View source for Chemistry:AB-CHMINACA

{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name = ''N''-[(2''S'')-1-Amino-3-methyl-1-oxobutan-2-yl]-1-(cyclohexylmethyl)indazole-3-carboxamide
| image = AB-CHMINACA.svg

<!--Clinical data-->
| tradename = 
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category = 
| legal_AU =
| legal_BR = F2
| legal_CA = Schedule II
| legal_UK = Class B
| legal_US = Schedule I
| legal_DE = Anlage II
| legal_UN = P II 
| legal_UN_comment = <ref>{{Cite web |title=Substance Details AB-CHMINACA |url=https://www.unodc.org/LSS/Substance/Details/45f2f4f5-3c8b-40f3-99d3-207d2666adc2 |access-date=2024-01-22}}</ref>
| legal_status = Illegal in China and Switzerland
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 1185887-21-1
| ATC_prefix = 
| ATC_suffix = 
| PubChem = 44206133
| KEGG = C22702
| ChemSpiderID      = 30646774
| smiles            = CC(C)[C@H](NC(=O)c1nn(CC2CCCCC2)c3ccccc13)C(N)=O
| StdInChI          = 1S/C20H28N4O2/c1-13(2)17(19(21)25)22-20(26)18-15-10-6-7-11-16(15)24(23-18)12-14-8-4-3-5-9-14/h6-7,10-11,13-14,17H,3-5,8-9,12H2,1-2H3,(H2,21,25)(H,22,26)/t17-/m0/s1
| StdInChIKey       = KJNZIEGLNLCWTQ-KRWDZBQOSA-N
| UNII = QG3J28E7L8

<!--Chemical data-->
| C=20 | H=28 | N=4 | O=2
}}

'''AB-CHMINACA''' is an [[Chemistry:Indazole|indazole]]-based synthetic cannabinoid. It is a potent [[Biology:Agonist|agonist]] of the CB<sub>1</sub> receptor (''K''<sub>i</sub>&nbsp;=&nbsp;0.78&nbsp;nM) and CB<sub>2</sub> receptor (''K''<sub>i</sub>&nbsp;=&nbsp;0.45&nbsp;nM) and fully substitutes for [[Biology:Tetrahydrocannabinol|Δ<sup>9</sup>-THC]] in rat discrimination studies, while being 16x more potent.<ref>{{cite journal | vauthors = Wiley JL, Marusich JA, Lefever TW, Antonazzo KR, Wallgren MT, Cortes RA, Patel PR, Grabenauer M, Moore KN, Thomas BF | display-authors = 6 | title = AB-CHMINACA, AB-PINACA, and FUBIMINA: Affinity and Potency of Novel Synthetic Cannabinoids in Producing Δ9-Tetrahydrocannabinol-Like Effects in Mice | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 354 | issue = 3 | pages = 328–39 | date = September 2015 | pmid = 26105953 | pmc = 4538877 | doi = 10.1124/jpet.115.225326 | url = http://jpet.aspetjournals.org/content/early/2015/06/23/jpet.115.225326.short | name-list-style = amp }}</ref><ref>[https://www.caymanchem.com/app/template/Product.vm/catalog/15434 AB-CHMINACA], Cayman Chemicals</ref> Continuing the trend seen in other cannabinoids of this generation, such as [[Chemistry:AB-FUBINACA|AB-FUBINACA]] and [[Chemistry:AB-PINACA|AB-PINACA]], it contains a [[Chemistry:Valine|valine]] amino acid amide residue as part of its structure, where older cannabinoids contained a naphthyl or [[Chemistry:Adamantane|adamantane]] residue.

