EG-2201

EG-2201
Names
	IUPAC name [9-(5-fluoropentyl)carbazol-3-yl]-naphthalen-1-ylmethanone
	Other names (9-(5-fluoropentyl)-9H-carbazol-3-yl)(naphthalen-1-yl)methanone
Identifiers
CAS Number	2365471-72-1;
3D model (JSmol)	Interactive image;
ChemSpider	DTXSID901342056;
PubChem CID	118796499;
UNII	X0IJ1PKG2Q;
CompTox Dashboard (EPA)	DTXSID901342056 ;
	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,1,6-7,17-18H2 Key: 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 [77 °F], 100 kPa). (what is ?) Infobox references

EG-2201 is a synthetic cannabinoid belonging to the indole-3-carboxamide family.^[1] 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.^[2]

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.^[3]

References

^ 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.
^ 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.
^ 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

Gaunitz, Franziska; Dahm, Patrick; Mogler, Lukas; Thomas, Andreas; Thevis, Mario; Mercer-Chalmers-Bender, Katja (June 2019). "In vitro metabolic profiling of synthetic cannabinoids by pooled human liver microsomes, cytochrome P450 isoenzymes, and Cunninghamella elegans and their detection in urine samples". Analytical and Bioanalytical Chemistry. 411 (16): 3561–3579. doi:10.1007/s00216-019-01837-8. ISSN 1618-2642. PMID 31183523.
Thevis, Mario; Kuuranne, Tiia; Geyer, Hans (2020). "Annual banned-substance review – Analytical approaches in human sports drug testing". Drug Testing and Analysis. 12 (1): 7–26. doi:10.1002/dta.2735. ISSN 1942-7611.
Alam, Ryan M.; Keating, John J. (2020). "Adding more "spice" to the pot: A review of the chemistry and pharmacology of newly emerging heterocyclic synthetic cannabinoid receptor agonists". Drug Testing and Analysis. 12 (3): 297–315. doi:10.1002/dta.2752. ISSN 1942-7611. PMID 31854124.

[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

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