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

Abstract:

: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.

journal_name

Drug Test Anal

authors

Wallach J,De Paoli G,Adejare A,Brandt SD

doi

10.1002/dta.1468

subject

Has Abstract

pub_date

2014-07-01 00:00:00

pages

633-50

issue

7-8

eissn

1942-7603

issn

1942-7611

journal_volume

6

pub_type

杂志文章
  • Docetaxel epimerization in silicone films: a case of drug excipient incompatibility.

    abstract::Docetaxel (DTX) is an anti-cancer compound derived from 10-deacetyl baccatin III which is indicated for treatment of breast, lung, prostate, gastro-esophageal, and head and neck cancers. Epimerization of DTX at the C-7 hydroxyl position has intrigued chemists and has been implicated in loss of potency, as well as in t...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.1617

    authors: Mohsin S,Arellano IH,Choudhury NR,Garg S

    更新日期:2014-10-01 00:00:00

  • Studies on the in vivo metabolism of methylstenbolone and detection of novel long term metabolites for doping control analysis.

    abstract::The anabolic-androgenic steroid methylstenbolone (MSTEN; 2α,17α-dimethyl-17β-hydroxy-5α-androst-1-en-3-one) is available as a so-called designer steroid or nutritional supplement. It is occasionally detected in doping control samples, predominantly tested and confirmed as the glucuronic acid conjugate of methylstenbol...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.2736

    authors: Piper T,Fusshöller G,Schänzer W,Lagojda A,Kuehne D,Thevis M

    更新日期:2019-11-01 00:00:00

  • Zebrafish (Danio rerio) water tank model for the investigation of drug metabolism: Progress, outlook, and challenges.

    abstract::Zebrafish (Danio rerio) water tank (ZWT) approach was investigated as an alternative model for metabolism studies based on six different experiments with four model compounds. Sibutramine was applied for the multivariate optimization of ZWT conditions, also for the comparison of the metabolism among ZWT, humans and mi...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.2523

    authors: Sardela VF,Anselmo CS,Nunes IKDC,Carneiro GRA,Dos Santos GRC,de Carvalho AR,Labanca BJ,Silva Oliveira D,Ribeiro WD,de Araujo ALD,Padilha MC,de Lima CKF,de Sousa VP,de Aquino Neto FR,Gualberto Pereira HM

    更新日期:2018-11-01 00:00:00

  • Determination of acetylcholinesterase activity by the Ellman assay: a versatile tool for in vitro research on medical countermeasures against organophosphate poisoning.

    abstract::Inhibition of acetylcholinesterase (AChE) is the main mechanism of action of organophosphorus compounds (OP), and AChE reactivators (oximes) are at present the only causal therapeutic approach. Being the key target of OP toxicity, AChE may serve as a valuable tool for diagnosis of OP exposure as well as for the invest...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章,评审

    doi:10.1002/dta.337

    authors: Worek F,Eyer P,Thiermann H

    更新日期:2012-03-01 00:00:00

  • Studies on the metabolism of the fentanyl-derived designer drug butyrfentanyl in human in vitro liver preparations and authentic human samples using liquid chromatography-high resolution mass spectrometry (LC-HRMS).

    abstract::Increasing numbers of new psychoactive substances (NPS) among them fentanyl derivatives has been reported by the European monitoring centre for drugs and drug addiction (EMCDDA). Butyrfentanyl is a new fentanyl derivative whose potency ratio was found to be seven compared to morphine and 0.13 compared to fentanyl. Sev...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.2111

    authors: Steuer AE,Williner E,Staeheli SN,Kraemer T

    更新日期:2017-07-01 00:00:00

  • The use of in vitro technologies and high-resolution/accurate-mass LC-MS to screen for metabolites of 'designer' steroids in the equine.

    abstract::Detection of androgenic-anabolic steroid abuse in equine sports requires knowledge of the drug's metabolism in order to target appropriate metabolites, especially where urine is the matrix of choice. Studying 'designer' steroid metabolism is problematic since it is difficult to obtain ethical approval for in vivo meta...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.250

    authors: Clarke A,Scarth J,Teale P,Pearce C,Hillyer L

    更新日期:2011-01-01 00:00:00

  • The use of dried blood spots for quantification of 15 antipsychotics and 7 metabolites with ultra-high performance liquid chromatography - tandem mass spectrometry.