== Side effects ==
There have been a number of reported cases of seizures, deaths, and psychotic episodes in relation to this synthetic cannabinoid.<ref>{{cite web | url=https://www.grassley.senate.gov/sites/default/files/news/upload/3-factor%20analysis%20AB-CHMINACA%20AB-PINACA%20THJ2201%2012172014.pdf | title=''N''-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-1''H''-indazole-3-carboxamide (AB-CHMINACA), ''N''-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1''H''-indazole-3-carboxamide (AB-PINACA) and [1-(5-fluoropentyl)-1''H''-indazol-3-yl](naphthalen-1-yl)methanone (THJ-2201). Background Information and Evaluation of 'Three Factor Analysis' (Factors 4, 5, and 6) for Temporary Scheduling. | publisher=Drug Enforcement Administration | date=December 2014 | access-date=7 August 2015}}</ref><ref>{{cite web | url=https://www.independent.co.uk/news/uk/home-news/vertex-police-warn-of-ticking-time-bomb-of-potentially-lethal-cannabis-substitute-10301030.html |archive-url=https://web.archive.org/web/20150605215437/http://www.independent.co.uk/news/uk/home-news/vertex-police-warn-of-ticking-time-bomb-of-potentially-lethal-cannabis-substitute-10301030.html |archive-date=2015-06-05 |url-access=limited |url-status=live | title=Vertex: Police warn of 'ticking time bomb' of potentially lethal cannabis substitute | work=The Independent | date=5 June 2015 | access-date=2 July 2015 | vauthors = Merrill J }}</ref><ref>{{cite journal | vauthors = Trecki J, Gerona RR, Schwartz MD | title = Synthetic Cannabinoid-Related Illnesses and Deaths | journal = The New England Journal of Medicine | volume = 373 | issue = 2 | pages = 103–7 | date = July 2015 | pmid = 26154784 | doi = 10.1056/NEJMp1505328 }}</ref><ref>{{cite journal | vauthors = Wurita A, Hasegawa K, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Suzuki O, Watanabe K | display-authors = 6 | title = Identification and quantification of metabolites of AB-CHMINACA in a urine specimen of an abuser | journal = Legal Medicine | volume = 19 | pages = 113–8 | date = March 2016 | pmid = 26257317 | doi = 10.1016/j.legalmed.2015.07.011 | url = http://www.legalmedicinejournal.com/article/S1344-6223%2815%2930011-0/abstract }}</ref><ref>{{cite web | url=http://www.richlandsource.com/news/no-criminal-charges-in-march-death-of-terrance-moxley/article_4a8029ea-67b9-11e5-a0f0-631f701f77ae.html | title=No criminal charges in March death of Terrance Moxley | publisher=Richland Source | date=30 September 2015 | access-date=2 October 2015 | vauthors = Schock B }}</ref><ref>{{cite journal | vauthors = Tyndall JA, Gerona R, De Portu G, Trecki J, Elie MC, Lucas J, Slish J, Rand K, Bazydlo L, Holder M, Ryan MF, Myers P, Iovine N, Plourde M, Weeks E, Hanley JR, Endres G, St Germaine D, Dobrowolski PJ, Schwartz M | display-authors = 6 | title = An outbreak of acute delirium from exposure to the synthetic cannabinoid AB-CHMINACA | journal = Clinical Toxicology | volume = 53 | issue = 10 | pages = 950–6 | date = November 2015 | pmid = 26555732 | doi = 10.3109/15563650.2015.1100306 | pmc = 9128755 | s2cid = 24724258 }}</ref><ref>{{cite journal | vauthors = Klavž J, Gorenjak M, Marinšek M | title = Suicide attempt with a mix of synthetic cannabinoids and synthetic cathinones: Case report of non-fatal intoxication with AB-CHMINACA, AB-FUBINACA, alpha-PHP, alpha-PVP and 4-CMC | journal = Forensic Science International | volume = 265 | pages = 121–4 | date = August 2016 | pmid = 26890319 | doi = 10.1016/j.forsciint.2016.01.018 }}</ref>

== Legal status ==
In 2015, AB-CHMINACA became a Schedule I controlled substance in the United States.<ref>{{cite journal | title = Schedules of controlled substances: temporary placement of three synthetic cannabinoids into schedule I. Final order | journal = Federal Register | volume = 80 | issue = 20 | pages = 5042–7 | date = January 2015 | pmid = 25730924 | url = https://www.gpo.gov/fdsys/pkg/FR-2015-01-30/pdf/2015-01776.pdf | last1 = Drug Enforcement Administration | first1 = Department of Justice }}</ref>

AB-CHMINACA is an [[Medicine:Drugs controlled by the German Betäubungsmittelgesetz|Anlage II]] controlled substance in Germany as of May 2015.<ref>{{cite web | url=http://www.gesetze-im-internet.de/btmg_1981/anlage_ii.html | title=Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel) | access-date=22 June 2015}}</ref>

As of October 2015 AB-CHMINACA is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref>

AB-CHMINACA is illegal in Switzerland as of December 2015.<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=Der Bundesrat}}</ref>

AB-CHMINACA is an illegal substance in Russian Federation.

== See also ==
{{div col|colwidth=30em}}
* [[Chemistry:5F-AB-PINACA|5F-AB-PINACA]]
* [[Chemistry:5F-ADB|5F-ADB]]
* [[Chemistry:5F-AMB|5F-AMB]]
* A-CHMINACA<ref>{{cite journal | vauthors = Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, Ellison R, Gerona R, Banister SD, Stove CP | display-authors = 6 | title = in Vitro Cannabinoid Receptor 1 Activity of Recently Detected Synthetic Cannabinoids 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA | journal = ACS Chemical Neuroscience | date = November 2020 | volume = 11 | issue = 24 | pages = 4434–4446 | pmid = 33253529 | doi = 10.1021/acschemneuro.0c00644 | s2cid = 227246346 }}</ref>
* [[Chemistry:AB-FUBINACA|AB-FUBINACA]]
* [[Chemistry:AB-CHFUPYCA|AB-CHFUPYCA]]
* [[Chemistry:AB-PINACA|AB-PINACA]]
* [[Chemistry:ADB-CHMINACA|ADB-CHMINACA]]
* [[Chemistry:ADB-FUBINACA|ADB-FUBINACA]]
* [[Chemistry:ADB-PINACA|ADB-PINACA]]
* [[Chemistry:ADBICA|ADBICA]]
* [[Chemistry:APICA (synthetic cannabinoid drug)|APICA]]
* [[Chemistry:APINACA|APINACA]]
* [[Chemistry:MDMB-CHMICA|MDMB-CHMICA]]
* [[Chemistry:MDMB-CHMINACA|MDMB-CHMINACA]]
* [[Chemistry:MDMB-FUBINACA|MDMB-FUBINACA]]
* [[Chemistry:PX-3|PX-3]]
{{Div col end}}

== References ==
{{Reflist}}

{{Cannabinoids}}
{{Cannabinoidergics}}

[[Category:Cannabinoids]]
[[Category:Designer drugs]]
[[Category:Cyclohexyl compounds]]

{{Sourceattribution|AB-CHMINACA}}