AB-CHMINACA
Chemical compound
- BR: Class F2 (Prohibited psychotropics)[1]
- CA: Schedule II
- DE: Anlage II (Authorized trade only, not prescriptible)
- UK: Class B
- US: Schedule I
- UN: Psychotropic Schedule II[2]
- Illegal in China and Switzerland
- N-[(2S)-1-Amino-3-methyl-1-oxobutan-2-yl]-1-(cyclohexylmethyl)indazole-3-carboxamide
- 1185887-21-1
Y
- 44206133
- 30646774
- QG3J28E7L8
- C22702
- DTXSID101009983
- Interactive image
- CC(C)[C@H](NC(=O)c1nn(CC2CCCCC2)c3ccccc13)C(N)=O
InChI
- InChI=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
- Key:KJNZIEGLNLCWTQ-KRWDZBQOSA-N
AB-CHMINACA is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor (Ki = 0.78 nM) and CB2 receptor (Ki = 0.45 nM) and fully substitutes for Δ9-THC in rat discrimination studies, while being 16x more potent.[3][4] Continuing the trend seen in other cannabinoids of this generation, such as AB-FUBINACA and AB-PINACA, it contains a valine amino acid amide residue as part of its structure, where older cannabinoids contained a naphthyl or adamantane residue.
Side effects
There have been a number of reported cases of seizures, deaths, and psychotic episodes in relation to this synthetic cannabinoid.[5][6][7][8][9][10][11]
Legal status
In 2015, AB-CHMINACA became a Schedule I controlled substance in the United States.[12]
AB-CHMINACA is an Anlage II controlled substance in Germany as of May 2015.[13]
As of October 2015 AB-CHMINACA is a controlled substance in China.[14]
AB-CHMINACA is illegal in Switzerland as of December 2015.[15]
AB-CHMINACA is an illegal substance in Russian Federation.
See also
References
- ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
- ^ "Substance Details AB-CHMINACA". Retrieved 2024-01-22.
- ^ Wiley JL, Marusich JA, Lefever TW, Antonazzo KR, Wallgren MT, Cortes RA, et al. (September 2015). "AB-CHMINACA, AB-PINACA, and FUBIMINA: Affinity and Potency of Novel Synthetic Cannabinoids in Producing Δ9-Tetrahydrocannabinol-Like Effects in Mice". The Journal of Pharmacology and Experimental Therapeutics. 354 (3): 328–39. doi:10.1124/jpet.115.225326. PMC 4538877. PMID 26105953.
- ^ AB-CHMINACA, Cayman Chemicals
- ^ "N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-1H-indazole-3-carboxamide (AB-CHMINACA), N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA) and [1-(5-fluoropentyl)-1H-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" (PDF). Drug Enforcement Administration. December 2014. Retrieved 7 August 2015.
- ^ Merrill J (5 June 2015). "Vertex: Police warn of 'ticking time bomb' of potentially lethal cannabis substitute". The Independent. Archived from the original on 2015-06-05. Retrieved 2 July 2015.
- ^ Trecki J, Gerona RR, Schwartz MD (July 2015). "Synthetic Cannabinoid-Related Illnesses and Deaths". The New England Journal of Medicine. 373 (2): 103–7. doi:10.1056/NEJMp1505328. PMID 26154784.
- ^ Wurita A, Hasegawa K, Minakata K, Gonmori K, Nozawa H, Yamagishi I, et al. (March 2016). "Identification and quantification of metabolites of AB-CHMINACA in a urine specimen of an abuser". Legal Medicine. 19: 113–8. doi:10.1016/j.legalmed.2015.07.011. PMID 26257317.
- ^ Schock B (30 September 2015). "No criminal charges in March death of Terrance Moxley". Richland Source. Retrieved 2 October 2015.
- ^ Tyndall JA, Gerona R, De Portu G, Trecki J, Elie MC, Lucas J, et al. (November 2015). "An outbreak of acute delirium from exposure to the synthetic cannabinoid AB-CHMINACA". Clinical Toxicology. 53 (10): 950–6. doi:10.3109/15563650.2015.1100306. PMC 9128755. PMID 26555732. S2CID 24724258.
