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グリセロールトリニトラート

Nitroglycerin

HCID 4510
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
55-63-0
標準SMILES
O=[N+]([O-])OCC(CO[N+](=O)[O-])O[N+](=O)[O-]
InChIKey
SNIOPGDIGTZGOP-UHFFFAOYSA-N
分子式
C3H5N3O9
平均分子量
227.09 g/mol
単同位体質量
227.00257875

概要

Glyceryl trinitrate solution appears as a colorless solution of glyceryl trinitrate (nitroglycerin) in water. If allowed to dry out, the remaining nitroglycerin is explosive.

名称と識別子

優先名称
Nitroglycerin
IUPAC
1,3-dinitrooxypropan-2-yl nitrate
現地名
グリセロールトリニトラート
英語名
Nitroglycerin
分子式
C3H5N3O9
分子量
227.09

名称と別名

nitroglycerinGlyceryl trinitrateTrinitroglycerinNitrostatNitroglycerineNitroglycerol55-63-0Glycerol trinitrateTrinitroglycerolNitro-durMinitranTrinitrin
名称をさらに表示
ニトロダームメディトランスニトロングミニトログリセリルトリニトラートミリスロール1,2,3-プロパントリイルトリス(ニトラート)ニトログリセリンニトロスタートグリセロールトリニトラート三硝酸グリセリンニトロスパン1,2,3-プロパントリオールトリニトラートジドレンニトロダームTTSグリセリン三硝酸ニトログリセロールトリニトログリセロールニトロペン1,2,3-プロパントリオールトリスニトラートNTGDiluted NitroglycerinTNGGTNNitroglicerinaSNGNitrol
NitronetTridilNitroglynNitrolingualNitrongNiongNitoraTransderm-nitro

物性

構造計算による物性

XLogP
1.6
極性表面積
165 Ų
水素結合供与体数
0
水素結合受容体数
9
回転可能結合数
5
重原子数
15
形式電荷
0
複雑度
218

実験および物理化学的性質

Chemical Classes · 2 件

Other Uses -> Explosives

Corrosives

Drugs · 2 件

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

SpringerMaterials PropertiesBoiling point
LogP · 4 件

log Kow = 1.62

1

1.62

1.62

TasteSweet, burning taste
Density · 6 件

1.6 (NIOSH, 2024) - Denser than water; will sink

1.5918 @ 25 °C/4 °C; 1.6009 @ 15 °C/4 °C

Heat of formation 1.63 kJ/g; heat of detonation 6.29 kJ/g; gas volume at STP 715 cm/g; activation energy 169 kJ/mol; collision constant, 17.1 log 10/s; applicable temp range 75-105 °C; detonation velocity 7.60 km/s and at density 1.59 g/cu m; vacuum stability at 100 °C ml gas per g per 40 hr at STP: explodes; weight loss at 100 °C 3-5%; explosion temp at 5 s, 220 °C (decomposes); effect of prolonged storage dec 3-4 days at 75 °C; relative impact test value 15% trinitrotoluene (TNT); friction pendulum: explode.

Relative density (water = 1): 1.6

1.6

1.5931 @ 20°C

Viscosity36.0 centipoise @ 20 °C
Color/Form · 3 件

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H200: (Deleted) Unstable Explosive [Danger Explosives]

P201, P202, P260, P262, P264, P270, P271, P273, P280, P281, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P372, P373, P380, P391, P401, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H201: (Deleted) Explosive; mass explosion hazard [Danger Explosives]

P210, P230, P240, P250, P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P370+P380, P372, P373, P391, P401, P403+P233, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 5 件

Chemical: 1,2,3-Propanetriol, trinitrate

1,2,3-Propanetriol, 1,2,3-trinitrate is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2,3-Propanetriol, 1,2,3-trinitrate are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: Glycerol trinitrate (EC: 200-240-8)

1,2,3-Propanetriol, trinitrate, <1% solution in alcohol: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - 1,2,3-Propanetriol, trinitrate: Human health tier II assessment
DOT Label · 5 件

Flammable Liquid

Explosive 1.1D Poison

Flammable Liquid

Flammable Liquid

Explosive 1.1D

Fire Hazards · 6 件

化学と産業

薬理情報

ATC Code · 6 件

C01DA02

C - Cardiovascular system

C - Cardiovascular system

QC - Cardiovascular system

QC - Cardiovascular system

C01DA02

Protein Binding · 1 件

After a sublingual dose of nitroglycerin, at concentrations in the plasma ranging from 50 to 500 ng/mL, plasma protein binding of nitroglycerin is about 60%. The plasma protein binding of the metabolites 1,2-dinitroglycerin is 60% and that of 1,3-dinitroglycerin is 30%.

