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	409.504 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N (what is  YN ?) Infobox references

EG-2201 (also known as NA-5F-PCZMO using EUDA systematic nomenclature ^[1] ) is a synthetic cannabinoid belonging to the indole-3-carboxamide family. ^[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 with a fluorinated alkyl chain and a naphthalene-based ketone moiety. These modifications enhance its receptor binding affinity.^{[ citation needed ]}

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.^{[ citation needed ]}

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. ^[4]

See also

• Controlled substances

References

1. Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403. PMID   36346325. S2CID   253396419.
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" . Drug Testing and Analysis. 10 (9): 1417–1429. doi:10.1002/dta.2398. ISSN   1942-7611. PMID   29726116.
3. 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.
4. 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. PMID   31724288.
• 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.