Cannabivarin

Extraction and isolation of cannabinoids from marijuana seizures and characterization by (1)H NMR allied to chemometric tools.[Pubmed:30193661]

Sci Justice. 2018 Sep;58(5):355-365.

Marijuana, a drug derived from the Cannabis sativa L. plant, is the world's most consumed illicit drug. In this paper, a total of 156 marijuana samples seized in the state of Espirito Santo (ES), Brazil were studied and analysed by proton nuclear magnetic resonance ((1)H NMR) spectroscopy to identify the major cannabinoids present. A crude extract of all samples was purified using high performance liquid chromatography so that these compounds could serve as reference substances. Nine fractions were obtained and analysed by (1)H NMR and gas chromatography-mass spectrometry (GC-MS), with five presented cannabinoids. (9)-THC (Delta(9)-trans-tetrahydrocannabinol), (9)-THCA ((9)-tetrahydrocannabinolic acid), (8)-THC ((8)-tetrahydrocannabinol), 11-hydroxycannabinol, CBV (Cannabivarin), and CBN (cannabinol) were found, and their chemical structures were confirmed by GC-MS. The latter compound was obtained with high purity ( approximately 100%), while the others were obtained as less complex mixtures with purity higher than 75% (except for Delta(8)-THC). Principal component analysis (PCA) was used on the (1)H NMR spectra of the 156 samples, and it was found that the samples were grouped according to the months, differentiating into two groups (from July 2014 to January 2015 and from February 2015 to July 2015), where non-grouping was observed from four macro-regions of the ES state (North, Central, Metropolitan, and South). The chemical profile of the seized samples was correlated to the (1)H NMR spectrum of an isolated CBN sub-fraction, in which the group formed by samples seized in the year 2015 presented lower CBN content in the chemical composition. From the PCA score plot, two groups of samples were confirmed using the partial least squares discriminant analysis and orthogonal projections to latent structures classification methods.

Iodine-Promoted Aromatization of p-Menthane-Type Phytocannabinoids.[Pubmed:29240420]

J Nat Prod. 2018 Mar 23;81(3):630-633.

Treatment with iodine cleanly converts various p-menthane-type phytocannabinoids and their carboxylated precursors into cannabinol (CBN, 1a). The reaction is superior to previously reported protocols in terms of simplicity and substrate range, which includes not only tricyclic tetrahydrocannabinols such as Delta(9)-THC (2a) but also bicyclic phytocannabinoids such as cannabidiol (CBD, 3a). Lower homologues from the viridin series (2c and 3c, respectively) afforded Cannabivarin (CBV), a non-narcotic compound that, when investigated against a series of ionotropic (thermo-TRPs) biological end-points of phytocannabinoids, retained the submicromolar TRPA1-activating and TRPM8-inhibiting properties of CBN, while also potently activating TRPV2. Treatment with iodine provides an easy access to CBN (1a) from crude extracts and side-cuts of the purification of Delta(9)-THC and CBD from respectively narcotic Cannabis sativa (marijuana) and fiber hemp, substantially expanding the availability of this compound and, in the case of fiber hemp, dissecting it from narcotic phytocannabinoids.

Distinction of synthetic cannabidiol, cannabichromene, and cannabivarin by GLC using on-column methylation.[Pubmed:1185546]

J Pharm Sci. 1975 Oct;64(10):1719-20.

The on-column flash methylation of synthetic cannabidiol, cannabichromene, and Cannabivarin by trimethylanillinium hydroxide offers a rapid, simple GLC method for their distinction. The phenolic groups of other cannabinoids are methylated by the procedure described.