(5Z,8Z,11Z,14Z)-N-[(2R)-1-hydroxypropan-2-yl]icosa-5,8,11,14-tetraenamide

• ChemBase ID: 132563
• Molecular Formular: C23H39NO2
• Molecular Mass: 361.56126
• Monoisotopic Mass: 361.29807949
• SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N[C@H](C)CO
• Canonical SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N[C@@H](CO)C
• InChI: 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

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 157182-49-5
• EC Number: 200-578-6
• MDL Number: MFCD00467914
• PubChem SID: 24896698; 162226840
• PubChem CID: 6321351

CALCULATED PROPERTIES

• Acid pKa: 15.0486
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.7303762
• LogD (pH = 7.4): 5.730377
• Log P: 5.730377
• Molar Refractivity: 117.384 cm^3
• Polarizability: 43.9922 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: 14 °C; 57.2 °F
• Optical Rotation: [α]/D +8.7°, c = 4 in chloroform(lit.)

Safety Information

• Storage Condition: desiccated; protect from light; under inert gas
• European Hazard Symbols: Flammable (F)
• UN Number: 1170
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11
• Safety Statements: 7-16
• GHS Pictograms: GHS02
• GHS Signal Word: Danger
• GHS Hazard statements: H225
• GHS Precautionary statements: P210
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1170 3/PG 2
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: mouse ... Cnr1(12801), Cnr2(12802)rat ... Cnr1(25248)

Product Information

• Purity: ≥96% (HPLC)
• Concentration: 5 mg/mL in absolute ethanol

DETAILS

Sigma Aldrich - M186

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.