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Methanandamide

BML-FA021

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Cannabinoid receptor ligand

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.

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Product Details

Alternative Name	(R)-(+)-Arachidonyl-1′-hydroxy-2′-propylamide, AM 356, N-(2-Hydroxy-1R-methylethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Appearance	Colorless oil.
CAS	157182-49-5
Couple Target	Cannabinoid receptor
Couple Type	Ligand
Formula	C₂₃H₃₉NO₂
MW	361.6
Purity	≥98% (TLC)
Solubility	Soluble in ethanol or DMSO (10mg/ml).

Handling & Storage

Use/Stability	As indicated on product label or CoA when stored as recommended. 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.
Long Term Storage	-20°C
Shipping	Dry Ice

Regulatory Status	RUO – Research Use Only

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
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
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
Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide: P.M. Zygmunt, et al.; Nature 400, 452 (1999), Abstract
Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase: W. Lang, et al.; J. Med. Chem. 42, 896 (1999), Abstract
Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand: A.D. Khanolkar, et al.; J. Med. Chem. 39, 4515 (1996), Abstract
Extrapyramidal effects of methanandamide, an analog of anandamide, the endogenous CB1 receptor ligand: J. Romero, et al.; Life Sci. 58, 1249 (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

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Methanandamide

BML-FA021

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