Pharmacodynamics · 1 件

Nitroglycerin causes the relaxation of vascular smooth muscles, causing arteriolar and venous dilatation. It increases blood flow to the myocardium and reduces cardiac preload and afterload, decreasing myocardial wall stress and ameliorating anginal symptoms. Nitroglycerin also reduces coronary artery spasm, decreasing systemic vascular resistance as well as systolic and diastolic blood pressure. Like other organic nitrates, repeated and prolonged administration of nitroglycerin can lead to the development of tolerance or desensitization of vascular smooth muscle to further nitroglycerin-induced vasorelaxation. This loss of efficacy may be associated with the inhibition of mitochondrial aldehyde dehydrogenase, which is an important enzyme involved in the bioactivation of nitroglycerin. Nitroglycerin tolerance may be accompanied by pro-oxidant effects, endothelial dysfunction, and increased sensitivity to vasoconstrictors.

Mechanism of Action · 5 件

Nitroglycerin is converted by mitochondrial aldehyde dehydrogenase in smooth muscle cells to nitric oxide (NO), a potent vasodilator. NO activates the enzyme guanylate cyclase, which converts guanosine triphosphate (GTP) to cyclic guanosine 3',5'-monophosphate (cGMP) in vascular smooth muscle and other tissues. cGMP is an endogenous vasodilator of vascular smooth muscle: it causes protein kinase-dependent phosphorylation and activates downstream cascades that promote relaxation and increased blood flow in veins, arteries and cardiac tissue. An _in vitro_ study using mouse aorta suggests that nitric oxide, an active metabolite of nitroglycerin, targets the natriuretic peptide receptors.

The drugs used to treat angina alleviate symptoms by increasing blood flow to the ischemic myocardium and/or by reducing myocardial oxygen requirements. ... /Nitrates/ reduce myocardial oxygen requirements through their effects on the systemic circulation. Their major systemic action is a reduction in venous tone, which leads to pooling of blood in peripheral veins, decreased venous return, and reduced ventricular volume and myocardial tension (preload). /Org nitrates/

関連反応

1 件
反応記録を作成
HRID 1156505 の反応式
HRID 1156505生成物としてuspto-grants-1982_06

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
55-63-0
PubChem CID
4510
DTXSID
DTXSID1021407
ChEMBL
CHEMBL730
ChEBI
CHEBI:28787
UNII
G59M7S0WS3
EC Number
200-240-8
Nikkaji
J4.491A

VISCOUS LIQUID

Pale-yellow, oily liquid

Colorless to pale-yellow, viscous liquid or solid (below 56 degrees F) Note: An explosive ingredient in dynamite (20-40%) with ethylene glycol dinitrate (80-60%).

Solubility · 6 件

0.1 % (NIOSH, 2024)

poor solubility in water

Sparingly sol in petroleum ether, liq petrolatum, glycerol.

One gram dissolves in 4 grams ethanol, 18 g methanol, 120 g carbon disulfide.

Miscible with glacial acetic acid, nitrobenzene, pyridine, ethylene bromide, dichloroethylene, ethyl acetate.

1 g in 800 ml water.

Flash Point · 4 件

Explodes (NIOSH, 2024)

518 °F (NFPA, 2010)

explodes

Explodes

Human Drugs · 4 件

Breast Feeding; Lactation; Milk, Human; Cardiovascular Agents; Vasodilator Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Antianginal medicines

Boiling Point · 6 件

Begins to decompose at 122-140 °F (NIOSH, 2024)

Explodes at 218 °C

BOILING POINT: 125 °C @ 2 MM HG

at 2kPa: 160 °C

Begins to decompose at 122-140 °F

Begins to decompose at 122-140 °F

物理化学的性質

融点
2.8 °; · 2.8°; mp 13.5°
沸点
368.78 °C · 368.78°C (rough estimate)
比重(密度)
1515 · d1515 1.599; d44 1.6144; d415 1.6009; d425 1.5918
屈折率
15 · nD15 1.474
闪点
12 °C · 12°C
貯蔵温度
-20 °C · -20°C
溶解性
アセトンおよび無水エタノールと混合可能
外見
解決
水溶解度
1.25 g/L · 1.25g/L(25℃)
比熱容量
1.03 J/ · Cp(gas): 1.03 J/(g·K), at 25℃
Henry's Law Constant
2.3 · 2.3×102 mol/(m3Pa) at 25℃, HSDB (2015)
Dielectric constant
19 · 19.0(20℃)
BCS Class
1 · 1
主な用途
医薬品(低分子化合物)
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
SMILES
O=[N+]([O-])OCC(CO[N+]([O-])=O)O[N+]([O-])=O
CAS データベース
55 · 55-63-0(CAS DataBase Reference)
NISTの化学物質情報
1 · 1,2,3-Propanetriol, trinitrate(55-63-0)
EPAの化学物質情報
Nitroglycerin (55-63-0)

化学的性質

化学的特性Nitroglycerin is a pale yellow liquid or crystalline solid (below 13℃).

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Health Hazards · 6 件

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Excerpt from NIOSH Pocket Guide for Nitroglycerine:

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

· Inhalation or contact with material may irritate or burn skin and eyes.

