(-)-5'-DMH-CBDMetabolically stable anandamide transport inhibitor CAS# 97452-63-6 |
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Quality Control & MSDS
3D structure
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| Cas No. | 97452-63-6 | SDF | Download SDF |
| PubChem ID | 126670 | Appearance | Powder |
| Formula | C25H38O2 | M.Wt | 370.57 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | (-)-5'-Dimethylheptyl-cannabidiol | ||
| Solubility | Soluble in ethanol (supplied pre-dissolved in anhydrous ethanol, 5mg/ml) | ||
| Chemical Name | 5-(2-methyloctan-2-yl)-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]benzene-1,3-diol | ||
| SMILES | CCCCCCC(C)(C)C1=CC(=C(C(=C1)O)C2C=C(CCC2C(=C)C)C)O | ||
| Standard InChIKey | MPJURNPNPDQYSY-LEWJYISDSA-N | ||
| Standard InChI | InChI=1S/C25H38O2/c1-7-8-9-10-13-25(5,6)19-15-22(26)24(23(27)16-19)21-14-18(4)11-12-20(21)17(2)3/h14-16,20-21,26-27H,2,7-13H2,1,3-6H3/t20-,21+/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Anandamide membrane transport inhibitor (IC50 = 14 μM) that is relatively metabolically stable. Displays some affinity for CB2 receptors but has only weak affinity for CB1 receptors and has no activity at VR1 receptors or FAAH. Anticonvulsive in vivo following systemic administration. |
(-)-5'-DMH-CBD Dilution Calculator
(-)-5'-DMH-CBD Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.6985 mL | 13.4927 mL | 26.9855 mL | 53.9709 mL | 67.4636 mL |
| 5 mM | 0.5397 mL | 2.6985 mL | 5.3971 mL | 10.7942 mL | 13.4927 mL |
| 10 mM | 0.2699 mL | 1.3493 mL | 2.6985 mL | 5.3971 mL | 6.7464 mL |
| 50 mM | 0.054 mL | 0.2699 mL | 0.5397 mL | 1.0794 mL | 1.3493 mL |
| 100 mM | 0.027 mL | 0.1349 mL | 0.2699 mL | 0.5397 mL | 0.6746 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Molecular targets for cannabidiol and its synthetic analogues: effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide.[Pubmed:11606325]
Br J Pharmacol. 2001 Oct;134(4):845-52.
1. (-)-Cannabidiol (CBD) is a non-psychotropic component of Cannabis with possible therapeutic use as an anti-inflammatory drug. Little is known on the possible molecular targets of this compound. We investigated whether CBD and some of its derivatives interact with vanilloid receptor type 1 (VR1), the receptor for capsaicin, or with proteins that inactivate the endogenous cannabinoid, anandamide (AEA). 2. CBD and its enantiomer, (+)-CBD, together with seven analogues, obtained by exchanging the C-7 methyl group of CBD with a hydroxy-methyl or a carboxyl function and/or the C-5' pentyl group with a di-methyl-heptyl (DMH) group, were tested on: (a) VR1-mediated increase in cytosolic Ca(2+) concentrations in cells over-expressing human VR1; (b) [(14)C]-AEA uptake by RBL-2H3 cells, which is facilitated by a selective membrane transporter; and (c) [(14)C]-AEA hydrolysis by rat brain membranes, which is catalysed by the fatty acid amide hydrolase. 3. Both CBD and (+)-CBD, but not the other analogues, stimulated VR1 with EC(50)=3.2 - 3.5 microM, and with a maximal effect similar in efficacy to that of capsaicin, i.e. 67 - 70% of the effect obtained with ionomycin (4 microM). CBD (10 microM) desensitized VR1 to the action of capsaicin. The effects of maximal doses of the two compounds were not additive. 4. (+)-5'-DMH-CBD and (+)-7-hydroxy-5'-DMH-CBD inhibited [(14)C]-AEA uptake (IC(50)=10.0 and 7.0 microM); the (-)-enantiomers were slightly less active (IC(50)=14.0 and 12.5 microM). 5. CBD and (+)-CBD were also active (IC(50)=22.0 and 17.0 microM). CBD (IC(50)=27.5 microM), (+)-CBD (IC(50)=63.5 microM) and (-)-7-hydroxy-CBD (IC(50)=34 microM), but not the other analogues (IC(50)>100 microM), weakly inhibited [(14)C]-AEA hydrolysis. 6. Only the (+)-isomers exhibited high affinity for CB(1) and/or CB(2) cannabinoid receptors. 7. These findings suggest that VR1 receptors, or increased levels of endogenous AEA, might mediate some of the pharmacological effects of CBD and its analogues. In view of the facile high yield synthesis, and the weak affinity for CB(1) and CB(2) receptors, (-)-5'-DMH-CBD represents a valuable candidate for further investigation as inhibitor of AEA uptake and a possible new therapeutic agent.
Anticonvulsant effects of the (-) and (+)isomers of cannabidiol and their dimethylheptyl homologs.[Pubmed:7071126]
Pharmacology. 1982;24(3):141-6.
The anticonvulsant actions of the (-) and (+)isomers of cannabidiol and dimethylheptyl-cannabidiol were studied with the maximal electroconvulsive shock model in mice. The ratio of the times for hindlimb extension and fore limb flexion was recorded as an anticonvulsant index. All the cannabinoids were anticonvulsant. They also potentiated pentobarbitone sleeping time. The (+)isomer was more active than the (-)isomer. Possible mechanisms of actions on receptors or membranes are discussed.
