Separation and structural characterization of the synthetic cannabinoids JWH-412 and 1-[(5-fluoropentyl)-1H-indol-3yl]-(4-methylnaphthalen-1-yl)methanone using GC–MS, NMR analysis and a flash chromatography system

Moosmann, Bjoern; Kneisel, Stefan; Girreser, Ulrich; Brecht, Volker; Westphal, Folker; Auwärter, Volker

doi:10.1016/j.forsciint.2011.12.010

Cited by 64 publications

(49 citation statements)

References 10 publications

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“…It was found that in case of AM-2201 intake, metabolites of JWH-018 were also present, presumably after enzymatic defluorination of AM-2201. MAM-2201 has presumably high affinity for the CB 1 receptor, because it is a chemical hybrid of two highly potent CB 1 agonists (JWH-122 and AM-2201 [31] ). This pattern was seen in many urine samples analyzed in our laboratory, although, for example, MAM-2201 and JWH-122 usually do not occur simultaneously in products (own unpublished data).…”

Section: Discussionmentioning

confidence: 99%

Acute intoxication by synthetic cannabinoids – Four case reports

Hermanns-Clausen

Kneisel

Hutter

et al. 2013

Drug Testing and Analysis

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Section: Discussionmentioning

confidence: 99%

Acute intoxication by synthetic cannabinoids – Four case reports

Hermanns-Clausen

Kneisel

Hutter

et al. 2013

Drug Testing and Analysis

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“…19,20 The incorporation of fluorine or methoxy substituents in SC analogs has proven a popular clandestine design trend. [23][24][25][26][27][28] These modifications are not restricted to 3-naphthoylindoles, and several regioisomers and homologues of methoxybenzoylindole SC RCS-4 (5) have also been reported 29,30 despite no precedent in the scientific literature, with position of methoxy substituent affecting cannabinoid potency in vitro. [23][24][25][26][27][28] These modifications are not restricted to 3-naphthoylindoles, and several regioisomers and homologues of methoxybenzoylindole SC RCS-4 (5) have also been reported 29,30 despite no precedent in the scientific literature, with position of methoxy substituent affecting cannabinoid potency in vitro.…”

Section: Introductionmentioning

confidence: 99%

The chemistry and pharmacology of synthetic cannabinoid SDB‐006 and its regioisomeric fluorinated and methoxylated analogs

Banister

Olson

Winchester

et al. 2018

Drug Testing and Analysis

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Synthetic cannabinoids are the largest and most structurally diverse class of new psychoactive substances, with manufacturers often using isomerism to evade detection and circumvent legal restriction. The regioisomeric methoxy- and fluorine-substituted analogs of SDB-006 (N-benzyl-1-pentyl-1H-indole-3-carboxamide) were synthesized and could not be differentiated by gas chromatography-mass spectrometry (GC-MS), but were distinguishable by liquid chromatography-quadrupole time-of-flight-MS (LC-QTOF-MS). In a fluorescence-based plate reader membrane potential assay, SDB-006 acted as a potent agonist at human cannabinoid receptors (CB EC = 19 nM). All methoxy- and fluorine-substituted analogs showed reduced potency compared to SDB-006, although the 2-fluorinated analog (EC = 166 nM) was comparable to known synthetic cannabinoid RCS-4 (EC = 146 nM). Using biotelemetry in rats, SDB-006 and RCS-4 evoked comparable reduction in body temperature (~0.7°C at a dose of 10 mg/kg), suggesting lower potency than the recent synthetic cannabinoid AB-CHMINACA (>2°C, 3 mg/kg).

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“…However, the range of analytes covered by these methods had to be expanded [10,11], as the number of different synthetic cannabinoids identified in herbal mixtures is continuously increasing [12][13][14][15][16][17]. The synthetic cannabinoids used in these products are mainly high-potency drugs [18][19][20].…”

Section: Introductionmentioning

confidence: 99%