AB-PINACA

化合物

AB-PINACA是一种有机化合物,化学式为C18H26N4O2。它最初由辉瑞公司于2009年作为镇痛药开发,[1][2]并在2012年于日本首次被鉴定为合成大麻素[3]

AB-PINACA
法律規範狀態
法律規範
识别信息
  • N-[(1S)-1-(Aminocarbonyl)-2-methylpropyl]-1-pentyl-1H-indazole-3-carboxamide
CAS号1445752-09-9  checkY
PubChem CID
ChemSpider
UNII
CompTox Dashboard英语CompTox Chemicals Dashboard (EPA)
化学信息
化学式C18H26N4O2
摩尔质量330.43 g·mol−1
3D模型(JSmol英语JSmol
  • CCCCCn1c2ccccc2c(n1)C(=O)N[C@@H](C(C)C)C(=O)N
  • InChI=1S/C18H26N4O2/c1-4-5-8-11-22-14-10-7-6-9-13(14)16(21-22)18(24)20-15(12(2)3)17(19)23/h6-7,9-10,12,15H,4-5,8,11H2,1-3H3,(H2,19,23)(H,20,24)/t15-/m0/s1
  • Key:GIMHPAQOAAZSHS-HNNXBMFYSA-N

它是潜在的CB1受体Ki = 2.87 nM,EC50 = 1.2 nM)和CB2受体Ki = 0.88 nM,EC50 = 2.5 nM)的激动剂。[4][5]

这种合成大麻素有不少相关死亡和住院病例报告。[6]

参见

参考文献

  1. ^ AB-PINACA. Cayman Chemical. [25 June 2015]. (原始内容存档于2015-06-26). 
  2. ^ Patent WO/2009/106980 - Indazole derivatives. [2023-01-26]. (原始内容存档于2016-05-27). 
  3. ^ Uchiyama N, Matsuda S, Wakana D, Kikura-Hanajiri R, Goda Y. 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 drugs in illegal products. Forensic Toxicology. 2012, 31: 93–100. S2CID 25242453. doi:10.1007/s11419-012-0171-4. 
  4. ^ Banister SD, Moir M, Stuart J, Kevin RC, Wood KE, Longworth M, et al. Pharmacology of Indole and Indazole Synthetic Cannabinoid Designer Drugs AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADB-PINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA, and 5F-ADBICA. ACS Chemical Neuroscience. September 2015, 6 (9): 1546–59. PMID 26134475. doi:10.1021/acschemneuro.5b00112. 
  5. ^ Wiley JL, Marusich JA, Lefever TW, Antonazzo KR, Wallgren MT, Cortes RA, et al. 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. September 2015, 354 (3): 328–39 [2023-01-26]. PMC 4538877 . PMID 26105953. doi:10.1124/jpet.115.225326. (原始内容存档于2023-01-30). 
  6. ^ Trecki J, Gerona RR, Schwartz MD. Synthetic Cannabinoid-Related Illnesses and Deaths. The New England Journal of Medicine. July 2015, 373 (2): 103–7. PMID 26154784. doi:10.1056/NEJMp1505328.