R(+)-Methanandamide

• Catalog No.: M186
• CAS Number: 157182-49-5
• M. F.: C23H39NO2
• M. W.: 361.56126
• Purity: ≥96% (HPLC)
• Storage: desiccated

SYNONYMS

• IUPAC name: (5Z,8Z,11Z,14Z)-N-[(2R)-1-hydroxypropan-2-yl]icosa-5,8,11,14-tetraenamide
• IUPAC Traditional name: methanandamide
• Synonyms: R(+)-Arachidonyl-1′-hydroxy-2′-propylamide; AM-356

DATABASE IDS

• MDL Number: MFCD00467914
• PubChem SID: 24896698
• EC Number: 200-578-6
• CAS Number: 157182-49-5

PROPERTIES

• Flash Point: 57.2 °F
• Optical Rotation: [α]/D +8.7°, c = 4 in chloroform(lit.)
• Flash Point: 14 °C
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada
• GHS Signal Word: Danger
• GHS Hazard statements: H225
• European Hazard Symbols: Flammable (F)
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• GHS Precautionary statements: P210
• RID/ADR: UN 1170 3/PG 2
• Risk Statements: 11
• Safety Statements: 7-16
• Storage Condition: desiccated
• Storage Condition: protect from light
• Storage Condition: under inert gas
• Storage Temperature: -20°C
• Hazard Class: 3
• UN Number: 1170
• Packing Group: 2
• German water hazard class: 2
• Concentration: 5 mg/mL in absolute ethanol
• Purity: ≥96% (HPLC)
• Gene Information: mouse ... Cnr1(12801), Cnr2(12802)rat ... Cnr1(25248)

DETAILS

Description (English)

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.
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.