Iodine-Promoted Aromatization of p-Menthane-Type Phytocannabinoids.
J Nat Prod
; 81(3): 630-633, 2018 03 23.
Article
em En
| MEDLINE
| ID: mdl-29240420
ABSTRACT
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 Δ9-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 Δ9-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.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Agonistas de Receptores de Canabinoides
/
Iodo
Tipo de estudo:
Guideline
Limite:
Humans
Idioma:
En
Ano de publicação:
2018
Tipo de documento:
Article