Pentaerithrityltetranitrat

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

1.773 at 20 °C/4 °C

1.77 g/cm³

1.773 @ 20°C

Tetragonal holohedra from acetone + alcohol

White crystalline

Tetragonal (acetone) prisms (acetone-alcohol)

less than 1 mg/mL at 72 °F (NTP, 1992)

Soluble in acetone. Sparingly soluble in alcohol, ether

Very soluble in acetone

Soluble in benzene, pyrene

Soluble in toluene; slightly soluble in methanol

Explodes at 205-215 °C

BP: 180 °C at 50 mm Hg

140.5 °C

138 °C

0.00000014 [mmHg]

1.36X10-7 mm Hg at 25 °C

Vapor pressure at 25 °C: negligible

Danger

H200: (Deleted) Unstable Explosive [Danger Explosives]

P201, P202, P281, P372, P373, P380, P401, and P501 (click each P-code to see the statement)

Danger

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

P210, P230, P240, P250, P280, P370+P380, P372, P373, P401, and P501 (click each P-code to see the statement)

Chemical: 1,3-Propanediol, 2,2-bis[(nitrooxy)methyl]-, dinitrate (ester)

1,3-Propanediol, 2,2-bis[(nitrooxy)methyl]-, 1,3-dinitrate is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Propanediol, 2,2-bis[(nitrooxy)methyl]-, 1,3-dinitrate 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)

Status: Active Update: 01-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13791

Pentaerythritol tetranitrate: Does not have an individual approval but may be used under an appropriate group standard

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.)

Explosive 1.1D

Explosive 1.1D

Explosive 1.1D

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

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

Flash point data for this compound are not available. It is probably combustible. (NTP, 1992)

Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion. Explosive.

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

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

SYMPTOMS: Symptoms of exposure to this compound may include a decrease in blood pressure, dyspnea, convulsions, cyanosis, headache, dizziness, postural hypotension, weakness, nausea, vomiting, pallor, sweating, collapse, rashes, coma, respiratory paralysis and formation of methemoglobin.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

DHHS/NTP; Toxicology and Carcinogenesis Studies of Pentaerythritol Tetranitrate (CAS No. 78-11-5) with 80% D-Lactose Monohydrate (PETN, NF) in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 365 (1989) NIH Publication No. 89-2820[Available from, as of April 4, 2003: http://ntp.niehs.nih.gov/ntp/htdocs/LT_rpts/tr365.pdf]

IPCS/Commission of the European Communities; International Chemical Safety Card on Pentaerythritol tetranitrate (April 2005).[Available from, as of December 30, 2009: http://www.inchem.org/pages/icsc.html]

D003; A solid waste containing pentaerythritol tetranitrate may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste.

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

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

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

In case of fire in the surroundings, use appropriate extinguishing media. Combat fire from a sheltered position.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

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

Rinse mouth. Refer for medical attention .

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

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

EYES: Check for contact lenses and remove them at once if present. You should then immediately flush eyes with water for 15 minutes. Do not use oil or ointment in eyes. Arrange immediate transportation to a medical facility.

If material on fire or involved in fire: use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Do not use water, dry chemical, or foam. Do not extinguish fire unless flow can be stopped. /Pentaerythrite tetranitrate mixture, desensitized, solid, n.o.s./

If material on fire or involved in fire: dangerously explosive. Do not fight fires in a cargo of explosives. Evacuate area and let burn. /Pentaerythrite tetranitrate; Pentaerythrite tetranitrate, wetted/

Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Pentaerythrite tetranitrate; Pentaerythrite tetranitrate, wetted/

In case of fire in the surroundings: use appropriate extinguishing media. Combat fire from a sheltered position.

Fireproof. Separated from strong oxidants. Store in an area without drain or sewer access.

Store below 40 °C (104 °F), preferably between 15 and 30 °C (59 and 86 °F), unless otherwise specified by manufacturer. Store in a tight container.

Store in a cool place in an airtight container. Protect from light.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Evacuate danger area! Consult an expert! ... Remove all ignition sources. Cover the spilled material with water. Carefully collect remainder, then remove to safe place. Do NOT wash away into sewer.

