M186

R(+)-Methanandamide

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

• Synonym(e): AM-356, R(+)-Arachidonyl-1′-hydroxy-2′-propylamide
• Empirische Formel (Hill-System): C₂₃H₃₉NO₂
• CAS-Nummer: 157182-49-5
• Molekulargewicht: 361.56
• EG-Nummer: 200-578-6
• MDL-Nummer: MFCD00467914
• UNSPSC-Code: 12352200
• PubChem Substanz-ID: 24896698

Eigenschaften

• Qualitätsniveau: 100
• Assay: ≥96% (HPLC)
• Optische Aktivität: [α]/D +8.7°, c = 4 in chloroform(lit.)
• Arzneimittelkontrolle: regulated under CDSA - not available from Sigma-Aldrich Canada
• Lagerbedingungen: desiccated; protect from light; under inert gas
• Konzentration: 5 mg/mL in absolute ethanol
• Lagertemp.: −20°C
• SMILES String: CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)N[C@H](C)CO
• 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
• InChIKey: SQKRUBZPTNJQEM-FQPARAGTSA-N
• Angaben zum Gen: mouse ... Cnr1(12801) , Cnr2(12802) ; rat ... Cnr1(25248)

Beschreibung

Biochem./physiol. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Sicherheitshinweise

• Piktogramme: GHS02,GHS07
• Signalwort: Danger
• H-Sätze: H225,H319
• P-Sätze: P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338
• Gefahreneinstufungen: Eye Irrit. 2 - Flam. Liq. 2
• Lagerklassenschlüssel: 3 - Flammable liquids
• WGK: WGK 2
• Flammpunkt (°F): 57.2 °F
• Flammpunkt (°C): 14 °C
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter