Crystallographic investigations of select cathinones: emerging illicit street drugs known as `bath salts'

The name `bath salts', for an emerging class of synthetic cathinones, is derived from an attempt to evade prosecution and law enforcement. These are truly illicit drugs that have psychoactive CNS (central nervous system) stimulant effects and they have seen a rise in abuse as recreational drugs in the last few years since first having been seen in Japan in 2006. The ease of synthesis and modification of specific functional groups of the parent cathinone make these drugs particularly difficult to regulate. MDPV (3,4‐methylenedioxypyrovalerone) is commonly encountered as its hydrochloride salt (C<sub>16</sub>H<sub>21</sub>NO<sub>3</sub>·HCl), in either the hydrated or the anhydrous forms. This `bath salt' has various names in the US, e.g. `Super Coke', `Cloud Nine', and `Ivory Wave', to name just a few. We report here the structures of two forms of the HCl salt, one as a mixed bromide/chloride salt, C<sub>16</sub>H<sub>22</sub>NO<sub>3</sub><sup>+</sup>·0.343Br<sup>−</sup>·0.657Cl<sup>−</sup> [systematic name: 1‐(benzo[d][1,3]dioxol‐5‐yl)‐2‐(pyrrolidin‐1‐ium‐1‐yl)pentan‐1‐one bromide/chloride (0.343/0.657)], and the other with the H<sub>7</sub>O<sub>3</sub><sup>+</sup> cation, as well as the HCl counter‐ion [systematic name: hydroxonium 1‐(benzo[d][1,3]dioxol‐5‐yl)‐2‐(pyrrolidin‐1‐ium‐1‐yl)pentan‐1‐one dichloride, H<sub>7</sub>O<sub>3</sub><sup>+</sup>·C<sub>16</sub>H<sub>22</sub>NO<sub>3</sub><sup>+</sup>·2Cl<sup>−</sup>]. This is one of a very few structures (11 to be exact) in which we have a new example of a precisely determined hydroxonium cation. During the course of researching the clandestine manufacture of MDPV, we were surprised by the fact that a common precursor of this illicit stimulant is known to be the fragrant species piperonal, which is present in the fragrances of orchids, most particularly in the case of the vanilla orchid. We found that MDPV can be made by a Grignard reaction of this heliotropin. This may also explain the unexpected appearance of the bromide counter‐ion in some of the salts we encountered (C<sub>16</sub>H<sub>21</sub>NO<sub>3</sub>·HBr), one of which is presented here [systematic name: 1‐(benzo[d][1,3]dioxol‐5‐yl)‐2‐(pyrrolidin‐1‐ium‐1‐yl)pentan‐1‐one bromide, C<sub>16</sub>H<sub>22</sub>NO<sub>3</sub><sup>+</sup>·Br<sup>−</sup>]. Complexation of MDPV with a forensic crystallizing reagent, HAuCl<sub>4</sub>, yields the tetrachloridoaurate salt of this drug, (C<sub>16</sub>H<sub>22</sub>NO<sub>3</sub>)[AuCl<sub>4</sub>]. The heavy‐metal complexing agent HAuCl<sub>4</sub> has been used for over a century to identify common quarternary nitrogen‐containing drugs via microscopic identification. Another street drug, called ethylone (3,4‐methylenedioxyethylcathinone), is regularly sold and abused as its hydrochloride salt (C<sub>12</sub>H<sub>15</sub>NO<sub>3</sub>·HCl), and its structure is herein described (systematic name: N‐{1‐[(benzo[d][1,3]dioxol‐5‐yl)carbonyl]ethyl}ethanaminium chloride, C<sub>12</sub>H<sub>16</sub>NO<sub>3</sub><sup>+</sup>·Cl<sup>−</sup>). Marketed and sold as a `bath salt', `plant feeder', or `cleaning product', this drug is nothing more than a slight chemical modification of the banned drug methylone (3,4‐methylenedioxymethcathinone). As with previously popular synthetic cathinones, the abuse of ethylone has seen a recent increase due to regulatory efforts on previous generations of cathinones that are now banned.     

Treewidth of the Line Graph of a Complete Graph

In recent articles by Grohe and Marx, the treewidth of the line graph of a complete graph is a critical example—in a certain sense, every graph with large treewidth “contains” . However, the treewidth of was not determined exactly. We determine the exact treewidth of the line graph of a complete graph.     

Eine vereinfachte Konstruktion des Soxhlet'schen Extraktions-Apparates

Ohne Zusammenfassung     

催化光度法测定痕量钒——钒(Ⅴ)-溴甲酚紫-过氧化氢体系

催化光度法测定钒已有报道[1～3],在0.45 mol·L-1磷酸介质及加热条件下,过氧化氢氧化溴甲酚紫褪色反应非常缓慢,而痕量钒对此反应具有较高的催化活性,且在一定浓度范围内,钒量与褪色反应程度呈线性关系,据此可建立测定痕量钒的方法.方法的检出限为1.9×10-6g·L-1,测定范围为0.003～1.8 mg·L-1.方法操作简便,重现性好,用于钢样中痕量钒的测定,结果满意.     

Bestimmung des Titans und Zirkoniums, ihre Trennung von anderen Elementen sowie von einander

Ohne Zusammenfassung     

Untersuchung von Wasser und Abwasser

Analytical and Bioanalytical Chemistry -     

Boundedness and Complete Distributivity

We extend the concept of constructive complete distributivity so as to make it applicable to ordered sets admitting merely bounded suprema. The KZ-doctrine for bounded suprema is of some independent interest and a few results about it are given. The 2-category of ordered sets admitting bounded suprema over which inhabited (classically non-empty) infima distribute is shown to be bi-equivalent to a 2-category defined in terms of idempotent relations. As a corollary we obtain a simple construction of the non-negative reals.