EG-018

EG-018
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act; Illegal in Japan;
Identifiers
	IUPAC name Naphthalen-1-yl-(9-pentylcarbazol-3-yl)methanone;
CAS Number	2219320-91-7;
PubChem CID	118796466;
ChemSpider	30922490;
UNII	5G2788GL5G;
CompTox Dashboard (EPA)	DTXSID001337258 ;
Chemical and physical data
Formula	C28H25NO
Molar mass	391.514 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCN1C2=C(C=C(C=C2)C(=O)C3=CC=CC4=CC=CC=C43)C5=CC=CC=C51;
	InChI InChI=1S/C28H25NO/c1-2-3-8-18-29-26-15-7-6-13-23(26)25-19-21(16-17-27(25)29)28(30)24-14-9-11-20-10-4-5-12-22(20)24/h4-7,9-17,19H,2-3,8,18H2,1H3; Key:FJMMDJDPNLZYLA-UHFFFAOYSA-N;

EG-018 is a carbazole-based synthetic cannabinoid that has been sold online as a designer drug.^[1]^[2]^[3]^[4]^[5] It acts as a partial agonist of the CB₁ and CB₂ receptor, with reasonably high binding affinity, but low efficacy in terms of inducing a signaling response.^[6]

Legal status

EG-018 is a controlled substance in Japan.^[7]

References

^ "EG 018". www.caymanchem.com.
^ Mogler, Lukas; Franz, Florian; Wilde, Maurice; Huppertz, Laura M.; Halter, Sebastian; Angerer, Verena; Moosmann, Bjoern; Auwärter, Volker (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:10.1002/dta.2398. ISSN 1942-7611. PMID 29726116.
^ Banister, Samuel D.; Connor, Mark (August 2018). The Chemistry and Pharmacology of Synthetic Cannabinoid Receptor Agonist New Psychoactive Substances: Evolution. Handbook of Experimental Pharmacology. Springer International Publishing. pp. 191–226. doi:10.1007/164_2018_144. ISBN 978-3-030-10561-7. PMID 30105473 – via Springer Link.
^ 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 1618-2650. PMID 31183523.
^ Diao, Xingxing; Carlier, Jeremy; Zhu, Mingshe; Huestis, Marilyn A. (July 2018). "Metabolism of the new synthetic cannabinoid EG-018 in human hepatocytes by high-resolution mass spectrometry". Forensic Toxicology. 36 (2): 304–312. doi:10.1007/s11419-018-0404-2. ISSN 1860-8973.
^ Gamage, Thomas F.; Barrus, Daniel G.; Kevin, Richard C.; Finlay, David B.; Lefever, Timothy W.; Patel, Purvi R.; Grabenauer, Megan A.; Glass, Michelle; McGregor, Iain S.; Wiley, Jenny L.; Thomas, Brian F. (April 2020). "In vitro and in vivo pharmacological evaluation of the synthetic cannabinoid receptor agonist EG-018". Pharmacology Biochemistry and Behavior: 172918. doi:10.1016/j.pbb.2020.172918. ISSN 0091-3057. PMID 32247816.
^ "指定薬物を指定する省令が公布されました｜厚生労働省". www.mhlw.go.jp (in Japanese). Ministry of Health, Labour and Welfare.

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[1] "EG 018". www.caymanchem.com.

[2] Mogler, Lukas; Franz, Florian; Wilde, Maurice; Huppertz, Laura M.; Halter, Sebastian; Angerer, Verena; Moosmann, Bjoern; Auwärter, Volker (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:10.1002/dta.2398. ISSN 1942-7611. PMID 29726116.

[3] Banister, Samuel D.; Connor, Mark (August 2018). The Chemistry and Pharmacology of Synthetic Cannabinoid Receptor Agonist New Psychoactive Substances: Evolution. Handbook of Experimental Pharmacology. Springer International Publishing. pp. 191–226. doi:10.1007/164_2018_144. ISBN 978-3-030-10561-7. PMID 30105473 – via Springer Link.

[4] 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 1618-2650. PMID 31183523.

[5] Diao, Xingxing; Carlier, Jeremy; Zhu, Mingshe; Huestis, Marilyn A. (July 2018). "Metabolism of the new synthetic cannabinoid EG-018 in human hepatocytes by high-resolution mass spectrometry". Forensic Toxicology. 36 (2): 304–312. doi:10.1007/s11419-018-0404-2. ISSN 1860-8973.

[6] Gamage, Thomas F.; Barrus, Daniel G.; Kevin, Richard C.; Finlay, David B.; Lefever, Timothy W.; Patel, Purvi R.; Grabenauer, Megan A.; Glass, Michelle; McGregor, Iain S.; Wiley, Jenny L.; Thomas, Brian F. (April 2020). "In vitro and in vivo pharmacological evaluation of the synthetic cannabinoid receptor agonist EG-018". Pharmacology Biochemistry and Behavior: 172918. doi:10.1016/j.pbb.2020.172918. ISSN 0091-3057. PMID 32247816.

[7] "指定薬物を指定する省令が公布されました｜厚生労働省". www.mhlw.go.jp (in Japanese). Ministry of Health, Labour and Welfare.

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Legal status

See also

References