See personalized New Product recommendations! Get personalized New Product recommendations! Register or Login for personalized New Product recommendations!

Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

N-Arachidonyl Maleimide

Cayman Chemical Item Number 10007517

NAM (CAS 876305-42-9)

N-Arachidonyl Maleimide (CAS 876305-42-9)

See more

Description

2-Arachidonoyl glycerol (2-AG) is an endogenous agonist of the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors.1,2,3 2-AG is present at relatively high levels in the central nervous system and is the most abundant molecular species of monoacylglycerol found in rat brain.1,4 Monoacylglycerol lipase (MGL) hydrolyzes 2-AG to arachidonic acid and glycerol, thereby terminating its biological actions.5 N-Arachidonyl maleimide (NAM) is a potent, irreversible inhibitor of MGL or MGL-like activity in rat cerebellar membranes, exhibiting an IC50 value of 140 nM.6 Inhibition of MGL by the sulfhydryl-reactive maleimide group of NAM suggests a critical cysteine residue is present in the substrate-binding site of the enzyme.

1 Stella, N., Schweitzer, P., and Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 773-778 (1997).

2 Sugiura, T., Kodaka, T., Nakane, S., et al. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J Biol Chem 274 2794-2801 (1999).

3 Ben-Shabat, S., Fride, E., Sheskin, T., et al. An entourage effect: Inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity. Eur J Pharmacol 353 23-31 (1998).

4 Kondo, S., Kondo, H., Nakane, S., et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: Identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through Ca2+-dependent and -independent mechanisms. FEBS Lett 429 152-156 (1998).

5 Dinh, T.P., Carpenter, D., Leslie, F.M., et al. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc Natl Acad Sci USA 99(16) 10819-10824 (2002).

6 Saario, S.M., Salo, O.M.H., Nevalainen, T., et al. Characterization of the sulfhydryl-sensitive site in the enzyme responsible for hydrolysis of 2-arachidonoyl-glycerol in rat cerebellar membranes. Chem Biol 12 649-656 (2005).

Synonyms
  • NAM
Formal Name eicosa-​5Z,​8Z,​11Z,​14Z-​tetraenyl-​1-​pyrrole-​2,​5-​dione
CAS Number 876305-42-9
Molecular Formula C24H35NO2
Formula Weight 369.5
Formulation A solution in ethanol
Purity >98%
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCN1C(=O)​C=CC1=O

Background Reading

Sugiura, T., Kodaka, T., Nakane, S., et al. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J Biol Chem 274 2794-2801 (1999).

Kondo, S., Kondo, H., Nakane, S., et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: Identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through Ca2+-dependent and -independent mechanisms. FEBS Lett 429 152-156 (1998).

Ben-Shabat, S., Fride, E., Sheskin, T., et al. An entourage effect: Inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity. Eur J Pharmacol 353 23-31 (1998).

Stella, N., Schweitzer, P., and Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 773-778 (1997).

Saario, S.M., Salo, O.M.H., Nevalainen, T., et al. Characterization of the sulfhydryl-sensitive site in the enzyme responsible for hydrolysis of 2-arachidonoyl-glycerol in rat cerebellar membranes. Chem Biol 12 649-656 (2005).

Dinh, T.P., Carpenter, D., Leslie, F.M., et al. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc Natl Acad Sci USA 99(16) 10819-10824 (2002).

Show all 6 Hide all but first 3

N-Arachidonyl Maleimide is available in the following screening library:

Size Price Quantity Subtotal
5 mg $43.00 $0.00
10 mg $82.00 $0.00
50 mg $344.00 $0.00
100 mg $602.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-11. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

2-Arachidonoyl Glycerol
Monoacylglycerol Lipase (human recombinant)
Monoacylglycerol Lipase Polyclonal Antibody
O-Arachidonoyl Glycidol Exclusive
WWL70 Exclusive
Show all 5 Hide all but first 3

Downloads

Batch-specific Information

Login to access batch-specific information

Cayman Chemical is a manufacturer, supplier and vendor of biochemical reagents, assay kits, antibodies, and proteins.

Other Resources
Management Team Company Profile Company History ChemAssistant Tools FAQs Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule Order Terms Browser Recommendation Privacy Statement Site Map

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2012 Cayman Chemical Company

Lost password?