{2-[bis(pyridin-2-ylmethyl)amino]ethyl}bis(pyridin-2-ylmethyl)amine

• ChemBase ID: 104575
• Molecular Formular: C26H28N6
• Molecular Mass: 424.54072
• Monoisotopic Mass: 424.23754493
• SMILES: C(CN(Cc1ncccc1)Cc1ncccc1)N(Cc1ncccc1)Cc1ncccc1
• Canonical SMILES: c1ccc(nc1)CN(Cc1ccccn1)CCN(Cc1ccccn1)Cc1ccccn1
• InChI: InChI=1S/C26H28N6/c1-5-13-27-23(9-1)19-31(20-24-10-2-6-14-28-24)17-18-32(21-25-11-3-7-15-29-25)22-26-12-4-8-16-30-26/h1-16H,17-22H2
• InChIKey: CVRXLMUYFMERMJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[bis(pyridin-2-ylmethyl)amino]ethyl}bis(pyridin-2-ylmethyl)amine
• IUPAC Traditional name: {2-[bis(pyridin-2-ylmethyl)amino]ethyl}bis(pyridin-2-ylmethyl)amine
• Synonyms: N,N,N′,N′-Tetrakis(2-pyridylmethyl)ethylenediamine; TPEN; N,N,N',N',-tetrakis(2-PYRIDYLMETHYL)ETHYLENEDIAMINE; N,N,N’,N’-Tetrakis-pyridin-2-ylmethyl-ethane-1,2-diamine; N,N,N',N'-Tetrakis(2-pyridylmethyl)-1,2-ethylenediamine

Database IDs

• CAS Number: 16858-02-9
• MDL Number: MFCD00036918
• Beilstein Number: 4211982
• PubChem SID: 24888924; 162091901; 24898538
• PubChem CID: 5519

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 1.7223662
• LogD (pH = 7.4): 2.5330105
• Log P: 2.5619042
• Molar Refractivity: 125.7412 cm^3
• Polarizability: 49.65382 Å^3
• Polar Surface Area: 58.04 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Brownish Orange Solid
• Melting Point: 110-112 °C; 115-117°C

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (NT); 98%
• Empirical Formula (Hill Notation): C26H28N6

DETAILS

MP Biomedicals - 02156458

Purity: 98%
Intracellular Zn^2+ chelator with low affinity for Mg^2+ and Ca^2+ . Used with QUIN 2 to measure free Ca^2+ in cells.

Sigma Aldrich - P4413

Biochem/physiol Actions
TPEN is a membrane-permeable zinc chelator; decreased the intracellular level of zinc and induced apoptosis (i.e., cell shrinkage and formation of apoptotic bodies with DNA fragmentation and formation of a typical DNA ladder pattern).

Sigma Aldrich - 87641

Biochem/physiol Actions
TPEN is a membrane-permeable zinc chelator; decreased the intracellular level of zinc and induced apoptosis (i.e., cell shrinkage and formation of apoptotic bodies with DNA fragmentation and formation of a typical DNA ladder pattern).
Other Notes
Chelating agent for intracellular heavy metals1

Toronto Research Chemicals - T296500

Membrane-permeable zinc chelator; decreased the intracellular level of zinc and induced apoptosis.

REFERENCES

• Chang, H.-R., et al.: J. Am. Chem. Soc., 112, 6814 (1990)
• Treves, S., et al.: Exp. Cell Res., 21, 339 (1990)
• Kolenko, V.M.: Apoptosis, 6, 419 (1990)
• Chimienti, F.: Biochem. Pharmacol., 62, 51 (2001)