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M186 Sigma

R(+)-Methanandamide

5 mg/mL in absolute ethanol, ≥96% (HPLC)

Synonym: AM-356, R(+)-Arachidonyl-1′-hydroxy-2′-propylamide

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cannabinoids, Cell Biology, Cell Signaling and Neuroscience,
InChI Key   SQKRUBZPTNJQEM-FQPARAGTSA-N
assay   ≥96% (HPLC)
optical activity   [α]/D +8.7°, c = 4 in chloroform(lit.)
drug control   regulated under CDSA - not available from Sigma-Aldrich Canada
storage condition   desiccated
  protect from light
  under inert gas
concentration   5 mg/mL in absolute ethanol
storage temp.   −20°C
Gene Information   mouse ... Cnr1(12801), Cnr2(12802)
rat ... Cnr1(25248)

Description

Packaging

5, 100 mg in glass bottle

Biochem/physiol Actions

R(+)-Methanandamide is metabolically stable congener of anandamide that has higher affinity for the cannabinoid receptor. Of the analogs tested, (R)-methanandamide exhibited the highest affinity for the cannabinoid receptor with a Ki of 20 +/- 1.6 nM, 4-fold lower than that of anandamide (Ki = 78 +/- 2 nM). (R)-methanandamide exhibits high stability to aminopeptidase hydrolysis. Experiments with mice have demonstrated that (R)-methanandamide also posseses cannabimimetric properties in vivo, as established by the four tests of hypothermia, hypokinesia, ring immobility, and antinociception.

Features and Benefits

This compound is featured on the Cannabinoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M186.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN1170 - class 3 - PG 2 - Ethanol, solution
WGK Germany 
2
Flash Point(F) 
57.2 °F
Flash Point(C) 
14 °C

Documents

Certificate of Analysis

Protocols & Articles
Peer-Reviewed Papers
15

References

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