Chemistry:List of miscellaneous designer cannabinoids

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Since the first synthetic cannabinoids were discovered in recreational drug products in 2008, new synthetic cannabinoids with no precedent in the scientific literature continue to be identified. These synthetic cannabinoids appear to be rationally designed by clandestine medicinal chemists. These unprecedented synthetic cannabinoids often feature alphanumeric code names intended to mimic the style of chemical nomenclature used by academic laboratories and pharmaceutical companies, and there is generally little, if any, information available regarding their pharmacology and toxicology at the time of first discovery.

  • 5F-AB-PINACA — the terminally fluorinated (5-fluoropentyl) analogue of AB-PINACA.[1]
  • 5F-AMB —
  • 5F-ADB —
  • 5F-NNE1 —
  • 5F-PCN —
  • 5F-SDB-006 — the terminally fluorinated (5-fluoropentyl) analogue of SDB-006.[2]
  • AB-001 — one of the earliest adamantane derivatives discovered as a designer cannabinoid. AB-001 was unknown in the scientific literature at the time of its discovery, and has since been characterized as a CB1 and CB2 agonist with weak cannabimimetic activity in rats.[3]
  • AB-005 —
  • AB-CHMINACA —
  • ADAMANTYL-THPINACA —
  • AMB-FUBINACA
  • APICA — also known as 2NE1 and SDB-001, APICA is the carboxamide analogue of AB-001 and was similarly unknown in the scientific literature at the time of its discovery. Like AB-001, APICA is a CB1 and CB2 agonist possessing moderate cannabimimetic potency in rats.[3]
  • APINACA — also known as AKB-48. APINACA is the indazole analogue of APICA.[4]
  • BB-22 —
  • BIM-018 — also known as JWH-018 benzimidazole analogue, is a 1,2-disubstituted benzimidazole analogue of JWH-018.
  • FAB-144 — the indazole analogue of XLR-11.
  • FDU-NNE1
  • FUB-144 — the N-(4-fluorobenzyl) analogue of UR-144 and XLR-11.
  • FUBIMINA — the terminally fluorinated (5-fluoro) analogue of BIM-018.
  • MDMB-CHMICA
  • MDMB-FUBINACA
  • MMB-2201
  • MN-18 — the indazole analogue of NNE1.
  • NM-2201 —
  • NNE1 — also known as NNEI, MN-24 and AM-6527, is the carboxamide analogue of JWH-018. NNE1 was first described in a paper by Abbott Laboratories in 2011.[5]
  • PB-22 —
  • PX-1 —
  • PX-2 —
  • PX-3 —
  • SDB-005 —
  • SDB-006 — is a benzylic analogue of APICA, and was discovered during research related to AB-001 and APICA.[3]
  • STS-135 — the terminally fluorinated (5-fluoro) analogue of APICA.[6] STS-135 is believed to be named after the STS-135 jet propulsion system, and functions as an agonist at CB1 and CB2 receptors.[2]
  • THJ-018 — the indazole analogue of JWH-018.[7]
  • THJ-2201 — the indazole analogue of AM-2201.[7][8][9][10]
  • WIN 55,212-2 —
  • XLR-11 — the terminally fluorinated (5-fluoro) analogue of UR-144.[2]
  • XLR-12 — the terminally trifluorinated (4,4,4-trifluorobutyl) analogue of UR-144.

See also

References

  1. ↑ Banister, S. D.; Moir, M.; Stuart, J.; Kevin, R. C.; Wood, K. E.; Longworth, M.; Wilkinson, S. M.; Beinat, C. et al. (Sep 2015). "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 Chem Neurosci 6 (9): 1546–59. doi:10.1021/acschemneuro.5b00112. PMID 26134475. 
  2. ↑ 2.0 2.1 2.2 Banister, SD; Stuart, J; Kevin, RC; Edington, A; Longworth, M; Wilkinson, SM; Beinat, C; Buchanan, AS et al. (2015). "Effects of Bioisosteric Fluorine in Synthetic Cannabinoid Designer Drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135". ACS Chem Neurosci 6 (8): 1445–58. doi:10.1021/acschemneuro.5b00107. PMID 25921407. https://zenodo.org/record/47750. 
  3. ↑ 3.0 3.1 3.2 Banister, SD; Wilkinson, SM; Longworth, M; Stuart, J; Apetz, N; English, K; Brooker, L; Goebel, C et al. (2013). "The Synthesis and Pharmacological Evaluation of Adamantane-Derived Indoles: Cannabimimetic Drugs of Abuse". ACS Chem Neurosci 4 (7): 1081–92. doi:10.1021/cn400035r. PMID 23551277. 
  4. ↑ Uchiyama, N.; Kawamura, M.; Kikura-Hanajiri, R.; Goda, Y. (2012). "URB-754: A new class of designer drug and 12 synthetic cannabinoids detected in illegal products". Forensic Science International 227 (1–3): 21–32. doi:10.1016/j.forsciint.2012.08.047. PMID 23063179. 
  5. ↑ Blaazer, A. R.; Lange, J. H. M.; Van der Neut, M. A. W.; Mulder, A.; Den Boon, F. S.; Werkman, T. R.; Kruse, C. G.; Wadman, W. J. (2011). "Novel indole and azaindole (pyrrolopyridine) cannabinoid (CB) receptor agonists: Design, synthesis, structure–activity relationships, physicochemical properties and biological activity". European Journal of Medicinal Chemistry 46 (10): 5086–5098. doi:10.1016/j.ejmech.2011.08.021. PMID 21885167. 
  6. ↑ Wilkinson, S. M.; Banister, S. D.; Kassiou, M. (2015). "Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids". Australian Journal of Chemistry 68: 4. doi:10.1071/CH14198. 
  7. ↑ 7.0 7.1 Xingxing Diao; Ariane Wohlfarth; Shaokun Pang; Karl B. Scheidweiler; Marilyn A. Huestis (October 2015). "High-Resolution Mass Spectrometry for Characterizing the Metabolism of Synthetic Cannabinoid THJ-018 and Its 5-Fluoro Analog THJ-2201 after Incubation in Human Hepatocytes". Clinical Chemistry 62 (1): 157–69. doi:10.1373/clinchem.2015.243535. PMID 26430074. 
  8. ↑ Shevyrin, Vadim; Melkozerov, Vladimir; Nevero, Alexander; Eltsov, Oleg; Morzherin, Yuri; Shafran, Yuri (2014). "3-Naphthoylindazoles and 2-naphthoylbenzoimidazoles as novel chemical groups of synthetic cannabinoids: Chemical structure elucidation, analytical characteristics and identification of the first representatives in smoke mixtures". Forensic Science International 242: 72–80. doi:10.1016/j.forsciint.2014.06.022. PMID 25036783. http://www.fsijournal.org/article/S0379-0738%2814%2900258-8/abstract. 
  9. ↑ Nahoko Uchiyama; Yoshihiko Shimokawa; Maiko Kawamura; Ruri Kikura-Hanajiri; Takashi Hakamatsuka (August 2014). "Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products". Forensic Toxicology 32 (2): 266–281. doi:10.1007/s11419-014-0238-5. 
  10. ↑ Xingxing Diao; Karl B. Scheidweiler; Ariane Wohlfarth; Mingshe Zhu; Shaokun Pang; Marilyn A. Huestis (2016). "Strategies to distinguish new synthetic cannabinoid FUBIMINA (BIM-2201) intake from its isomer THJ-2201: metabolism of FUBIMINA in human hepatocytes". Forensic Toxicology 34 (2): 256–267. doi:10.1007/s11419-016-0312-2. PMID 27547265. 



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