EG-2201: Difference between revisions

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	* {{Cite journal \|last=Alam \|first=Ryan M. \|last2=Keating \|first2=John J. \|date=2020 \|title=Adding more “spice” to the pot: A review of the chemistry and pharmacology of newly emerging heterocyclic synthetic cannabinoid receptor agonists \|url=https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/10.1002/dta.2752 \|journal=Drug Testing and Analysis \|language=en \|volume=12 \|issue=3 \|pages=297–315 \|doi=10.1002/dta.2752 \|issn=1942-7611}}		* {{Cite journal \|last=Alam \|first=Ryan M. \|last2=Keating \|first2=John J. \|date=2020 \|title=Adding more “spice” to the pot: A review of the chemistry and pharmacology of newly emerging heterocyclic synthetic cannabinoid receptor agonists \|url=https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/10.1002/dta.2752 \|journal=Drug Testing and Analysis \|language=en \|volume=12 \|issue=3 \|pages=297–315 \|doi=10.1002/dta.2752 \|issn=1942-7611}}

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Revision as of 22:12, 2 January 2025

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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	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,1,6-7,17-18H2Key: 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.

References

Sources

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.
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.
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, retrieved 2025-01-02
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.
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.

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