Trigonal planar at N7, N8, and N9
Tetrahedral at C1, C2, and C3
Dihedral at N7, N8, and N9
7700 m s−1
Std enthalpy of
−370 kJ mol−1
Std enthalpy of
−1.529 MJ mol−1
C01DA02 (WHO) C05AE01 (WHO)
US: C (Risk not ruled out)
Intravenous, by mouth, under the tongue, topical
AU: S3 (Pharmacist only)
GHS signal word
GHS hazard statements
H202, H205, H241, H301, H311, H331, H370
GHS precautionary statements
P210, P243, P250, P260, P264, P270, P271, P280, P302+352, P410
US health exposure limits (NIOSH):
C 0.2 ppm (2 mg/m3) [skin]
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Nitroglycerin (NG), also known as nitroglycerine, trinitroglycerin
(TNG), trinitroglycerine, nitro, glyceryl trinitrate (GTN), or
1,2,3-trinitroxypropane, is a heavy, colorless, oily, explosive liquid
most commonly produced by nitrating glycerol with white fuming nitric
acid under conditions appropriate to the formation of the nitric acid
ester. Chemically, the substance is an organic nitrate compound rather
than a nitro compound, yet the traditional name is often retained.
Invented in 1847, nitroglycerin has been used as an active ingredient
in the manufacture of explosives, mostly dynamite, and as such it is
employed in the construction, demolition, and mining industries. Since
the 1880s, it has been used by the military as an active ingredient,
and a gelatinizer for nitrocellulose, in some solid propellants, such
as cordite and ballistite.
Nitroglycerin is a major component in double-based smokeless
gunpowders used by reloaders. Combined with nitrocellulose, there are
hundreds of powder combinations used by rifle, pistol, and shotgun
In medicine, for over 130 years nitroglycerin has been used as a
potent vasodilator (dilation of the vascular system) to treat heart
conditions, such as angina pectoris and chronic heart failure. Though
it was previously known that these beneficial effects are due to
nitroglycerin being converted to nitric oxide, a potent venodilator,
it was not until 2002 that the enzyme for this conversion was
discovered to be mitochondrial aldehyde dehydrogenase.
Nitroglycerin is available in sublingual tablets, sprays, and
1.1 Wartime production rates
2 Instability and desensitization
5 Use as an explosive and a propellant
6 Medical use
7 Industrial exposure
8 See also
10 External links
Nitroglycerin was the first practical explosive produced that was
stronger than black powder. It was first synthesized by the Italian
Ascanio Sobrero in 1847, working under Théophile-Jules
Pelouze at the University of Turin. Sobrero initially called his
discovery pyroglycerine and warned vigorously against its use as an
Nitroglycerin was later adopted as a commercially useful explosive by
Alfred Nobel, who experimented with safer ways to handle the dangerous
compound after his younger brother, Emil Oskar Nobel, and several
factory workers were killed in an explosion at the Nobels' armaments
factory in 1864 in Heleneborg, Sweden.
One year later, Nobel founded
Alfred Nobel & Company in Germany
and built an isolated factory in the Krümmel hills of
Hamburg. This business exported a liquid combination of nitroglycerin
and gunpowder called "Blasting Oil", but this was extremely unstable
and difficult to handle, as evidenced in numerous catastrophes. The
buildings of the Krümmel factory were destroyed twice.
In April 1866, three crates of nitroglycerin were shipped to
California for the Central Pacific Railroad, which planned to
experiment with it as a blasting explosive to expedite the
construction of the 1,659-foot (506 m)-long Summit
the Sierra Nevada Mountains. One of the crates exploded, destroying a
Wells Fargo company office in
San Francisco and killing 15 people.
This led to a complete ban on the transportation of liquid
nitroglycerin in California. The on-site manufacture of nitroglycerin
was thus required for the remaining hard-rock drilling and blasting
required for the completion of the
First Transcontinental Railroad
First Transcontinental Railroad in
Liquid nitroglycerin was widely banned elsewhere as well, and these
legal restrictions led to
Alfred Nobel and his company's developing
dynamite in 1867. This was made by mixing nitroglycerin with
diatomaceous earth ("kieselgur" in German) found in the Krümmel
hills. Similar mixtures, such as "dualine" (1867), "lithofracteur"
(1869), and "gelignite" (1875), were formed by mixing nitroglycerin
with other inert absorbents, and many combinations were tried by other
companies in attempts to get around Nobel's tightly held patents for
Dynamite mixtures containing nitrocellulose, which increases the
viscosity of the mix, are commonly known as "gelatins".
