APICA: Difference between revisions

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'''APICA''' (also known as '''SDB-001''', and '''2NE1''') is a novel synthetic [[psychoactive class::cannabinoid]] that produces modified [[cannabis|cannabis-like]] effects when [[routes of administration|administered]]. It has been shown to act as a potent [[agonist]] for the CB1 and CB2 [[cannabinoid]] [[receptors]].<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>

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> a naming convention shared by the closely related chemical [[AKB48]]. In 2011, the two chemicals were first identified in Japan as a mixture in a product sold under the name "Fragrance Powder".<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 Toxicology (2012) 30: 114-125. https://doi.org/10.1007/s11419-012-0136-7</ref> ~~2NE1~~ has since been available for sale as a grey-area [[research chemical]] through online vendors.

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> a naming convention shared by the closely related chemical [[AKB48]]. In 2011, the two chemicals were first identified in Japan as a mixture in a product sold under the name "Fragrance Powder".<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 Toxicology (2012) 30: 114-125. https://doi.org/10.1007/s11419-012-0136-7</ref> APICA has since been available for sale as a grey-area [[research chemical]] through online vendors.

Synthetic cannabinoids are commonly [[smoked]] or [[vaporized]] to achieve a quick [[onset]] of effects and rapid [[offset]]. There is little information available about the use of ~~2NE1~~ via other [[routes of administration]], although as with other synthetic cannabinoids ~~2NE1~~ could be expected to be [[orally]] active when dissolved in a lipid, which may significantly extend its [[duration]]. It is insoluble in water, but dissolves in ethanol and lipids.{{citation needed}}

Synthetic cannabinoids are commonly [[smoked]] or [[vaporized]] to achieve a quick [[onset]] of effects and rapid [[offset]]. There is little information available about the use of APICA via other [[routes of administration]], although as with other synthetic cannabinoids it could be expected to be [[orally]] active when dissolved in a lipid, which may significantly extend its [[duration]]. It is insoluble in water, but dissolves in ethanol and lipids.{{citation needed}}

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. ~~Adequate~~ independent research and [[harm reduction practices]] are strongly advised if choosing to use this substance.

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. Thorough independent research and [[harm reduction practices]] are strongly advised if choosing to use this substance.

==Chemistry==

APICA, or N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide, is a synthetic [[Chemical class::indole cannabinoid]]. Like many synthetic cannabinoids, it can be considered to be composed of four linked structures: core, bridge, head, and tail.<ref>Synthetic cannabinoids in Europe - Interactive: demystifying the chemistry (EMCDDA) | http://www.emcdda.europa.eu/topics/pods/synthetic-cannabinoids</ref> In APICA, the core indole group is substituted at R1 with a pentyl chain tail and at R3 with a carboxamide bridge linking to an adamantyl head.

~~AOUCA~~ can be considered an analog of both [[AKB48]], which features an indazole in place of APICA's indole group, and [[STS-135]], in which the pentyl tail is further substituted with a terminal fluorine.

APICA can be considered an analog of both [[AKB48]], which features an indazole in place of APICA's indole group, and [[STS-135]], in which the pentyl tail is further substituted with a terminal fluorine.

==Pharmacology==

APICA acts as a full agonist of the cannabinoid [[receptors]], with similar potency at both [[CB1]] and [[CB2]]. In vivo experiments measuring the response of rats to APICA and similar drugs found that APICA had similar potency to Δ9-[[THC]] and around a third the potency of [[JWH-018]]. In comparison to these other cannabinoids, APICA appeared to elicit a longer duration of effect. Caution should be exercised in interpreting studies using animals, however, as effects may differ significantly in humans.<ref>Banister SD, Wilkinson SM, Longworth M, et al. The Synthesis and Pharmacological Evaluation of Adamantane-Derived Indoles: Cannabimimetic Drugs of Abuse. ACS Chemical Neuroscience. 2013;4(7):1081-1092. doi:10.1021/cn400035r. (PMC/NCBI) | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3715837/</ref>

APICA acts as a full agonist of the cannabinoid [[receptors]], with similar potency at both [[CB1]] and [[CB2]]. In vivo experiments measuring the response of rats to APICA and similar drugs found that APICA had a similar potency to Δ9-[[THC]] and around a third the potency of [[JWH-018]]. In comparison to these other cannabinoids, APICA appeared to elicit a longer duration of effect. Caution should be exercised in interpreting studies using animals, however, as effects may differ significantly in humans.<ref>Banister SD, Wilkinson SM, Longworth M, et al. The Synthesis and Pharmacological Evaluation of Adamantane-Derived Indoles: Cannabimimetic Drugs of Abuse. ACS Chemical Neuroscience. 2013;4(7):1081-1092. doi:10.1021/cn400035r. (PMC/NCBI) | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3715837/</ref>

Pharmacological studies have reported EC50 values of 6.89 ± 0.11nM at CB1 and 7.54 ± 0.11nM at CB2.<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</ref> It is likely that APICA shares many of the in vivo properties of [[Δ9-THC]]. However, the role of these interactions and how they result in the cannabinoid high has yet to be scientifically validated.

