N,N-diethyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

• ChemBase ID: 155063
• Molecular Formular: C10H15N5
• Molecular Mass: 205.2596
• Monoisotopic Mass: 205.13274551
• SMILES: CCN(CC)c1cc(nc2n1ncn2)C
• Canonical SMILES: CCN(c1cc(C)nc2n1ncn2)CC
• InChI: InChI=1S/C10H15N5/c1-4-14(5-2)9-6-8(3)13-10-11-7-12-15(9)10/h6-7H,4-5H2,1-3H3
• InChIKey: GSNOZLZNQMLSKJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N,N-diethyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
• IUPAC Traditional name: trapidil
• Synonyms: AR 12008; Avantrin; N,N-diethyl-5-methyl-[1,2,4]Triazolo[1,5-a]pyrimidin-7-amine; Rocornal; Trapymin; Trapymine; Trapidil

Database IDs

• CAS Number: 15421-84-8
• EC Number: 239-434-2
• MDL Number: MFCD00193104
• PubChem SID: 162249201
• PubChem CID: 5531

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.2548602
• LogD (pH = 7.4): 1.2548734
• Log P: 1.2548735
• Molar Refractivity: 71.3755 cm^3
• Polarizability: 21.788668 Å^3
• Polar Surface Area: 46.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥15 mg/mL
• Apperance: white to tan powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C10H15N5

DETAILS

Sigma Aldrich - SML0071

Biochem/physiol Actions
Trapidil is an antiplatelet agent that acts in part as a phosphodiesterase inhibitor and as a competitive inhibitor of the platelet-derived growth factor (PDGF) receptor. Trapidil, with its vasodilator and NO releasing effect may have some potential to diminish the tissue injury. Trapidil suppresses platelet-derived growth factor (PDGF)-induced vascular smooth muscle cell (VSMC) proliferation by inhibiting Raf-1/extracellular signal-regulated kinase (ERK) via cAMP/protein kinase A (PKA). In addn. to cAMP/PKA activation, trapidil inhibits RhoA/ROCK activation.