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| Names | |
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| IUPAC name -naphthalen-1-ylmethanone | |
| Other names (9-(5-fluoropentyl)-9H-carbazol-3-yl)(naphthalen-1-yl)methanone | |
| Identifiers | |
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| 3D model (JSmol) | |
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InChI
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SMILES
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| 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
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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
- IUPAC name: -naphthalen-1-ylmethanone - Molecular formula: C28H24FNO - Molar mass: 409.5 g/mol - Structure: 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
1. 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.
2. 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.
3. 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).
4. 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).
5. 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).
See Also
- Synthetic cannabinoids - Controlled substances