Misplaced Pages

EG-2201

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

This is an old revision of this page, as edited by Wikishovel (talk | contribs) at 07:50, 2 January 2025 (→Chemical properties: these are best left in the infobox). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 07:50, 2 January 2025 by Wikishovel (talk | contribs) (→Chemical properties: these are best left in the infobox)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
This article includes a list of references, related reading, or external links, but its sources remain unclear because it lacks inline citations. Please help improve this article by introducing more precise citations. (January 2025) (Learn how and when to remove this message)
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

Sources

  • Mogler L, Franz F, Wilde M, Huppertz LM, Halter S, Angerer V, Moosmann B, Auwärter V. (September 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: (https://doi.org/10.1002/dta.2398). PMID 29726116.
  • Kavanagh P, Angelov D, McNamara S, Brandt SD. (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: (https://doi.org/10.1007/s00216-019-01837-8). PMID 31183523.
  • Brandt SD, Bowden MJ, Tosh DK, Halldin C, Dastmalchi S, et al. (August 2018). "The Chemistry and Pharmacology of Synthetic Cannabinoid Receptor Agonist New Psychoactive Substances: Evolution". *New Psychoactive Substances*. DOI: (https://doi.org/10.1007/164_2018_144).
  • Potts, AJ, Cano, C, Thomas, SHL, Hill, SL. (2020). "Synthetic cannabinoid receptor agonists: classification and nomenclature". *Clinical Toxicology*. 58 (2): 82–98. DOI: (https://doi.org/10.1080/15563650.2019.1661425).
  • 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: (https://doi.org/10.1002/dta.2735).
This article has not been added to any content categories. Please help out by adding categories to it so that it can be listed with similar articles. (January 2025)
EG-2201 Add topic