Following the discovery that amyl nitrite helped alleviate chest pain,
William Murrell experimented with the use of nitroglycerin to
alleviate angina pectoris and to reduce the blood pressure. He began
treating his patients with small diluted doses of nitroglycerin in
1878, and this treatment was soon adopted into widespread use after
Murrell published his results in the journal
The Lancet in
1879. A few months before his death in 1896,
Alfred Nobel was
prescribed nitroglycerine for this heart condition, writing to a
friend: "Isn't it the irony of fate that I have been prescribed
nitro-glycerin, to be taken internally! They call it Trinitrin, so as
not to scare the chemist and the public."  The medical
establishment also used the name "glyceryl trinitrate" for the same
Wartime production rates
Large quantities of nitroglycerin were manufactured during World War I
World War II
World War II for use as military propellants and in military
engineering work. During World War I, HM Factory, Gretna, the largest
propellant factory in Britain, produced about 800 tonne of cordite RDB
per week. This amount required at least 336 tons of nitroglycerin per
week (assuming no losses in production). The
Royal Navy had its own
factory at the
Cordite Factory, Holton Heath in Dorset,
England. A large cordite factory was also built in Canada during World
War I. The Canadian Explosives Limited cordite factory at Nobel,
Ontario, was designed to produce 1,500,000 lb (680 t) of
cordite per month, requiring about 286 tonnes of nitroglycerin per
Instability and desensitization
In its pure form, nitroglycerin is a contact explosive, with physical
shock causing it to explode, and it degrades over time to even more
unstable forms. This makes nitroglycerin highly dangerous to transport
or use. In its undiluted form, it is one of the world's most powerful
explosives, comparable to the more recently developed
RDX and PETN.
Early in its history, it was discovered that liquid nitroglycerin can
be "desensitized" by cooling it to about 5 to 10 °C (40 to
50 °F). At this temperature nitroglycerin freezes, contracting
upon solidification. Thawing it out can be extremely sensitizing,
especially if impurities are present or the warming is too rapid.
It is possible to chemically "desensitize" nitroglycerin to a point
where it can be considered approximately as "safe" as modern high
explosives, such as by the addition of approximately 10% to 30%
ethanol, acetone, or dinitrotoluene. (The percentage varies with
the desensitizing agent used.) Desensitization requires extra effort
to reconstitute the "pure" product. Failing this, it must be assumed
that desensitized nitroglycerin is substantially more difficult to
detonate, possibly rendering it useless as an explosive for practical
A serious problem in the use of nitroglycerin results from its high
freezing point 13 °C (55 °F). Solid nitroglycerin is much
less sensitive to shock than the liquid, a feature that is common in
explosives. In the past, nitroglycerin was often shipped in the frozen
state, but this resulted in a high number of accidents during the
thawing process just before its use. This disadvantage is overcome by
using mixtures of nitroglycerin with other polynitrates. For example,
a mixture of nitroglycerin and ethylene glycol dinitrate freezes at
−29 °C (−20 °F).
Nitroglycerin and any diluents can certainly deflagrate (i.e., burn).
The explosive power of nitroglycerin derives from detonation: energy
from the initial decomposition causes a strong pressure wave that
detonates the surrounding fuel. This is a self-sustained shock wave
that propagates through the explosive medium at 30 times the speed of
sound as a near-instantaneous pressure-induced decomposition of the
fuel into a white-hot gas.
Detonation of nitroglycerin generates gases
that would occupy more than 1,200 times the original volume at
ordinary room temperature and pressure. The heat liberated raises the
temperature to about 5,000 °C (9,000 °F). This is
entirely different from deflagration, which depends solely upon
available fuel regardless of pressure or shock. The decomposition
results in much higher ratio of energy to gas moles released compared
to other explosives, making it one of the hottest detonating high
Nitroglycerin can be produced by acid catalyzed nitration of glycerol
The industrial manufacturing process often reacts glycerol with a
nearly 1:1 mixture of concentrated sulfuric acid and concentrated
nitric acid. This can be produced by mixing white fuming nitric
acid—a quite expensive pure nitric acid in which the oxides of
nitrogen have been removed, as opposed to red fuming nitric acid,
which contains nitrogen oxides—and concentrated sulfuric acid. More
often, this mixture is attained by the cheaper method of mixing fuming
sulfuric acid, also known as oleum—sulfuric acid containing excess
sulfur trioxide—and azeotropic nitric acid (consisting of about 70
percent nitric acid, with the rest being water).