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

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

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

Evacuate danger area! Consult an expert! Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Remove all ignition sources. Cover the spilled material with water. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

SRP: Contaminated protective clothing should be segregated in a manner so that results in no direct personal contact by personnel who handle, dispose of, or clean the clothing. Quality assurance procedures to confirm the efficacy of the cleaning procedures should be implemented prior to the decontaminated protective clothing being returned for reuse by the workers. Contaminated clothing (including shoes/socks) should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

If material not on fire and not involved in fire: keep sparks, flames, and other sources of ignition away. Keep spilled material wet. Wet spilled material before picking it up. Do not attempt to sweep up dry material. /Pentaerythrite tetranitrate; Pentaerythrite tetranitrate, wetted/

If material not on fire and not involved in fire: keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. /Pentaerythrite tetranitrate mixture, desensitized, solid, n.o.s./

For more Preventive Measures (Complete) data for Pentaerythritol tetranitrate (11 total), please visit the HSDB record page.

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

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

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

Methemoglobinemia can be treated with supplemental oxygen and methylene blue 1% solution administered intravenously slowly over five minutes followed by IV flush with normal saline. Methylene blue restores the iron in hemoglobin to its normal (reduced) oxygen-carrying state. (L1613)

This study examined whether pentaerythrityl tetranitrate (PETN), a tolerance-devoid exogenous donor of nitric oxide (NO), could attenuate functional and morphological changes in the rat thoracic aorta evoked by 6-week NO synthase inhibition by NG-nitro-L-arginine methyl ester (L-NAME). Systolic blood pressure in L-NAME + PETN-treated rats (163 +/- 1 mm Hg) was significantly lower than in L-NAME-treated rats (172 +/- 2 mm Hg) but was still higher than in age-matched controls (126 +/- 2 mm Hg). Six weeks of treatment of rats with L-NAME significantly inhibited endothelium-dependent relaxation of the isolated thoracic aorta induced by acetylcholine. The inhibitory effect of L-NAME was entirely reversed by the simultaneous treatment with PETN. The enhancing effect of L-NAME on noradrenaline-induced contraction was antagonised by long-term treatment with PETN. Wall thickness, cross-sectional area and wall/diameter ratio of the thoracic aorta in L-NAME-treated rats were markedly increased. In the L-NAME + PETN-treated rats, the increment of these parameters was significantly lower. The results suggest that PETN administered to rats during development of NO-deficient hypertension prevented functional impairment and at the same time reduced structural changes in the thoracic aorta induced by long-term inhibition of NO synthase.

The chronic admin of long acting nitrates had been reported to produce tolerance, thus decr the therapeutic effect of subsequently admin nitroglycerin. ... A pharmacologic study of ten patients demonstrated that a partial tolerance to nitroglycerin developed after as little as one week of pentaerythritol tetranitrate therapy. /Nitroglycerin interactions/

LC50; Species: Daphnia magna (Water flea, age <24 hr); Conditions: freshwater, static, 22 °C; Concentration: 9,700 mg/L for 24 hr (95% confidence interval: 7,500-12,600 mg/L) /formulated product/

LC50; Species: Daphnia magna (Water flea, age <24 hr); Conditions: freshwater, static, 22 °C; Concentration: 8,500 mg/L for 48 hr (95% confidence interval: 5,800-12,400 mg/L) /formulated product/

