2,3,4-tris(nitrooxy)butyl nitrate

• ChemBase ID: 1390
• Molecular Formular: C4H6N4O12
• Molecular Mass: 302.11004
• Monoisotopic Mass: 301.99822165
• SMILES: O([N+](=O)[O-])C(C(O[N+](=O)[O-])CO[N+](=O)[O-])CO[N+](=O)[O-]
• Canonical SMILES: [O-][N+](=O)OC(C(O[N+](=O)[O-])CO[N+](=O)[O-])CO[N+](=O)[O-]
• InChI: InChI=1S/C4H6N4O12/c9-5(10)17-1-3(19-7(13)14)4(20-8(15)16)2-18-6(11)12/h3-4H,1-2H2
• InChIKey: SNFOERUNNSHUGP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3,4-tris(nitrooxy)butyl nitrate
• IUPAC Traditional name: 2,3,4-tris(nitrooxy)butyl nitrate
• Brand Name: Tetranitrin; Tetranitrol; Cardilate; Cardiloid; Cardivell; Cardiwell
• Synonyms: Erythritol tetranitrate; 1,2,3,4-Butanetetralyl tetranitrate; ETN; Eritritile tetranitrato [dcit]; Eritrityl tetranitrate; Eritrityli tetranitras [inn-latin]; Erythritol tetranitrate; Erythrol tetranitrate; Meso-erythritol tetranitrate; Nitroerythrit; Nitroerythrite; Nitroerythrol; Tetranitrate d'eritrityle [inn-french]; Tetranitrato de eritritilo [inn-spanish]; Erythrityl Tetranitrate

Database IDs

• CAS Number: 7297-25-8
• PubChem SID: 160964850
• PubChem CID: 5284553; 23723
• CHEBI ID: 60072
• Chemspider ID: 4447608
• Unique Ingredient Identifier: 35X333P19D
• Wikipedia Title: Erythritol_tetranitrate

CALCULATED PROPERTIES

JChem

• H Acceptors: 12
• H Donor: 0
• LogD (pH = 5.5): 1.2304573
• LogD (pH = 7.4): 1.2304573
• Log P: 1.2304573
• Molar Refractivity: 53.2546 cm^3
• Polarizability: 19.872093 Å^3
• Polar Surface Area: 220.2 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.68
• LOG S: -3.19
• Solubility (Water): 1.95e-01 g/l

PROPERTIES

Physical Property

• Melting Point: 61°C
• Boiling Point: Decomposes at 160 °C

Safety Information

• Explosive Velocity: 8000-8100 m/s
• Friction Sensitivity: Medium
• Shock Sensitivity: Medium (2.0 Nm)
• RE Factor: 1.60

DETAILS

DrugBank - DB01613

• Drug Groups: approved
• Description: A vasodilator with general properties similar to nitroglycerin. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1020)
• Indication: For the prevention of angina.
• Pharmacology: Erythrityl Tetranitrate is a vasodilator with general properties similar to nitroglycerin.
• Toxicity: Symptoms of overdose include increased intracranial pressure, with any or all of persistent throbbing headache, confusion, and moderate fever; Vertigo; Palpitations; Visual disturbances; Nausea and vomiting (possibly with colic and even bloody diarrhea); Syncope (especially in the upright posture); Air hunger and dyspnea, later followed by reduced ventilatory effort; Diaphoresis, with the skin either flushed or cold and clammy; Heart block and bradycardia; Paralysis; Coma; Seizures; Death.
• Affected Organisms: Humans and other mammals