M186

R(+)-Methanandamide

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

• Synonym(s): AM-356, R(+)-Arachidonyl-1′-hydroxy-2′-propylamide
• Empirical Formula (Hill Notation): C₂₃H₃₉NO₂
• CAS Number: 157182-49-5
• Molecular Weight: 361.56
• UNSPSC Code: 12352200
• PubChem Substance ID: 24896698
• EC Number: 200-578-6
• MDL number: MFCD00467914
• Assay: ≥96% (HPLC)
• Quality level: 100
• Storage condition: desiccated; protect from light; under inert gas

Properties

• Product Name: R(+)-Methanandamide, 5 mg/mL in absolute ethanol, ≥96% (HPLC)
• InChI key: SQKRUBZPTNJQEM-FQPARAGTSA-N
• InChI: 1S/C23H39NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(26)24-22(2)21-25/h7-8,10-11,13-14,16-17,22,25H,3-6,9,12,15,18-21H2,1-2H3,(H,24,26)/b8-7-,11-10-,14-13-,17-16-/t22-/m1/s1
• SMILES string: CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)N[C@H](C)CO
• 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
• Quality Level: 100
• Gene Information: mouse ... Cnr1(12801), Cnr2(12802) ; rat ... Cnr1(25248)

Description

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.

Safety Information

• pictograms: GHS02,GHS07
• signalword: Danger
• hcodes: H225,H319
• pcodes: P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Flam. Liq. 2
• Storage Class: 3 - Flammable liquids
• wgk: WGK 2
• flash_point_f: 57.2 °F
• flash_point_c: 14 °C
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter