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Submit Review(R)-(+)-Methanandamide
Description: Potent and selective CB1 agonist
Chemical Name: (R)-N-(2-Hydroxy-1-methylethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Purity: ≥98% (HPLC)
Biological Activity for (R)-(+)-Methanandamide
Stable anandamide analog that is a selective agonist for the CB1 receptor (Ki values are 20 and 815 nM for CB1 and CB2 receptors respectively). Also displays agonist activity at vanilloid receptors.
Water Soluble Emulsion also available.
Technical Data for (R)-(+)-Methanandamide
| M. Wt | 361.57 |
| Formula | C23H39NO2 |
| Storage | Desiccate at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 157182-49-5 |
| PubChem ID | 6321351 |
| InChI Key | SQKRUBZPTNJQEM-FQPARAGTSA-N |
| Smiles | O=C(N[C@H](C)CO)CCC\C=C/C\C=C/C/C=C\C/C=C\CCCCC |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Product Datasheets for (R)-(+)-Methanandamide
References for (R)-(+)-Methanandamide
References are publications that support the biological activity of the product.
Abadji et al (1994) (R)-Methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability. J.Med.Chem. 37 1889 PMID: 8021930
Carriero et al (1998) A detailed characterization of the effects of four cannabinoid agonists on operant lever pressing. Psychopharmacology (Berl.) 137 147 PMID: 9630001
Khanolkar et al (1996) Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J.Med.Chem. 39 4515 PMID: 8893848
Zygmunt et al (1999) Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide. Nature 400 452 PMID: 10440374
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Keywords: (R)-(+)-Methanandamide, (R)-(+)-Methanandamide supplier, Potent, selective, CB1, agonists, Cannabinoids, Receptors, cb1r, 1121, Tocris Bioscience
7 Citations for (R)-(+)-Methanandamide
Citations are publications that use Tocris products. Selected citations for (R)-(+)-Methanandamide include:
Grace et al (2014) Identification of a pharmacological target for genioglossus reactivation throughout sleep. Nat Chem Biol 37 41 PMID: 24470694
Korossy-Mruk et al (2013) Neonatal DSP-4 treatment modifies antinociceptive effects of the CB1 receptor agonist methanandamide in adult rats. Neurotox Res 23 39 PMID: 22488162
Mendiguren and Pineda (2009) Effect of the CB(1) receptor antagonists rimon. and AM251 on the firing rate of dorsal raphe nucleus neurons in rat brain slices. Br J Pharmacol 158 1579 PMID: 19845674
Carney et al (2009) Cannabinoid regulation of nitric oxide synthase I (nNOS) in neuronal cells. J Neuroimmune Pharmacol 4 338 PMID: 19365734
Cenni et al (2006) Differential effect of cannabinoid agonists and endocannabinoids on histamine release from distinct regions of the rat brain. Eur J Neurosci 24 1633 PMID: 17004927
Nieri et al (2006) Modulation of P-glycoprotein activity by cannabinoid molecules in HK-2 renal cells. Br J Pharmacol 148 682 PMID: 16715117
Justinova et al (2008) Blockade of THC-seeking behavior and relapse in monkeys by the cannabinoid CB(1)-receptor antagonist rimon. Neuropsychopharmacology 33 2870 PMID: 18305459
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Low affinity CB1 agonist.
By
Jonathan Fay on 05/30/2019
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: COSH-1
Used as an agonist to induce a spectroscopic change of a fluorescent reporter attached to trans-membrane helix six of purified CB1.
Literature in this Area
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