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J Nat Prod. 2019 Dec 31. doi: 10.1021/acs.jnatprod.9b00876. [Epub ahead of print]

Isolation of a High-Affinity Cannabinoid for the Human CB1 Receptor from a Medicinal Cannabis sativa Variety: Δ9-Tetrahydrocannabutol, the Butyl Homologue of Δ9-Tetrahydrocannabinol.

Author information

1
Department of Life Sciences , University of Modena and Reggio Emilia , Via Campi 103 , 41125 Modena , Italy.
2
Mediteknology s.r.l. , Via Arnesano , 73100 Lecce , Italy.
3
CNR NANOTEC , Campus Ecotekne, Via Monteroni , 73100 Lecce , Italy.
4
Department of Experimental Medicine, Division of Pharmacology , Università della Campania "L. Vanvitelli" , Via Santa Maria di Costantinopoli 16 , 80138 Naples , Italy.
5
Department of Chemistry , Sapienza University of Rome , Piazzale Aldo Moro 5 , 00185 Rome , Italy.

Abstract

The butyl homologues of Δ9-tetrahydrocannabinol, Δ9-tetrahydrocannabutol (Δ9-THCB), and cannabidiol, cannabidibutol (CBDB), were isolated from a medicinal Cannabis sativa 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 Δ9-THC, Δ9-THCB, showed an affinity for the human CB1 (Ki = 15 nM) and CB2 receptors (Ki = 51 nM) comparable to that of (-)-trans9-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 Δ9-THCB in order to reveal possible analgesic and anti-inflammatory properties. The tetrad test in mice showed a partial agonistic activity of Δ9-THCB toward the CB1 receptor.

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