View source for Chemistry:ADB-CHMINACA

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

<!--Clinical data-->
| tradename =  
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category =  
| legal_AU = 
| legal_BR = F2
| legal_CA = Schedule II
| legal_DE = Anlage II
| legal_UK = Class B
| legal_US = Schedule I
| legal_UN = P II 
| legal_UN_comment = <ref>{{Cite web |title=Substance Details ADB-CHMINACA |url=https://www.unodc.org/LSS/Substance/Details/c3c5f5b0-9f29-4fa9-a341-eea44ea193c2 |access-date=2024-01-22}}</ref>
| legal_status = Illegal in Singapore, Sweden, Switzerland
| routes_of_administration =

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

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 1185887-13-1
| ATC_prefix =  
| ATC_suffix =  
| PubChem = 68894304
| ChemSpiderID      = 48059556
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = SL4C60689M
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C22698
| smiles            = CC(C)(C)[C@H](NC(=O)c1nn(CC2CCCCC2)c3ccccc13)C(N)=O
| StdInChI          = 1S/C21H30N4O2/c1-21(2,3)18(19(22)26)23-20(27)17-15-11-7-8-12-16(15)25(24-17)13-14-9-5-4-6-10-14/h7-8,11-12,14,18H,4-6,9-10,13H2,1-3H3,(H2,22,26)(H,23,27)/t18-/m1/s1
| StdInChIKey       = ZWCCSIUBHCZKOY-GOSISDBHSA-N

<!--Chemical data-->
| C=21 | H=30 | N=4 | O=2 
}}

'''ADB-CHMINACA''' (also known as '''ADMB-CHMINACA'''<ref>{{cite journal |last1=Pulver |first1=Benedikt |last2=Fischmann |first2=Svenja |last3=Gallegos |first3=Ana |last4=Christie |first4=Rachel |title=EMCDDA framework and practical guidance for naming synthetic cannabinoids |journal=Drug Testing and Analysis |date=March 2023 |volume=15 |issue=3 |pages=255–276 |doi=10.1002/dta.3403}}</ref> and '''MAB-CHMINACA''') is an [[Chemistry:Indazole|indazole]]-based synthetic cannabinoid. It is a potent [[Biology:Agonist|agonist]] of the CB<sub>1</sub> receptor with a binding affinity of ''K''<sub>i</sub>&nbsp;=&nbsp;0.289&nbsp;nM and was originally developed by [[Company:Pfizer|Pfizer]] in 2009 as an [[Biology:Analgesic|analgesic]] medication.<ref>{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/16616 | title=MAB-CHMINACA | publisher=Cayman Chemical | access-date=16 June 2015}}</ref><ref>{{cite patent | url= https://www.google.com/patents/WO2009106980A3 | country = WO | number = 2009/106980 | title = Indazole derivatives | inventor = Buchler IP, Hayes MJ, Hegde SG, Hockerman SL, Jones DE, Kortum SW, Rico JG, Tenbrink RE, Wu KK | assign1 = Pfizer Inc. | pubdate = 3 September 2009 | postscript = . }}</ref> It was identified in cannabinoid blends in Japan in early 2015.<ref>{{cite journal | vauthors = Wurita A, Hasegawa K, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Watanabe K, Suzuki O | title=Identification and quantitation of 5-fluoro-ADB-PINACA and MAB-CHMINACA in dubious herbal products | date=July 2015 | journal=Forensic Toxicology | volume=33 | issue=2 | pages=213–220 | doi=10.1007/s11419-015-0264-y| s2cid=207289143 }}</ref>

== Side effects ==

There have been a number of reported cases of deaths and hospitalizations in relation to this synthetic cannabinoid.<ref>{{cite journal | vauthors = Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Watanabe K, Suzuki O | display-authors = 6 | title = Postmortem distribution of MAB-CHMINACA in body fluids and solid tissues of a human cadaver | journal = Forensic Toxicology | volume = 33 | issue = 2 | pages = 380–387 | date = July 2015 | pmid = 26257834 | pmc = 4525191 | doi = 10.1007/s11419-015-0272-y }}</ref><ref>{{cite web | url=https://www.nytimes.com/2015/04/25/health/surge-in-hospital-visits-linked-to-a-drug-called-spice-alarms-health-officials.html | title=Potent 'Spice' Drug Fuels Rise in Visits to Emergency Room | work=The New York Times | date=24 April 2015 | access-date=29 June 2015 | vauthors = Schwarz A }}</ref><ref>{{cite web | url=http://www.aapcc.org/press/43/ | title=American Association of Poison Control Centers Issues Warning About Reemerging Synthetic Drugs | publisher=American Association of Poison Control Centers | date=23 April 2015 | access-date=29 June 2015}}</ref><ref>{{cite web | url=http://www.adph.org/news/assets/150511.pdf | title=Synthetic cannabinoid users can exhibit bizarre and violent behaviors, hospitalizations after use increase in Alabama over past week | publisher=Alabama Department of Public Health | date=11 May 2015 | access-date=29 June 2015}}</ref><ref>{{cite web | url = http://www.drugscouts.de/de/pillenwarnung/todesf%C3%A4lle-zusammenhang-mit-adb-chminaca | title=Todesfälle in Zusammenhang mit ADB-CHMINACA | publisher=Drug Scouts | date=7 May 2015 | access-date=29 June 2015}}</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 = 103–107 | date = July 2015 | pmid = 26154784 | doi = 10.1056/NEJMp1505328 }}</ref><ref>{{cite news | url=http://www.huffingtonpost.com/2015/05/08/synthetic-marijuana-hospitalizations_n_7241772.html | title=There's Been A Sudden, Alarming Spike In Hospitalizations Caused By Synthetic Marijuana | work=Huffington Post | date=8 May 2015 | access-date=8 August 2015 | vauthors = Collins D }}</ref><ref>{{cite journal | vauthors = Adamowicz P, Gieroń J | title = Acute intoxication of four individuals following use of the synthetic cannabinoid MAB-CHMINACA | journal = Clinical Toxicology | volume = 54 | issue = 8 | pages = 650–654 | date = September 2016 | pmid = 27227269 | doi = 10.1080/15563650.2016.1190016 | s2cid = 23133855 }}</ref>

