NNE1

NNE1
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B;
Identifiers
	IUPAC name N-1-naphthalenyl-1-pentyl-1H-indole-3-carboxamide;
CAS Number	1338925-11-3;
PubChem CID	54752945;
ChemSpider	26613275;
UNII	7FVT9P642K;
CompTox Dashboard (EPA)	DTXSID50716467 ;
Chemical and physical data
Formula	C24H24N2O
Molar mass	356.469 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCn1cc(c2c1cccc2)C(=O)Nc1cccc2c1cccc2;
	InChI InChI=1S/C24H24N2O/c1-2-3-8-16-26-17-21(20-13-6-7-15-23(20)26)24(27)25-22-14-9-11-18-10-4-5-12-19(18)22/h4-7,9-15,17H,2-3,8,16H2,1H3,(H,25,27); Key:GWCQNKRMTGVYIZ-UHFFFAOYSA-N;

NNE1 (also known as NNEI, MN-24 and AM-6527) is an indole-based synthetic cannabinoid, representing a molecular hybrid of APICA and JWH-018^[1] that is an agonist for the cannabinoid receptors, with K_i values of 60.09 nM at CB₁ and 45.298 nM at CB₂ and EC₅₀ values of 9.481 nM at CB₁ and 1.008 nM at CB₂.^[2] It was invented by Abbott and has a CB₁ receptor pEC₅₀ of 8.9 with around 80x selectivity over the related CB₂ receptor.^[3] It is suspected that metabolic hydrolysis of the amide group of NNE1 may release 1-naphthylamine, a known carcinogen, given the known metabolic liberation (and presence as an impurity) of amantadine in the related compound APINACA, and NNE1 was banned in New Zealand in 2012 as a temporary class drug to stop it being used as an ingredient in then-legal synthetic cannabis products.^[4] NNE1 was subsequently found to be responsible for the death of a man in Japan in 2014.^[5]

References

^ Uchiyama N, Matsuda S, Kawamura M, Shimokawa Y, Kikura-Hanajiri R, Aritake K, et al. (October 2014). "Characterization of four new designer drugs, 5-chloro-NNEI, NNEI indazole analog, α-PHPP and α-POP, with 11 newly distributed designer drugs in illegal products". Forensic Science International. 243: 1–13. doi:10.1016/j.forsciint.2014.03.013. PMID 24769262.
^ Gamage TF, Farquhar CE, Lefever TW, Marusich JA, Kevin RC, McGregor IS, et al. (May 2018). "Molecular and Behavioral Pharmacological Characterization of Abused Synthetic Cannabinoids MMB- and MDMB-FUBINACA, MN-18, NNEI, CUMYL-PICA, and 5-Fluoro-CUMYL-PICA". The Journal of Pharmacology and Experimental Therapeutics. 365 (2): 437–446. doi:10.1124/jpet.117.246983. PMC 5932312. PMID 29549157.
^ Blaazer AR, Lange JH, van der Neut MA, Mulder A, den Boon FS, Werkman TR, et al. (October 2011). "Novel indole and azaindole (pyrrolopyridine) cannabinoid (CB) receptor agonists: design, synthesis, structure-activity relationships, physicochemical properties and biological activity". European Journal of Medicinal Chemistry. 46 (10): 5086–98. doi:10.1016/j.ejmech.2011.08.021. PMID 21885167.
^ New Zealand Government Gazette, Notice Number 7051, 1 November 2012
^ Sasaki C, Saito T, Shinozuka T, Irie W, Murakami C, Maeda K, et al. (January 2015). "A case of death caused by abuse of a synthetic cannabinoid N -1-naphthalenyl-1-pentyl-1H -indole-3-carboxamide". Forensic Toxicology. 33 (1): 165–169. doi:10.1007/s11419-014-0246-5. S2CID 13524298.

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[1] Uchiyama N, Matsuda S, Kawamura M, Shimokawa Y, Kikura-Hanajiri R, Aritake K, et al. (October 2014). "Characterization of four new designer drugs, 5-chloro-NNEI, NNEI indazole analog, α-PHPP and α-POP, with 11 newly distributed designer drugs in illegal products". Forensic Science International. 243: 1–13. doi:10.1016/j.forsciint.2014.03.013. PMID 24769262.

[2] Gamage TF, Farquhar CE, Lefever TW, Marusich JA, Kevin RC, McGregor IS, et al. (May 2018). "Molecular and Behavioral Pharmacological Characterization of Abused Synthetic Cannabinoids MMB- and MDMB-FUBINACA, MN-18, NNEI, CUMYL-PICA, and 5-Fluoro-CUMYL-PICA". The Journal of Pharmacology and Experimental Therapeutics. 365 (2): 437–446. doi:10.1124/jpet.117.246983. PMC 5932312. PMID 29549157.

[3] Blaazer AR, Lange JH, van der Neut MA, Mulder A, den Boon FS, Werkman TR, et al. (October 2011). "Novel indole and azaindole (pyrrolopyridine) cannabinoid (CB) receptor agonists: design, synthesis, structure-activity relationships, physicochemical properties and biological activity". European Journal of Medicinal Chemistry. 46 (10): 5086–98. doi:10.1016/j.ejmech.2011.08.021. PMID 21885167.

[4] New Zealand Government Gazette, Notice Number 7051, 1 November 2012

[5] Sasaki C, Saito T, Shinozuka T, Irie W, Murakami C, Maeda K, et al. (January 2015). "A case of death caused by abuse of a synthetic cannabinoid N -1-naphthalenyl-1-pentyl-1H -indole-3-carboxamide". Forensic Toxicology. 33 (1): 165–169. doi:10.1007/s11419-014-0246-5. S2CID 13524298.

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See also

References