The black market for new psychoactive substances has been constantly evolving and the substances that appear on this market cause a considerable number of issues, in extreme cases leading to human deaths. While monitoring the drug black market, we detected a sample of a dissociative anesthetic methoxphenidine, the salt of which contained an unusual anion in the form of bromo- and chloro-zincate complex. Concerning the unknown and potentially hazardous properties of this sample, we performed an in vitro cytotoxicity screening in cell lines of various origins (e.g., kidney, liver, bladder) which was compared with the toxicity results of the methoxphenidine standard prepared for this purpose. The street methoxphenidine sample exhibited markedly higher toxicity than the standard, which was probably caused by the anion impurity. Since it is not usual to analyze anions in salts of novel psychoactive substances, but such samples may be commonly available at the drug black market, we have developed a method for their identification with X-ray powder diffraction (XRPD), which also enabled us to distinguish between different polymorphs/solvates of methoxphenidine that were crystallized in the laboratory. XRPD offers additional data about samples, which may not be discovered by routine techniques, and in some cases, they may help to find out essential information.

• Keywords
• X-ray powder diffraction, crystal structure, cytotoxicity, dissociative anesthetic, inorganic impurity, methoxphenidine, new psychoactive substances, novel synthetic drug,
• MeSH
• Anesthetics, Dissociative adverse effects   MeSH
• X-Ray Diffraction methods   MeSH
• Cells, Cultured MeSH
• Humans MeSH
• Piperidines adverse effects   MeSH
• Psychotropic Drugs adverse effects   MeSH
• Illicit Drugs adverse effects   MeSH
• Check Tag
• Humans MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• 1-(1-(2-methoxyphenyl)-2-phenylethyl)piperidine MeSH Browser
• Anesthetics, Dissociative MeSH
• Piperidines MeSH
• Psychotropic Drugs MeSH
• Illicit Drugs MeSH

Degradation of anthocyanins involves scission of the flavonoid skeleton yielding 2,4,6-trihydroxybenzaldehyde (phloroglucinaldehyde, PGA) and a phenolic acid. However, the process is not finished with the formation of PGA, as the consequent condensation of two PGA molecules providing colored hydroxylated anthraquinones was observed for the first time. This process was studied using a combination of preparative column chromatography, nuclear magnetic resonance, liquid chromatography/high resolution tandem mass spectrometry (LC/HRMS2), and quantum calculations using density functional theory. 1,3,5,7-tetrahydroxyanthraquinone (anthrachrysone) and its isomers were found to rise during heating (95 °C) in a buffered PGA model solution (phosphate buffer, pH 7). These compounds were detected in heated red wine after an increase of its pH value. The concentration of the identified anthrachrysone in the red wine reached 0.01 mg·L-1. Presence of those compounds could therefore indicate involvement of certain steps in the processing of plant materials rich in anthocyanins (e.g., utilization of a higher temperature and/or reduction of acidity) or long-term transformation of anthocyanins (potentially, for instance, in archaeological findings such as wine or fruit residues). Additionally, measurement of wine-soil suspensions proved an increase of their pH to the values suitable for anthocyanin cleavage (neutral to slightly alkaline; reached using soil from archaeologically well-known Bull Rock Cave). Although not found in artificially prepared samples (imitations) or authentic materials so far, according to our results the above mentioned conditions are suitable for the formation of tetrahydroxylated anthraquinone derivatives and their monitoring would be beneficial.

• Keywords
• anthocyanin, degradation, hydroxyanthraquinone, phloroglucinaldehyde, wine,
• MeSH
• Food Analysis * methods   MeSH
• Anthocyanins chemistry   MeSH
• Anthraquinones analysis   chemistry   MeSH
• Chromatography, Liquid MeSH
• Mass Spectrometry MeSH
• Models, Molecular MeSH
• Molecular Structure MeSH
• Wine analysis   MeSH
• Chromatography, High Pressure Liquid MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• Anthocyanins MeSH
• Anthraquinones MeSH