Chemistry of Cannabis

Hazekamp, Arno; Fischedick, Justin T.; Díez, Mónica Llano; Lubbe, Andrea; Ruhaak, Renee L.

doi:10.1016/b978-008045382-8.00091-5

Cited by 54 publications

(82 citation statements)

References 250 publications

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“…As customary, the sum of THC and its acidic precursor THCA is reported as “total THC content.” Similarly, the sum of CBD and CBDA is reported as “total CBD content.” It should be noted that delta-8-THC and CBN are not originally produced by the cannabis plant, but are formed as degradation products of THC by exposure to heat or light, or by prolonged storage (Hazekamp et al, 2010). …”

Section: Resultsmentioning

confidence: 99%

Evaluating the Effects of Gamma-Irradiation for Decontamination of Medicinal Cannabis

Hazekamp¹

2016

Front. Pharmacol.

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In several countries with a National medicinal cannabis program, pharmaceutical regulations specify that herbal cannabis products must adhere to strict safety standards regarding microbial contamination. Treatment by gamma irradiation currently seems the only method available to meet these requirements. We evaluated the effects of irradiation treatment of four different cannabis varieties covering different chemical compositions. Samples were compared before and after standard gamma-irradiation treatment by performing quantitative UPLC analysis of major cannabinoids, as well as qualitative GC analysis of full cannabinoid and terpene profiles. In addition, water content and microscopic appearance of the cannabis flowers was evaluated. This study found that treatment did not cause changes in the content of THC and CBD, generally considered as the most important therapeutically active components of medicinal cannabis. Likewise, the water content and the microscopic structure of the dried cannabis flowers were not altered by standard irradiation protocol in the cannabis varieties studied. The effect of gamma-irradiation was limited to a reduction of some terpenes present in the cannabis, but keeping the terpene profile qualitatively the same. Based on the results presented in this report, gamma irradiation of herbal cannabis remains the recommended method of decontamination, at least until other more generally accepted methods have been developed and validated.

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Section: Resultsmentioning

confidence: 99%

Evaluating the Effects of Gamma-Irradiation for Decontamination of Medicinal Cannabis

Hazekamp¹

2016

Front. Pharmacol.

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“…1945 Until the 1990s') and the specific case of cannabis is discussed in much greater detail in another chapter of this volume. 154 In another example, Boelsma et al 155 investigated the effect of G. biloba extract EGb 761 on skin blood flow in healthy volunteers using laser Doppler flowmetry and the accompanying changes in urinary metabolites in urine using a combination of NMR spectroscopy and multivariate data analysis (MVDA). Following EGb 761 treatment, the overall mean skin blood flow was significantly reduced as compared with placebo.…”

Section: Extracts As Medicines?mentioning

confidence: 99%

Ethnopharmacology and Drug Discovery

Heinrich¹

2013

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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“…The NMR spectra of 1 suggested a partial structure similar to that of cannabisin A, but with only one of the two tyramine moieties. In accordance with the molecular formula, the 13 C NMR data (l " Table 1) in combination with analysis of the HSQC spectrum revealed 26 carbon signals due to 2 methylenes, 10 aromatic methines, and 14 quaternary carbons (2 esters carbonyls, 5 oxygenated, and 7 olefinic). The 1 H, 13 C, and HSQC NMR spectra (l " Table 1) revealed signals attributable to arylnaphtalene and tyramine moieties.…”

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confidence: 92%

“…In accordance with the molecular formula, the 13 C NMR data (l " Table 1) in combination with analysis of the HSQC spectrum revealed 26 carbon signals due to 2 methylenes, 10 aromatic methines, and 14 quaternary carbons (2 esters carbonyls, 5 oxygenated, and 7 olefinic). The 1 H, 13 C, and HSQC NMR spectra (l " Table 1) revealed signals attributable to arylnaphtalene and tyramine moieties. The tyramine moiety was supported by the HMBC correlations from H-2″ and H-6″ to C-1″ and C-4″ and from H 2 -7″ to C-8″ and C-1″.…”

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confidence: 92%

“…Hempseed cakes, the by-products of this industry, are not currently considered as having high economic added value. But hempseed and its residue are sources of amide compounds derived from caffeic acid [10][11][12][13], among which some possess predominant radical scavenging activity [14]. With the aim to find novel natural compounds useful for the development of new treatments, we performed a biological and phytochemistry study of the extracts from hempseed cakes.…”

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confidence: 99%

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In Vitro Mammalian Arginase Inhibitory and Antioxidant Effects of Amide Derivatives Isolated from the Hempseed Cakes (Cannabis sativa)

Bourjot

Zedet

Demange

et al. 2017

PMIO

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!In an effort to identify novel inhibitors of arginase, a phytochemical study was performed on hempseed cakes (Cannabis sativa L.). It led to the isolation of a new lignanamide, cannabisin I (1), together with seven known lignanamides, cannabisins A, B, C, F, M, 3,3′-demethylgrossamide, grossamide, and two phenylpropanoid amides, N-trans-caffeoyltyramine and N-trans-caffeoyloctopamine, among which was later identified for the first time from C. sativa. Their structures were elucidated by comprehensive analysis of NMR spectroscopy and mass spectrometry data. These compounds were evaluated on mammal arginase (purified liver bovine arginase), showing that N-trans-caffeoyltyramine exhibited the higher activity with an IC 50 value of 20.9 µM, which remains, however, less active than the reference compound S-(2-boronoethyl)-l-cysteine (IC 50 = 4.3 µM). Radical scavenging capacity of these compounds was determined by the ORAC-FL method. All tested cannabisins displayed antioxidant activity close to or better than the reference compounds. N-trans-Caffeoyltyramine has both arginase inhibitory property and antioxidant capacity.

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Chemistry of Cannabis

Cited by 54 publications

References 250 publications

Evaluating the Effects of Gamma-Irradiation for Decontamination of Medicinal Cannabis

Evaluating the Effects of Gamma-Irradiation for Decontamination of Medicinal Cannabis

Ethnopharmacology and Drug Discovery

In Vitro Mammalian Arginase Inhibitory and Antioxidant Effects of Amide Derivatives Isolated from the Hempseed Cakes (Cannabis sativa)

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