- ^ Klavž J, Gorenjak M, Marinšek M (August 2016). "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". Forensic Science International. 265: 121–4. doi:10.1016/j.forsciint.2016.01.018. PMID 26890319.
- ^ Drug Enforcement Administration, Department of Justice (January 2015). "Schedules of controlled substances: temporary placement of three synthetic cannabinoids into schedule I. Final order" (PDF). Federal Register. 80 (20): 5042–7. PMID 25730924.
- ^ "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)". Retrieved 22 June 2015.
- ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
- ^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien". Der Bundesrat.
- ^ Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, et al. (November 2020). "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". ACS Chemical Neuroscience. 11 (24): 4434–4446. doi:10.1021/acschemneuro.0c00644. PMID 33253529. S2CID 227246346.
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| Cannabibutols |
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| Active metabolites |
- Arachidonoyl ethanolamide (AEA; anandamide)
- 2-Arachidonoylglycerol (2-AG)
- 2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
- 2-Oleoylglycerol (2-OG)
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- N-Arachidonylglycine (NAGly)
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- N-Arachidonoyl serotonin (AA-5-HT)
- Docosatetraenoylethanolamide (DEA)
- Lysophosphatidylinositol (LPI)
- Oleamide
- Oleoylethanolamide (OEA)
- Palmitoylethanolamide (PEA)
- RVD-Hpα
- Stearoylethanolamide (SEA)
- O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
cannabinoid
receptor
agonists /
neocannabinoids
| Classical cannabinoids (dibenzopyrans) |
|
|---|---|
| Non-classical cannabinoids |
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| Eicosanoids |
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| Hydrocarbons | |
| Indazole carboxamides | |
| Indazole-3- carboxamides |
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| Indole-3-carboxamides |
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| Indole-3-carboxylates | |
| Naphthoylindazoles | |
| Naphthoylindoles |
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| Naphthoylpyrroles | |
| Naphthylmethylindenes | |
| Naphthylmethylindoles | |
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| Pyrazolecarboxamides |
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| Quinolinyl esters | |
| Tetramethylcyclo- propanoylindazoles | |
| Tetramethylcyclo- propanoylindoles | |
| Tetramethylcyclo- propylindoles | |
| Others |
|
enhancers
(inactivation inhibitors)
- 4-Nonylphenylboronic acid
- AM-404
- Arachidonoyl serotonin
- Arvanil
- BIA 10-2474
- Biochanin A
- CAY-10401
- CAY-10429
- Genistein
- Guineesine
- IDFP
- JNJ 1661010
- JNJ-42165279
- JZL184
- JZL195
- Kaempferol
- LY-2183240
- MK-4409
- O-1624
- O-2093
- Oleoylethanolamide (OEA)
- Olvanil
- Palmitoylethanolamide (PEA)
- PF-04457845
- PF-622
- PF-750
- PF-3845
- PHOP
- URB-447
- URB-597
- URB-602
- URB-754
- VDM-11
(antagonists/inverse
agonists/antibodies)
- AM-251
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- AM-4113
- AM-6527
- AM-6545
- BML-190
- Brizantin (Бризантин)
- CAY-10508
- CB-25
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- Dietressa (Диетресса)
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- Hemopressin
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- JTE-907
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- MK-9470
- NESS-0327
- NIDA-41020
- O-606
- O-1184
- O-1248
- O-1918
- O-2050
- O-2654
- Otenabant (CP-945,598)
- PF-514273
- PipISB
- PSB-SB-487
- Rimonabant (SR141716)
- Rosonabant (E-6776)
- SR-144,528
- Surinabant (SR147778)
- Taranabant (MK-0364)
- TM-38837
- VCHSR
- See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
- List of: AM cannabinoids
- JWH cannabinoids
- Designer drugs § Synthetic cannabimimetics