Hazards SummaryAllergic contact dermatitis reported in workers manufacturing explosives and pharmaceuticals; [Kanerva, p. 1820] Listed by ACGIH in a table of agents that may cause methemoglobinemia in the nonoccupational setting;
DOT ID and Guide · 4 件

1204 127

3064 127

1204 127(< or = 1% solution in alcohol)

3064 127(1-5% solution in alcohol)

FDA Requirements · 2 件

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl nitroglycerin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Drug preparations intended for human use containing certain "coronary vasodilators". The Food and Drug Administraton finds that the following "coronary vasodilators" are extensively regarded by physicians as safe and useful as employed under medical supervision for the management of angina pectoris in some patients. Nitroglycerin is included on this list.

Reactive Group · 5 件

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Alcohols and Polyols

Alcohols and Polyols

Alcohols and Polyols

EC ClassificationSymbol: E, T+, N; R: 3-26/27/28-33-51/53; S: (1/2)-33-35-36/37-45-61
UN ClassificationUN Hazard Class: 1.1D (Desensitized); UN Subsidiary Risks: 6.1 (Desensitized)
Special Reports · 2 件

Curry SH, Aburawi SM; Biopharm Drug Dispos 6 (3): 235-80 (1985)

Abrams J; Am J Med 76 (6A): 38-46 (1984). A review on long-acting nitrates and nitroglycerin, especially for treatment of angina and congestive heart failure. Oral, sublingual, transdermal, and buccal formulations are discussed.

安全と保護具

Fire Fighting · 6 件

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer immediately for medical attention.

Accidental Release Measures · 4 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 6 件

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Excerpt from NIOSH Pocket Guide for Nitroglycerine:

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

General First Aid:

Safe StorageStore only if stabilized. Store in an area without drain or sewer access. Fireproof. Well closed. Separated from food and feedstuffs.
Exposure Control and Personal Protection · 3 件

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

0.01 [ppm] (Value applies for the sum of the concentrations of Ethylene glycol dinitrate, Nitroglycerin and Propylene glycol dinitrate in the air.)[German Research Foundation (DFG)]

Fire Fighting ProceduresIf material on fire or involved in fire: Dangerously explosive. Do not fight fires in a cargo of explosives. Evacuate area and let burn. If the material is on fire or involved in fire consider evacuation of one mile radius.
Storage Conditions · 2 件

Nitroglycerin injections are practically colorless and stable in their intact containers. The solutions are not explosive. Storage should be at room temperature; the containers should be protected from freezing. Exposure to light, even high intensity light, does not adversely affect nitroglycerin stability. /nitroglycerin injections/

Store at room temp not above 25 °C (77 °F). Do not refrigerate. /Nitroglycerin trans dermal systems/

Cleanup Methods · 2 件

Nitro-compounds and nitrate ester are cathodically reduced from industrial wastewaters.

Solvent used to remove nitroglycerin from nitration plant effluent was dinitrotoluene.

Nonfire Spill Response · 5 件

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

Disposal Methods · 2 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

Spillage Disposal · 1 件

Evacuate danger area! Consult an expert! Personal protection: complete protective clothing including self-contained breathing apparatus. Remove all ignition sources. Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

毒性情報

Interactions · 5 件

Alcoholic beverages may precipitate /nitroglycerin/ poisoning and increase its severity.

Some interactions, for which there is quantitative supporting evidence, are not readily explained by direct effect on biotransformation, although this may play contributory role. This appears to be case with interactions between ... Phenobarbitone and ... Nitroglycerin

Alcohol may enhance sensitivity to the hypotensive effects of /nitroglycerin/.

The marked interaction of nitroglycerin with ethanol has prompted investigation of the possible biochemical mechanism of interaction. The activity of liver alcohol dehydrogenase has been shown to be decreased by nitroglycerin levels.

For more Interactions (Complete) data for NITROGLYCERIN (7 total), please visit the HSDB record page.

