Methanandamide

Cannabinoid receptor ligand



BML-FA021-0005	5 mg	77.00 USD

BML-FA021-0025	25 mg	247.00 USD
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Replaces Prod. #: ALX-340-030

Amidase resistant cannabinoid receptor (CB) agonist (CB₁: K_i=20nM; CB₂: K_i=815nM). The most potent of the series of methyl-anandamides. About 4-fold higher binding affinity for cannabinoid receptor CB₁ than anandamide (Prod. No. BML-FA017) in the presence of PMSF. Does also bind to TRPV1 (K_i=4.67µM). Inhibits motor behavior resembling the effectts of THC rather than anadamide.

Product Details

Alternative Name:	(R)-(+)-Arachidonyl-1'-hydroxy-2'-propylamide, AM 356, N-(2-Hydroxy-1R-methylethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide

Formula:	C₂₃H₃₉NO₂

MW:	361.6

CAS:	157182-49-5

Purity:	≥98% (TLC)

Appearance:	Colorless oil.

Solubility:	Soluble in ethanol or DMSO (10mg/ml).

Shipping:	Dry Ice

Long Term Storage:	-20°C

Use/Stability:	Stable for at least 1 year after receipt when stored, as supplied, at -80°C. Stock solutions are stable for up to 1 month at -20°C.

Handling:	Protect from light and oxygen. Keep under inert gas.

Regulatory Status:	RUO - Research Use Only

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Product Literature References

Antagonism of discriminative stimulus effects of Delta(9)-THC and (R)-methanandamide in rats: T.U. Jarbe, et al.; Psychopharmacology (Berlin) 184, 36 (2006), Abstract;

R(+)-methanandamide elicits a cyclooxygenase-2-dependent mitochondrial apoptosis signaling pathway in human neuroglioma cells: K. Eichele, et al.; Pharm. Res. 23, 90 (2006), Abstract;

Up-regulation of cyclooxygenase-2 expression is involved in R(+)-methanandamide-induced apoptotic death of human neuroglioma cells: B. Hinz, et al.; Mol. Pharmacol. 66, 1643 (2004), Abstract; Full Text

Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens: R.A. Ross, et al.; Br. J. Pharmacol. 132, 631 (2001), Abstract;

Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase: W. Lang, et al.; J. Med. Chem. 42, 896 (1999), Abstract;

Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide: P.M. Zygmunt, et al.; Nature 400, 452 (1999), Abstract;

Extrapyramidal effects of methanandamide, an analog of anandamide, the endogenous CB1 receptor ligand: J. Romero, et al.; Life Sci. 58, 1249 (1996), Abstract;

Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand: A.D. Khanolkar, et al.; J. Med. Chem. 39, 4515 (1996), Abstract;

(R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability: V. Abadji, et al.; J. Med. Chem. 37, 1889 (1994), Abstract;