Deschloroketamine

Deschloroketamine
Legal status
Legal status	CA: Schedule I; DE: NpSG (Industrial and scientific use only); UK: Class B; Illegal in Latvia;
Identifiers
	IUPAC name 2-Phenyl-2-(methylamino)cyclohexanone;
CAS Number	7063-30-1 ; hydrochloride: 4631-27-0 ;
PubChem CID	437168;
ChemSpider	386687;
UNII	B0J1D1S3EI; hydrochloride: H3MA78UVN7 ;
ChEMBL	ChEMBL2068808;
CompTox Dashboard (EPA)	DTXSID701342024 DTXSID10595730, DTXSID701342024 ;
Chemical and physical data
Formula	C13H17NO
Molar mass	203.285 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CNC1(CCCCC1=O)c2ccccc2;
	InChI InChI=1S/C13H17NO/c1-14-13(10-6-5-9-12(13)15)11-7-3-2-4-8-11/h2-4,7-8,14H,5-6,9-10H2,1H3; Key:ZAGBSZSITDFFAF-UHFFFAOYSA-N;

Deschloroketamine (DXE, DCK, 2'-Oxo-PCM) is a dissociative anesthetic^[1]^[2] that has been sold online as a designer drug.^[3]^[4]^[5]^[6]^[7] It has also been proposed for the treatment of bacterial, fungal, viral or protozoal infections and for immunomodulation at doses of 2 mg per day.^[8]

Legal status

Deschloroketamine is illegal in Latvia,^[9] and is covered by blanket bans in Canada and the UK.^{[citation needed]}

References

^ Robins EG, Zhao Y, Khan I, Wilson A, Luthra SK, Rstad E (March 2010). "Synthesis and in vitro evaluation of (18)F-labelled S-fluoroalkyl diarylguanidines: Novel high-affinity NMDA receptor antagonists for imaging with PET". Bioorganic & Medicinal Chemistry Letters. 20 (5): 1749–51. doi:10.1016/j.bmcl.2010.01.052. PMID 20138515.
^ US 3254124, Stevens CL, "Aminoketones and methods for their production", published 31 May 1966
^ Frison G, Zamengo L, Zancanaro F, Tisato F, Traldi P (January 2016). "Characterization of the designer drug deschloroketamine (2-methylamino-2-phenylcyclohexanone) by gas chromatography/mass spectrometry, liquid chromatography/high-resolution mass spectrometry, multistage mass spectrometry, and nuclear magnetic resonance". Rapid Communications in Mass Spectrometry. 30 (1): 151–60. Bibcode:2016RCMS...30..151F. doi:10.1002/rcm.7425. PMID 26661982.
^ "Alerta: descloroketamina vendida como ketamina en Barcelona" (in Spanish). Energy Control. Retrieved 2 October 2015.
^ Villalba J (27 March 2015). "Los efectos desconocidos de la sequía de ketamina" (in Spanish). Vice. Retrieved 2 October 2015.
^ Knibbs J (22 October 2015). "Party-drug testing shows its worth". The Medical Republic.
^ Hájková K, Jurásek B, Čejka J, Štefková K, Páleníček T, Sýkora D, Kuchař M (October 2019). "Synthesis and identification of deschloroketamine metabolites in rats' urine and a quantification method for deschloroketamine and metabolites in rats' serum and brain tissue using liquid chromatography tandem mass spectrometry". Drug Testing and Analysis. 12 (3): 343–360. doi:10.1002/dta.2726. PMID 31670910. S2CID 204975994.
^ DE 4409671, Preiss D, Tatar A, "Use of 2-methylamino-2-phenylcyclohexanone for the treatment of bacterial, fungal, viral or protozoal infections and for immunomodulation", published 23 May 1995
^ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" [Regulations on Narcotic Drugs, Psychotropic Substances and Precursors Controlled in Latvia] (in Latvian). Ministry of Health of the Republic of Latvia. Archived from the original on 4 March 2016. Retrieved 29 October 2015.

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[1] Robins EG, Zhao Y, Khan I, Wilson A, Luthra SK, Rstad E (March 2010). "Synthesis and in vitro evaluation of (18)F-labelled S-fluoroalkyl diarylguanidines: Novel high-affinity NMDA receptor antagonists for imaging with PET". Bioorganic & Medicinal Chemistry Letters. 20 (5): 1749–51. doi:10.1016/j.bmcl.2010.01.052. PMID 20138515.

[2] US 3254124, Stevens CL, "Aminoketones and methods for their production", published 31 May 1966

[3] Frison G, Zamengo L, Zancanaro F, Tisato F, Traldi P (January 2016). "Characterization of the designer drug deschloroketamine (2-methylamino-2-phenylcyclohexanone) by gas chromatography/mass spectrometry, liquid chromatography/high-resolution mass spectrometry, multistage mass spectrometry, and nuclear magnetic resonance". Rapid Communications in Mass Spectrometry. 30 (1): 151–60. Bibcode:2016RCMS...30..151F. doi:10.1002/rcm.7425. PMID 26661982.

[4] "Alerta: descloroketamina vendida como ketamina en Barcelona" (in Spanish). Energy Control. Retrieved 2 October 2015.

[5] Villalba J (27 March 2015). "Los efectos desconocidos de la sequía de ketamina" (in Spanish). Vice. Retrieved 2 October 2015.

[6] Knibbs J (22 October 2015). "Party-drug testing shows its worth". The Medical Republic.

[7] Hájková K, Jurásek B, Čejka J, Štefková K, Páleníček T, Sýkora D, Kuchař M (October 2019). "Synthesis and identification of deschloroketamine metabolites in rats' urine and a quantification method for deschloroketamine and metabolites in rats' serum and brain tissue using liquid chromatography tandem mass spectrometry". Drug Testing and Analysis. 12 (3): 343–360. doi:10.1002/dta.2726. PMID 31670910. S2CID 204975994.

[8] DE 4409671, Preiss D, Tatar A, "Use of 2-methylamino-2-phenylcyclohexanone for the treatment of bacterial, fungal, viral or protozoal infections and for immunomodulation", published 23 May 1995

[9] "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" [Regulations on Narcotic Drugs, Psychotropic Substances and Precursors Controlled in Latvia] (in Latvian). Ministry of Health of the Republic of Latvia. Archived from the original on 4 March 2016. Retrieved 29 October 2015.

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Legal status

See also

References