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X-ray powder diffraction data for (S)-Deschloroketamine hydrochloride, C13H18ClNO

Published online by Cambridge University Press:  21 June 2017

J. Maixner ,
B. Jurásek ,
M. Kohout ,
M. Kuchař  and
P. Kačer
J. Maixner*
Affiliation:
Central Laboratories, University of Chemistry and Technology Prague, Technická 5, 166 28 Prague 6, Czech Republic
B. Jurásek
Affiliation:
Department of Chemistry of Natural Compounds, Faculty of Food and Biochemical Technology, University of Chemistry and Technology Prague, Technická 5, 166 28 Prague 6, Czech Republic Forensic Laboratory of Biologically Active Substances, University of Chemistry and Technology Prague, Technická 5, Prague 6, 166 28, Czech Republic
M. Kohout
Affiliation:
Department of Organic Chemistry, University of Chemistry and Technology Prague, Technická 5, CZ-166 28 Prague 6, Czech Republic
M. Kuchař
Affiliation:
Department of Chemistry of Natural Compounds, Faculty of Food and Biochemical Technology, University of Chemistry and Technology Prague, Technická 5, 166 28 Prague 6, Czech Republic Forensic Laboratory of Biologically Active Substances, University of Chemistry and Technology Prague, Technická 5, Prague 6, 166 28, Czech Republic
P. Kačer
Affiliation:
Department of Organic Technology, University of Chemistry and Technology Prague, Technická 5, CZ-166 28 Prague 6, Czech Republic
*
a) Author to whom correspondence should be addressed. Electronic mail: jaroslav.maixner@vscht.cz

Abstract

X-ray powder diffraction data, unit-cell parameters, and space group for S-2-(methylamino)-2-phenylcyclohexan-1-one hydrochloride, C13H18ClNO, are reported [a = 6.578 (1) Å, b = 13.250 (2) Å, c = 15.096 (2) Å, β = 91.619 (3)°, unit-cell volume V = 1315(1) Å3, Z = 4, and space group P21]. All measured lines were indexed and are consistent with the P21 space group. No detectable impurities were observed.

Keywords

X-ray powder diffractiondeschloroketamineNSDnew synthetic drugsnew psychoactive substancesdesigner drugsdissociative anesthetics

Information

Type
New Diffraction Data
Information
Powder Diffraction , Volume 32 , Issue 3 , September 2017 , pp. 193 - 195
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Copyright
Copyright © International Centre for Diffraction Data 2017 

I. INTRODUCTION

2-(Methylamino)-2-phenylcyclohexan-1-one (deschloroketamine) belongs by its structure among arylcyclohexylamines. Arylcyclohexylamines are typical representative of dissociative anesthetics (Frison et al., Reference Frison, Zamengo, Zancanaro, Tisato and Traldi2016). Deschloroketamine is a structural analogue of ketamine, which is still used in healthcare as an anesthetic and recently it has been tested also for its long-lasting antidepressant effects (Dolgin, Reference Dolgin2013; Frison et al., Reference Frison, Zamengo, Zancanaro, Tisato and Traldi2016). Deschloroketamine was originally designed for the treatment of bacterial, fungal and viral diseases, but it did not find any pharmaceutical application (Preiss and Tatar, Reference Preiss and Tatar1995, Reference Preiss and Tatar2000). It started to appear on the black market with New Psychoactive Substances (NPS) as a substitute for methoxetamine, which was listed among prohibited substances by law by the Member States of the European Union (Frison et al., Reference Frison, Zamengo, Zancanaro, Tisato and Traldi2016; Jurásek and Kuchař, Reference Jurásek and Kuchař2016). Here, we present powder data for deschlorketamine hydrochloride.

We have inspected the CSD database (Allen, Reference Allen2002) and the PDF4+ database (ICDD, 2015) and have not found any entry for this organic substance C13H18ClNO in the mentioned databases. Therefore we have decided to characterize this compound by X-ray powder diffraction technique.

II. EXPERIMENTAL

A. Synthesis

Synthesis of deschloroketamine hydrochloride was carried out according to Lambdasyn instructions (Lambdasyn, 2015) and Stevens patents (Stevens and Parke, Reference Stevens and Parke1966; Stevens et al., Reference Stevens, Hanson and Taylor1966). (1-Hydroxycyclopentyl)phenyl-N-methylketimine was dissolved in decalin (10 ml) and stirred 4 h at 190 °C in a microwave reactor. Then the reaction mixture was cooled down and treated with a solution of hydrogen chloride in diethylether. The precipitated solid (title compound, Figure 1) was filtered, washed with acetone and recrystallized from a methanol/diethyl ether mixture. Deschloroketamine hydrochloride was isolated as a white solid polycrystalline material. The structure was confirmed by NMR analysis.

