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      Identification and quantitation of two cannabimimetic phenylacetylindoles JWH-251 and JWH-250, and four cannabimimetic naphthoylindoles JWH-081, JWH-015, JWH-200, and JWH-073 as designer drugs in illegal products

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      Forensic Toxicology
      Springer Nature

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          'Spice' and other herbal blends: harmless incense or cannabinoid designer drugs?

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            Spice: a never ending story?

            On January 22nd 2009, the German Health Authorities prohibited several non-traditional cannabinoids, that proved to be the active components in popular "Bio-Designer-Drugs" like "Spice" and analogous products. The recent detection of CP 47,497-C8 in Europe and Japan documents that these products have already spread world wide. We synthesized several potentially interesting alkylaminoindoles (alkylchain C(3) to C(7)) and isolated CP 47,497-C8 from "Spice Gold". The compounds were purified and characterized by NMR and mass spectrometry methods. With the aid of these authentic references we were able to detect and quantify added psychoactive compounds in different herbal blends. All samples that were acquired before the prohibition in December 2008 contained either CP 47,497-C8 (5.4-11.0mg/g) or JWH-018 (2.3mg/g). Some samples acquired in March 2009, 4 weeks after the prohibition took place, still contained CP 47,497-C8 (3.0-3.3mg/g) but JWH-018 was not detected anymore. Instead it was replaced by its non-regulated C(4)-homolog JWH-073 (5.8-22.9 mg/g). Furthermore some of the new products did not contain any non-traditional cannabinoids. To our knowledge this is the first report of the appearance JWH-073 as a new designer drug. The data and method presented here will facilitate and accelerate the detection of these compounds in complex matrices.
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              Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs.

              Numerous cannabinoids have been synthesized that are extremely potent in all of the behavioral assays conducted in our laboratory. An important feature in increasing potency has been the substitution of a dimethylheptyl (DMH) side chain for the pentyl side chain. Our previous studies have shown that (-)-11-OH-delta 8-THC-dimethylheptyl was 80-1150 times more potent than delta 9-THC. Stereospecificity was demonstrated by its (+)-enantiomer which was more than 1400-7500 times less potent. A related series of DMH cannabinoid analogs has recently been synthesized and preliminary evaluations reported here. (-)-11-OH-delta 9-THC-DMH was found to be equipotent with (-)-11-OH-delta 8-THC-DMH. The aldehyde (-)-11-oxo-delta 9-THC-DMH was 15-50 times more potent than delta 9-THC. Surprisingly, (-)-11-carboxy-delta 9-THC-DMH was also active, being slightly more potent than delta 9-THC. In the bicyclic cannabinoid series, the length and bulk of the side chain were found to be equally important. Aminoalkylindoles, which are structurally dissimilar from classical cannabinoids, have been found to exhibit a pharmacological profile similar to delta 9-THC. Though not extremely potent in vivo, they appear to represent an entirely new approach to studying the actions of the cannabinoids. The structural diversity and wide-ranging potencies of the analogs described herein provide the opportunity to develop a pharmacophore for the cannabinoids using molecular modeling techniques.
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                Author and article information

                Journal
                Forensic Toxicology
                Forensic Toxicol
                Springer Nature
                1860-8965
                1860-8973
                January 2011
                November 2010
                : 29
                : 1
                : 25-37
                Article
                10.1007/s11419-010-0100-3
                e62d09c9-8395-4632-904c-25c64298ea03
                © 2011
                History

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