The sulfuric acid produces protonated nitric acid species, which are
attacked by glycerol's nucleophilic oxygen atoms. The nitro group is
thus added as an ester C-O-NO2 and water is produced. This is
different from an electrophilic aromatic substitution reaction in
which nitronium ions are the electrophile.
The addition of glycerol results in an exothermic reaction (i.e., heat
is produced), as usual for mixed-acid nitrations. If the mixture
becomes too hot, it results in a runaway reaction, a state of
accelerated nitration accompanied by the destructive oxidation of
organic materials by the hot nitric acid and the release of poisonous
nitrogen dioxide gas at high risk of an explosion. Thus, the glycerin
mixture is added slowly to the reaction vessel containing the mixed
acid (not acid to glycerin). The nitrator is cooled with cold water or
some other coolant mixture and maintained throughout the glycerin
addition at about 22 °C (72 °F), much below which the
esterification occurs too slowly to be useful. The nitrator vessel,
often constructed of iron or lead and generally stirred with
compressed air, has an emergency trap door at its base, which hangs
over a large pool of very cold water and into which the whole reaction
mixture (called the charge) can be dumped to prevent an explosion, a
process referred to as drowning. If the temperature of the charge
exceeds about 30 °C (86 °F) (actual value varying by
country) or brown fumes are seen in the nitrator's vent, then it is
Use as an explosive and a propellant
Main articles: Dynamite, Ballistite, Cordite, smokeless powder, and
Alfred Nobel's patent application from 1864
The main use of nitroglycerin, by tonnage, is in explosives such as
dynamite and in propellants.
Nitroglycerin is an oily liquid that may explode when subjected to
heat, shock or flame.
Alfred Nobel developed the use of nitroglycerin as a blasting
explosive by mixing nitroglycerin with inert absorbents, particularly
"kieselguhr," or diatomaceous earth. He named this explosive dynamite
and patented it in 1867. It was supplied ready for use in the form
of sticks, individually wrapped in greased waterproof paper. Dynamite
and similar explosives were widely adopted for civil engineering
tasks, such as in drilling highway and railroad tunnels, for mining,
for clearing farmland of stumps, in quarrying, and in demolition work.
Likewise, military engineers have used dynamite for construction and
Nitroglycerin was also used as an ingredient in military propellants
for use in firearms.
Nitroglycerin has been used in conjunction with hydraulic fracturing,
a process used to recover oil and gas from shale formations. The
technique involves displacing and detonating nitroglycerin in natural
or hydraulically induced fracture systems, or displacing and
detonating nitroglycerin in hydraulically induced fractures followed
by wellbore shots using pelletized TNT.
Nitroglycerin has an advantage over some other high explosives, that
on detonation it produces practically no visible smoke. Therefore, it
is useful as an ingredient in the formulation of various kinds of
Its sensitivity has limited the usefulness of nitroglycerin as a
military explosive, and less sensitive explosives such as TNT, RDX,
HMX have largely replaced it in munitions. It remains important in
military engineering, and combat engineers still use dynamite.
Alfred Nobel then developed ballistite, by combining nitroglycerin and
guncotton. He patented it in 1887.
Ballistite was adopted by a number
of European governments, as a military propellant. Italy was the first
to adopt it. The British Government and the Commonwealth governments
adopted cordite instead, which had been developed by Sir Frederick
Sir James Dewar
Sir James Dewar of the United Kingdom in 1889. The original
Cordite Mk I consisted of 58% nitroglycerin, 37% guncotton, and 5.0%
Ballistite and cordite were both manufactured in the
forms of cords.
Smokeless powders were originally developed using nitrocellulose as
the sole explosive ingredient. Therefore, they were known as
single-base propellants. A range of smokeless powders that contain
both nitrocellulose and nitroglycerin, known as double-base
propellants, were also developed. Smokeless powders were originally
supplied only for military use, but they were also soon developed for
civilian use and were quickly adopted for sports. Some are known as
sporting powders. Triple-base propellants contain nitrocellulose,
nitroglycerin, and nitroguanidine, but are reserved mainly for
extremely high-caliber ammunition rounds such as those used in tank
cannons and naval artillery.
