N-Ethylnorketamine

N-Ethylnorketamine
Clinical data
ATC code	none;
Legal status
Legal status	CA: Schedule I; DE: NpSG (Industrial and scientific use only); UK: Class B;
Identifiers
	IUPAC name 2-(2-Chlorophenyl)-2-(ethylamino)cyclohexan-1-one;
CAS Number	1354634-10-8;
PubChem CID	57483649;
ChemSpider	35805667;
UNII	TLL3802A3P;
CompTox Dashboard (EPA)	DTXSID501030493 ;
Chemical and physical data
Formula	C14H18ClNO
Molar mass	251.75 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc2ccccc2C1(NCC)CCCCC1=O;
	InChI InChI=1S/C14H18ClNO/c1-2-16-14(10-6-5-9-13(14)17)11-7-3-4-8-12(11)15/h3-4,7-8,16H,2,5-6,9-10H2,1H3; Key:ITBBBZIIFJJMDU-UHFFFAOYSA-N;

N-Ethylnorketamine (ethketamine, NENK, 2-Cl-2'-Oxo-PCE) is a designer drug which is presumed to have similar properties to ketamine, a dissociative anesthetic drug with hallucinogenic and sedative effects. It has been sold over the internet since around September 2012, and identified in seized drug samples by analytical laboratories in the UK and other European countries.^[1]

It is an NMDA receptor antagonist. In mice its antidepressant effects are dependent on activation of AMPA and 5-HT2 receptors, as blocking those abolishes said activity.^[2]

Legal Status

As of October 2015 NENK is a controlled substance in the United Kingdom,^[3] China,^[4] and the US state of Alabama.^[5]

References

^ Advisory Council on the Misuse of Drugs (ACMD) Methoxetamine Report (2012)
^ Sayson LV, Botanas CJ, Custodio RJ, Abiero A, Kim M, Lee HJ, et al. (July 2019). "The novel methoxetamine analogs N-ethylnorketamine hydrochloride (NENK), 2-MeO-N-ethylketamine hydrochloride (2-MeO-NEK), and 4-MeO-N-ethylketamine hydrochloride (4-MeO-NEK) elicit rapid antidepressant effects via activation of AMPA and 5-HT2 receptors". Psychopharmacology. 236 (7): 2201–2210. doi:10.1007/s00213-019-05219-x. PMID 30891619. S2CID 253743164.
^ Explanatory Memorandum to the Misuse of Drugs (1971) Amendment Order 2013
^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
^ "Alabama Senate Bill 333 - Controlled substances, Schedule I, additional synthetic controlled substances and analogue substances included in, trafficking in controlled substance analogues, requisite weight increased, Secs. 13A-12-231, 20-2-23 am'd". March 2014. Retrieved 28 September 2015.

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[1] Advisory Council on the Misuse of Drugs (ACMD) Methoxetamine Report (2012)

[Sayson_2019-2] Sayson LV, Botanas CJ, Custodio RJ, Abiero A, Kim M, Lee HJ, et al. (July 2019). "The novel methoxetamine analogs N-ethylnorketamine hydrochloride (NENK), 2-MeO-N-ethylketamine hydrochloride (2-MeO-NEK), and 4-MeO-N-ethylketamine hydrochloride (4-MeO-NEK) elicit rapid antidepressant effects via activation of AMPA and 5-HT2 receptors". Psychopharmacology. 236 (7): 2201–2210. doi:10.1007/s00213-019-05219-x. PMID 30891619. S2CID 253743164.

[3] Explanatory Memorandum to the Misuse of Drugs (1971) Amendment Order 2013

[4] "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.

[5] "Alabama Senate Bill 333 - Controlled substances, Schedule I, additional synthetic controlled substances and analogue substances included in, trafficking in controlled substance analogues, requisite weight increased, Secs. 13A-12-231, 20-2-23 am'd". March 2014. Retrieved 28 September 2015.

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