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1.
Forensic Sci Int ; 360: 112074, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38823217

ABSTRACT

Synthetic cathinones, which are novel psychoactive substances, have caused major social problems worldwide. A substance called 2-methyl-4'-(methylthio)-2-morpholinopropiophenone (MMMP), which is employed as a commercial industrial photoinitiator for triggering polymerization, has a basic cathinone backbone; however, few reports regarding MMMP have been published. In the current study, three potential metabolites of MMMP-namely hydroxy-MMMP (HO-MMMP), HO-MMMP-sulfoxide (HO-MMMP-SO), and HO-MMMP-sulfone (HO-MMMP-SO2)-were successfully synthesized, and MMMP and these three potential metabolites were used as standards to establish an analytic method based on liquid chromatography-tandem mass spectrometry for the quantitative analysis of urine. This analytic method and related parameters-including dynamic range, limit of quantification, selectivity, precision, accuracy, carryover effect, matrix effect, interference, and dilution integrity-were optimized and validated. Forty urine samples from 1,691 individuals who abused drugs were determined to contain MMMP, HO-MMMP, HO-MMMP-SO, or HO-MMMP-SO2; the results of this study indicate that approximately 2.37 % of drug abusers in Taiwan consumed MMMP in 2023. These 40 urine samples were analyzed to investigate the metabolism of MMMP in humans. The results indicate that HO-MMMP-SO is the main metabolite in human urine. This study recommends HO-MMMP-SO with a concentration of 2 ng/mL as a target and cutoff value, respectively, for identifying individuals who have consumed MMMP.


Subject(s)
Psychotropic Drugs , Tandem Mass Spectrometry , Humans , Psychotropic Drugs/urine , Psychotropic Drugs/analysis , Chromatography, Liquid , Propiophenones/urine , Substance Abuse Detection/methods , Illicit Drugs/analysis , Morpholines/urine , Morpholines/analysis , Limit of Detection
2.
J Forensic Sci ; 69(2): 688-697, 2024 Mar.
Article in English | MEDLINE | ID: mdl-38095302

ABSTRACT

Ketamine deemed as a psychoactive substance has gained popularity for recreational use owing to its hallucinogenic and dissociative effects. Understanding the synthetic processes of ketamine can provide essential clues for law enforcement officers against illicit ketamine manufacturing. In this case report, a chemical company was being monitored by law enforcement officers due to its importation of precursors and materials that could be used for the synthesis of illicit drugs. After materials and products seized from this chemical company were employed for analyses using gas chromatography-mass spectrometry, liquid chromatography-high-resolution mass spectrometry, and nuclear magnetic resonance analyses, ketamine, hydroxylamine, 2-chlorophenyl cyclopentyl ketone, and cyclopentanone p-toluenesulfonylhydrazone were identified. In addition, a novel process for the synthesis of ketamine precursor 2-chlorophenyl cyclopentyl ketone from cyclopentanone p-toluenesulfonylhydrazone and 2-chlorobenzaldehyde was validated. This is the first report to uncover this novel process for the synthesis of 2-chlorophenyl cyclopentyl ketone and can be used to increase awareness among law enforcement officers and forensic practitioners about these novel starting materials for the synthesis of ketamine.


Subject(s)
Illicit Drugs , Ketamine , Ketones , Ketamine/analysis , Cyclopentanes , Illicit Drugs/chemistry
3.
Forensic Sci Int ; 341: 111501, 2022 Dec.
Article in English | MEDLINE | ID: mdl-36274344

ABSTRACT

Identifying new psychoactive substances (NPSs) and their metabolites is essential for regulating such substances for purposes of law enforcement and forensics. NPSs can be regulated on the basis of their chemical structures before they become a critical threat to society. Further, NPS metabolites can be targeted for analysis in urine, blood, and hair. This case study reports an incident in which 10 bags with approximately 15 g of crystalline material were seized from suspects by law enforcement officers and sent to the laboratory for confirmation. Gas chromatography-mass spectrometry, liquid chromatography-high-resolution mass spectrometry, and nuclear magnetic resonance (NMR) were employed to analyze these materials. The analyses revealed that the materials were a new ketamine analog, 2-fluorodeschloro-N-ethyl-ketamine (2-FDCNEK). Single-crystal X-ray diffraction (SXRD) analysis was also employed to confirm this result. In addition, metabolites of 2-FDCNEK were investigated using a fungal model and a urine sample from an abuser. The results suggest that 2-FDCNEK and 2-fluorodeschoro-norketamine are optimal metabolites for biological samples. This report presents the mass fragmentation, NMR analysis, and SXRD data of 2-FDCNEK. In addition, it provides suggestions regarding metabolites of 2-FDCNEK for law enforcement and forensic purposes, thereby facilitating the detection of this new ketamine analog.


Subject(s)
Ketamine , Ketamine/analysis , Chromatography, Liquid , Gas Chromatography-Mass Spectrometry/methods , Mass Spectrometry , Hair/chemistry , Substance Abuse Detection/methods
4.
Org Lett ; 4(25): 4439-42, 2002 Dec 12.
Article in English | MEDLINE | ID: mdl-12465907

ABSTRACT

[reaction: see text] A series of novel 9,9-diarylfluorene-capped oligothiophenes were synthesized by Suzuki coupling reactions in good yields. The color of the emissions can be controlled by varying the conjugation length of the oligothiophene core. The bulky and rigid terminal groups of the resulting oligomers are significantly beneficial for their high morphological and thermal stability. These new oligothiophenes exhibit intriguing reversible oxidation and reduction redox behavior.

5.
J Am Chem Soc ; 124(39): 11576-7, 2002 Oct 02.
Article in English | MEDLINE | ID: mdl-12296705

ABSTRACT

Novel ter(9,9-diarylfluorene)s were synthesized by a Suzuki-coupling reaction of 2-bromofluorene (1) and 2,7-fluorenediboronic ester derivatives (3) with high isolated yields (63-86%). The X-ray structure analysis of ter(9,9'-spirobifluorene) (4aa) revealed that the conjugated chromophore adopts a helical conformation. This conformation effectively releases the steric interaction between the fluorene moieties and prevents inter-chromophore interactions. The introduction of aryl groups at the C9 position of fluorene was highly beneficial to the thermal and morphological stability of these oligomers. These terfluorenes exhibit intense blue fluorescence with excellent quantum yields both in solution ( approximately 100%) and in solid state (66-90%), and possess interesting reversible redox properties. Highly efficient blue light-emitting OLED devices were fabricated using 4aa and 4cc as emitters as well as hole transporters. The devices exhibit low turn-on voltage ( approximately 3 V) and high EL external quantum efficiency (2.5-3%).

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