The Identification of Unreacted Precursors, Impurities, and By-Products in Clandestinely Produced Phencyclidine Preparations

Angelos, Sanford A.; Raney, Jack K.; Skowronski, Gerald T.; Wagenhofer, Ronald J.

doi:10.1520/jfs12963j

Cited by 11 publications

(5 citation statements)

References 11 publications

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“…In addition to the fact that the injected analogues were hydrochloride salts (protonated ammonium salts serve as better leaving groups than the free base analytes, and reduced formation when the free base was injected) it seemed also noteworthy to consider the electron-donating properties of the 4'methoxy group. [27] However, it might be worth noting that, as far as PCP is concerned, cyclohexenylbenzene may also be formed during organic synthesis [28] and/or pyrolysis. In comparison, the 3-methoxy group might not have stabilized the carbocation in that manner which meant that the elimination could have been much slower.…”

Section: Resultsmentioning

confidence: 99%

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Preparation and analytical characterization of 1‐(1‐phenylcyclohexyl)piperidine (PCP) and 1‐(1‐phenylcyclohexyl)pyrrolidine (PCPy) analogues

Wallach

Paoli

Adejare

et al. 2013

Drug Testing and Analysis

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Classic examples of psychoactive arylcycloalkylamines include ketamine and 1-(1-phenylcyclohexyl)piperidine (PCP) and many others serve as important structural templates for neuropharmacological research. The recent emergence of PCP analogues that can be obtained from internet retailers requires the implementation of appropriate monitoring strategies for harm reduction purposes. Access to analytical data plays a key part when encountering these substances, especially if reference material is not available. The present study describes the synthesis of three substituted 1-(1-phenylcyclohexyl)piperidines, (3-MeO-, 4-MeO- and 3-Me-PCP) and three substituted 1-(1-phenylcyclohexyl)pyrrolidine analogues (3-MeO-, 4-MeO- and 3-Me-PCPy). Analytical characterizations of all six arylcyclohexylamines and their primary 1-phenylcyclohexanamine intermediates included gas chromatography ion trap electron- and chemical ionization and high resolution mass spectrometry, liquid chromatography electrospray hybrid triple-quadrupole linear ion trap tandem mass spectrometry, infrared, diode array detection and (1) H and (13) C nuclear magnetic resonance (NMR) spectroscopy. Solvent (CDCl3 vs. d6 -DMSO) and protonation effects (free bases vs hydrochloride salts) were studied in order to investigate the impact on shifts and splitting patterns, for example, when attempting to assign separate axial and equatorial proton chemical shifts of NMR spectra. Differentiation between the isomeric 3-MeO-/4-MeO-PCP and PCPy analogues was feasible under mass spectral conditions. Gas chromatography analysis appeared to induce notable degradation of the 4-MeO-substituted analytes, especially when dealing with the HCl salts which led to the detection of the substituted 1-phenylcyclohex-1-ene nucleus. This phenomenon was observed to be less pronounced with the 3-MeO isomers, possibly due to the resonance properties of the para-methoxy group followed by more facile elimination of the amine.

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Section: Resultsmentioning

confidence: 99%

“…In all three cases the corresponding alkene was 2-cyclohexenylthiophene. [27] However, it might be worth noting that, as far as PCP is concerned, cyclohexenylbenzene may also be formed during organic synthesis [28] and/or pyrolysis. [29][30][31]…”

Section: Resultsmentioning

confidence: 99%

Preparation and analytical characterization of 1‐(1‐phenylcyclohexyl)piperidine (PCP) and 1‐(1‐phenylcyclohexyl)pyrrolidine (PCPy) analogues

Wallach

Paoli

Adejare

et al. 2013

Drug Testing and Analysis

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“…As the name suggests, a PCP bucket laboratory is a series of reactions, each of which is performed in its own bucket (Figure 44) (Angelos, Raney, Skowronski, & Wagenhofer, 1990; Cone, Vaupel, & Buchwald, 1980; Frank, 1983; Khan et al, 2012). The first bucket is used to synthesize the PCP precursor 1‐piperidinyl cyclohexanecarbonitrile (PCC).…”

Section: Phencyclidinementioning

confidence: 99%

“…The PCC formed in the first bucket is added to the third bucket, along with additional ether. The Grignard reagent prepared in the second bucket is then slowly added to the third bucket, and the mixture is allowed to react for 2–3 hr (Allen et al, 1993; Angelos et al, 1990; Ballinger & Marshman, 1979; Frank, 1983; A. T. Shulgin & MacLean, 1976). During the reaction of PCC and the Grignard reagent, the nucleophilic attack occurs at the alpha carbon and not at the carbon of the cyanide group as normally occurs during Grignard reactions; this is due to the electron deficiency of the alpha carbon (Allen et al, 1993; Maddox et al, 1965; Yoshimura, Ohgo, & Sato, 1964).…”

Section: Phencyclidinementioning

confidence: 99%

Identification and associated hazards of clandestine drug laboratories

Norman

Ciesielski

Wagner

2020

WIREs Forensic Science

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The production of illicit drugs at clandestine laboratory operations is a world‐wide problem with many associated public health hazards. This review describes many laboratory types that might be encountered by the clandestine laboratory response personnel, describing the materials and processes associated with different clandestine laboratories to aid in awareness and hazard identification. Clandestine laboratories generally create products according to market forces, including the end‐user expectations with regard to product appearance (e.g., as solid or liquid, in powder or tablet formulation) and potency. The clandestine laboratories use different materials, and processes depending on the laboratory's access to precursors, their ability to produce quantities sufficient to meet market demands, and also their ability to circumvent local, national and international laws and regulations. The information presented here is aimed at both laboratory‐based scientists and analysts who have to understand the classical methods for production, which are still used, and consider novel methods using alternative precursors. It is important to be cognizant of the emerging drugs and drug analogues, how these are considered under the law, and how they can be safely collected for analysis. Clandestine laboratory responders must consider the information presented here from the perspective of the risks associated with the drugs, precursors, waste materials and equipment. As clandestine laboratories and drug markets are constantly evolving, responders need to consistently pursue ongoing education, research, and collaboration with the constant review and assessment of the emerging drugs and precursors seized during operations and reported on regional and international forums. This article is categorized under: Forensic Chemistry and Trace Evidence > Controlled and Emerging Drug Compounds Toxicology > Drug Analysis Crime Scene Investigation > Crime Scene Examination

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“…PCP extracted from urine was detected by GC/NPD with acetylated column packing material (281). A GC/MS procedure has been developed m which the 13 major components, including PCP and PCC, found in typical clandestine mixtures may be screened for and identified (282). Impurities found in the two principal methods of the manufacture of Nethyl-l-phencyclohexylamine (cyclohexamine, PCE) were identified by using proton NMR, FT-IR, and capillary GC/MS (283).…”

mentioning

confidence: 99%