    abstract::Therapeutic drug monitoring of antipsychotics is important in optimizing individual therapy. In psychiatric populations, classical venous blood sampling is experienced as frightening. Interest in alternative techniques, like dried blood spots (DBS), has consequently increased. A fast and easy to perform DBS method for...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.1698

    authors: Patteet L,Maudens KE,Stove CP,Lambert WE,Morrens M,Sabbe B,Neels H

    更新日期:2015-06-01 00:00:00

  • Nanoparticle technology: amplifying the effective sensitivity of biomarker detection to create a urine test for hGH.

    abstract::Several clinical-grade immunoassays exist for the specific measurement of hGH or its isoforms in blood but there is an urgent need to apply these same reliable assays to the measurement of hGH in urine as a preferred 'non-invasive' biofluid. Unfortunately, conventional hGH immunoassays cannot attain the sensitivity re...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章,评审

    doi:10.1002/dta.96

    authors: Fredolini C,Tamburro D,Gambara G,Lepene BS,Espina V,Petricoin EF 3rd,Liotta LA,Luchini A

    更新日期:2009-09-01 00:00:00

  • Subject-based steroid profiling and the determination of novel biomarkers for DHT and DHEA misuse in sports.

    abstract::Doping with natural steroids can be detected by evaluating the urinary concentrations and ratios of several endogenous steroids. Since these biomarkers of steroid doping are known to present large inter-individual variations, monitoring of individual steroid profiles over time allows switching from population-based to...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.206

    authors: Van Renterghem P,Van Eenoo P,Sottas PE,Saugy M,Delbeke F

    更新日期:2010-11-01 00:00:00

  • A new technique for spectrophotometric determination of pseudoephedrine and guaifenesin in syrup and synthetic mixture.

    abstract::The accuracy in predicting different chemometric methods was compared when applied on ordinary UV spectra and first order derivative spectra. Principal component regression (PCR) and partial least squares with one dependent variable (PLS1) and two dependent variables (PLS2) were applied on spectral data of pharmaceuti...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.235

    authors: Riahi S,Hadiloo F,Milani SM,Davarkhah N,Ganjali MR,Norouzi P,Seyfi P

    更新日期:2011-05-01 00:00:00

  • Methylhexanamine is not detectable in Pelargonium or Geranium species and their essential oils: A multi-centre investigation.

    abstract::In an earlier study, we developed two sensitive and reliable procedures for gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-tandem mass spectrometry (LC-MS/MS) analysis of methylhexaneamine (MHA) in P. graveolens plant materials and volatile oils. None of the analyzed plant materials or oils sho...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章,多中心研究

    doi:10.1002/dta.1726

    authors: ElSohly MA,Gul W,Tolbert C,ElSohly KM,Murphy TP,Avula B,Chittiboyina AG,Wang M,Khan IA,Yang M,Guo D,Zhang WD,Su J

    更新日期:2015-07-01 00:00:00

  • Head-twitch response in rodents induced by the hallucinogen 2,5-dimethoxy-4-iodoamphetamine: a comprehensive history, a re-evaluation of mechanisms, and its utility as a model.

    abstract::Two primary animal models persist for assessing hallucinogenic potential of novel compounds and for examining the pharmacological and neurobiological substrates underlying the actions of classical hallucinogens, the two-lever drug discrimination procedure and the drug-induced head-twitch response (HTR) in rodents. The...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章,评审

    doi:10.1002/dta.1333

    authors: Canal CE,Morgan D

    更新日期:2012-07-01 00:00:00

  • Annual banned-substance review: analytical approaches in human sports drug testing.

    abstract::The annual update of the list of prohibited substances and doping methods as issued by the World Anti-Doping Agency (WADA) allows the implementation of most recent considerations of performance manipulation and emerging therapeutics into human sports doping control programmes. The annual banned-substance review for hu...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章,评审

    doi:10.1002/dta.128

    authors: Thevis M,Kuuranne T,Geyer H,Schänzer W

    更新日期:2010-04-01 00:00:00

  • Potency of Δ9 -tetrahydrocannabinol and other cannabinoids in cannabis in England in 2016: Implications for public health and pharmacology.

    abstract::In 2005 and 2008, studies reported that cannabis in England had become dominated by the sinsemilla (unseeded female) form. The average potency (Δ9 -tetrahydrocannabinol [THC] content) of this material had doubled over the previous decade. Cannabis resin then circulating contained approximately equal ratios of THC and ...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.2368

    authors: Potter DJ,Hammond K,Tuffnell S,Walker C,Di Forti M

    更新日期:2018-04-01 00:00:00

  • Altitude training causes haematological fluctuations with relevance for the Athlete Biological Passport.

