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EG-2201

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EG-2201
Names
IUPAC name -naphthalen-1-ylmethanone
Other names (9-(5-fluoropentyl)-9H-carbazol-3-yl)(naphthalen-1-yl)methanone
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C28H24FNO/c29-17-6-1-7-18-30-26-14-5-4-12-23(26)25-19-21(15-16-27(25)30)28(31)24-13-8-10-20-9-2-3-11-22(20)24/h2-5,8-16,19H,1,6-7,17-18H2Key: LYDDINAZVHIBGP-UHFFFAOYSA-N
SMILES
  • C1=CC=C2C(=C1)C=CC=C2C(=O)C3=CC4=C(C=C3)N(C5=CC=CC=C54)CCCCCF
Properties
Chemical formula C28H24FNO
Molar mass 409.5 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N (what is  ?) Infobox references
Chemical compound

EG-2201 is a synthetic cannabinoid belonging to the indole-3-carboxamide family. 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.

Chemical properties

EG-2201 comprises a carbazole core with a fluorinated alkyl chain and a naphthalene-based ketone moiety. These modifications enhance its receptor binding affinity.

Pharmacology

EG-2201 acts as a potent agonist of the cannabinoid receptor type 1 (CB1), producing effects similar to THC. Its synthetic modifications result in increased potency and altered pharmacokinetics, making it more hazardous.

Legal status

The legal status of EG-2201 varies globally:

  • United States: Classified as a Schedule I substance under the Controlled Substances Act.
  • European Union: Banned in several member states.
  • Japan: Controlled under the Narcotics and Psychotropics Control Act.

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.

See also

References

  1. 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". Drug Testing and Analysis. 10 (9): 1417–1429. doi:10.1002/dta.2398. ISSN 1942-7611. PMID 29726116.
  2. Potts, A. J.; Cano, C.; Thomas, S. H. L.; Hill, S. L. (2020-02-01). "Synthetic cannabinoid receptor agonists: classification and nomenclature". Clinical Toxicology. 58 (2): 82–98. doi:10.1080/15563650.2019.1661425. ISSN 1556-3650. PMID 31524007.
  3. 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", New Psychoactive Substances, vol. 252, Cham: Springer International Publishing, pp. 191–226, doi:10.1007/164_2018_144, ISBN 978-3-030-10560-0, PMID 30105473, retrieved 2025-01-02

Sources

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