Blasting gelatin, also known as gelignite, was invented by Nobel in
1875, using nitroglycerin, wood pulp, and sodium or potassium
nitrates. This was an early low-cost, flexible explosive.
Main article: Medical use of nitroglycerin
Nitroglycerin belongs to a group of drugs called nitrates, which
includes many other nitrates like isosorbide dinitrate (Isordil) and
isosorbide mononitrate (Imdur, Ismo, Monoket). These agents all
exert their effect by being converted to nitric oxide in the body by
mitochondrial aldehyde dehydrogenase, and nitric oxide is a potent
In medicine, nitroglycerin is used as a medicine for angina pectoris,
a painful symptom of ischemic heart disease caused by inadequate flow
of blood and oxygen to the heart and as a potent antihypertensive
Nitroglycerin corrects the imbalance between the flow of oxygen
and blood to the heart. At low doses, nitroglycerin will dilate
veins more than arteries, thereby reducing preload (volume of blood in
the heart after filling); this is thought to be its primary mechanism
of action. By decreasing preload, the heart has less blood to pump
which decreases oxygen requirement since the heart doesn't have to
work as hard. Additionally, having a smaller preload reduces the
ventricular transmural pressure (pressure exerted on the walls of the
heart), which decreases the compression of heart arteries to allow
more blood to flow through the heart. At higher doses, it also dilates
arteries, thereby reducing afterload (decreasing the pressure against
which the heart must pump). Improved myocardial oxygen demand vs
oxygen delivery ratio leads to the following therapeutic effects
during episodes of angina pectoris: subsiding of chest pain, decrease
of blood pressure, increase of heart rate, and orthostatic
hypotension. Patients experiencing angina when doing certain physical
activities can often prevent symptoms by taking nitroglycerin 5 to 10
minutes before the activity. Overdoses may generate
Nitroglycerin is available in tablets, ointment, solution for
intravenous use, transdermal patches, or sprays administered
sublingually. Some forms of nitroglycerin last much longer in the body
than others. It has been shown that continuous exposure to nitrates
can cause the body to stop responding normally to this medicine.
Experts recommend that the patches be removed at night, allowing the
body a few hours to restore its responsiveness to nitrates.
Shorter-acting preparations of nitroglycerin can be used several times
a day with less risk of developing tolerance.
first used by
William Murrell to treat angina attacks in 1878, with
the discovery published that same year.
Infrequent exposure to high doses of nitroglycerin can cause severe
headaches known as "NG head" or "bang head". These headaches can be
severe enough to incapacitate some people; however, humans develop a
tolerance to and dependence on nitroglycerin after long-term exposure.
Withdrawal can (rarely) be fatal; withdrawal symptoms include
chest pain and heart problems and if unacceptable may be treated with
re-exposure to nitroglycerin or other suitable organic nitrates.
For workers in nitroglycerin (NTG) manufacturing facilities, the
effects of withdrawal sometimes include "Sunday
Heart Attacks" in
those experiencing regular nitroglycerin exposure in the workplace,
leading to the development of tolerance for the venodilating effects.
Over the weekend, the workers lose the tolerance and, when they are
re-exposed on Monday, the drastic vasodilation produces a fast heart
rate, dizziness, and a headache, this is referred to as "Monday
People can be exposed to nitroglycerin in the workplace by breathing
it in, skin absorption, swallowing it, or eye contact. The
Occupational Safety and Health Administration
Occupational Safety and Health Administration (OSHA) has set the legal
limit (permissible exposure limit) for nitroglycerin exposure in the
workplace as 0.2 ppm (2 mg/m3) skin exposure over an 8-hour
workday. The National Institute for Occupational Safety and Health
(NIOSH) has set a recommended exposure limit (REL) of 0.1 mg/m2
skin exposure over an 8-hour workday. At levels of 75 mg/m3,
nitroglycerin is immediately dangerous to life and health.
Ethylene glycol dinitrate
List of investigational sexual dysfunction drugs
^ a b
^ "NIOSH Pocket Guide to Chemical Hazards #0456". National Institute
for Occupational Safety and Health (NIOSH).
