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Isolation of new phytocannabinoids from Cannabis sativa L

(-)-trans-Δ9-tetraidrocannabibutolo(-)-trans-Δ9-tetraidrocannabiforolocannabidibutolCannabidiolCannabis

Introduction

Identification of new phytocannabinoids with the same structure as Δ9-THC and CBD but with four- and seven-membered alkyl side chains. These new phytocannabinoids have been called (-) – trans-Δ9-tetrahydrocannabibu-tol (Δ9-THCB), cannabidibutol (CBDB), (-) – trans-Δ9-tetrahydrocannabifo-rolo (Δ9-THCP) and cannabidiforol (CBDP); all were isolated and fully characterized. Their stereochemical configuration is assigned by correspondence to the same obtained by stereoselective synthesis.

Technical features

New phytocannabinoids were isolated from the medicinal variety Cannabis sativa (FM2) (-) – trans-Δ9-tetrahydrocannabibutol (Δ9-THCB), cannabidibutol (CBDB), (-) – trans-Δ9-tetrahydrocannabiforol (Δ9-THCP) and cannabidiforol ( CBDP). Full spectroscopic and spectrometric characterization were also performed on all isolated compounds, including NMR, UV, IR, ECD and HRMS. The binding activity of Δ9-THCP on the human CB1 receptor in vitro (Ki = 1.2 nM) was similar to that of CP55940 (Ki = 0.9 nM), a potent complete CB1 agonist. In the cannabinoid tetrad drug test, Δ9-THCP induced hypomotility, analgesia, catalepsy and decreased rectal temperature, indicating a cannabimimetic activity superior to THC. Δ9-tetrahydrocannabutol was isolated from C. Sativa and tested for possible anti-inflammatory activity in mice. Other tests are necessary for its commercialization but with scientific evidence already established. State of development: TRL 4.

Possible Applications

  • New formulations for analgesics;
  • Anti – inflammatories.

Advantages

  • Greater therapeutic efficacy.