== Legal status ==
In the United States, ADB-CHMINACA is a Schedule I controlled substance.<ref>{{cite journal | vauthors = ((Drug Enforcement Administration)) | title = Schedules of Controlled Substances: Extension of Temporary Placement of MAB–CHMINACA in Schedule I of the Controlled Substances Act. Temporary rule; temporary scheduling order; extension | journal = Federal Register | volume = 83 | issue = 20 | pages = 4411–4412 | date = January 2018 | pmid = 29461023 }}</ref>  Prior to its listing at the federal level in 2018, Louisiana placed ADB-CHMINACA on its Schedule I list by emergency scheduling in 2014.<ref>{{cite web | url=http://dhh.louisiana.gov/index.cfm/newsroom/detail/3161 | title=Gov. Jindal and State Officials Ban New Synthetic Marijuana Compound | access-date=16 June 2015}}</ref>

Sweden's public health agency suggested to classify ADB-CHMINACA as hazardous substance on November 10, 2014.<ref>{{cite web | url=http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2014/november/cannabinoider-foreslas-bli-klassade-som-halsofarlig-vara/ | title=Cannabinoider föreslås bli klassade som hälsofarlig vara | publisher=Folkhälsomyndigheten | access-date=29 June 2015}}</ref>

ADB-CHMINACA is listed in the Fifth Schedule of the Misuse of Drugs Act (MDA) and therefore illegal in Singapore as of May 2015.<ref>{{cite web | url=http://www.cnb.gov.sg/Libraries/CNB_Newsroom_Files/CNB_NR_-_30_Apr_2015.sflb.ashx | title=CNB NEWS RELEASE | publisher=Central Narcotics Bureau (CNB) | date=30 April 2015 | access-date=24 July 2015 | archive-url=https://web.archive.org/web/20150715045305/http://www.cnb.gov.sg/Libraries/CNB_Newsroom_Files/CNB_NR_-_30_Apr_2015.sflb.ashx | archive-date=15 July 2015 | url-status=dead }}</ref>

ADB-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>

== Metabolism ==
Ten ADB-CHMINACA major metabolites were identified in several incubations with cryopreserved human hepatocytes. Most transformations occurred at the cyclohexylmethyl tail of the compound.<ref>{{cite journal | vauthors = Carlier J, Diao X, Sempio C, Huestis MA | title = Identification of New Synthetic Cannabinoid ADB-CHMINACA (MAB-CHMINACA) Metabolites in Human Hepatocytes | journal = The AAPS Journal | volume = 19 | issue = 2 | pages = 568–577 | date = March 2017 | pmid = 28070717 | doi = 10.1208/s12248-016-0037-5 | doi-access = free }}</ref>

== See also ==
{{div col|colwidth=30em}}
* [[Chemistry:5F-AB-PINACA|5F-AB-PINACA]]
* [[Chemistry:5F-ADB|5F-ADB]]
* [[Chemistry:5F-AMB|5F-AMB]]
* [[Chemistry:5F-APINACA|5F-APINACA]]
* [[Chemistry:AB-FUBINACA|AB-FUBINACA]]
* [[Chemistry:AB-CHFUPYCA|AB-CHFUPYCA]]
* [[Chemistry:AB-CHMINACA|AB-CHMINACA]]
* [[Chemistry:AB-PINACA|AB-PINACA]]
* [[Chemistry:ADB-BINACA|ADB-BINACA]]
* [[Chemistry:ADB-FUBINACA|ADB-FUBINACA]]
* [[Chemistry:ADB-HEXINACA|ADB-HEXINACA]]
* [[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]]
[[Category:Carboxamides]]

{{Sourceattribution|ADB-CHMINACA}}