ChemicalBook > CAS DataBase List > 5-METHYL-4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-1,3-BENZENEDIOL

5-METHYL-4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-1,3-BENZENEDIOL

Product Name
5-METHYL-4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-1,3-BENZENEDIOL
CAS No.
317321-41-8
Chemical Name
5-METHYL-4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-1,3-BENZENEDIOL
Synonyms
O-1602;O 1602,O1602;O-1602, 10 mM in DMSO;5-Methyl-4-[(1R,6R)-3-methyl-6-(1-cyclohexen-1-yl]-1,3-benzenediol;5-METHYL-4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-1,3-BENZENEDIOL;1,3-Benzenediol, 5-methyl-4-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-
CBNumber
CB2136206
Molecular Formula
C17H22O2
Formula Weight
258.36
MOL File
317321-41-8.mol
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5-METHYL-4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-1,3-BENZENEDIOL Property

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H319Causes serious eye irritation

H336May cause drowsiness or dizziness

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
10006803
Product name
O-1602
Purity
≥98%
Packaging
1mg
Price
$29
Updated
2024/03/01
Cayman Chemical
Product number
10006803
Product name
O-1602
Purity
≥98%
Packaging
5mg
Price
$109
Updated
2024/03/01
Cayman Chemical
Product number
10006803
Product name
O-1602
Purity
≥98%
Packaging
10mg
Price
$162
Updated
2024/03/01
Cayman Chemical
Product number
10006803
Product name
O-1602
Purity
≥98%
Packaging
25mg
Price
$302
Updated
2024/03/01
Tocris
Product number
2797
Product name
O-1602
Purity
≥97%(HPLC)
Packaging
10
Price
$227
Updated
2021/12/16
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5-METHYL-4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-1,3-BENZENEDIOL Chemical Properties,Usage,Production

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 GRAFSTR?M. 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

5-METHYL-4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-1,3-BENZENEDIOL Preparation Products And Raw materials

Raw materials

Preparation Products

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5-METHYL-4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-1,3-BENZENEDIOL Suppliers

China 41 India 1 Switzerland 1 United Kingdom 1 United States 6 USA 1 Global 51

317321-41-8, 5-METHYL-4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-1,3-BENZENEDIOLRelated Search:

5-METHYL-4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-1,3-BENZENEDIOL 4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL

  • 5-METHYL-4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-1,3-BENZENEDIOL
  • O-1602
  • 5-Methyl-4-[(1R,6R)-3-methyl-6-(1-cyclohexen-1-yl]-1,3-benzenediol
  • 1,3-Benzenediol, 5-methyl-4-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-
  • O 1602,O1602
  • O-1602, 10 mM in DMSO
  • 317321-41-8
  • Cannabinoid receptor