Target Organscardiovascular system, blood, skin, central nervous system
Ecotoxicity ValuesLC50 Bluegill 1.28 mg/l/96 hr @ pH 6.0. /Static bioassay/
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 180(SRC), determined from a log Kow of 1.62(2) and a regression-derived equation(3), indicates that nitroglycerin is expected to have moderate mobility in soil(SRC). Volatilization of nitroglycerin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.3X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 2.0X10-4 mm Hg(4), and water solubility, 1,380 mg/l(5). Nitroglycerin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Hydrolysis under alkaline conditions may be important based upon half-lives of 37 and 96 days at pH 9 and 25 and 18 °C, respectively(6). Biodegradation of nitroglycerin occurs rapidly using batch reactors and digestors(7,8), but its rate of biodegradation in soil is unknown(SRC). Nitroglycerin (10 ppm initial concn) was completely biodegraded in 13 days using river water and river water/sediment microcosms obtained from a river near a munitions facility(9), which may suggest biodegradation can occur in soils(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 180(SRC), determined from a log Kow of 1.62(2) and a regression-derived equation(3), indicates that nitroglycerin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.3X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 2.0X10-4 mm Hg(4), and water solubility, 1,380 mg/l(5). According to a classification scheme(6), an estimated BCF of 4(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is expected to be an important environmental fate process under alkaline conditions based on half-lives of 37 and 96 days at pH 9 and 25 and 18 °C, respectively(8). Nitroglycerin was completely biodegraded in 13 days using river water and river water/sediment microcosms obtained from a river near a munitions facility in Virginia(9). Nitroglycerin may undergo photolysis in water slowly in sunlit surface water(9). The half-life for nitroglycerin (5.8 ppm) in distilled water, filtered river water and filtered pond water exposed to sunlight were 116, 57 and 73 days, respectively(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nitroglycerin, which has a vapor pressure of 2.0X10-4 mm Hg at 20 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase nitroglycerin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 15 days(SRC), calculated from its rate constant of 1.1X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase nitroglycerin may be removed from the air by wet and dry deposition(SRC). Nitroglycerin absorbs light above 290 nm weakly and may be susceptible to direct photolysis(4), but the kinetics of this reaction in the atmosphere are not known(SRC).

Adverse Effects · 2 件

Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

Nitroglycerin has many adverse effects of significance, most resulting from the vasodilatory effects of the medication. These include:

Exposure Routes · 2 件

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Toxicity Summary · 2 件

IDENTIFICATION: Glyceryl trinitrate is used as an anti-anginal vasodilating agent. It slightly volatile odorless oily liquid with sweet, aromatic and pungent taste. Soluble in water, ethanol, methanol and miscible with ether, acetone and chloroform. Indications: Prophylaxis and treatment of angina and left ventricular failure. Control of hypertension during cardiac surgery. Congestive cardiac failure unresponsive to usual therapy. HUMAN EXPOSURE: Main risks and target organs: Toxic effects of glyceryl trinitrate are caused by vasodilatation and methemoglobinemia. Venous and arterial vasodilatation causes lowering of blood pressure leading to shock. Heart, blood vessels and red blood cells are the target organs in glyceryl trinitrate poisoning. Summary of clinical effects: Features of poisoning may appear within a few minutes to one hour or more after exposure. There is tachycardia and hypotension followed by bradycardia and collapse. Flushing of the face, headache, dizziness, restlessness, syncope, convulsions and coma may be present. Some of the other features are vomiting, diarrhoea, cyanosis and methaemoglobinaemia and respiratory failure. Effects of glyceryl trinitrate are enhanced by alcohol. Contraindications to the use of glyceryl trinitrate is in patients with hypo, head injury, severe anemia, cerebral hemorrhage and in patients predisposed to closed-angle glaucoma. Intravenous administration contraindicated in constrictive pericarditis and uncorrected hypovolaemia. Routes of entry: Oral: Toxic effects can occur by ingestion. Inhalation: Inhalation of dust may cause toxic effects. Dermal: Toxic effects may occur when absorbed through skin. Prolonged skin contact can cause skin eruptions. Parenteral: Toxic effects can occur by the administration of excessive intravenous doses. Absorption by route of exposure: Oral: Glyceryl trinitrate is readily absorbed from the oral mucosa but rapidly metabolized so that it has only a fleeting duration of action. It is also readily absorbed from the gastrointestinal tract, but owing to extensive first-pass metabolism in the liver its bioavailability is reduced. A study involving 5 healthy persons indicated a bioavailability of less than 1% following administration by mouth of glyceryl trinitrate capsule and oral solution. However the weakly pharmacologically active dinitrate metabolites reached relatively high concentrations after oral glyceryl trinitrate administration and it was suggested that these metabolites may be responsible for the activity of oral glyceryl trinitrate. Dermal: Glyceryl trinitrate is also absorbed through the skin from an ointment base. Distribution by route of exposure: The time to peak concentration depends on the route of administration; it occurs after 2 minutes, 40 minutes and one hour after sublingual, oral and dermal administration respectively. Bioavailability is 38% after sublingual and 1% for oral administration. Biological half-life by route of exposure: This drug has a very short plasma half life. Elimination half-life of nitroglycerin is 1.7 to 2.9 minutes. When glyceryl trinitrate was given sublingually peak plasma concentrations appeared within 4 minutes and at least half of the intact glyceryl trinitrate was cleared from the blood in 1 to 3 minutes. Peak plasma concentration following dermal application of 45 mg nitroglycerin ointment occurred in about 1 hour. Metabolism: Glyceryl trinitrate is metabolized by hydrolysis to dinitrates and the mononitrate. The half-life for dinitrate metabolites is about 40 minutes approximately 20 times that of glyceryl trinitrate. Elimination by route of exposure: In 10 healthy volunteers given glyceryl trinitrate 560 ug sublingually, about 22% of the administered dose was excreted in the urine after 24 hours mainly as the mononitrate. Mode of action Toxicodynamics: Glyceryl trinitrate has dilator properties on vascular smooth muscle in virtually all vascular beds. The beneficial effects in therapeutic doses and the effects seen with overdose are attributable to the physiologic consequences of systemic venous and arteriolar vasodilatation. The cardiac preload, systemic blood pressure and systemic vascular resistance all show a progressive decrease. A state of hypotension and circulatory collapse and shock may result. methemoglobinemia may occur in patients following an overdose or after therapy. Pharmacodynamics: Glyceryl trinitrate relaxes smooth muscle including vascular smooth muscle, and reduces systolic blood pressure. It is thought that the anti-anginal effect mainly depends on reducing myocardial oxygen demand by means of peripheral vasodilatation which causes decreased venous return permitting a reduction in left ventricular volume and energy expenditure. The effect of glyceryl trinitrate in relaxing coronary vessels is not considered to increase appreciably coronary blood flow. Interactions: Alcohol enhances the effects of glyceryl trinitrate. Undue dizziness and faint feeling may occur when sublingual nitrates are taken with beta-adrenoceptor blocking drugs. Complete AV block has been reported after use of sublingual nitrates in patients receiving lignocaine by infusion. Even cardiac asystole may occur. Disopyramide (by producing dryness in mouth) may prevent dissolution of sublingual isosorbide dinitrate tablets. This may also occur with tricyclic antidepressants. Delayed dissolution of glyceryl trinitrate tablets in patients with dry mouths has been reported in a patient taking imipramine and in another patient treated with atropine. A patient developed resistance to the effects of heparin on two occasions directly after intravenous administration of glyceryl trinitrate. The interactions could not be attributed to propylene glycol in the solvent since resistance also occurred during administration of a formulation of glyceryl trinitrate without propylene glycol. Explosion flush has been observed in patients with transdermal patch when electric defibrillation was performed. Main adverse effects: The toxicity of the nitrates is unaffected by the chemical form or by the route of administration and all the nitrates have a common profile of adverse effects. Hypotension, reflex tachycardia and palpitations may occur. Postural hypotension and syncope is seen, especially in elderly patients. Rarely severe bradycardia has been reported. Throbbing headache is quite common. This symptoms is likely to recede as tolerance develops. Peripheral edema is also frequently seen. Transient hypoxemia with precipitation of angina is seen occasionally. Transient cerebral ischemic episodes unrelated to changes in blood pressure are rarely seen. In patients with cerebrovascular disease, it is recommended to initiate treatment with small doses. Although tolerance has long been associated with nitrates, its clinical implications are not clear. Tolerance is best defined as a decreasing pharmacological effect over time, often with a need for an increasing dose to achieve a given action. Tolerance may be partial or incomplete and may occur to one aspect of nitrate therapy and not to others. Disappearance of the throbbing headache is useful. However, due to an attenuation of the antihypertensive effect, these agents are not useful in the long term management of hypertension. The part played by the arterial and venous side of the circulation pertaining to the development of tolerance is not clear. By having a long (approximately 8 hours) nitrate free interval, the development of tolerance may be avoided or reduced. Decreasing the number of daily doses of glyceryl trinitrate also helps to achieve this effect. Sustained release preparations are more likely to produce tolerance than the short acting preparations.

