5-Methyl-4-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-1,3-benzenediol

Product Name5-Methyl-4-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-1,3-benzenediol
CAS317321-41-8
MFC17H22O2
MW258.36
EINECS
MOL File317321-41-8.mol

Chemical Properties

Boiling point	401.6±45.0 °C(Predicted)
Density	1.073±0.06 g/cm3(Predicted)
storage temp.	Store at -20°C
solubility	Soluble in methyl acetate (supplied pre-dissolved -10mg/ml)
form	Powder
pka	9.92±0.45(Predicted)
color	White to light yellow

Usage And Synthesis

Description

O-1602 is an agonist of GPR55 (EC₅₀ = 13 nM in a GTPγS binding assay) and a derivative of the GPR55 agonist abnormal cannabidiol . It is selective for GPR55 over cannabinoid (CB) receptor 1 (CB₁) and CB₂ (EC₅₀s = >30 μM for both in GTPγS binding assays). O-1602 (50 μM) reduces growth of Mz-ChA-1, HuCCT-1, CC-LP-1, and SG231 cholangiocarcinoma cells and reduces tumor growth in a Mz-ChA-1 mouse xenograft model when administered at a dose of 10 mg/kg per day. O-1602 increases calcium mobilization and lipogenesis in 3T3-L1 adipocytes in a concentration-dependent manner and increases food intake and fat mass in rats; however, this effect was also observed in mice lacking GPR55. O-1602 reduces movement-induced firing of nociceptive C fibers in a rat model of inflammatory joint pain. It also decreases IL-6 and TNF-α levels and myeloperoxidase activities in the plasma, lungs, and pancreas in a mouse model of acute pancreatitis.

Uses

O-1602 is an analog of cannabidiol that is a potent agonist at the GPR55 cannabinoid receptor.

Biological Activity

Analog of cannabidiol that is a potent agonist at the GPR55 cannabinoid receptor (EC 50 values are 13, > 30000 and > 30000 nM for GPR55, CB 1 and CB 2 receptors respectively). Induces activation of RhoA, cdc42 and rac1.

in vivo

O-1602 (10 mg/kg, ip; once daily for 14 consecutive days) decreases levels of serum corticosterone, TNF-α, IL-1β, and IL-6^[1].
O-1602 (10 mg/kg, ip; once daily for 14 consecutive days) increases hippocampal GPR55 protein expression ^[1].
O-1602 (10 mg/kg, ip; once daily for 14 consecutive days) significantly increases DCX expression in the DG ^[1].
O-1602 (10 mg/kg, ip; once daily for 14 consecutive days) significantly decreases the number of microglia in the hippocampus ^[1].
O-1602 (10 mg/kg, ip; once daily for 14 consecutive days) increases expression levels of NLRP3, ASC, and Caspase-1 in the hippocampus ^[1].
O-1602 (0.1 mg/kg,ip; subchronically infused for 7 days) decreases the percentage of fat utilization over total energy consumption and decreases metabolic use of lipids leading to elevated fat deposition rates^[2].
O-1602 (0.04 and 0.4 μg/h/rat, ip; for 7 days) increases the the amount of fat mass with O-1602 at the dose of 0.4 μg/h/rat^[2].

Animal Model:	the model of METH-induced anxiety- and depression-like behaviors ^[1]
Dosage:	10 mg/kg, once daily for 14 consecutive days
Administration:	Intraperitoneal injection (i.p.)
Result:	Increased both time spent in the center area of the open field test and time exploring the open arms in the elevated plus maze test. Reduced immobility time in the forced swim and tail suspension tests.

Animal Model:	Adult male Sprague–Dawley rats (Harlam Iberica, Barcelona, Spain) (250–275 g, 10–12 weeks old)^[2]
Dosage:	0.1, 0.5 and 1 mg/kg
Administration:	Intraperitoneal injection (i.p.)
Result:	Did not modify food intake and body weight gain.Increased the fat mass.

storage

Store at -20°C

References

[1] T. B. VREE. Identification in hashish of tetrahydrocannabinol, cannabidiol and cannabinol analogues with a methyl side-chain[J]. Journal of Pharmacy and Pharmacology, 1972, 24 1: 7-12. DOI: 10.1111/j.2042-7158.1972.tb08857.x
[2] KARIN GRAFSTRM. Effects of long term storage on secondary metabolite profiles of cannabis resin[J]. Forensic science international, 2019, 301: Pages 331-340. DOI: 10.1016/j.forsciint.2019.05.035

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