6-APB: Difference between revisions

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==Pharmacology==

6-APB is a [[serotonin]]–[[norepinephrine]]–[[dopamine]] [[reuptake inhibitor]] (SNDRI) with Ki values of 117, 150, and 2698 nM for the norepinephrine transporter (NET), dopamine transporter (DAT), and serotonin transporter (SERT), respectively.<ref name="6APBpharm1"> Iversen L, Gibbons S, Treble R, Setola V, Huang XP, Roth BL (2013). "Neurochemical profiles of some novel psychoactive substances". Eur. J. Pharmacol. 700 (1-3): 147–51. PMID 23261499. https://doi.org10.1016/j.ejphar.2012.12.006</ref> 6-APB also possesses additional activity as a [[releasing agent]] of these [[monoamine neurotransmitters]].<ref> Rickli A, Kopf S, Hoener MC, Liechti ME (2015). "Pharmacological profile of novel psychoactive benzofurans". Br. J. Pharmacol. 172 (13): 3412–25. PMID 25765500. https://doi.org/10.1111/bph.13128</ref>

6-APB is a [[serotonin]]–[[norepinephrine]]–[[dopamine]] [[reuptake inhibitor]] (SNDRI) with Ki values of 117, 150, and 2698 nM for the norepinephrine transporter (NET), dopamine transporter (DAT), and serotonin transporter (SERT), respectively.<ref name="6APBpharm1">Iversen L, Gibbons S, Treble R, Setola V, Huang XP, Roth BL (2013). "Neurochemical profiles of some novel psychoactive substances". Eur. J. Pharmacol. 700 (1-3): 147–51. PMID 23261499. https://doi.org10.1016/j.ejphar.2012.12.006</ref> 6-APB also possesses additional activity as a [[releasing agent]] of these [[monoamine neurotransmitters]].<ref>Rickli A, Kopf S, Hoener MC, Liechti ME (2015). "Pharmacological profile of novel psychoactive benzofurans". Br. J. Pharmacol. 172 (13): 3412–25. PMID 25765500. https://doi.org/10.1111/bph.13128</ref>

6-APB is a potent [[Agonists#Types of agonist|full agonist]] of the serotonin 5-HT2B receptor (Ki = 3.7 nM)<ref name="6APBpharm1" />, with higher affinity for this target than any other site.<ref name="5HT2C">Canal CE, Murnane KS (2017). "The serotonin 5-HT2C receptor and the non-addictive nature of classic hallucinogens". J. Psychopharmacol. (Oxford). 31 (1): 127–143. PMID 27903793. https://doi.org/10.1177/0269881116677104</ref> Moreover, unlike MDMA, 6-APB shows 100-fold selectivity for the 5-HT2B receptor over the 5-HT2A and 5-HT2C receptors.<ref name="5HT2C"

6-APB is a potent [[Agonists#Types of agonist|full agonist]] of the serotonin 5-HT2B receptor (Ki = 3.7 nM)<ref name="6APBpharm1" />, with higher affinity for this target than any other site.<ref name="5HT2C">Canal CE, Murnane KS (2017). "The serotonin 5-HT2C receptor and the non-addictive nature of classic hallucinogens". J. Psychopharmacol. (Oxford). 31 (1): 127–143. PMID 27903793. https://doi.org/10.1177/0269881116677104</ref> Moreover, unlike MDMA, 6-APB shows 100-fold selectivity for the 5-HT2B receptor over the 5-HT2A and 5-HT2C receptors.<ref name="5HT2C" /><ref>US patent 7045545, Karin Briner, Joseph Paul Burkhart, Timothy Paul Burkholder, Matthew Joseph Fisher, William Harlan Gritton, Daniel Timothy Kohlman, Sidney Xi Liang, Shawn Christopher Miller, Jeffrey Thomas Mullaney, Yao-Chang Xu, Yanping Xu, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 19 January 2000, issued 16 May 2006</ref>

/><ref>US patent 7045545, Karin Briner, Joseph Paul Burkhart, Timothy Paul Burkholder, Matthew Joseph Fisher, William Harlan Gritton, Daniel Timothy Kohlman, Sidney Xi Liang, Shawn Christopher Miller, Jeffrey Thomas Mullaney, Yao-Chang Xu, Yanping Xu, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 19 January 2000, issued 16 May 2006</ref>

Aside from the 5-HT2B receptor, 6-APB has also been found to bind with high affinity to the α2C-adrenergic receptor subtype (Ki = 45 nM), although the clinical significance of this action is unknown.<ref name="6APBpharm1 />