Signs and Symptoms · 5 件

Headache. Nausea. Flushing of the face. Dizziness.

MAY BE ABSORBED! Further see Inhalation.

Redness. Pain.

Flushing of the face. Headache. Dizziness. Nausea. Vomiting. Shock or collapse.

throbbing headache; dizziness; nausea, vomiting, abdominal pain; hypotension; flush; palpitations; methemoglobinemia; delirium, central nervous system depression; angina; skin irritation

Effluent ConcentrationsWastewater from the Radford Army Munitions plant contained 1,566 mg/l of nitroglycerin(1). Nitroglycerin has been identified, not quantified, in the waste streams of munitions factories and pharmaceutical plants(2).
ICSC Environmental DataThe substance is toxic to aquatic organisms.
Soil Adsorption/Mobility · 1 件

The Koc of nitroglycerin is estimated as 180(SRC), using a log Kow of 1.62(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that nitroglycerin is expected to have moderate mobility in soil(SRC).

Human Toxicity Excerpts · 5 件

/HUMAN EXPOSURE STUDIES/ Withdrawal of coronary vasodilators such as nitroglycerin ... caused sudden death in industrial workers who were exposed all week on the job and then abstained from the chemical on weekends. They were adapted and dependent on the continuous presence of these cmpds to maintain a minimum level of coronary flow.

/HUMAN EXPOSURE STUDIES/ /Symptoms of nitroglycerin toxicity include:/ A prompt fall in blood pressure. A roaring sound in the ears; a headache which is persistent and throbbing, with associated vertigo; a generalized tingling sensation, palpitations, and visual disturbances. The skin is flushed and perspiring, later cold and cyanotic. Nausea and vomiting. The ingestion of nitrites may also cause colic and diarrhea. Syncope, especially when attempting to stand upright. Methemoglobinemia, with attendant cyanosis and anoxia. Hyperpnea; later dyspnea and slow breathing. The pulse may be slow, dicrotic and intermittent. Increased intraocular tension and intracranial pressure. Collapse and coma, followed by clonic convulsions. Death due to circulatory collapse.

