N-(2-fluoroethyl)-2-methylicosa-5,8,11,14-tetraenamide

• ChemBase ID: 155731
• Molecular Formular: C23H38FNO
• Molecular Mass: 363.5523232
• Monoisotopic Mass: 363.29374306
• SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCC(C)C(=O)NCCF
• Canonical SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCC(C(=O)NCCF)C
• InChI: InChI=1S/C23H38FNO/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(2)23(26)25-21-20-24/h7-8,10-11,13-14,16-17,22H,3-6,9,12,15,18-21H2,1-2H3,(H,25,26)
• InChIKey: HMMNZALKMVCHHZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-fluoroethyl)-2-methylicosa-5,8,11,14-tetraenamide
• IUPAC Traditional name: N-(2-fluoroethyl)-2-methylicosa-5,8,11,14-tetraenamide
• Synonyms: 2-Methyl-2′-fluoro AEA; Fluoromethanandamide; O-689; (±)-2-Methylarachidonoyl-2′-fluoroethylamide

Database IDs

• CAS Number: 166100-39-6
• EC Number: 200-578-6
• MDL Number: MFCD01862615
• PubChem SID: 162249869
• PubChem CID: 5353617

CALCULATED PROPERTIES

• Acid pKa: 15.1477165
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 6.747879
• LogD (pH = 7.4): 6.7478805
• Log P: 6.7478805
• Molar Refractivity: 115.8476 cm^3
• Polarizability: 43.026287 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: ethanol solution
• Flash Point: 14 °C; 57.2 °F

Safety Information

• 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

Product Information

• Purity: ≥95%
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C23H38NOF

DETAILS

Sigma Aldrich - M1438

Biochem/physiol Actions
An analog of arachidonylethanolamide (anandamide) that is a potent, selective CB1 cannabinoid receptor agonist. The methyl group at the C-2 position of arachidonic acid gives the compound enhanced metabolic stability. It can fully substitute for Δ9-THC in animal self-administration tests.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M1438.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.