Nitroglycerin

Base Information

• Chemical Name: Nitroglycerin
• CAS No.: 55-63-0
• Deprecated CAS: 105469-31-6,80066-48-4,8013-23-8,9010-02-0,100292-13-5,100292-13-5,8013-23-8,9010-02-0
• Molecular Formula: C3H5N3O9
• Molecular Weight: 227.087
• Hs Code.: 2920900002
• European Community (EC) Number: 200-240-8
• ICSC Number: 0186
• UN Number: 0144,0143
• UNII: G59M7S0WS3
• DSSTox Substance ID: DTXSID1021407
• Wikipedia: Nitroglycerin
• Wikidata: Q162867
• NCI Thesaurus Code: C29294
• RXCUI: 4917
• Pharos Ligand ID: 8JZKV6G7YNVM
• Metabolomics Workbench ID: 43033
• ChEMBL ID: CHEMBL730
• Mol file: 55-63-0.mol

Synonyms:Anginine;Dynamite;Gilustenon;Glyceryl Trinitrate;Nitrangin;Nitro Bid;Nitro Dur;Nitro-Bid;Nitro-Dur;NitroBid;Nitrocard;Nitroderm;Nitroderm TTS;NitroDur;Nitroglycerin;Nitroglyn;Nitrol;Nitrolan;Nitrong;Nitrospan;Nitrostat;Perlinganit;Susadrin;Sustac;Sustak;Sustonit;Transderm Nitro;Tridil;Trinitrate, Glyceryl;Trinitrin;Trinitrolong

Chemical Property of Nitroglycerin

Chemical Property:

• Appearance/Colour: Colorless to pale-yellow, viscous liquid or solid
• Vapor Pressure: 3.82E-07mmHg at 25°C
• Melting Point: 144 - 146oC
• Refractive Index: 1.508
• Boiling Point: 295.782 °C at 760 mmHg
• Flash Point: 145.658 °C
• PSA: 165.15000
• Density: 1.672 g/cm³
• LogP: 0.54950
• Storage Temp.: ?20°C
• Solubility.: Miscible with acetone and with anhydrous ethanol
• Water Solubility.: 1.25g/L(25 oC)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 227.00257875
• Heavy Atom Count: 15
• Complexity: 219
• Transport DOT Label: Explosive 1.1D

Purity/Quality:

99.9% ^*data from raw suppliers

Diluted Nitroglycerin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): E, T+, N
• Hazard Codes: E,T+,N,Xn,T
• Statements: 11-51/53-33-26/27/28-3-36-20/21/22-23/24/25
• Safety Statements: 7-16-61-45-36/37-35-33-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Explosives
• Canonical SMILES: C(C(CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-]
• Recent ClinicalTrials: The Intra-arterial Vasospasm Trial
• Recent EU Clinical Trials: Evaluation of myocardial uptake of CardioCell in patients with non-ischaemic heart failure using the CIRCULATE catheter for transcoronary administration of pharmacologic and cell-based agents (CIRCULATE-PLUS)
• Recent NIPH Clinical Trials: Distal-Radial Approach using transdermal NitroGlycerine patch
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is irritating to the eyes. The substance may cause effects on the cardiovascular system. This may result in lowering of blood pressure. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. Repeated exposure leads to marked tolerance and short absence from exposure may lead to sudden death.
• Uses: Glyceryl trinitrate (GTN; nitroglycerin) is a representative compound from the organic nitrate ester family. Introduced in 1879, it has been used as a therapeutic agent in the treatment of angina pectoris. In the later part of the nineteenth century, the explosive property of nitroglycerin was discovered, and it then became the active component of dynamite. Glyceryl trinitrate, ethylene glycol dinitrate, and other nitrate esters are commonly used in military and mining explosives. In preparing dynamite, these nitrate esters are absorbed in a dope of oxidizing salts and various inert fillers. Vasodilator (coronary) Minitran (3M Pharmaceuticals); Nitro-Bid (Sanofi Aventis); Nitro-Dur (Key); Nitrol (Rorer); Nitrolingual (Pohl Boskamp); Nitrostat (Pfizer); Transderm-Nitro (Novartis). Nitroglycerin has medicinal use as a vasodilator. The main medical use of nitroglycerin is to treat angina pectoris. Nitroglycerin was first used to treat this condition in the late 19th century. It is prescribed today in various forms (tablet, ointment, patches, and injection) for patients who suffer from angina pectoris. Nitroglycerin is marketed under various trade names: Nitro-Dur, Nitrostat, Nitrospan, Nitro-Bid, and Tridil. When used in medications, the name glyceryl trinitrate is often used instead of nitroglycerin. Nitroglycerin is an explosive agent contained in dynamite and an antianginal and vasodilator treatment. It is a well-known irritant in dynamite manufacturers. It can also cause allergic reactions in employees of manufacturers of explosives, or in the pharmaceutical industries. Nitroglycerin can cross react with isosorbide dinitrate.
• Description: Nitroglycerin is an oily, poisonous, clear to pale yellow, explosive liquid.Nitroglycerin is made by nitrating glycerol. Early industrial processes used a batch process in which glycerol was added to a mixture with approximately equal volumes of nitric acid and sulfuric acid.The sulfuric acid serves to ionize the nitric acid and removes water formed in the nitration process.
• Indications: Nitroglycerin (also isosorbide nitrate) relaxes isolated strips of human corpus cavernosum. Its mechanism involves the stimulation of guanylate cyclase. Clinically, nitroglycerin has been of limited use in the treatment of ED.
• Clinical Use: Nitroglycerin is used extensively as an explosive in dynamite.A solution of the ester, if spilled or allowed to evaporate,will leave a residue of nitroglycerin. To prevent anexplosion of the residue, the ester must be decomposed byadding alkali. Even so, the material dispensed is so dilutethat the risk of explosions does not exist. It has a strong vasodilatingaction and, because it is absorbed through theskin, is prone to cause headaches among workers associatedwith its manufacture. This transdermal penetration is whynitroglycerin is useful in a patch formulation. In medicine, ithas the action typical of nitrites, but its action develops moreslowly and is of longer duration. Of all the known coronaryvasodilatory drugs, nitroglycerin is the only one capable ofstimulating the production of coronary collateral circulationand the only one able to prevent experimental myocardialinfarction by coronary occlusion.
• Drug interactions: Potentially hazardous interactions with other drugs Anticoagulants: infusion of GTN reduces anticoagulant effect of heparins. Antidepressants: tricyclics may reduce effect of sublingual tablets due to dry mouth. Antimuscarinics: may reduce effect of sublingual tablets due to dry mouth. Avanafil, sildenafil, tadalafil, vardenafil: hypotensive effect significantly enhanced - avoid concomitant use. Riociguat: avoid concomitant use due to risk of hypotension.

Technology Process of Nitroglycerin

There total 9 articles about Nitroglycerin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → glycerin trinitrate (55-63-0,9010-02-0)

Guidance literature:

With carbon dioxide; dinitrogen pentoxide; at 0 ℃; for 0.5h; under 45004.5 - 60006 Torr; Autoclave;

DOI:10.1016/j.mencom.2012.03.004

Reference yield: 90.83%

glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → 1,3-bis(nitrooxy)propan-2-ol (623-87-0) + glyceryl 1,2-dinitrate (621-65-8) + glycerin trinitrate (55-63-0,9010-02-0)

Guidance literature:

With sulfuric acid; sulfur trioxide; nitric acid; at 40 - 50 ℃; for 0.00116667 - 0.00238889h;

Reference yield: 73.0%

oxiranyl-methanol (556-52-5) → glycerin trinitrate (55-63-0,9010-02-0)

Guidance literature:

With dinitrogen pentoxide; aluminium trichloride; In dichloromethane; at 0 - 10 ℃; for 4h; in armoured cupboards;

DOI:10.1016/S0040-4020(01)87978-3

upstream raw materials:

glycerol

1,3-bis(nitrooxy)propan-2-ol

glyceryl 1,2-dinitrate

oxiranyl-methanol

Downstream raw materials:

N,N-dimethylhydroxylamine

N-ethyl-N-hydroxy-ethanamine

nitric acid

glyceric acid

Refernces

• 1、 Kazakov, A. I.,Kirpichev, E. P.,Lagodzinskaya, G. V.,Andrienko, L. P.,Yunda, N. G.,et al.. "STUDY OF NITRATION EQUILIBRIUM IN THE GLYCERIN-AQUEOUS NITRIC ACID SYSTEM. 2. CHANGES IN ΔH AND ΔS IN THE NITRATION REACTION". . p. 1565 - 1570. Retrieved 1990.
• 2、 -. "Continuous production nitroglycerin tablet (by machine translation)". Paragraph 0070-0073. . Retrieved 2020/08/27.
• 3、 -. "Methods of producing glycidyl nitrate". Page/Page column 11; 12. . Retrieved 2020/03/04.