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It is advised that those with severe pre-existing mental conditions should not ingest these substances due to the way they strongly amplify [[emotion enhancement|one's current state of mind and emotions]]. Also, as with [[THC]] and [[cannabis]], prolonged usage of synthetic [[cannabinoids]] including APICA may increase one's disposition to mental illness and psychosis,<ref>Causal association between cannabis and psychosis: examination of the evidence - The British Journal of Psychiatry Jan 2004, 184 (2) 110-117 | http://bjp.rcpsych.org/content/184/2/110.short</ref> particularly in vulnerable individuals with risk factors for psychotic illnesses (like a past or family history of schizophrenia).<ref>Every-Palmer, S. [[Synthetic cannabinoid]] use and psychosis: an explorative study. Journal of Drug and Alcohol Dependence 2011.</ref><ref>“Spice” Girls: Synthetic Cannabinoid Intoxication - The Journal of Emergency Medicine Volume 40, Issue 3, March 2011, Pages 296–299 (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0736467910008802</ref><ref>A Teenager With Agitation: Higher Than She Should Have Climbed - Pediatric Emergency Care: June 2010 - Volume 26 - Issue 6 - pp 462-465 | http://journals.lww.com/pec-online/Abstract/2010/06000/A_Teenager_With_Agitation__Higher_Than_She_Should.16.aspx</ref>

As synthetic cannabinoids are active in the milligram range (with below 5mg being a common dose), it is important to [[Dosage|use proper precautions when dosing]] to avoid a negative experience and injury to ~~one self~~ or others.

As synthetic cannabinoids are active in the milligram range (with below 5mg being a common dose), it is important to [[Dosage|use proper precautions when dosing]] to avoid a negative experience and injury to oneself or others.

It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.

