Chemistry:EG-2201

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EG-2201 (also known as NA-5F-PCZMO using EUDA systematic nomenclature[1]) is a synthetic cannabinoid derived from a carbazole core group.[2] It has been identified as a designer drug and is structurally related to other synthetic cannabinoids, such as EG-018 and MDMB-CHMCZCA. It is primarily used illicitly due to its psychoactive effects, which mimic delta-9-tetrahydrocannabinol (THC), the active ingredient in cannabis.[3]

Chemical properties

EG-2201 comprises a carbazole core group with a 5-fluoropentyl tail group, a methanone linker group, and a napthylenyl linked group. The use of a carbazole core group may increase CB2 receptor affinity compared to less bulky core groups like indoles and indazoles.[3][4]

Pharmacology

EG-2201 acts as an agonist of both human cannabinoid receptors, CB1 and CB2, at an affinity of 22.4 ± 12.8 nM and 4.36 ± 2.91 nM, respectively.[4]

Risks and toxicity

Limited toxicity studies exist for EG-2201, but related synthetic cannabinoids are associated with seizures, cardiovascular events, and psychiatric disturbances. Its metabolic byproducts may also be toxic.[5]

See also

  • Controlled substances

References

  1. ↑ "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis 15 (3): 255–276. March 2023. doi:10.1002/dta.3403. PMID 36346325. 
  2. ↑ Mogler, Lukas; Franz, Florian; Wilde, Maurice; Huppertz, Laura M.; Halter, Sebastian; Angerer, Verena; Moosmann, Bjoern; Auwärter, Volker (2018). "Phase I metabolism of the carbazole-derived synthetic cannabinoids EG-018, EG-2201, and MDMB-CHMCZCA and detection in human urine samples" (in en). Drug Testing and Analysis 10 (9): 1417–1429. doi:10.1002/dta.2398. ISSN 1942-7611. PMID 29726116. https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/10.1002/dta.2398. 
  3. ↑ 3.0 3.1 Potts, A. J.; Cano, C.; Thomas, S. H. L.; Hill, S. L. (2020-02-01). "Synthetic cannabinoid receptor agonists: classification and nomenclature" (in en). Clinical Toxicology 58 (2): 82–98. doi:10.1080/15563650.2019.1661425. ISSN 1556-3650. PMID 31524007. https://www.tandfonline.com/doi/full/10.1080/15563650.2019.1661425. 
  4. ↑ 4.0 4.1 Schoeder, Clara T.; Hess, Cornelius; Madea, Burkhard; Meiler, Jens; Müller, Christa E. (16 April 2017). "Pharmacological evaluation of new constituents of “Spice”: synthetic cannabinoids based on indole, indazole, benzimidazole and carbazole scaffolds" (in en). Forensic Toxicology 36 (2): 385–403. doi:10.1007/s11419-018-0415-z. ISSN 1860-8965. PMID 29963207. PMC 6002460. http://link.springer.com/10.1007/s11419-018-0415-z. 
  5. ↑ Banister, Samuel D.; Connor, Mark (2018), Maurer, Hans H.; Brandt, Simon D., eds., "The Chemistry and Pharmacology of Synthetic Cannabinoid Receptor Agonist New Psychoactive Substances: Evolution" (in en), New Psychoactive Substances (Cham: Springer International Publishing) 252: pp. 191–226, doi:10.1007/164_2018_144, ISBN 978-3-030-10560-0, PMID 30105473, http://link.springer.com/10.1007/164_2018_144, retrieved 2025-01-02 



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