^ "Hazard Rating Information for NFPA Fire Diamonds". Archived from
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Kitagawa, K; Nakayama, KI; et al. (2005). "An essential role for
mitochondrial aldehyde dehydrogenase in nitroglycerin bioactivation".
Proc. Natl. Acad. Sci. USA. 102 (34): 12159–12164.
PMC 1189320 . PMID 16103363.
^ Sobrero, Ascagne (1847) "Sur plusieur composés détonants produits
avec l'acide nitrique et le sucre, la dextrine, la lactine, la mannite
et la glycérine" (On several detonating compounds produced with
nitric acid and sugar, dextrin, lactose, mannitol, and glycerine),
Comptes rendus, 24 : 247–248.
^ Sobrero, Ascanio (1849) "Sopra alcuni nuovi composti fulminanti
ottenuti col mezzo dell’azione dell’acido nitrico sulle sostante
organiche vegetali" (On some new explosive products obtained by the
action of nitric acid on some vegetable organic substances), Memorie
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195–201. On p. 197, Sobrero names nitroglycerine "pyroglycerine":
"Quelle gocciole costituiscono il corpo nuovo di cui descriverò ora
le proprietà, e che chiamerò Piroglicerina." (Those drops constitute
the new substance whose properties I will now describe, and which I
will call "pyroglycerine".)
^ NobelPrize.org: Emil Nobel.
^ NobelPrize.org: Krümmel Archived 10 July 2006 at the Wayback
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Nitroglycerin as a remedy for angina
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Alfred Nobel and the History of Dynamite". About.com
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WebBook page for C3H5N3O9
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The Tallini Tales of Destruction Detailed and horrific stories of the
historical use of nitroglycerin-filled torpedoes to restart petroleum
Dynamite and TNT at
The Periodic Table of Videos
The Periodic Table of Videos (University of
Nitric oxide signaling modulators
Nitroxyl anion (NO−; oxonitrate(1-), hyponitrite anion)
Nitric oxide (NO⋅; nitrogen monoxide)
Nitrosonium (NO+; nitrosyl cation)
Cinaciguat (BAY 58-2667)
Riociguat (BAY 63-2521)
Diethylene glycol dinitrate
Diethylene glycol dinitrate (DEGDN)
Erythritol tetranitrate (ETN)
Ethylene glycol dinitrate
Ethylene glycol dinitrate (EGDN; nitroglycol)
Isosorbide mononitrate (ISMN)
Isosorbide dinitrate (ISDN)
Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)
Nitroglycerin (glyceryl trinitrate (GTN))
Pentaerithrityl tetranitrate (PETN)
Propylene glycol dinitrate
Propylene glycol dinitrate (PGDN)
Sodium trioxodinitrate (Angeli's salt)
2); O-Nitroso compounds (alkyl nitrites):
Amyl nitrite (isoamyl
nitrite, isopentyl nitrite)
Isobutyl nitrite (2-methylpropyl nitrite)
tert-Butyl nitrite; S-Nitroso compounds (thionitrites): LA810
S-Nitrosocysteine (SNC, CysNO, SNO-Cys)
S-Nitrosoglutathione (GSNO, SNOG)
SNO-vWF; N-Nitroso compounds (e.g., nitrosamines): SIN-1A
Nitrosyl compounds: Metal nitrosyl complexes: Roussin's black salt
Roussin's red salt
Sodium nitroprusside (SNP)
NONOates (diazeniumdiolates): Diethylamine/NO (DEA/NO)
Methylamine hexamethylene methylamine/NO (MAHMA/NO)
Heterocyclic compounds: Furoxans: Furoxan
REC15/2739; Sydnonimines: Feprosidnine
Nitroarginine (NNA, NOARG)
Nitroarginine (NNA, NOARG)
Asymmetric dimethylarginine (ADMA)
Nitroarginine methyl ester (NAME)
Indirect/downstream NO modulators: ACE inhibitors/AT-II receptor
antagonists (e.g., captopril, losartan)
ETB receptor antagonists (e.g., bosentan)
L-Type calcium channel
L-Type calcium channel blockers (e.g., dihydropyridines: nifedipine)
Nebivolol (beta blocker)
PDE5 inhibitors (e.g., sildenafil)
Statins (e.g., simvastatin)
See also: Receptor/signaling modulators