@@ Line 3: / Line 3: @@
 '''APICA''' (also known as '''SDB-001''', and '''2NE1''') is a novel synthetic [[psychoactive class::cannabinoid]] that produces modified [[cannabis|cannabis-like]] effects when [[routes of administration|administered]]. It has been shown to act as a potent [[agonist]] for the CB1 and CB2 [[cannabinoid]] [[receptors]].<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>
-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> a naming convention shared by the closely related chemical [[AKB48]]. In 2011, the two chemicals were first identified in Japan as a mixture in a product sold under the name "Fragrance Powder".<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 Toxicology (2012) 30: 114-125. https://doi.org/10.1007/s11419-012-0136-7</ref> 2NE1 has since been available for sale as a grey-area [[research chemical]] through online vendors.
+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> a naming convention shared by the closely related chemical [[AKB48]]. In 2011, the two chemicals were first identified in Japan as a mixture in a product sold under the name "Fragrance Powder".<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 Toxicology (2012) 30: 114-125. https://doi.org/10.1007/s11419-012-0136-7</ref> APICA has since been available for sale as a grey-area [[research chemical]] through online vendors.
-Synthetic cannabinoids are commonly [[smoked]] or [[vaporized]] to achieve a quick [[onset]] of effects and rapid [[offset]]. There is little information available about the use of 2NE1 via other [[routes of administration]], although as with other synthetic cannabinoids 2NE1 could be expected to be [[orally]] active when dissolved in a lipid, which may significantly extend its [[duration]]. It is insoluble in water, but dissolves in ethanol and lipids.{{citation needed}}
+Synthetic cannabinoids are commonly [[smoked]] or [[vaporized]] to achieve a quick [[onset]] of effects and rapid [[offset]]. There is little information available about the use of APICA via other [[routes of administration]], although as with other synthetic cannabinoids it could be expected to be [[orally]] active when dissolved in a lipid, which may significantly extend its [[duration]]. It is insoluble in water, but dissolves in ethanol and lipids.{{citation needed}}
-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. Adequate independent research and [[harm reduction practices]] are strongly advised if choosing to use this substance.
+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. Thorough independent research and [[harm reduction practices]] are strongly advised if choosing to use this substance.
 ==Chemistry==
 APICA, or N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide, is a synthetic [[Chemical class::indole cannabinoid]]. Like many synthetic cannabinoids, it can be considered to be composed of four linked structures: core, bridge, head, and tail.<ref>Synthetic cannabinoids in Europe - Interactive: demystifying the chemistry (EMCDDA) | http://www.emcdda.europa.eu/topics/pods/synthetic-cannabinoids</ref> In APICA, the core indole group is substituted at R<sub>1</sub> with a pentyl chain tail and at R<sub>3</sub> with a carboxamide bridge linking to an adamantyl head.
-AOUCA can be considered an analog of both [[AKB48]], which features an indazole in place of APICA's indole group, and [[STS-135]], in which the pentyl tail is further substituted with a terminal fluorine.
+APICA can be considered an analog of both [[AKB48]], which features an indazole in place of APICA's indole group, and [[STS-135]], in which the pentyl tail is further substituted with a terminal fluorine.
 ==Pharmacology==
-APICA acts as a full agonist of the cannabinoid [[receptors]], with similar potency at both [[CB1]] and [[CB2]]. In vivo experiments measuring the response of rats to APICA and similar drugs found that APICA had similar potency to Δ9-[[THC]] and around a third the potency of [[JWH-018]]. In comparison to these other cannabinoids, APICA appeared to elicit a longer duration of effect. Caution should be exercised in interpreting studies using animals, however, as effects may differ significantly in humans.<ref>Banister SD, Wilkinson SM, Longworth M, et al. The Synthesis and Pharmacological Evaluation of Adamantane-Derived Indoles: Cannabimimetic Drugs of Abuse. ACS Chemical Neuroscience. 2013;4(7):1081-1092. doi:10.1021/cn400035r. (PMC/NCBI) | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3715837/</ref>
+APICA acts as a full agonist of the cannabinoid [[receptors]], with similar potency at both [[CB1]] and [[CB2]]. In vivo experiments measuring the response of rats to APICA and similar drugs found that APICA had a similar potency to Δ9-[[THC]] and around a third the potency of [[JWH-018]]. In comparison to these other cannabinoids, APICA appeared to elicit a longer duration of effect. Caution should be exercised in interpreting studies using animals, however, as effects may differ significantly in humans.<ref>Banister SD, Wilkinson SM, Longworth M, et al. The Synthesis and Pharmacological Evaluation of Adamantane-Derived Indoles: Cannabimimetic Drugs of Abuse. ACS Chemical Neuroscience. 2013;4(7):1081-1092. doi:10.1021/cn400035r. (PMC/NCBI) | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3715837/</ref>
 Pharmacological studies have reported EC<sub>50</sub> values of 6.89 ± 0.11nM at CB1 and 7.54 ± 0.11nM at CB2.<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</ref> It is likely that APICA shares many of the in vivo properties of [[Δ9-THC]]. However, the role of these interactions and how they result in the cannabinoid high has yet to be scientifically validated.
@@ Line 67: / Line 67: @@
 It is advised that those with severe pre-existing mental conditions should not ingest these substances due to the way they strongly amplify [[emotion enhancement|one's current state of mind and emotions]]. Also, as with [[THC]] and [[cannabis]], prolonged usage of synthetic [[cannabinoids]] including APICA may increase one's disposition to mental illness and psychosis,<ref>Causal association between cannabis and psychosis: examination of the evidence - The British Journal of Psychiatry Jan 2004, 184 (2) 110-117  | http://bjp.rcpsych.org/content/184/2/110.short</ref> particularly in vulnerable individuals with risk factors for psychotic illnesses (like a past or family history of schizophrenia).<ref>Every-Palmer, S. [[Synthetic cannabinoid]] use and psychosis: an explorative study. Journal of Drug and Alcohol Dependence 2011.</ref><ref>“Spice” Girls: Synthetic Cannabinoid Intoxication - The Journal of Emergency Medicine  Volume 40, Issue 3, March 2011, Pages 296–299 (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0736467910008802</ref><ref>A Teenager With Agitation: Higher Than She Should Have Climbed - Pediatric Emergency Care: June 2010 - Volume 26 - Issue 6 - pp 462-465 | http://journals.lww.com/pec-online/Abstract/2010/06000/A_Teenager_With_Agitation__Higher_Than_She_Should.16.aspx</ref>
-As synthetic cannabinoids are active in the milligram range (with below 5mg being a common dose), it is important to [[Dosage|use proper precautions when dosing]] to avoid a negative experience and injury to one self or others.
+As synthetic cannabinoids are active in the milligram range (with below 5mg being a common dose), it is important to [[Dosage|use proper precautions when dosing]] to avoid a negative experience and injury to oneself or others.
 It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.