ADB-FUBHQUCA explained

Iupac Name:(S)-N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1,4-dihydroquinoline-3-carboxamide
Width:200px
Pubchem:165361603
Smiles:NC(=O)[C@@H](NC(=O)C=1Cc2ccccc2N(C=1)Cc1ccc(F)cc1)C(C)(C)C
C:23
H:26
F:1
N:3
O:2
Stdinchi:1S/C23H26FN3O2/c1-23(2,3)20(21(25)28)26-22(29)17-12-16-6-4-5-7-19(16)27(14-17)13-15-8-10-18(24)11-9-15/h4-11,14,20H,12-13H2,1-3H3,(H2,25,28)(H,26,29)
Stdinchikey:WEFDGWANUSMUJL-UHFFFAOYSA-N

ADB-FUBHQUCA is a synthetic cannabinoid receptor agonist that has been sold as a designer drug, first reported in 2022.[1] It is related to the previously reported compound ADB-FUBICA but with the central indole ring system expanded to a 1,4-dihydroquinoline structure. This breaks the aromaticity of the ring system, and ADB-FUBHQUCA is relatively low in potency compared to related compounds where the aromatic core is retained.[2] [3] [4] [5] [6] [7] [8] [9] [10] [11] [12] [13]

See also

Notes and References

  1. Web site: New Substance Report. 118. ADB-FUBHQUCA . AIPSIN monitoring . 18 February 2022 . ru .
  2. Web site: Cumyl-PeGaClone and other recently encountered synthetic cannabinoid receptor agonists. A review of the evidence on their use and harms. . Advisory Council on the Misuse of Drugs . Government Digital Service, UK Government . 2022 .
  3. Andrews R, Jorge R, Christie R, Gallegos A . From JWH-018 to OXIZIDS: Structural evolution of synthetic cannabinoids in the European Union from 2008 to present day . Drug Testing and Analysis . 15 . 4 . 378–387 . April 2023 . 36507715 . 10.1002/dta.3422 . 254610773 . free .
  4. Ferrarini PL, Calderone V, Cavallini T, Manera C, Saccomanni G, Pani L, Ruiu S, Gessa GL . 6 . Synthesis and biological evaluation of 1,8-naphthyridin-4(1H)-on-3-carboxamide derivatives as new ligands of cannabinoid receptors . Bioorganic & Medicinal Chemistry . 12 . 8 . 1921–1933 . April 2004 . 15051060 . 10.1016/j.bmc.2004.01.035 .
  5. Stern E, Muccioli GG, Millet R, Goossens JF, Farce A, Chavatte P, Poupaert JH, Lambert DM, Depreux P, Hénichart JP . 6 . Novel 4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives as new CB2 cannabinoid receptors agonists: synthesis, pharmacological properties and molecular modeling . Journal of Medicinal Chemistry . 49 . 1 . 70–79 . January 2006 . 16392793 . 10.1021/jm050467q .
  6. Manera C, Benetti V, Castelli MP, Cavallini T, Lazzarotti S, Pibiri F, Saccomanni G, Tuccinardi T, Vannacci A, Martinelli A, Ferrarini PL . 6 . Design, synthesis, and biological evaluation of new 1,8-naphthyridin-4(1H)-on-3-carboxamide and quinolin-4(1H)-on-3-carboxamide derivatives as CB2 selective agonists . Journal of Medicinal Chemistry . 49 . 20 . 5947–5957 . October 2006 . 17004710 . 10.1021/jm0603466 .
  7. Stern E, Muccioli GG, Bosier B, Hamtiaux L, Millet R, Poupaert JH, Hénichart JP, Depreux P, Goossens JF, Lambert DM . 6 . Pharmacomodulations around the 4-oxo-1,4-dihydroquinoline-3-carboxamides, a class of potent CB2-selective cannabinoid receptor ligands: consequences in receptor affinity and functionality . Journal of Medicinal Chemistry . 50 . 22 . 5471–5484 . November 2007 . 17915849 . 10.1021/jm070387h .
  8. Manera C, Cascio MG, Benetti V, Allarà M, Tuccinardi T, Martinelli A, Saccomanni G, Vivoli E, Ghelardini C, Di Marzo V, Ferrarini PL . 6 . New 1,8-naphthyridine and quinoline derivatives as CB2 selective agonists . Bioorganic & Medicinal Chemistry Letters . 17 . 23 . 6505–6510 . December 2007 . 17942307 . 10.1016/j.bmcl.2007.09.089 .
  9. Pasquini S, Botta L, Semeraro T, Mugnaini C, Ligresti A, Palazzo E, Maione S, Di Marzo V, Corelli F . 6 . Investigations on the 4-quinolone-3-carboxylic acid motif. 2. Synthesis and structure-activity relationship of potent and selective cannabinoid-2 receptor agonists endowed with analgesic activity in vivo . Journal of Medicinal Chemistry . 51 . 16 . 5075–5084 . August 2008 . 18680276 . 10.1021/jm800552f .
  10. Manera C, Saccomanni G, Adinolfi B, Benetti V, Ligresti A, Cascio MG, Tuccinardi T, Lucchesi V, Martinelli A, Nieri P, Masini E, Di Marzo V, Ferrarini PL . 6 . Rational design, synthesis, and pharmacological properties of new 1,8-naphthyridin-2(1H)-on-3-carboxamide derivatives as highly selective cannabinoid-2 receptor agonists . Journal of Medicinal Chemistry . 52 . 12 . 3644–3651 . June 2009 . 19435366 . 10.1021/jm801563d .
  11. Pasquini S, Ligresti A, Mugnaini C, Semeraro T, Cicione L, De Rosa M, Guida F, Luongo L, De Chiaro M, Cascio MG, Bolognini D, Marini P, Pertwee R, Maione S, Di Marzo V, Corelli F . 6 . Investigations on the 4-quinolone-3-carboxylic acid motif. 3. Synthesis, structure-affinity relationships, and pharmacological characterization of 6-substituted 4-quinolone-3-carboxamides as highly selective cannabinoid-2 receptor ligands . Journal of Medicinal Chemistry . 53 . 16 . 5915–5928 . August 2010 . 20718492 . 10.1021/jm100123x .
  12. Pasquini S, De Rosa M, Pedani V, Mugnaini C, Guida F, Luongo L, De Chiaro M, Maione S, Dragoni S, Frosini M, Ligresti A, Di Marzo V, Corelli F . 6 . Investigations on the 4-quinolone-3-carboxylic acid motif. 4. Identification of new potent and selective ligands for the cannabinoid type 2 receptor with diverse substitution patterns and antihyperalgesic effects in mice . Journal of Medicinal Chemistry . 54 . 15 . 5444–5453 . August 2011 . 21702498 . 10.1021/jm200476p .
  13. Pasquini S, De Rosa M, Ligresti A, Mugnaini C, Brizzi A, Caradonna NP, Cascio MG, Bolognini D, Pertwee RG, Di Marzo V, Corelli F . 6 . Investigations on the 4-quinolone-3-carboxylic acid motif. 6. Synthesis and pharmacological evaluation of 7-substituted quinolone-3-carboxamide derivatives as high affinity ligands for cannabinoid receptors . European Journal of Medicinal Chemistry . 58 . 30–43 . December 2012 . 23085772 . 10.1016/j.ejmech.2012.09.035 .

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