    abstract::The impact of altitude training on haematological parameters and the Athlete Biological Passport (ABP) was evaluated in international-level elite athletes. One group of swimmers lived high and trained high (LHTH, n = 10) for three to four weeks at 2130 m or higher whereas a control group (n = 10) completed a three-wee...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.1757

    authors: Bonne TC,Lundby C,Lundby AK,Sander M,Bejder J,Nordsborg NB

    更新日期:2015-08-01 00:00:00

  • Synthesis and identification of deschloroketamine metabolites in rats' urine and a quantification method for deschloroketamine and metabolites in rats' serum and brain tissue using liquid chromatography tandem mass spectrometry.

    abstract::Deschloroketamine (2-(methylamino)-2-phenyl-cyclohexanone) is a ketamine analog belonging to a group of dissociative anesthetics, which have been distributed within the illicit market since 2015. However, it was also being sold as 'ketamine' misleading people to believe that they were getting genuine ketamine. Dissoci...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.2726

    authors: Hájková K,Jurásek B,Čejka J,Štefková K,Páleníček T,Sýkora D,Kuchař M

    更新日期:2020-03-01 00:00:00

  • Detection of erythropoiesis stimulating agents in urine samples using a capillary Western system.

    abstract::The presence of erythropoiesis stimulating agents (ESAs) in the urine samples collected from athletes is detected using traditional Western blotting following either size-based separation (SDS/SAR-PAGE) or isoelectric focusing (IEF). Although there is an important testing effort, there is little doubt that ESAs are st...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.2528

    authors: Desharnais P,Naud JF,Ayotte C

    更新日期:2018-11-01 00:00:00

  • Hair analysis as a useful procedure for detection of vapour exposure to chemical warfare agents: simulation of sulphur mustard with methyl salicylate.

    abstract::Chemical warfare agents (CWA) are highly toxic compounds which have been produced to kill or hurt people during conflicts or terrorist attacks. Despite the fact that their use is strictly prohibited according to international convention, populations' exposure still recently occurred. Development of markers of exposure...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.1659

    authors: Spiandore M,Piram A,Lacoste A,Josse D,Doumenq P

    更新日期:2014-06-01 00:00:00

  • Determination of cannabinoids in hemp nut products in Taiwan by HPLC-MS/MS coupled with chemometric analysis: quality evaluation and a pilot human study.

    abstract::Hemp nuts are mature cannabis seeds obtained after shelling and that are commonly used in traditional Chinese medicine for treating functional constipation. In this work, we screened hemp nut products, classified them, and verified the legality of consuming them. A total of 18 products were purchased from Taiwan, Chin...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.2062

    authors: Chang CW,Tung CW,Tsai CC,Wu YT,Hsu MC

    更新日期:2017-06-01 00:00:00

  • Quantification of six cannabinoids and metabolites in oral fluid by liquid chromatography-tandem mass spectrometry.

    abstract::Δ(9) -Tetrahydrocannabinol (THC) is the most commonly analyzed cannabinoid in oral fluid (OF); however, its metabolite 11-nor-9-carboxy-THC (THCCOOH) offers the advantage of documenting active consumption, as it is not detected in cannabis smoke. Analytical challenges such as low (ng/L) THCCOOH OF concentrations hampe...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.1753

    authors: Desrosiers NA,Scheidweiler KB,Huestis MA

    更新日期:2015-08-01 00:00:00

  • GHB and synthetic cathinones: clinical effects and potential consequences.

    abstract::Designer drugs belong to a group of legally or illegally produced substances that are structurally and pharmacologically very similar to illicit drugs. In the past, designer drugs were often used during all-night dance parties, but they are now consumed in multiple settings from college bars to parks to private house ...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章,评审

    doi:10.1002/dta.210

    authors: Karila L,Reynaud M

    更新日期:2011-09-01 00:00:00

  • Hair analysis can provide additional information in doping and forensic cases involving clostebol.

    abstract::Clostebol is a synthetic anabolic androgenic steroid, with potential use as a performance-enhancing drug if taken for long periods in order to produce the desired effect. Recently, the use of medications containing clostebol acetate has led to the suspension of several athletes in various sports. Previous studies have...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.2469

    authors: Salomone A,Gerace E,Di Corcia D,Alladio E,Vincenti M,Kintz P

    更新日期:2019-01-01 00:00:00

  • Liposomes as potential masking agents in sport doping. Part 2: Detection of liposome-entrapped haemoglobin by flow cytofluorimetry.

