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55-63-0 molecular structure
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2,3-bis(nitrooxy)propyl nitrate

ChemBase ID: 608
Molecular Formular: C3H5N3O9
Molecular Mass: 227.0865
Monoisotopic Mass: 227.00257876
SMILES and InChIs

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

Cite this record

CBID:608 http://www.chembase.cn/molecule-608.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
55-63-0
EC Number
200-240-8
Beilstein Number
1802063
PubChem SID
160964071
46509120
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 0.93584067  LogD (pH = 7.4) 0.93584067 
Log P 0.93584067  Molar Refractivity 40.5981 cm3
Polarizability 15.065297 Å3 Polar Surface Area 165.15 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 1.25  LOG S -3.05 
Solubility (Water) 2.04e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Bioassay(PubChem)
Solubility
acetone, ether, benzene, alcohol expand Show data source
slightly in water expand Show data source
Slightly soluble expand Show data source
Apperance
Colorless liquid expand Show data source
Melting Point
14°C expand Show data source
Boiling Point
50°C (explodes) expand Show data source
Density
1.6 g cm-3 (at 15 °C) expand Show data source
Partition Coefficient
2.154 expand Show data source
Hydrophobicity(logP)
1 expand Show data source
Std enthalpy of combustion
-1.529 MJ mol-1 expand Show data source
Std enthalpy of formation
-370 kJ mol-1 expand Show data source
European Hazard Symbols
Explosive Explosive (E) expand Show data source
Nature polluting Nature polluting (N) expand Show data source
Highly toxic Highly toxic (T+) expand Show data source
UN Number
0143, 0144, 1204, 3064, 3319 expand Show data source
Risk Statements
R3, R12, R26/27/28, R33, R51/53 expand Show data source
Safety Statements
S1/2, S33, S35, S36/37, S45, S53, S61 expand Show data source
EU Index
603-034-00-X expand Show data source
NFPA704
NFPA 704 diagram
3
2
4
expand Show data source
Explosive Velocity
7700 m s-1 expand Show data source
Friction Sensitivity
High expand Show data source
Shock Sensitivity
High expand Show data source
RE Factor
1.50 expand Show data source
Admin Routes
Intravenous, Oral, Sublingual, Topical, Transdermal expand Show data source
Bioavailability
<1% expand Show data source
Half Life
3 min expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
S3 (Australia) expand Show data source
Pregnancy Category
C (US) expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00727 external link
Item Information
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

REFERENCES

REFERENCES

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PATENTS

PATENTS

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