[1-(Tetrahydropyran-4-ylmethyl)-1H-indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone: a new synthetic cannabinoid identified on the drug market

Zuba, Dariusz; Geppert, Bogna; Sekuła, Karolina; Żaba, Czesław

doi:10.1007/s11419-013-0191-8

Cited by 14 publications

(6 citation statements)

References 26 publications

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“…In recent years, several new psychoactive substances (NPS) have been found and identified in illicit drug products [1][2][3][4][5][6][7]. Among the NPS, synthetic cannabinoids and synthetic cathinones are most frequently detected and have become serious social problems [1,7].…”

Section: Introductionmentioning

confidence: 99%

Identification and characterization of α-PVT, α-PBT, and their bromothienyl analogs found in illicit drug products

et al. 2015

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Recently, thienyl derivatives of cathinones have appeared on the market as new psychoactive substances (NPS). In this study, identification and characterization of 2-(pyrrolidin-1-yl)-1-(thiophen-2-yl)pentan-1-one (a-PVT), 2-(pyrrolidin-1-yl)-1-(thiophen-2-yl)butan-1-one (a-PBT), and their bromothienyl analogs disclosed in illicit products are described. In our analysis, some analogous compounds of a-PVT, which had a bromine substitution on the thiophene ring, were identified in the samples containing a-PVT; 1-(4-bromothiophen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one, 1-(5-bromothiophen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one, and 1-(4,5-dibromothiophen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one by comparing the analytical data with synthetic reference standards. We also observed 1-(4-bromothiophen-2-yl)-2-(pyrrolidin-1-yl)butan-1-one and 1-(5-bromothiophen-2-yl)-2-(pyrrolidin-1-yl)butan-1-one from a powder product, in which a-PBT was detected. The brominated a-PVTs were also found when overbrominated 1-(thiophen-2-yl)pentan-1-one reacted with pyrrolidine, and they are suspected to be the by-products of a-PVT synthesis. In Japan, cathinone derivatives with a phenyl group as the aromatic ring have been widely controlled by generic scheduling. To escape from such a regulation, analogs with different aromatic groups such as a-PVT and a-PBT appeared on the illicit market of psychoactive compounds. To our knowledge, this is the first report describing identification of a-PBT, and bromothienyl analogs of both a-PVT and a-PBT in illicit drug products. The synthetic method and analytical data shown in this study will be useful for identification of the thienyl derivatives of cathinone analogs.

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Section: Introductionmentioning

confidence: 99%

Identification and characterization of α-PVT, α-PBT, and their bromothienyl analogs found in illicit drug products

et al. 2015

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“…The potential for adulteration of botanical raw material with synthetic cannabinoids [67] is also a concern where analysis relies on methods with inherent low discrimination, such as Fourier-transform infrared (FTIR) spectroscopy. Due to the relatively large molecular size of cannabinoids, key structural features that appear between 500 and 1,500 cm –1 are difficult to interpret, making the differentiation of cannabinoid species problematic from FTIR spectra alone [68]. …”

Section: Validation Characteristics For Analytical Proceduresmentioning

confidence: 99%

Developing Robust Standardised Analytical Procedures for Cannabinoid Quantification: Laying the Foundations for an Emerging Cannabis-Based Pharmaceutical Industry

Welling¹,

Liu²,

Hazekamp³

et al. 2019

Med Cannabis Cannabinoids

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The plant genus Cannabis is a prolific producer of unique pharmaceutically relevant metabolites, commonly referred to as cannabinoids. Robust and standardised methods for the quantification of cannabinoids within botanical and drug forms is a critical step forward for an emerging Cannabis-based pharmaceutical industry, which is poised for rapid expansion. Despite a growing body of analytical methods for the quantification of cannabinoids, few have been validated using internationally accredited guidelines. Moreover, standardised methods have yet to be developed for application at various stages of manufacture as well as for different levels of processing and refinement. Validation parameters for establishing robust standardised methods for cannabinoid quantification within Cannabis-based drug forms are critically discussed. Determining an appropriate level of specificity (discrimination) among heterogeneous botanical matrices as well as evaluating accuracy (recovery) and inter-laboratory precision (reproducibility) within strict and volatile regulatory environments are potential obstacles to the establishment of robust analytical procedures. We argue that while some of these challenges remain unique to Cannabis, others are common to botanical-based drug development and manufacture. In order to address potential barriers to analytical method standardisation, a collaborative research initiative inclusive of academic and commercial stakeholders is proposed.

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“…Pounded roots and leaves of L. leonurus are added to the drinking water of poultry by traditional farmers in South Africa to prevent sickness, as well as to treat gallsickness (anaplasmosis) in their cattle (Hulme, 1954as quoted by Hutchings, 1996and McGaw and Eloff, 2008 Zuba et al (2013) report that in the first years of the 21 st century numerous herbal products were advertised, particularly over the internet, as legal alternatives to cannabis. L. leonurus was one of these herbal products, amongst others such as Nymphaea caerulea Savigny, Turnera diffusa Willd.…”

Section: Ethnoveterinary Usesmentioning

confidence: 99%

“Wild cannabis”: A review of the traditional use and phytochemistry of Leonotis leonurus

Nsuala

Enslin

Viljoen

2015

Journal of Ethnopharmacology

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[1-(Tetrahydropyran-4-ylmethyl)-1H-indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone: a new synthetic cannabinoid identified on the drug market

Cited by 14 publications

References 26 publications

Identification and characterization of α-PVT, α-PBT, and their bromothienyl analogs found in illicit drug products

Identification and characterization of α-PVT, α-PBT, and their bromothienyl analogs found in illicit drug products

Developing Robust Standardised Analytical Procedures for Cannabinoid Quantification: Laying the Foundations for an Emerging Cannabis-Based Pharmaceutical Industry

“Wild cannabis”: A review of the traditional use and phytochemistry of Leonotis leonurus

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