Iodine-Promoted Aromatization of p‑Menthane-Type
Phytocannabinoids
Posted on 2017-12-14 - 19:22
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.
CITE THIS COLLECTION
DataCite
3 Biotech
3D Printing in Medicine
3D Research
3D-Printed Materials and Systems
4OR
AAPG Bulletin
AAPS Open
AAPS PharmSciTech
Abhandlungen aus dem Mathematischen Seminar der Universität Hamburg
ABI Technik (German)
Academic Medicine
Academic Pediatrics
Academic Psychiatry
Academic Questions
Academy of Management Discoveries
Academy of Management Journal
Academy of Management Learning and Education
Academy of Management Perspectives
Academy of Management Proceedings
Academy of Management Review
Pollastro, Federica; Caprioglio, Diego; Marotta, Patrizia; Schiano Moriello, Aniello; Petrocellis, Luciano De; Taglialatela-Scafati, Orazio; et al. (2017). Iodine-Promoted Aromatization of p‑Menthane-Type
Phytocannabinoids. ACS Publications. Collection. https://doi.org/10.1021/acs.jnatprod.7b00946
or
Select your citation style and then place your mouse over the citation text to select it.
SHARE
Usage metrics
Read the peer-reviewed publication
AUTHORS (7)
FP
Federica Pollastro
DC
Diego Caprioglio
PM
Patrizia Marotta
AS
Aniello Schiano Moriello
LP
Luciano De Petrocellis
OT
Orazio Taglialatela-Scafati
GA
Giovanni Appendino