New ketamine analogue: 2-fluorodeschloro-N-ethyl-ketamine and its suggested metabolites

Yen, Yu-Chun; Tsai, Yi-Shiuan; Su, Wen-Liang; Huang, Deng-Ying; Wu, Heng; Tseng, Shih-Hao; Wang, Hsiao-Hui; Chiu, Chu-Yin; Wang, Chung-Feng; Liu, Chunyi; Chyueh, San‐Chong

doi:10.1016/j.forsciint.2022.111501

Cited by 7 publications

(3 citation statements)

References 25 publications

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“…The following are the common EI-MS fragmentation patterns (as shown in Scheme 2 ) on the basis of the GC-Q-TOF/MS analysis of eight ketamine analogue reference substances [ 18 ]: (i) The nitrogen atom of ketamine analogues is initially ionized via EI. (ii) Second, the α-cleavage of the carbon bond C 1 -C 2 in the cyclohexanone moiety stabilizes the positive charge on the nitrogen atom, followed by the neutral loss of a CO (28 Da) and a five-membered ring formed to generate the stable fragment a via the fragmentation pathway 1 or the neutral loss of a CO (28 Da) to generate the unstable fragment b via the fragmentation pathway 2.…”

Section: Resultsmentioning

confidence: 99%

“…Ketamine analogues yield the fragment k by the cleavage of the carbon bond via the fragmentation pathway 8. 238.09952 220.08894 (Path 10), 207.05742 (Path 9), 179.06247 (Path 9), 125.01547 (Path 9), 16 222.12936 204.11887 (Path 10), 191.08719 (Path 9), 163.09216 (Path 9), 109.04510 (Path 282.04880 264.03821 (Path 10), 251.00664 (Path 9), 223.01180 (Path 9), 168.96486 (Path 9), 17 252.11505 234.10452 (Path 10), 207.05725 (Path 9), 179.06230 (Path 9), 125.01538 (Path 9), 16 232.16963 214.15903 (Path 10), 187.11192 (Path 9), 159.11699 (Path 9), 105.07034 (PathThe following are the common EI-MS fragmentation patterns (as shown in Sc on the basis of the GC-Q-TOF/MS analysis of eight ketamine analogue referen stances[18]: (i) The nitrogen atom of ketamine analogues is initially ionized via Second, the α-cleavage of the carbon bond C1-C2 in the cyclohexanone moiety st the positive charge on the nitrogen atom, followed by the neutral loss of a CO (28 a five-membered ring formed to generate the stable fragment a via the fragme pathway 1 or the neutral loss of a CO (28 Da) to generate the unstable fragment b fragmentation pathway 2. (iii) The unstable fragment b is prone to causing hy transfers to generate the fragment c, leading to the radical approach to the positiv gen atom.…”

mentioning

confidence: 98%

“…(Path 1, 2), 160.1127 (Path 3), 146.1042 (Path 5), 132.0811 (Path 4, 7), 117.0699 (Path 6), 104.0500 (Path 7), 91.0546 (Path 8), 77.0389 (Path 8) 2 217.1463 189.1518 (Path 1, 2), 174.1283 (Path 3), 160.1144 (Path 5), 146.0970 (Path 4), 132.0813 (Path 7), 117.0701 (Path 6), 104.0500 (Path 7), 91.0546 (Path 8), 77.0389 (Path 8) 3 247.1567 219.1619 (Path 1, 2), 204.1387 (Path 3), 190.1301 (Path 5), 176.1085 (Path 4), 162.0915 (Path 7), 147.0805 (Path 6), 134.0603 (Path 7), 121.0650 (Path 8),91.0539 (Path 8), 77.0388 (Path 8) 4 237.0913 209.0965 (Path 1, 2), 194.0732 (Path 3), 180.0591 (Path 5), 166.0418 (Path 7), 145.0885 (Path 1) 138.0105 (Path 7), 125.0151 (Path 8), 115.0542 (Path 6), 102.0341 (Path 7), 75.0229 (Path 8) 5 221.1205 193.1265 (Path 1, 2), 178.1034 (Path 3), 164.0942 (Path 5), 150.0718 (Path 4, 7), 135.0606 (Path 6), 122.0406 (Path 7), 115.0547 (Path 6), 109.0542 (Path 8), 102.0345 (Path 7), 75.0232 (Path 8) 6 281.0423 253.0480 (Path 1, 2), 238.0219 (Path 3), 224.0092 (Path 5), 209.9915 (Path 4, 7), 194.9801 (Path 6), 181.9616 (Path 7), 168.9652 (Path 8), 145.0900 (Path 1), 115.0553 (Path 6), 102.0470 (Path 7), 75.0229 (Path 8) 7 251.1072 223.1125 (Path 1, 2), 208.0890 (Path 3), 194.0758 (Path 5), 180.0579 (Path 4), 166.0423 (Path 7), 151.0312 (Path 6), 138.0108 (Path 7), 125.0156 (Path 8), 115.0545, 102.0342 (Path 8), 75.0232 (Path 8) 8 231.1617 203.1669 (Path 1, 2), 188.1438 (Path 3), 174.1284 (Path 5), 160.1124 (Path 4), 146.0967 (Path 7), 131.0855 (Path 6), 118.0654 (Path 7), 105.0701 (Path 8), 91.0544 (Path 8), 77.0387 (Path 8) (Path 10), 191.08719 (Path 9), 163.09216 (Path 9), 109.04510 (Path 9) 6 282.04880 264.03821 (Path 10), 251.00664 (Path 9), 223.01180 (Path 9), 168.96486 (Path 9), 172.08832 7 252.11505 234.10452 (Path 10), 207.05725 (Path 9), 179.06230 (Path 9), 125.01538 (Path 9), 163.03096 8 232.16963 214.15903 (Path 10), 187.11192 (Path 9), 159.11699 (Path 9), 105.07034 (Path 9) Molecules 2023, 28, 6510 5 of 14The following are the common EI-MS fragmentation patterns (as shown in Scheme 2) on the basis of the GC-Q-TOF/MS analysis of eight ketamine analogue reference substances[18]: (i) The nitrogen atom of ketamine analogues is initially ionized via EI. (ii) Second, the α-cleavage of the carbon bond C 1 -C 2 in the cyclohexanone moiety stabilizes the positive charge on the nitrogen atom, followed by the neutral loss of a CO (28 Da) and a five-membered ring formed to generate the stable fragment a via the fragmentation pathway 1 or the neutral loss of a CO(28 Da) to generate the unstable fragment b via the fragmentation pathway 2.…”