Aside from the 5-HT2B receptor, 6-APB has also been found to bind with high affinity to the α2C-adrenergic receptor subtype (Ki = 45 nM), although the clinical significance of this action is unknown.<ref name="6APBpharm1" />

The potent agonism of the 5-HT2B receptor makes it likely that 6-APB would be cardiotoxic with chronic or long-term use, as seen with other 5-HT2B receptor agonists such as the withdrawn serotonergic anorectic [https://en.wikipedia.org/wiki/Fenfluramine fenfluramine].<ref name="6APBpharm1" /><ref>Advisory Council on the Misuse of Drugs, Jeremy Browne (4 June 2013). "Temporary class drug order on benzofury and NBOMe compounds - letter from ACMD". GOV.UK.</ref>

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*'''Australia and New Zealand:''' Certain countries contain a "substantially similar" catch-all clause in their drug law, such as New Zealand and Australia. This includes 6-APB as it is similar in chemical structure to the class A drug MDA, meaning 6-APB may be viewed as a controlled substance analogue in these jurisdictions.{{citation needed}}

*'''Canada:''' 6-APB is Schedule III in Canada as it is an analogue of MDA. The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.{{citation needed}}

*'''Germany:''' 6-APB is illegal ~~in Germany~~.<ref>{{cite web|url=http://archive.is/QEKft|accessdate=2018-01-12|title=Anlage II BtMG - Einzelnorm)}}</ref>

*'''Germany:''' 6-APB is controlled under Anlage II of the BtMG, making it illegal to manufacture, import, possess, sell, or transfer it without a license.<ref>{{cite web|url=http://archive.is/QEKft|accessdate=2018-01-12|title=Anlage II BtMG - Einzelnorm)}}</ref>

*'''Italy:''' 6-APB is illegal in Italy.<ref>http://www.salute.gov.it/imgs/C_17_pagineAree_3729_listaFile_itemName_0_file.pdf</ref>

*'''Sweden:''' 6-APB is prohibited in Sweden as a "health hazard" as of 2009.{{citation needed}}

