N,N-dimethyl-5-[(4-phenylphenyl)methyl]-1H-1,2,3,4-tetrazole-1-carboxamide

• ChemBase ID: 128140
• Molecular Formular: C17H17N5O
• Molecular Mass: 307.34978
• Monoisotopic Mass: 307.14331019
• SMILES: CN(C)C(=O)n1nnnc1Cc1ccc(cc1)c1ccccc1
• Canonical SMILES: CN(C(=O)n1nnnc1Cc1ccc(cc1)c1ccccc1)C
• InChI: InChI=1S/C17H17N5O/c1-21(2)17(23)22-16(18-19-20-22)12-13-8-10-15(11-9-13)14-6-4-3-5-7-14/h3-11H,12H2,1-2H3
• InChIKey: GZNIYOXWFCDBBJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N,N-dimethyl-5-[(4-phenylphenyl)methyl]-1H-1,2,3,4-tetrazole-1-carboxamide
• IUPAC Traditional name: N,N-dimethyl-5-[(4-phenylphenyl)methyl]-1,2,3,4-tetrazole-1-carboxamide
• Synonyms: LY-2183240; 1H-Tetrazole-1-carboxamide, 5-([1,1′-biphenyl]-4-ylmethyl)-N,N-dimethyl-; 5-Biphenyl-4-ylmethyl-tetrazole-1-carboxylic acid dimethylamide; LY2183240

Database IDs

• CAS Number: 874902-19-9
• MDL Number: MFCD08703123
• PubChem SID: 162222454
• PubChem CID: 11507802
• Wikipedia Title: LY-2183240

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.2672813
• LogD (pH = 7.4): 2.2672813
• Log P: 2.2672813
• Molar Refractivity: 90.3578 cm^3
• Polarizability: 34.412334 Å^3
• Polar Surface Area: 63.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H17N5O

DETAILS

Sigma Aldrich - L9044

Biochem/physiol Actions
Regioisomer 1-5 of LY2183240 is a potent inhibitor of anandamide uptake (IC50= 15 nM). The compound inhibits FAAH (IC50=2.1 nM) and some other brain serine proteases. After systemic administration to rodents, LY2182340 elevates brain anandamide levels and shows efficacy in a rodent model of persistent pain (ED50=1.37 mg/kg). Regioisomer 2-5 of LY2183240 is less active. The compound is more potent than N-(4-Hydroxyphenyl)-arachidonylamide (AM-404), which inhibits anandamide transport at IC50=1mM.