(R)-(+)-Methanandamide

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Cat.No. 1121 - (R)-(+)-Methanandamide | C23H39NO2 | CAS No. 157182-49-5
Description: Potent and selective CB1 agonist
Chemical Name: (R)-N-(2-Hydroxy-1-methylethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Purity: ≥98% (HPLC)
Datasheet
Citations (6)
Literature

Biological Activity

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. Also available in water-soluble emulsion (Cat. No. 1782).

Technical Data

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.

All Tocris products are intended for laboratory research use only.

Solubility Data

SolubilitySoluble in ethanol (supplied pre-dissolved in anhydrous ethanol, 5mg/ml)

Preparing Stock Solutions

The following data is based on the product molecular weight 361.57. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.77 mL 13.83 mL 27.66 mL
5 mM 0.55 mL 2.77 mL 5.53 mL
10 mM 0.28 mL 1.38 mL 2.77 mL
50 mM 0.06 mL 0.28 mL 0.55 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

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: Potent selective CB1 agonists Cannabinoids Receptors cb1r CB1 Receptors

6 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 rimonabant 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

Justinova et al (2008) Blockade of THC-seeking behavior and relapse in monkeys by the cannabinoid CB(1)-receptor antagonist rimonabant. Neuropsychopharmacology 33 2870 PMID: 18305459

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


Do you know of a great paper that uses (R)-(+)-Methanandamide from Tocris? If so please let us know.

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