(R)-MethanandamideA potent CB1 agonist and VR agonist

(R)-Methanandamide (CAS 157182-49-5)

(R)-Methanandamide | CAS 157182-49-5 is rated 5.0 out of 5 by 1.
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Synonym: N-(1R-methyl-2-hydroxy-ethyl) arachidonoyl amine
Application: A potent CB1 agonist and VR agonist
CAS Number: 157182-49-5
Purity: 98%
Molecular Weight: 361.57
Molecular Formula: C23H39NO2
* Refer to Certificate of Analysis for lot specific data (including water content).
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(R)-Methanandamide is a derivative of Anandamide (sc-200790) with a stereodefined methyl group introduced on the hydroxyethylamine moiety of the parent compound. (R)-Methanandamide demonstrates higher affinity at the cannabinoid CB1 receptor (Ki = 20 nM) than Anandamide itself (Ki = 78 nM). (R)-Methanandamide is described to be markedly stable to aminopeptidase hydrolysis as compared to Anandamide. Low concentrations of (R)-Methanandamide, preferentially activating the CB1 receptors, are demonstrated to produce antinociception, while high concentrations of (R)-Methanandamide preferentially activate the VR(vanilloid receptors) and produce pronociceptive effects. (R)-Methanandamide is an activator of CB2.


References

1. Abadji, V., et al. 1994. J. Med. Chem. 37: 1889-1893. PMID: 8021930
2. Khanolkar, A.D., et al. 1996. J. Med. Chem. 39: 4515-4519. PMID: 8893848
3. Romero, J., et al. 1996. Life Sci. 58: 1249-1257. PMID: 8614278
4. Fischer, M.J. and Messlinger, K. 2007. Cephalalgia. 27: 422-428. PMID: 17448180
5. Rasmussen, B.A., et al. 2010. Eur. J. Pharmacol. 627: 150-155. PMID: 19879869

Appearance :
Oil
Physical State :
Liquid
Solubility :
Soluble in ethanol, and DMSO (10 mg/ml).
Storage :
Store at -20° C
Boiling Point :
529.03° C at 760 mmHg (Predicted)
Density :
0.94 g/mL (Predicted)
Refractive Index :
n20D 1.50 (Predicted)
Optical Activity :
α20/D 8.7°, c = 4 in chloroform
Ki Data :
CB1 receptor: Ki= 20 nM; CB2 receptor: Ki= 815 nM; TRPV1: Ki= 4.67 µM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
1
PubChem CID :
6321351
MDL Number :
MFCD00467914
SMILES :
CCCCC/C=C\\C/C=C\\C/C=C\\C/C=C\\CCCC(=O)N[C@H](C)CO

Download SDS (MSDS)

Certificate of Analysis

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(R)-Methanandamide  Product Citations

See how others have used (R)-Methanandamide. Click on the entry to view the PubMed entry .

Citations 1 to 1 of 1 total

PMID: # 19401177  Rasmussen, BA. et al. 2009. Brain Res. -.

Citations 1 to 1 of 1 total
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Rated 5 out of 5 by from Relevant assays for usage as analytical standards Relevant assays for usage as analytical standards.
Date published: 2015-05-28
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