/HUMAN EXPOSURE STUDIES/ Workers without demonstrable organic vascular disease have been reported to have an incr in the incidence of acute coronary syndromes during the 24 to 72 hr period away from the work environment.

/HUMAN EXPOSURE STUDIES/ Right coronary arterial segments that appeared angiographically normal before admin of nitroglycerin showed narrowing after sublingual admin. Evidence against admin of nitrates before coronary arteriography.

For more Human Toxicity Excerpts (Complete) data for NITROGLYCERIN (7 total), please visit the HSDB record page.

法規制情報

FDA Requirements · 2 件

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl nitroglycerin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Drug preparations intended for human use containing certain "coronary vasodilators". The Food and Drug Administraton finds that the following "coronary vasodilators" are extensively regarded by physicians as safe and useful as employed under medical supervision for the management of angina pectoris in some patients. Nitroglycerin is included on this list.

RCRA Requirements · 1 件

U081; As stipulated in 40 CFR 261.33, when nitroglycerine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

CERCLA Reportable Quantities · 1 件

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

DHS Chemicals of Interest (COI) · 6 件

Nitroglycerine

A Commercial Grade

5000

A Commercial Grade

400

Explosive chemical that can be released at a facility.

Federal Drinking Water GuidelinesEPA 5 ug/l

安全データ

OEL
STEL: 0.1 mg/m3 [skin]
wgk
3
IDLA
75 mg/m3
tsca
TSCA listed
ridadr
UN 3064 3/PG II (NITROGLYCERIN, SOLUTION IN ALCOHOL with more than 1 % but not more than 5 % nitroglycerin)
毒性
LD50 oral in rabbit: 1607mg/kg
PRTR法
第1種指定化学物質
hs_code
2920900002
risk_code
11-51/53-33-26/27/28-3-36-20/21/22-23/24/25
化審法
2-1574
hazard_code
E,T+,N,Xn,T
safety_code
7-16-61-45-36/37-35-33-26
hazard_class
1.1A
packing_group
I
環境リスク評価
ニトログリセリン(55-63-0)
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 4 OralFlam. Liq. 2
ストレージクラス
3 - Flammable liquids
有毒物質データの
55-63-0(Hazardous Substances Data)

Although it predominately affects vascular smooth muscle /nitroglycerin/, the bronchioles, gastrointestinal tract (including biliary system), ureters, and uterus are affected. Free radicals of nitric oxide may activate guanylate cyclase, resulting in increased synthesis of cyclic GMP. Nitric oxide may combine with sulfhydryl groups in the endothelium and produce S-nitrosothiols, which stimulate guanylate cyclase production. N-acetyl-cycteine may enhance this process by providing a source of sulfhydryl groups. Cyclic GMP appears to reduce stored calcium and interfere with calcium-activated smooth muscle contractions.

Organic nitrates... lead to the formation of the reactive free radical nitric oxide, which can activate guanylyl cyclase and increase the synthesis of cyclic GMP in smooth muscle and other tissues... A cyclic GMP-dependent protein kinase catalyzes the phosphorylation of various proteins in smooth muscle. Eventually, the light chain of myosin is dephosphorylated. Phosphorylation of the myosin chain regulates the maintenance of the contractile state in smooth muscle.

Nitrates also may alter the prostaglandin system by inhibiting thromboxane synthetase and permitting preferential formation of prostacyclin over thromboxane A2. Both of these two short-acting vasoactive substances are formed from prostaglandin precursors. Prostacyclin is a potent vasodilator which causes smooth muscle relaxation through phosphorylation of the myosin light chain kinase. This reduces its ability to to be activated by calciun and calmodulin.

Biological Half-Life · 4 件

Following intravenous administration, the plasma half-life is about three minutes. The estimated plasma half-life following sublingual administration is approximately six minutes. The elimination half-lives of metabolites 1,2-dinitroglycerin and 1,3-dinitroglycerin range between 32 to 26 minutes.

Half-life 2.3 + or - 0.6 minutes.

The plasma half-life of nitroglycerin has been estimated at 1 to 3 minutes, representing the alpha distribution, and also at about 7.5 minutes.

The elim half-life of 1,2- and 1,3-dinitroglycerin is 36 and 32 min, respectively.

Metabolism/Metabolites · 6 件

Mitochondrial aldehyde dehydrogenase 2 (ALDH2) promotes the bioactivation of nitroglycerin. Nitroglycerin is metabolized to nitrite; 1,2-glyceryl dinitrate; and 1,3 glyceryl dinitrate. Nitrite is further metabolized to nitric oxide. 1,2- and 1,3-dinitroglycerols are less biologically active than nitroglycerin but they have longer half-lives, which explains some prolonged effects of nitrates. Both dinitrates are finally metabolized to glycerol, carbon dioxide, and mononitrates that do not have vasodilatory actions. Nitroglycerin can also chemically react with a thiol to generate an intermediate S-nitrosothiol, which resulted in further production of nitric oxide.

