AB-FUBINACA: Difference between revisions

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{{SubstanceBox/AB-FUBINACA}}
{{SubstanceBox/AB-FUBINACA}}


'''AB-FUBINACA''' ('''N-[(1S)-1-(Aminocarbonyl)-2-methylpropyl]-1-[(4-fluorophenyl)methyl]-1H-indazole-3-carboxamide''') is a drug that acts as a potent agonist for the [[Psychoactive class::cannabinoid]] [[receptor]]s which produces subjective effects somewhat similar to that of [[cannabis]]. It was originally developed by Pfizer in 2009 as an [[analgesic]] medication,<ref>The cannabinoid receptors (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/12432948</ref> but was never pursued for human use. Subsequently in 2012, this compound was discovered as an ingredient in synthetic cannabis blends in Japan<ref>Uchiyama, N.; Matsuda, S.; Wakana, D.; Kikura-Hanajiri, R.; Goda, Y. (2012). "New cannabimimetic indazole derivatives, N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA) and N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (AB-FUBINACA) identified as [[designer drug]]s in illegal products".</ref> along with a related compound [[AB-PINACA]] which had not previously been reported.
'''AB-FUBINACA''' is a novel synthetic [[Psychoactive class::cannabinoid]] compound. Members of this group produce cannabis-like effects when [[administered]].
 
AB-FUBINACA was originally developed by Pfizer in 2009 as an [[analgesic]] medication,<ref>The cannabinoid receptors (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/12432948</ref> but was not pursued for human use. Subsequently in 2012, it was discovered as an ingredient in synthetic cannabis blends in Japan<ref>Uchiyama, N.; Matsuda, S.; Wakana, D.; Kikura-Hanajiri, R.; Goda, Y. (2012). "New cannabimimetic indazole derivatives, N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA) and N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (AB-FUBINACA) identified as [[designer drug]]s in illegal products".</ref> along with a related compound [[AB-PINACA]] which had not previously been reported.


Cannabinoids are commonly smoked or vaporized to achieve a quick [[onset]] of effects and rapid [[offset]]. AB-FUBINACA 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.
Cannabinoids are commonly smoked or vaporized to achieve a quick [[onset]] of effects and rapid [[offset]]. AB-FUBINACA 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 [[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.
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 higher toxicity]]. It is strongly discouraged to take this substance for extended periods of time or in high doses.
==Chemistry==
==Chemistry==
AB-FUBINACA, or N-[(1S)-1-(Aminocarbonyl)-2-methylpropyl]-1-[(4-fluorophenyl)methyl]-1H-indazole-3-carboxamide, is a synthetic [[Chemical class::indazole cannabinoid]] drug as it contains a substituted indazole core. A 4-substituted fluorophenyl group is bound to this indazole core through a methyl group at R<sub>1</sub> of the indazole. This indazole is substituted at R<sub>3</sub> with a carboxamide group. The terminal amine of this carboxamide is bonded to a substituted propyl chain with an aminocarbonyl group at R<sub>1</sub> and a methyl group at R<sub>2</sub>.
AB-FUBINACA, or N-[(1S)-1-(Aminocarbonyl)-2-methylpropyl]-1-[(4-fluorophenyl)methyl]-1H-indazole-3-carboxamide, is a synthetic [[Chemical class::indazole cannabinoid]] drug as it contains a substituted indazole core. A 4-substituted fluorophenyl group is bound to this indazole core through a methyl group at R<sub>1</sub> of the indazole. This indazole is substituted at R<sub>3</sub> with a carboxamide group. The terminal amine of this carboxamide is bonded to a substituted propyl chain with an aminocarbonyl group at R<sub>1</sub> and a methyl group at R<sub>2</sub>.
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Tolerance to many of the effects of AB-FUBINACA [[Time to full tolerance::develops with prolonged and repeated use]]. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). AB-FUBINACA presents cross-tolerance with [[Cross-tolerance::all [[cannabinoids]]]], meaning that after the consumption of AB-FUBINACA all cannabinoids will have a reduced effect.
Tolerance to many of the effects of AB-FUBINACA [[Time to full tolerance::develops with prolonged and repeated use]]. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). AB-FUBINACA presents cross-tolerance with [[Cross-tolerance::all [[cannabinoids]]]], meaning that after the consumption of AB-FUBINACA all cannabinoids will have a reduced effect.


==Legal issues==
==Legal status==
*'''United Kingdom''' - AB-FUBINACA is a class B drug under the third-generation synthetic cannabinoids generic definition, which came into effect on the 14th December 2016 and is illegal to possess, produce, supply, or import. <ref>The Misuse of Drugs Act 1971 (Amendment) Order 2016 (Legislation.gov.uk) | http://www.legislation.gov.uk/uksi/2016/1109/made</ref>
*'''United Kingdom''' - AB-FUBINACA is a class B drug under the third-generation synthetic cannabinoids generic definition, which came into effect on the 14th December 2016 and is illegal to possess, produce, supply, or import. <ref>The Misuse of Drugs Act 1971 (Amendment) Order 2016 (Legislation.gov.uk) | http://www.legislation.gov.uk/uksi/2016/1109/made</ref>
*'''USA:''' In January 2014, AB-FUBINACA was designated as a Schedule I controlled substance in the United States.<ref>Four Postmortem Case Reports with Quantitative Detection of the Synthetic Cannabinoid, 5F-PB-22 (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/24876364</ref>
*'''United States''' In January 2014, AB-FUBINACA was designated as a Schedule I controlled substance in the United States.<ref>Four Postmortem Case Reports with Quantitative Detection of the Synthetic Cannabinoid, 5F-PB-22 (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/24876364</ref>
*'''Germany''': On December 13, 2014 AB-FUBINACA was added to the controlled substance act ("BtMG"), making it illegal to produce, sell or possess.<ref>Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften (28. BtMÄndV)| http://www.buzer.de/gesetz/11392/a189949.htm</ref>
*'''Germany''': On December 13, 2014 AB-FUBINACA was added to the controlled substance act ("BtMG"), making it illegal to produce, sell or possess.<ref>Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften (28. BtMÄndV)| http://www.buzer.de/gesetz/11392/a189949.htm</ref>
*'''Latvia:''' AB-FUBINACA is a Schedule I drug.<ref>Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (Indazola-3-karbonilatvasinājumi) | http://likumi.lv/doc.php?id=121086</ref>
*'''Latvia:''' AB-FUBINACA is a Schedule I drug.<ref>Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (Indazola-3-karbonilatvasinājumi) | http://likumi.lv/doc.php?id=121086</ref>
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*[https://en.wikipedia.org/wiki/AB-FUBINACA AB-FUBINACA (Wikipedia)]
*[https://en.wikipedia.org/wiki/AB-FUBINACA AB-FUBINACA (Wikipedia)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=2634 AB-FUBINACA (Isomer Design)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=2634 AB-FUBINACA (Isomer Design)]
===Discussion===
*[https://www.ukchemicalresearch.org/Thread-AB-FUBINACA AB-FUBINACA (UKCR)]
*[https://www.ukchemicalresearch.org/Thread-AB-FUBINACA AB-FUBINACA (UKCR)]


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[[Category:Cannabinoid]]
[[Category:Cannabinoid]]
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Substance]]