10.1021/acs.jnatprod.9b00876.s001
Pasquale Linciano
Pasquale
Linciano
Cinzia Citti
Cinzia
Citti
Livio Luongo
Livio
Luongo
Carmela Belardo
Carmela
Belardo
Sabatino Maione
Sabatino
Maione
Maria Angela Vandelli
Maria Angela
Vandelli
Flavio Forni
Flavio
Forni
Giuseppe Gigli
Giuseppe
Gigli
Aldo Laganà
Aldo
Laganà
Carmela Maria Montone
Carmela Maria
Montone
Giuseppe Cannazza
Giuseppe
Cannazza
Isolation of
a High-Affinity Cannabinoid for the Human
CB1 Receptor from a Medicinal <i>Cannabis sativa</i> Variety:
Δ<sup>9</sup>‑Tetrahydrocannabutol, the Butyl Homologue
of Δ<sup>9</sup>‑Tetrahydrocannabinol
American Chemical Society
2019
CB 2 receptors
cannabinoid
Medicinal Cannabis sativa Variety
Δ 9
THCB
Cannabis sativa variety
spectroscopic
UV
Human CB 1 Receptor
homologue
CB 1 receptor
FM
ECD
K i
THC-like binding affinity
NMR
nM
CBDB
HRMS
IR
-Δ
butyl
2019-12-31 13:38:29
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Isolation_of_a_High-Affinity_Cannabinoid_for_the_Human_CB1_Receptor_from_a_Medicinal_i_Cannabis_sativa_i_Variety_sup_9_sup_Tetrahydrocannabutol_the_Butyl_Homologue_of_sup_9_sup_Tetrahydrocannabinol/11482215
The butyl homologues of Δ<sup>9</sup>-tetrahydrocannabinol,
Δ<sup>9</sup>-tetrahydrocannabutol (Δ<sup>9</sup>-THCB),
and cannabidiol, cannabidibutol (CBDB), were isolated from a medicinal <i>Cannabis sativa</i> variety (FM2) inflorescence. Appropriate
spectroscopic and spectrometric characterization, including NMR, UV,
IR, ECD, and HRMS, was carried out on both cannabinoids. The chemical
structures and absolute configurations of the isolated cannabinoids
were confirmed by comparison with the spectroscopic data of the respective
compounds obtained by stereoselective synthesis. The butyl homologue
of Δ<sup>9</sup>-THC, Δ<sup>9</sup>-THCB, showed an affinity
for the human CB1 (<i>K</i><sub>i</sub> = 15 nM) and CB2
receptors (<i>K</i><sub>i</sub> = 51 nM) comparable to that
of (−)-<i>trans</i>-Δ<sup>9</sup>-THC. Docking
studies suggested the key bonds responsible for THC-like binding affinity
for the CB1 receptor. The formalin test in vivo was performed on Δ<sup>9</sup>-THCB in order to reveal possible analgesic and anti-inflammatory
properties. The tetrad test in mice showed a partial agonistic activity
of Δ<sup>9</sup>-THCB toward the CB1 receptor.