@@ Line 24: / Line 24: @@
 ==Pharmacology==
--APB is a [[serotonin]]–[[norepinephrine]]–[[dopamine]] [[reuptake inhibitor]] (SNDRI) with Ki values of 117, 150, and 2698 nM for the norepinephrine transporter (NET), dopamine transporter (DAT), and serotonin transporter (SERT), respectively.<ref name="6APBpharm1"> Iversen L, Gibbons S, Treble R, Setola V, Huang XP, Roth BL (2013). "Neurochemical profiles of some novel psychoactive substances". Eur. J. Pharmacol. 700 (1-3): 147–51. PMID 23261499. https://doi.org10.1016/j.ejphar.2012.12.006</ref> 6-APB also possesses additional activity as a [[releasing agent]] of these [[monoamine neurotransmitters]].<ref> Rickli A, Kopf S, Hoener MC, Liechti ME (2015). "Pharmacological profile of novel psychoactive benzofurans". Br. J. Pharmacol. 172 (13): 3412–25. PMID 25765500. https://doi.org/10.1111/bph.13128</ref>
+-APB is a [[serotonin]]–[[norepinephrine]]–[[dopamine]] [[reuptake inhibitor]] (SNDRI) with Ki values of 117, 150, and 2698 nM for the norepinephrine transporter (NET), dopamine transporter (DAT), and serotonin transporter (SERT), respectively.<ref name="6APBpharm1">Iversen L, Gibbons S, Treble R, Setola V, Huang XP, Roth BL (2013). "Neurochemical profiles of some novel psychoactive substances". Eur. J. Pharmacol. 700 (1-3): 147–51. PMID 23261499. https://doi.org10.1016/j.ejphar.2012.12.006</ref> 6-APB also possesses additional activity as a [[releasing agent]] of these [[monoamine neurotransmitters]].<ref>Rickli A, Kopf S, Hoener MC, Liechti ME (2015). "Pharmacological profile of novel psychoactive benzofurans". Br. J. Pharmacol. 172 (13): 3412–25. PMID 25765500. https://doi.org/10.1111/bph.13128</ref>
--APB is a potent [[Agonists#Types of agonist|full agonist]] of the serotonin 5-HT<sub>2B</sub> receptor (Ki = 3.7 nM)<ref name="6APBpharm1" />, with higher affinity for this target than any other site.<ref name="5HT2C">Canal CE, Murnane KS (2017). "The serotonin 5-HT2C receptor and the non-addictive nature of classic hallucinogens". J. Psychopharmacol. (Oxford). 31 (1): 127–143. PMID 27903793. https://doi.org/10.1177/0269881116677104</ref> Moreover, unlike MDMA, 6-APB shows 100-fold selectivity for the 5-HT<sub>2B</sub> receptor over the 5-HT<sub>2A</sub> and 5-HT<sub>2C</sub> receptors.<ref name="5HT2C"
+-APB is a potent [[Agonists#Types of agonist|full agonist]] of the serotonin 5-HT<sub>2B</sub> receptor (Ki = 3.7 nM)<ref name="6APBpharm1" />, with higher affinity for this target than any other site.<ref name="5HT2C">Canal CE, Murnane KS (2017). "The serotonin 5-HT2C receptor and the non-addictive nature of classic hallucinogens". J. Psychopharmacol. (Oxford). 31 (1): 127–143. PMID 27903793. https://doi.org/10.1177/0269881116677104</ref> Moreover, unlike MDMA, 6-APB shows 100-fold selectivity for the 5-HT<sub>2B</sub> receptor over the 5-HT<sub>2A</sub> and 5-HT<sub>2C</sub> receptors.<ref name="5HT2C" /><ref>US patent 7045545, Karin Briner, Joseph Paul Burkhart, Timothy Paul Burkholder, Matthew Joseph Fisher, William Harlan Gritton, Daniel Timothy Kohlman, Sidney Xi Liang, Shawn Christopher Miller, Jeffrey Thomas Mullaney, Yao-Chang Xu, Yanping Xu, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 19 January 2000, issued 16 May 2006</ref>
- /><ref>US patent 7045545, Karin Briner, Joseph Paul Burkhart, Timothy Paul Burkholder, Matthew Joseph Fisher, William Harlan Gritton, Daniel Timothy Kohlman, Sidney Xi Liang, Shawn Christopher Miller, Jeffrey Thomas Mullaney, Yao-Chang Xu, Yanping Xu, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 19 January 2000, issued 16 May 2006</ref>
-Aside from the 5-HT<sub>2B</sub> receptor, 6-APB has also been found to bind with high affinity to the α<sub>2C</sub>-adrenergic receptor subtype (Ki = 45 nM), although the clinical significance of this action is unknown.<ref name="6APBpharm1 />
+Aside from the 5-HT<sub>2B</sub> receptor, 6-APB has also been found to bind with high affinity to the α<sub>2C</sub>-adrenergic receptor subtype (Ki = 45 nM), although the clinical significance of this action is unknown.<ref name="6APBpharm1" />
 The potent agonism of the 5-HT<sub>2B</sub> receptor makes it likely that 6-APB would be cardiotoxic with chronic or long-term use, as seen with other 5-HT<sub>2B</sub> receptor agonists such as the withdrawn serotonergic anorectic [https://en.wikipedia.org/wiki/Fenfluramine fenfluramine].<ref name="6APBpharm1" /><ref>Advisory Council on the Misuse of Drugs, Jeremy Browne (4 June 2013). "Temporary class drug order on benzofury and NBOMe compounds - letter from ACMD". GOV.UK.</ref>
@@ Line 188: / Line 187: @@
 *'''Australia and New Zealand:''' Certain countries contain a "substantially similar" catch-all clause in their drug law, such as New Zealand and Australia. This includes 6-APB as it is similar in chemical structure to the class A drug MDA, meaning 6-APB may be viewed as a controlled substance analogue in these jurisdictions.{{citation needed}}
 *'''Canada:''' 6-APB is Schedule III in Canada as it is an analogue of MDA. The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.{{citation needed}}
-*'''Germany:''' 6-APB is illegal in Germany.<ref>{{cite web|url=http://archive.is/QEKft|accessdate=2018-01-12|title=Anlage II BtMG - Einzelnorm)}}</ref>
+*'''Germany:''' 6-APB is controlled under Anlage II of the BtMG, making it illegal to manufacture, import, possess, sell, or transfer it without a license.<ref>{{cite web|url=http://archive.is/QEKft|accessdate=2018-01-12|title=Anlage II BtMG - Einzelnorm)}}</ref>
 *'''Italy:''' 6-APB is illegal in Italy.<ref>http://www.salute.gov.it/imgs/C_17_pagineAree_3729_listaFile_itemName_0_file.pdf</ref>
 *'''Sweden:''' 6-APB is prohibited in Sweden as a "health hazard" as of 2009.{{citation needed}}