... Glyceryl ... /mononitrate is/ major circulating ... /metabolite/ of nitroglycerin.

The metabolism of nitroglycerin... appears to involve reduced glutathione in a reaction catalyzed by an enzyme known as organic nitrate reductase, which is predominantly located in the soluble fraction of liver homogenate.

Nitroglycerin is degraded in the liver by reductive hydrolysis and partially in plasma by spontaneous hydrolysis... The major urinary metabolites include glyceryl mononitrate, 1,2-glyceryl dinitrate and 1,3-glyceryl dinitrate... Reactive hydrolysis in the liver by hepatic inorganic nitrate reductase leads to the formation of the free nitric oxide radical.

Initial hydrolytic reduction by interaction of inorganic nitrate with reduced glutathione occurs both spontaneously and with enzymes, which can be extracted fron the soluble fraction of the liver.

For more Metabolism/Metabolites (Complete) data for NITROGLYCERIN (6 total), please visit the HSDB record page.

FDA Pharmacological Classification · 6 件

G59M7S0WS3

NITROGLYCERIN

Established Pharmacologic Class [EPC] - Nitrate Vasodilator

Chemical Structure [CS] - Nitrates

Physiologic Effects [PE] - Vasodilation

Nitroglycerin is a Nitrate Vasodilator. The physiologic effect of nitroglycerin is by means of Vasodilation.

MeSH Pharmacological Classification · 2 件

Drugs used to cause dilation of the blood vessels.

Substances that are energetically unstable and can produce a sudden expansion of the material, called an explosion, which is accompanied by heat, pressure and noise. Other things which have been described as explosive that are not included here are explosive action of laser heating, human performance, sudden epidemiological outbreaks, or fast cell growth.

Absorption, Distribution and Excretion · 6 件

Nitroglycerin is rapidly absorbed and is often used in emergency situations for this reason. After a sublingual dose of 0.5 mg of nitroglycerin in patients with ischemic heart disease, the peak concentration (Cmax) was 2.56 ng/mL and the mean Tmax was 4.4 minutes. The Cmax following a 0.6mg dose of sublingual nitroglycerin was 2.1 ng/mL and the Tmax was 7.2 minutes. The absolute bioavailability following sublingual administration was about 40%. The bioavailability of nitroglycerin depends on several factors, such as mucosal metabolism and hydration status, which both affect the absorption of sublingual drugs.

Metabolism is the main route by which nitroglycerin is eliminated from the body.

The volume of distribution of nitroglycerin is 3 L/kg.

The estimated clearance following intravenous administration is 1 L/kg/min. The apparent clearance after a sublingual dose was 21.9 L/min in a pharmacokinetic study of patients with ischemic heart disease and angina.

In human beings, peak concentrations of nitroglycerin are found in plasma within 4 min of sublingual administration.

volume of distribution 3.3 + or - 1.2 L/kg

Cellular LocationsCytoplasm

用途と製造

Uses · 6 件

Used in the production of dynamite and other explosives, rocket fuel and pharmaceuticals; [HSDB]

An OSHA Class A explosive (1910.109).

High explosive, production of dynamite and other explosives

Combating fires in oil wells

Rocket propellants

MEDICATION

ImpuritiesNitric acid, arising from imperfect washing, hydrolysis or thermal aging (eg heating to 50 °C)
U.S. Production · 2 件

2023: 8,500,000 - <10,000,000 lb

(1973) 2.6X10+10 G (EST SALES)

Consumer UsesEnergy Releasers (explosives, motive propellant)
Industry UsesOther
Methods of Manufacturing · 2 件

By dropping glycerol through cooled, mixed acid and stirring, followed by repeated washing with water.

It is prepared by continuous two-phase nitration of glycerol in anhydrous mixed acid. The mass ratio of pure anhydrous glycerol (H2O less than 0.5%) and 50:50 mixed acid is 1:5. The product is washed with aqueous sodium carbonate or bicarbonate.

Formulations/Preparations · 5 件

GRADES: TECHNICAL

Nitrostat contains 0.15 mg or 0.3 mg or 0.4 mg or 0.6 mg nitroglycerin and polyethylene glycol 4000 units per tablet.

Nitro-Dur contains 2% w/w nitroglycerin.

Nitroglyn contains 1/10, 1/25 or 1/50 gr nitroglycerin per tablet.

For more Formulations/Preparations (Complete) data for NITROGLYCERIN (12 total), please visit the HSDB record page.