    abstract::This work presents an analytical procedure for the identification and characterization of liposome-entrapped haemoglobins, based on flow cytofluorimetry. Flow cytofluorimetric detection is carried out following labelling by two distinct fluorescent reagents, an anti-haemoglobin antibody, fluorescein isothiocyanate con...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.1956

    authors: Esposito S,Colicchia S,de la Torre X,Donati F,Mazzarino M,Botrè F

    更新日期:2017-02-01 00:00:00

  • GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: regioisomers related to 4-Br-2,5-DMA (DOB).

    abstract::A series of regioisomeric bromodimethoxyamphetamines have mass spectra essentially equivalent to the controlled drug substance 4-Br-2,5-dimethoxyamphetamine (4-Br-2,5-DMA; DOB); all have molecular weight of 274 and major fragment ions in their electron ionization mass spectra at m/z 44 and m/z 230/232. The trifluoroac...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.409

    authors: Maher HM,Awad T,DeRuiter J,Randall Clark C

    更新日期:2012-07-01 00:00:00

  • An investigation of the stability of emerging new psychoactive substances.

    abstract::The evolving nature of new psychoactive substances (NPS) - often referred to as 'legal highs', 'designer drugs' or 'bath salts' - presents an evolving challenge for toxicologists. Apart from the detection and identification of these compounds, further analytical challenges may arise from the presence of possible metab...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.1576

    authors: Soh YN,Elliott S

    更新日期:2014-07-01 00:00:00

  • Circulating microRNAs as long-term biomarkers for the detection of erythropoiesis-stimulating agent abuse.

    abstract::MicroRNAs (miRNAs) are small, non-protein coding transcripts involved in many cellular and physiological mechanisms. Recently, a new class of miRNA called 'circulating miRNAs' was found in cell-free body fluids such as plasma and urine. Circulating miRNAs have been shown to be very stable, specific, and sensitive biom...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.370

    authors: Leuenberger N,Jan N,Pradervand S,Robinson N,Saugy M

    更新日期:2011-11-01 00:00:00

  • Determination of cocaine, cocaine metabolites and cannabinoids in single hairs by MALDI Fourier transform mass spectrometry--preliminary results.

    abstract::In a preliminary test, four single hairs of a drug abuser were analyzed for the presence of drugs by MALDI Fourier transform mass spectrometry (MALDI-FTMS). Washed hair strains were directly fixed on a sample plate using pressure stable, double-sided adhesive tape; α-cyano-4-hydroxycinnamic acid matrix was manually sp...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.1453

    authors: Musshoff F,Arrey T,Strupat K

    更新日期:2013-05-01 00:00:00

  • Metabolites of lorazepam: Relevance of past findings to present day use of LC-MS/MS in analytical toxicology.

    abstract::The advent of liquid chromatography-tandem mass spectrometry (LC-MS/MS), with the sensitivity it confers, permits the analysis of both phase I and II drug metabolites that in the past would have been difficult to target using other techniques. These metabolites may have relevance to current analytical toxicology emplo...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.305

    authors: Turfus SC,Braithwaite RA,Cowan DA,Parkin MC,Smith NW,Kicman AT

    更新日期:2011-10-01 00:00:00

  • In vivo metabolism of the designer anabolic steroid hemapolin in the thoroughbred horse.

    abstract::Hemapolin (2α,3α-epithio-17α-methyl-5α-androstan-17β-ol) is a designer steroid that is an ingredient in several "dietary" and "nutritional" supplements available online. As an unusual chemical modification to the steroid A-ring could allow this compound to pass through antidoping screens undetected, the metabolism of ...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.2769

    authors: Waller CC,Weththasinghe SA,McClure L,Cawley AT,Suann C,Suann E,Sutherland E,Cooper E,Heather A,McLeod MD

    更新日期:2020-06-01 00:00:00

  • Evaluation of fibronectin 1 in one dried blood spot and in urine after rhGH treatment.

    abstract::Since the appearance of recombinant human growth hormone (rhGH) in the 1980s, its expansion and acquisition through the black market has increased, so the detection of its abuse continues to be a challenge. New biomarkers that are more reliable and sensitive, allowing a larger detection window, are still needed. In th...

    journal_title:Drug testing and analysis

    pub_type: 杂志文章

    doi:10.1002/dta.2108

    authors: Ferro P,Ventura R,Pérez-Mañá C,Farré M,Segura J

    更新日期:2017-07-01 00:00:00