Figure 1.

(Color online) Structural formula of (S)-2-(Methylamino)-2-phenylcyclohexan-1-one hydrochloride..

Deschloroketamine was prepared as racemate. We used chiral separation to obtain (S)-deschloroketamine.

B. Specimen preparation

Sample was prepared by careful grinding in an agate mortar and front-loaded into the specimen holder.

C. Diffraction data collection and reduction

The diffraction pattern for the title compound was collected at room temperature with an X'Pert PRO θ–θ powder diffractometer with parafocusing Bragg-Brentano geometry using CuKα radiation (λ = 1.5418 Å, Ni filter, generator setting: 40 kV, 30 mA). An ultrafast X'Celerator detector was employed to collect XRD data over the angular range from 4° to 70°2θ with a step size of 0.017°2θ and a counting time of 81.28 s step−1.

The software package HighScore Plus V 3.0e (PANalytical, Almelo, Netherlands) was used to smooth the data, to fit the background and the top of smoothed peak method was used to determine the peak positions and intensities of the diffraction peaks.

III. RESULTS AND DISCUSSION

The experimental powder diffraction pattern is depicted in Figure 2. Automatic indexing of results obtained using DICVOL04 (Boultif and Louër, Reference Boultif and Louër2004) show that title compound C13H18ClNO is monoclinic with space group P21 and unit-cell parameters: a = 6.578 (1)  Å, b = 13.250 (2)  Å, c = 15.096 (2) Å, β = 91.619 (3)°, unit-cell volume V = 1315(1) Å3, and Z = 4. The figures of merits are F20 = 124.8(0.0050, 32) (Smith and Snyder, Reference Smith and Snyder1979) and M20 = 45.5 (de Wolff, Reference de Wolff1968). All measured lines (Table 1) were indexed and are consistent with the P21 space group.

Figure 2.

(Color online) X-ray powder diffraction pattern of title compound using CuK α radiation (λ = 1.5418 Å).

Table I.

Indexed X-ray powder diffraction data for C13H18ClNO. Only the peaks with I rel of 1 or greater are presented [a = 6.578 (1), b = 13.250 (2), c = 15.096 (2) Å, β = 91.619 (3)°, unit-cell volume V = 1315(1) Å3, Z = 4, and space group P21]. All lines were indexed and are consistent with the P21 space group. The d-values were calculated using CuKα radiation (λ = 1.5418 Å).

SUPPLEMENTARY MATERIAL

The supplementary material for this article can be found at https://doi.org/10.1017/S0885715617000586.

ACKNOWLEDGEMENTS

Financial support from specific university research (MSMT No 20-SVV/2016), Ministry of Interior of the Czech Republic (MV0/VI20152020048), the Czech Science Foundation (grant no 16-17689Y), the National Programme for Sustainability (NPU I LO1215) Ministry – 34870/2013) and GACR project 16-25747S.

References

Allen, F. H. (2002). “The Cambridge Structural Database: a quarter of a million crystal structures and rising,” Acta Cryst. B58, 380–388.CrossRefGoogle Scholar
Boultif, A. and Louër, D. (2004). “Powder pattern indexing with the dichotomy method,” J. Appl. Crystallogr. 37, 724–731.CrossRefGoogle Scholar
de Wolff, P. M. (1968).“A simplified criterion for the reliability of a powder pattern,” J. Appl. Crystallogr. 1, 108–113.CrossRefGoogle Scholar
Dolgin, E. (2013). “Rapid antidepressant effects of ketamine ignite drug discovery,” Nat. Med. 19, 8–8.CrossRefGoogle ScholarPubMed
Frison, G., Zamengo, L., Zancanaro, F., Tisato, F., and Traldi, P. (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 Commun. Mass Spectrom. 30, 151–160.CrossRefGoogle ScholarPubMed
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Preiss, D. and Tatar, A. (1995). “Use of 2-methylamino-2-phenylcyclohexanone for the treatment of bacterial, fungal, viral or protozoal infections and for immunomodulation,” Patent DE4409671C1.Google Scholar
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Figure 0

Figure 1. (Color online) Structural formula of (S)-2-(Methylamino)-2-phenylcyclohexan-1-one hydrochloride..

Figure 1

Figure 2. (Color online) X-ray powder diffraction pattern of title compound using CuKα radiation (λ = 1.5418 Å).

Figure 2

Table I. Indexed X-ray powder diffraction data for C13H18ClNO. Only the peaks with Irel of 1 or greater are presented [a = 6.578 (1), b = 13.250 (2), c = 15.096 (2) Å, β = 91.619 (3)°, unit-cell volume V = 1315(1) Å3, Z = 4, and space group P21]. All lines were indexed and are consistent with the P21 space group. The d-values were calculated using CuKα radiation (λ = 1.5418 Å).

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