lipid, which can increase the duration significantly. Like other [[cannabinoid]]s, it is insoluble in water but dissolves in [[ethanol]] and lipids.

The name 2NE1 appears to be a reference to the South Korean all-girl K-Pop group.<ref>2NE1 (Wikipedia) | https://en.wikipedia.org/wiki/2NE1</ref> It was first identified in Japan as a constituent of a brown powder sold in late 2011 under the name "Fragrance Powder" as a mixture with its [[indazole]] analog [[AKB48]]<ref>Nahoko Uchiyama, Maiko Kawamura, Ruri Kikura-Hanajiri, Yukihiro Goda. "Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide(APINACA), and detection of five synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB-13 (CRA-13), and AM-1248, as designer drugs in illegal products" Forensic Toxicol (2012) 30: 114-125;doi:10.1007/s11419-012-0136-7 (SpringerLink) | http://link.springer.com/article/10.1007/s11419-012-0136-7</ref> and has since been available for sale as a grey area [[research chemical]] through online vendors.

Cannabinoids are commonly [[smoked]] or [[vaporized]] to achieve a quick [[onset]] of effects and rapid [[offset]]. 2NE1 is [[oral]]ly active when dissolved in a lipid, which can increase the duration significantly. Like other [[cannabinoid]]s, it is insoluble in water but dissolves in [[ethanol]] and lipids. Unlike many novel designer cannabinoids, its metabolism has been described in the scientific literature.<ref>Tim Sobolevsky, Ilya Prasolov and Grigory Rodchenkov. "Study on the phase I metabolism of novel synthetic cannabinoids, APICA and its fluorinated analogue". Drug Testing and Analysis. 2015;7(2);131-142;doi:10.1002/dta.1756 (Pubmed / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/25428705</ref>.

Unlike [[cannabis]], the chronic abuse of [[synthetic cannabinoids]] has been [[Synthetic_cannabinoid#Deaths|associated with multiple deaths]] and [[Synthetic cannabinoid#Harm potential|more dangerous side effects and toxicity]] in general. Therefore, it is strongly discouraged to take this substance for extended periods of time or in excessive doses.

==Chemistry==

2NE1, or N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide, is a synthetic [[Chemical class::indole cannabinoid]] as it contains a substituted indole group. This indole moeity is substituted at R<sub>1</sub> with a pentyl chain, a substitution shared with [[JWH-018]]. Additionally, the indole is substituted at R<sub>3</sub> with a carboxamide group. This carboxamide group is N-substituted at its terminal amine group with an adamantane group. This group consists of four fused cyclohexane rings in a unique structure called a diamondoid. 2NE1 can be considered the indole analogue of [[AKB48]] and the pentyl analogue of [[STS-135]].

