Structural Analysis and Characterization of 4-F-α-PVP Analog 4-F-3-Methyl-α- PVP Hydrochloride

doi:10.12116/j.issn.1004-5619.2021.311002

Abstract

Abstract:

Objective To identify 1-（4-fluorophenyl）-2-（1-pyrrolidinyl） pentan-1-one （4-F-α-PVP） analog 1-（4-fluoro-3-methyl phenyl）-2-（1-pyrrolidinyl） pentan-1-one （4-F-3-Methyl-α-PVP） hydrochloride without reference substance. Methods The direct-injection electron ionization-mass spectrometry （EI-MS）, GC-MS, electrospray ionization-high resolution mass spectrometry （ESI-HRMS）, ultra-high performance liquid chromatography-high resolution tandem mass spectrometry （UPLC-HRMS/MS）, nuclear magnetic resonance （NMR）, ion chromatography and Fourier transform infrared spectroscopy （FTIR） were integrated utilized to achieve the structural analysis and characterization of the unknown compound in the sample, and the cleavage mechanism of the fragment ions was deduced by EI-MS and UPLC-HRMS/MS. Results By analyzing the direct-injection EI-MS, GC-MS, ESI-HRMS and UPLC-HRMS/MS of the compound in the samples, it was concluded that the unknown compound was a structural analog of 4-F-α-PVP, possibly with one more methyl group in the benzene ring. According to the analysis results of ¹H-NMR and ¹³C-NMR, it was further proved that the methyl group is located at the 3-position of the benzene ring. Since the actual number of hydrogen in ¹H-NMR analysis was one more than 4-F-3-Methyl-α-PVP neutral molecule, it was inferred that the compound existed in the form of salt. Ion chromatography analysis results showed that the compound contained chlorine anion （content 11.14%-11.16%）, with the structural analysis of main functional group information by FTIR, the unknown compound was finally determined to be 4-F-3-Methyl-α-PVP hydrochloride. Conclusion A comprehensive method using EI-MS, GC-MS, ESI-HRMS, UPLC-HRMS/MS, NMR, ion chromatography and FTIR to identify 4-F-3-Methyl-α-PVP hydrochloride in samples is established, which will be helpful for the forensic science laboratory to identify this compound or other analog compounds.

Key words: forensic medicine, toxicological analysis, new psychoactive substance, high resolution mass spectrometry, nuclear magnetic resonance, 4-F-3-Methyl-α-PVP hydrochloride, structural analysis

CLC Number:

DF795.1

Hao-yang WANG, Jian WU, Qian ZHANG, Xin-feng MIN, Xiu-yan LIU, Yin-long GUO. Structural Analysis and Characterization of 4-F-α-PVP Analog 4-F-3-Methyl-α- PVP Hydrochloride[J]. Journal of Forensic Medicine, 2023, 39(2): 144-150.

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URL: http://www.fyxzz.cn/EN/10.12116/j.issn.1004-5619.2021.311002

http://www.fyxzz.cn/EN/Y2023/V39/I2/144

Figures/Tables 10

References 13

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质荷比（m/z）	相对丰度/%
220	1.80
137	7.49
126	100.00
109	10.04
96	5.94
84	5.66
55	6.25

质荷比（m/z）	相对丰度/%
220	1.80
137	7.49
126	100.00
109	10.04
96	5.94
84	5.66
55	6.25

位置	碳谱		氢谱
位置	δ（¹³C）/×10^-6	峰型	δ（¹H）/×10^-6	质子数	峰型
1	14.06	单峰	0.78	3	三重峰
2	18.76	单峰	1.24~1.35	2	多重峰
3	32.89	单峰	2.03	2	多重峰
4	66.20	单峰	5.72	1	多重峰
5	52.60	单峰	3.36~3.81	2	双-多重峰
6	23.80	单峰	2.11~2.22	2	双-多重峰
7	23.65	单峰	2.11~2.22	2	双-多重峰
8	52.40	单峰	3.36~3.81	2	双-多重峰
9	132.84（J=7.0 Hz）	双峰	7.93	1	双重峰
10	14.56（J=3.2 Hz）	双峰	2.27	3	双重峰
11	116.01（J=17.9 Hz）	双峰	7.05	1	多重峰
12	129.38（J=9.7 Hz）	双峰	7.96	1	多重峰
13	126.48（J=17.9 Hz）	双峰	-	-	-
14	165.40（J=257.1 Hz）	双峰	-	-	-
15	131.40（J=2.9 Hz）	双峰	-	-	-
16	195.25	单峰	-	-	-
HCl	-		11.49	1	宽单峰

位置	碳谱		氢谱
位置	δ（¹³C）/×10^-6	峰型	δ（¹H）/×10^-6	质子数	峰型
1	14.06	单峰	0.78	3	三重峰
2	18.76	单峰	1.24~1.35	2	多重峰
3	32.89	单峰	2.03	2	多重峰
4	66.20	单峰	5.72	1	多重峰
5	52.60	单峰	3.36~3.81	2	双-多重峰
6	23.80	单峰	2.11~2.22	2	双-多重峰
7	23.65	单峰	2.11~2.22	2	双-多重峰
8	52.40	单峰	3.36~3.81	2	双-多重峰
9	132.84（J=7.0 Hz）	双峰	7.93	1	双重峰
10	14.56（J=3.2 Hz）	双峰	2.27	3	双重峰
11	116.01（J=17.9 Hz）	双峰	7.05	1	多重峰
12	129.38（J=9.7 Hz）	双峰	7.96	1	多重峰
13	126.48（J=17.9 Hz）	双峰	-	-	-
14	165.40（J=257.1 Hz）	双峰	-	-	-
15	131.40（J=2.9 Hz）	双峰	-	-	-
16	195.25	单峰	-	-	-
HCl	-		11.49	1	宽单峰

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