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Study on the Mass Spectrometry Fragmentation Patterns for Rapid Screening and Structure Identification of Ketamine Analogues in Illicit Powders

Fan,

Gao,

Chen

et al. 2023

Molecules

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Ketamine analogues have been emerging in recent years and are causing severe health and social problems worldwide. Ketamine analogues use 2-phenyl-2-aminocyclohexanone as the basic structure and achieve physiological reactions similar to or even more robust than the prototype of ketamine by changing the substituents on the benzene ring (R1 and R2) and amine group (RN1). Therefore, the mass spectrometry (MS) fragmentation pathways and fragments of ketamine analogues have certain regularity. Eight ketamine analogues are systematically investigated by GC-QTOF/MS and LC-Q-Orbitrap MS/MS with the positive mode of electrospray ionization. The MS fragmentation patterns of ketamine analogues are summarized according to high-resolution MS data. The α-cleavage of carbon bond C1-C2 in the cyclohexanone moiety and further losses of CO, methyl radical, ethyl radical and propyl radical are the characteristic fragmentation pathways of ketamine analogues in EI-MS mode. The loss of H2O or the sequential loss of RN1NH2, CO and C4H6 are the distinctive fragmentation pathways of ketamine analogues in ESI-MS/MS mode. Moreover, these MS fragmentation patterns are first introduced for the rapid screening of ketamine analogues in suspicious powder. Furthermore, the structure of the ketamine analogue in suspicious powder is 2-(Methylamino)-2-(o-tolyl)cyclohexan-1-one, which is further confirmed by NMR. This study contributes to the identification of the chemical structure of ketamine analogues, which can be used for the rapid screening of ketamine analogues in seized chemicals.

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confidence: 99%

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confidence: 98%

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confidence: 99%

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Study on the Mass Spectrometry Fragmentation Patterns for Rapid Screening and Structure Identification of Ketamine Analogues in Illicit Powders

Fan,

Gao,

Chen

et al. 2023

Molecules

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Identification of three unexpected new psychoactive substances at an Australian drug checking service

Algar,

Lawes,

Carroll

et al. 2024

Drug Testing and Analysis

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Drug checking is a harm reduction measure that provides people with the opportunity to confirm the identity and purity of substances before consumption. The CanTEST Health and Drug Checking Service is Australia's first fixed‐site drug checking service, where clients can learn about the contents of the samples they provide while receiving tailored harm reduction and health advice. Three samples were recently presented to the service with the expectation of 4‐fluoromethylphenidate (4F‐MPH) 1, methoxetamine (MXE) 2 and 3‐methylmethcathinone (3‐MMC) 3. The identity of all three samples did not meet these expectations and remained unknown on‐site, as no high confidence identifications were obtained. However, further analysis by nuclear magnetic resonance spectroscopy, high resolution gas chromatography‐electron ionisation‐mass spectrometry and liquid chromatography‐electrospray ionisation‐mass spectrometry at the nearby Australian National University allowed for the structure elucidation of the three samples as 4‐fluoro‐α‐pyrrolidinoisohexanophenone (4F‐α‐PiHP) 4, 1‐(4‐fluorobenzyl)‐4‐methylpiperazine (4F‐MBZP) 5 and N‐propyl‐1,2‐diphenylethylamine (propylphenidine) 6, respectively. Given all three samples were not of the expected identity and have not yet been described as new psychoactive substances in the literature, this study presents a full characterisation of each compound. As exemplified by this rapid identification of three unexpected new psychoactive substances, drug checking can be used as an effective method to monitor the unregulated drug market.

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Arylcyclohexamine type drugs

Warriner,

Dargan,

Wood

2024

Comprehensive Analytical Chemistry

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New ketamine analogue: 2-fluorodeschloro-N-ethyl-ketamine and its suggested metabolites

Cited by 7 publications

References 25 publications

Study on the Mass Spectrometry Fragmentation Patterns for Rapid Screening and Structure Identification of Ketamine Analogues in Illicit Powders

Study on the Mass Spectrometry Fragmentation Patterns for Rapid Screening and Structure Identification of Ketamine Analogues in Illicit Powders

Identification of three unexpected new psychoactive substances at an Australian drug checking service

Arylcyclohexamine type drugs

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