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 {{SubstanceBox/2NE1}}
-'''2NE1''' ('''APICA''', '''JWH-018 adamantyl carboxamide''', '''N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide''') is a drug that acts as a potent [[agonist]] for the CB1 and CB2 [[cannabinoid]] [[receptor]]s<ref>Samuel D. Banister, Jordyn Stuart, Richard C. Kevin, Amelia Edington, Mitchell Longworth, Shane M. Wilkinson, Corinne Beinat, Alexandra S. Buchanan, David E. Hibbs, Michelle Glass, Mark Connor, Iain S. McGregor, and Michael Kassiou. "Effects of Bioisosteric Fluorine in Synthetic Cannabinoid Designer Drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135" Chemical Neuroscience. 2015;6(8);1445-1458;doi:10.1021/acschemneuro.5b00107 (Pubmed / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/25921407</ref> which produces subjective effects somewhat similar to that of [[cannabis]] with a short duration and an emphasis on intense physical sensations. The name 2NE1 appears to be a reference to the South Korean all-girl KPop group with that name.<ref>2NE1 (Wikipedia) | https://en.wikipedia.org/wiki/2NE1</ref> Its metabolism has been described in the scientific literature.<ref>Tim Sobolevsky, Ilya Prasolov and Grigory Rodchenkov. "Study on the phase I metabolism of novel synthetic cannabinoids, APICA and its fluorinated analogue". Drug Testing and Analysis. 2015;7(2);131-142;doi:10.1002/dta.1756 (Pubmed / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/25428705</ref>. It was first identified in Japan as a constituent of a brown powder sold in late 2011 under the name "Fragrance Powder" as a mixture with its [[indazole]] analogue AKB48<ref>Nahoko Uchiyama, Maiko Kawamura, Ruri Kikura-Hanajiri, Yukihiro Goda. "Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide(APINACA), and detection of five synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB-13 (CRA-13), and AM-1248, as designer drugs in illegal products" Forensic Toxicol (2012) 30: 114-125;doi:10.1007/s11419-012-0136-7 (SpringerLink) | http://link.springer.com/article/10.1007/s11419-012-0136-7</ref> and has been available for sale as a grey area [[research chemical]] through online vendors.
+'''2NE1''' (also known as '''APICA''' or '''JWH-018 adamantyl carboxamide''') is a novel synthetic designer [[psychoactive class::cannabinoid]]. It has been shown to act as a potent [[agonist]] for the CB1 and CB2 [[cannabinoid]] [[receptor]]s<ref>Samuel D. Banister, Jordyn Stuart, Richard C. Kevin, Amelia Edington, Mitchell Longworth, Shane M. Wilkinson, Corinne Beinat, Alexandra S. Buchanan, David E. Hibbs, Michelle Glass, Mark Connor, Iain S. McGregor, and Michael Kassiou. "Effects of Bioisosteric Fluorine in Synthetic Cannabinoid Designer Drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135" Chemical Neuroscience. 2015;6(8);1445-1458;doi:10.1021/acschemneuro.5b00107 (Pubmed / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/25921407</ref> and has been reported to produce subjective effects somewhat similar to that of [[cannabis]], albeit with a short duration and an emphasis on intense physical sensations.
-Cannabinoids are commonly smoked or vaporized to achieve a quick [[onset]] of effects and rapid [[offset]]. 2NE1 is [[oral]]ly active when dissolved in a lipid, which can increase the duration significantly. Like other [[cannabinoid]]s, it is insoluble in water but dissolves in [[ethanol]] and lipids.
+The name 2NE1 appears to be a reference to the South Korean all-girl K-Pop group.<ref>2NE1 (Wikipedia) | https://en.wikipedia.org/wiki/2NE1</ref> It was first identified in Japan as a constituent of a brown powder sold in late 2011 under the name "Fragrance Powder" as a mixture with its [[indazole]] analog [[AKB48]]<ref>Nahoko Uchiyama, Maiko Kawamura, Ruri Kikura-Hanajiri, Yukihiro Goda. "Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide(APINACA), and detection of five synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB-13 (CRA-13), and AM-1248, as designer drugs in illegal products" Forensic Toxicol (2012) 30: 114-125;doi:10.1007/s11419-012-0136-7 (SpringerLink) | http://link.springer.com/article/10.1007/s11419-012-0136-7</ref> and has since been available for sale as a grey area [[research chemical]] through online vendors.
+Cannabinoids are commonly [[smoked]] or [[vaporized]] to achieve a quick [[onset]] of effects and rapid [[offset]]. 2NE1 is [[oral]]ly active when dissolved in a lipid, which can increase the duration significantly. Like other [[cannabinoid]]s, it is insoluble in water but dissolves in [[ethanol]] and lipids. Unlike many novel designer cannabinoids, its metabolism has been described in the scientific literature.<ref>Tim Sobolevsky, Ilya Prasolov and Grigory Rodchenkov. "Study on the phase I metabolism of novel synthetic cannabinoids, APICA and its fluorinated analogue". Drug Testing and Analysis. 2015;7(2);131-142;doi:10.1002/dta.1756 (Pubmed / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/25428705</ref>.
 Unlike [[cannabis]], the chronic abuse of [[synthetic cannabinoids]] has been [[Synthetic_cannabinoid#Deaths|associated with multiple deaths]] and [[Synthetic cannabinoid#Harm potential|more dangerous side effects and toxicity]] in general. Therefore, it is strongly discouraged to take this substance for extended periods of time or in excessive doses.
 ==Chemistry==
 NE1, or N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide, is a synthetic [[Chemical class::indole cannabinoid]] as it contains a substituted indole group. This indole moeity is substituted at R<sub>1</sub> with a pentyl chain, a substitution shared with [[JWH-018]]. Additionally, the indole is substituted at R<sub>3</sub> with a carboxamide group.  This carboxamide group is N-substituted at its terminal amine group with an adamantane group. This group consists of four fused cyclohexane rings in a unique structure called a diamondoid. 2NE1 can be considered the indole analogue of [[AKB48]] and the pentyl analogue of [[STS-135]].