Molecular structure of (R)-Methanandamide, CAS Number: 157182-49-5
(R)-Methanandamide (CAS 157182-49-5)
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Alternate Names:
N-(1R-methyl-2-hydroxy-ethyl) arachidonoyl amine
Application:
(R)-Methanandamide is a potent CB1 agonist and VR agonist
CAS Number:
157182-49-5
Purity:
98%
Molecular Weight:
361.57
Molecular Formula:
C23H39NO2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
Available in US only.
Available in US only.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
(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.
(R)-Methanandamide (CAS 157182-49-5) References
- Effects of delta-9-tetrahydrocannabinol and (R)-methanandamide on open-field behavior in rats. | Järbe, TU., et al. 1998. Behav Pharmacol. 9: 169-74. PMID: 10065936
- Cannabinoid receptor and WIN-55,212-2-stimulated [35S]GTPgammaS binding and cannabinoid receptor mRNA levels in several brain structures of adult male rats chronically exposed to R-methanandamide. | Romero, J., et al. 1999. Neurochem Int. 34: 473-82. PMID: 10402222
- (R)-Methanandamide and delta9-tetrahydrocannabinol-induced operant rate decreases in rats are not readily antagonized by SR-141716A. | Järbe, TU., et al. 2003. Eur J Pharmacol. 466: 121-7. PMID: 12679148
- Anandamide prodrugs. 1. Water-soluble phosphate esters of arachidonylethanolamide and R-methanandamide. | Juntunen, J., et al. 2003. Eur J Pharm Sci. 19: 37-43. PMID: 12729860
- The cannabinoid receptor antagonist SR-141716 does not readily antagonize open-field effects induced by the cannabinoid receptor agonist (R)-methanandamide in rats. | Järbe, TU., et al. 2003. Pharmacol Biochem Behav. 75: 809-21. PMID: 12957223
- Enhancement of androgen receptor expression induced by (R)-methanandamide in prostate LNCaP cells. | Sánchez, MG., et al. 2003. FEBS Lett. 555: 561-6. PMID: 14675774
- Cannabinoid and vanilloid effects of R(+)-methanandamide in the hemisected meningeal preparation. | Fischer, MJ. and Messlinger, K. 2007. Cephalalgia. 27: 422-8. PMID: 17448180
- Methanandamide blocks amphetamine-induced behavioral sensitization in rats. | Rasmussen, BA., et al. 2010. Eur J Pharmacol. 627: 150-5. PMID: 19879869
- (R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability. | Abadji, V., et al. 1994. J Med Chem. 37: 1889-93. PMID: 8021930
- Extrapyramidal effects of methanandamide, an analog of anandamide, the endogenous CB1 receptor ligand. | Romero, J., et al. 1996. Life Sci. 58: 1249-57. PMID: 8614278
- Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. | Khanolkar, AD., et al. 1996. J Med Chem. 39: 4515-9. PMID: 8893848
- (R)-methanandamide, but not anandamide, substitutes for delta 9-THC in a drug-discrimination procedure. | Burkey, RT. and Nation, JR. 1997. Exp Clin Psychopharmacol. 5: 195-202. PMID: 9260067
- Delta9-THC training dose as a determinant for (R)-methanandamide generalization in rats. | Järbe, TU., et al. 1998. Psychopharmacology (Berl). 140: 519-22. PMID: 9888629
Activator of:
CB1, CB2, and VR.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
(R)-Methanandamide, 5 mg | sc-200792 | 5 mg | $57.00 | |||
| US: Only available in the US | ||||||
(R)-Methanandamide, 25 mg | sc-200792A | 25 mg | $179.00 | |||
| US: Only available in the US | ||||||