Identification of a Novel Synthetic Cathinone CMMP

doi:10.12116/j.issn.1004-5619.2024.340103

Abstract

Abstract:

Objective To establish a method to identify an unknown substance based on the combined use of gas chromatography-quadrupole time-of-flight mass spectrometry （GC-QTOF-MS）, ultra-high performance liquid chromatography-quadrupole/electrostatic field orbitrap high resolution mass spectrometry （UPLC-Q/Orbitrap HRMS）and nuclear magnetic resonance （NMR） techniques. Methods The unknown substance was dissolved in methanol and was detected by GC-QTOF-MS and UPLC-Q/Orbitrap HRMS, and was dissolved in methanol-d4 to be detected by NMR. Results The main characteristics ion peaks of components with retention time of 9.67 min in GC-QTOF-MS measured were 84.080 8, 110.999 7, 128.107 0 （base peak）, 138.994 7, etc. The protonated molecular ion peak m/z in UPLC-Q/Orbitrap HRMS was 268.109 3. It was inferred that the unknown substance was an analog of the synthetic cathinone substance 2-methyl-1-[4-（methylthio）phenyl]-2-morpholinopropan-1-one （MTMP） by comparing the mass spectrum information and molecular structure of MTMP. NMR analysis confirmed it as a novel N-morpholine substituted synthetic cathinone substance 1-（4-chlorophenyl）-2-methyl-2-morpholinopropan-1-one （CMMP）. Conclusion The method established in this study can be used for structural confirmation of CMMP.

Key words: forensic medicine, toxicological analysis, new psychoactive substance （NPS）, synthetic cathinones, 2-methyl-1-[4-（methylthio）phenyl]-2-morpholinopropan-1-one （MTMP）, 1-（4-chlorophenyl）-2-methyl-2-morpholinopropan-1-one （CMMP）, high resolution mass spectrometry （HRMS）, N-morpholine substituted

CLC Number:

Si-yang HE, Qian-ya DENG, Shui-qing ZHENG, Chun-fang NI, Wen-juan SUN, Fang-qi CAO, Chen LIANG, Fei-jun GONG. Identification of a Novel Synthetic Cathinone CMMP[J]. Journal of Forensic Medicine, 2024, 40(6): 550-556.

Figures/Tables 12

References 18

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碳原子编号	δ（¹³C）/ ×10^-6	δ（¹H）/ ×10^-6	氢核数目	峰型	偶合常数（J）/Hz
1	141.14	-	-	-	-
2，6	132.08	7.98	2	双峰	8.4
3，5	130.22	7.58	2	双峰	8.4
4	133.87	-	-	-	-
7	199.34	-	-	-	-
8	74.93	-	-	-	-
9，12	49.05	3.37	4	单峰	-
10，11	65.19	3.99，4.12	4	多重峰	-
13，14	20.81	1.87	6	单峰	-

碳原子编号	δ（¹³C）/ ×10^-6	δ（¹H）/ ×10^-6	氢核数目	峰型	偶合常数（J）/Hz
1	141.14	-	-	-	-
2，6	132.08	7.98	2	双峰	8.4
3，5	130.22	7.58	2	双峰	8.4
4	133.87	-	-	-	-
7	199.34	-	-	-	-
8	74.93	-	-	-	-
9，12	49.05	3.37	4	单峰	-
10，11	65.19	3.99，4.12	4	多重峰	-
13，14	20.81	1.87	6	单峰	-

碎片离子	实测质量数	碎片分子式	理论质量数	误差/ ×10^-6
A	128.107 0	C₇H₁₄NO⁺	128.107 0	0
B	84.080 8	C₅H₁₀N⁺	84.080 8	0
C	70.065 2	C₄H₈N⁺	70.065 1	1.43
D	56.049 6	C₃H₆N⁺	56.049 5	1.78
E
CMMP	138.994 7	C₇H₄ClO⁺	138.994 5	1.44
MTMP	151.021 3	C₈H₇OS⁺	151.021 2	0.66
F
CMMP	110.999 7	C₆H₄Cl⁺	110.999 6	0.90
MTMP	123.026 2	C₇H₇S⁺	123.026 3	-0.81

碎片离子	实测质量数	碎片分子式	理论质量数	误差/ ×10^-6
A	128.107 0	C₇H₁₄NO⁺	128.107 0	0
B	84.080 8	C₅H₁₀N⁺	84.080 8	0
C	70.065 2	C₄H₈N⁺	70.065 1	1.43
D	56.049 6	C₃H₆N⁺	56.049 5	1.78
E
CMMP	138.994 7	C₇H₄ClO⁺	138.994 5	1.44
MTMP	151.021 3	C₈H₇OS⁺	151.021 2	0.66
F
CMMP	110.999 7	C₆H₄Cl⁺	110.999 6	0.90
MTMP	123.026 2	C₇H₇S⁺	123.026 3	-0.81

碎片离子	实测质量数	碎片分子式	理论质量数	误差/×10^-6
［M+H］⁺
CMMP	268.109 3	C₁₄H₁₉NO₂Cl⁺	268.109 9	-2.61
MTMP	280.136 0	C₁₅H₁₂NO₂S⁺	280.136 6	-2.14
A′
CMMP	181.041 1	C₁₀H₁₀OCl⁺	181.041 5	-2.21
MTMP	193.067 7	C₁₁H₁₃OS⁺	193.068 2	-2.59
B′
CMMP	153.046 2	C₉H₁₀Cl⁺	153.046 6	-2.61
MTMP	165.073 0	C₁₀H₁₃S⁺	165.073 2	-1.21
C′	128.106 9	C₇H₁₄NO⁺	128.107 0	-0.78
D′	88.076 0	C₄H₁₀NO⁺	88.075 7	3.41