General Manufacturing Information · 2 件

Explosives Manufacturing

1,2,3-Propanetriol, 1,2,3-trinitrate: ACTIVE

応用分野 · 6 件

解説ニトログリセリン,グリセリンの硝酸エステル。NGと略記される。1846年イタリアのソブレロによって初めて合成された。ソブレロ自身は、ニトログリセリンの爆発性があまりに激しいので使い物にならないと考えた。しかし、この強力な爆発威力に注目した人々によって鉱山で発破(はっぱ)用に使われていたが、たいへん敏感な液体で、岩の割れ目に流れ込んだりして予期しない爆発事故をおこした。また、凝固点が低いので冬には凍結し、それを溶かすときにも爆発事故をおこした。 ニトログリセリンは、それまで使われてきた黒色火薬の7倍の爆破威力があったが、黒色火薬と違って、導火線で点火したのでは燃えるだけで確実に爆発させることはできなかった。スウェーデンのノーベルは、ニトログリセリンを確実に爆発させるために雷管を発明(1864)して、ニトログリセリンおよびそれに続くダイナマイトの爆破薬としての用途を確立した。 ニトログリセリンはそのもの単独では危険すぎたので、ノーベルはそれを安全にして使える珪藻土(けいそうど)ダイナマイトおよびゼラチンダイナマイトを発明して、ニトログリセリンの爆薬原料としての用途を確立した。また、ニトログリセリンを窒素量12%前後のニトロセルロースと混ぜて高性能のダブルベース無煙火薬(バリスタイト)を発明した。このように、ニトログリセリンを実用化するためにノーベルの果たした役割は大きい。

用途ダイナマイトの基材、狭心症の薬。液体のままニトログリセリンが工場外にでることはなく、工場内でダイナマイトに変えられる。また無煙火薬の主剤とする

説明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.

来歴It was first prepared in 1846 by the Italian chemist Ascanio Sobrero (1812–1888), who nitrated glycerol using a mixture of nitric acid and sulfuric acid. Sobrero, who was injured in an explosion doing his research, realized the compound’s danger and abandoned work on nitroglycerin. Twenty years after Sobrero’s discovery, Alfred Nobel (1833–1896) developed its use commercially. Nobel mixed nitroglycerin with other substances, searching for a safe way to transport it and make it less sensitive to heat and pressure.nitroglycerin when it was first marketed,and Nobel continued to experiment with methods to make nitroglycerin safer.One of these was mixing nitroglycerin with materials to make a solid form of nitroglycerin. Nobel discovered that when nitroglycerin was mixed with a silica-based diatomaceous earth material called kieselguhr,a relatively stable product resulted.The mixture produced a paste that Nobel could pack into cardboard tubes;these could then be inserted into holes drilled into rock structures and detonated.In 1867,Nobel patented his mixture and called it dynamite,a name derived from the Greek word dunamis, meaning power.Nobel also perfected a blasting cap made from mercury fulminate (Hg(ONC)2) and potassium chlorate (KClO3) to detonate the nitroglycerin.

使用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.

一般的な説明Colorless to pale-yellow, viscous liquid or solid (below 56°F). (Note: An explosive ingredient in dynamite (20-40%) with ethylene glycol dinitrate (80-60%).).

調製方法 · 1 件

Nitroglycerin is made by nitrating glycerol.Early industrial processes used a batch processin which glycerol was added to a mixture with approximately equal volumes of nitric acidand sulfuric acid.The sulfuric acid serves to ionize the nitric acid and removes water formedin the nitration process.Removing the water formed in nitration increases the yield of nitroglycerin.Acids and water must be removed from the desired nitroglycerin through a washingprocess. The production of nitroglycerin is highly exothermic,and it is important to keepthe temperature below room temperature to prevent an explosion. Early production methodsused cooling coils in the nitration vessels to regulate the temperature.During the latter halfof the 20th century, safer continuous production methods replaced batch processes.In thesemethods much smaller reactors are required,as glycerol is reacted with the acids.

上流・下流製品情報

上流原料

硝酸硫酸水素グリセロールエタノール

下流製品

1,2,3-プロパントリオール1,2-ジニトラートグリセロール2-ニトラートL-グリセロール1,3-ジニトラート

補足説明

定義ChEBI: A nitroglycerol that is glycerol in which the hydrogen atoms of all three hydroxy groups are replaced by nitro groups. It acts as a prodrug, releasing nitric oxide to open blood vessels and so alleviate heart pain.

Overdose toxicity from nitroglycerin is mainly a consequence of increased vasodilatory response. Hypotension, venous pooling, increased vasodilation, and reduced cardiac output can be expected in these patients. Compensatory effects, such as tachycardia and palpitations, can also be expected. Vasodilation and venous pooling can increase the amount of blood in the cranial space, resulting in increased intracranial pressures; this can cause persistent, throbbing headaches, along with confusion, fever, vertigo, nausea, vomiting, and visual disturbances. As intracranial pressure increases, symptoms will progress to dyspnea secondary to a reduced respiratory effort, heart block, bradycardia, paralysis, seizures, coma, and, eventually, death.