2,3-bis(nitrooxy)propyl nitrate

• ChemBase ID: 608
• Molecular Formular: C3H5N3O9
• Molecular Mass: 227.0865
• Monoisotopic Mass: 227.00257876
• SMILES: O([N+](=O)[O-])C(CO[N+](=O)[O-])CO[N+](=O)[O-]
• Canonical SMILES: [O-][N+](=O)OC(CO[N+](=O)[O-])CO[N+](=O)[O-]
• InChI: InChI=1S/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2
• InChIKey: SNIOPGDIGTZGOP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-bis(nitrooxy)propyl nitrate
• IUPAC Systematic name: 2,3-Bis(nitrooxy)propyl nitrate
• IUPAC Traditional name: 2,3-bis(nitrooxy)propyl nitrate
• Brand Name: Nitrospan; Nitrostat; Tridil; Transderm Nitro; Nitro-Dur; Nitrolingual Pump Spray; Natispray; Minitran; Nitronet; Nitrocap; Nitrong parenteral; Cellegesic; Rectogesic
• Synonyms: TNG; NTG; NG; Nitroglycerine; Trinitroglycerin; Glyceryl trinitrate; nitroglycerin ointment; Nitroglycerin; 1,3-Dinitrooxypropan-2-yl nitrate; Propane-1,2,3-triyl trinitrate

Database IDs

• CAS Number: 55-63-0
• EC Number: 200-240-8
• Beilstein Number: 1802063
• PubChem SID: 46509120; 160964071
• PubChem CID: 4510
• CHEBI ID: 28787
• ATC CODE: C05AE01; C01DA02
• CHEMBL: 730
• Chemspider ID: 4354
• DrugBank ID: DB00727
• Gmelin ID: 165859
• KEGG ID: D00515
• MeSH Name: Nitroglycerin
• Unique Ingredient Identifier: G59M7S0WS3
• Wikipedia Title: Nitroglycerin

CALCULATED PROPERTIES

JChem

• H Acceptors: 9
• H Donor: 0
• LogD (pH = 5.5): 0.93584067
• LogD (pH = 7.4): 0.93584067
• Log P: 0.93584067
• Molar Refractivity: 40.5981 cm^3
• Polarizability: 15.065297 Å^3
• Polar Surface Area: 165.15 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.25
• LOG S: -3.05
• Solubility (Water): 2.04e-01 g/l

PROPERTIES

Physical Property

• Solubility: acetone, ether, benzene, alcohol; slightly in water; Slightly soluble
• Apperance: Colorless liquid
• Melting Point: 14°C
• Boiling Point: 50°C (explodes)
• Density: 1.6 g cm^-3 (at 15 °C)
• Partition Coefficient: 2.154
• Hydrophobicity(logP): 1
• Std enthalpy of combustion: -1.529 MJ mol^-1
• Std enthalpy of formation: -370 kJ mol^-1

Safety Information

• European Hazard Symbols: Explosive (E); Nature polluting (N); Highly toxic (T+)
• UN Number: 0143, 0144, 1204, 3064, 3319
• Risk Statements: R3, R12, R26/27/28, R33, R51/53
• Safety Statements: S1/2, S33, S35, S36/37, S45, S53, S61
• EU Index: 603-034-00-X
• NFPA704:
  

  3

  2

  4
• Explosive Velocity: 7700 m s^-1
• Friction Sensitivity: High
• Shock Sensitivity: High
• RE Factor: 1.50

Pharmacology Properties

• Admin Routes: Intravenous, Oral, Sublingual, Topical, Transdermal
• Bioavailability: <1%
• Half Life: 3 min
• Metabolism: Hepatic
• Legal Status: S3 (Australia)
• Pregnancy Category: C (US)

DETAILS

DrugBank - DB00727

• Drug Groups: approved; investigational
• Description: A volatile vasodilator which relieves angina pectoris by stimulating guanylate cyclase and lowering cytosolic calcium. [PubChem]
• Indication: For the prevention of angina
• Pharmacology: Nitroglycerin, an organic nitrate, is available in many forms as a vasodilator. Nitroglycerin is used in the treatement of angina pectoris and perioperative hypertension, to produce controlled hypotension during surgical procedures, to treat hypertensive emergencies, and to treat congestive heart failure associated with myocardial infarction.
• Toxicity: 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
• Biotransformation: Hepatic, cytochrome P450 (P450) is a key enzyme of organic nitrate biotransformation
• Half Life: 3 minutes
• Distribution: * 3 L/kg
• Clearance: * 1 L/kg/min
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com