LC50; Species: Pimephales promelas (Fathead minnow, weight 1 g, length 43 mm); Conditions: freshwater, static, 21 °C, pH 7.1, hardness 35 mg/L CaCO3; Concentration: 27,000 mg/L for 96 hr (95% confidence interval: 9,500-76,000 mg/L) /formulated product/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 650(SRC), determined from a structure estimation method(2), indicates that pentaerythritol tetranitrate is expected to have low mobility in soil(SRC). Volatilization of pentaerythritol tetranitrate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-9 atm-cu m/mole(SRC), derived from its vapor pressure of 1.36X10-7 mm Hg(3) and water solubility of 43 mg/L(4). Pentaerythritol tetranitrate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Microbial cultures isolated from soil and sewage sludge were capable of utilizing pentaerythritol tetranitrate as a sole nitrogen source(5,6), suggesting that pentaerythritol tetranitrate may biodegrade in the terrestrial environment(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 650(SRC), determined from a structure estimation method(2), indicates that pentaerythritol tetranitrate 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 1.3X10-9 atm-cu m/mole(SRC), derived from its vapor pressure of 1.36X10-7 mm Hg(4) and water solubility of 43 mg/L(5). According to a classification scheme(6), an estimated BCF of 17(SRC), from an estimated log Kow of 2.4(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Microbial cultures isolated from river water and sewage sludge were capable of utilizing pentaerythritol tetranitrate as a sole nitrogen source(9), suggesting that pentaerythritol tetranitrate may biodegrade in the aquatic environment(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pentaerythritol tetranitrate, which has a vapor pressure of 1.36X10-7 mm Hg at 25 °C(2), is expected to partially exist in the particulate phase and the vapor phase in the ambient atmosphere. Vapor-phase pentaerythritol tetranitrate will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 9.9 days, calculated from its rate constant of 1.6X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase pentaerythritol tetranitrate may be removed from the air by wet or dry deposition(SRC). Pentaerythritol tetranitrate contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

The substance can be absorbed into the body by inhalation and by ingestion.

Oral (L313) ; Dermal (L313) ; inhalation (L313)

Nitrate's toxicity is a result of it's conversion to nitrite once in the body. Nitrite causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen. (A2450, L1613)

Dizziness. Headache.

Redness.

Dizziness. Headache.

Nitrate and nitrite poisoning causes methemoglobinemia. Symptoms include cyanosis, cardiac dysrhythmias and circulatory failure, and progressive central nervous system (CNS) effects. CNS effects can range from mild dizziness and lethargy to coma and convulsions. (L1137)

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=78-11-5]

Using a structure estimation method based on molecular connectivity indices(1), the Koc of pentaerythritol tetranitrate can be estimated to be 650(SRC). According to a classification scheme(2), this estimated Koc value suggests that pentaerythritol tetranitrate is expected to have low mobility in soil.

/HUMAN EXPOSURE STUDIES/ Patch tests in 20 persons gave no evidence of skin irritation or sensitization. Although some cases of mild illness and dermatitis have been attributed to contact with PETN in ordnance plants, it is apparent that PETN is relatively nontoxic ...

/SIGNS AND SYMPTOMS/ No effect is observed in humans after 64 mg orally.

/SIGNS AND SYMPTOMS/ Tests on patients with open angle glaucoma and white eyes subject to angle closure glauocoma produced no elevation of intraocular pressure when an ordinary amount of drug was given by mouth as in the treatment of angina pectoris.

/SIGNS AND SYMPTOMS/ The acute effects of exposure to PETN are similar to those of nitroglycerin. Hypotension and increased respiratory rate may both occur, but to a lesser degree than is observed with nitroglycerin. In contrast to nitroglycerin, little reflex tachycardia is observed with PETN. Dyspnea and convulsions have also been reported.

For more Human Toxicity Excerpts (Complete) data for Pentaerythritol tetranitrate (13 total), please visit the HSDB record page.

D003; A solid waste containing pentaerythritol tetranitrate may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste.

PETN

A Commercial Grade

5000

A Commercial Grade

400

Explosive chemical that can be released at a facility.

C - Cardiovascular system

QC - Cardiovascular system

Organic nitrate which causes systemic vasodilation, decreasing cardiovascular preload. Nitrate enters vascular smooth muscle and converted to nitric oxide (NO) which acts as a cellular messenger, leading to activation of cyclic GMP and, therefore, vasodilation. The nitrovasodilator group of drugs relaxes most smooth muscles in the body, including those in the walls of arteries and veins, and selectively dilate large coronary vessels. Lower doses of nitrates increase coronary blood flow without significantly affecting systemic arterial pressure. Higher doses, especially if repeated frequently, decrease systolic and diastolic blood pressure as well as cardiac output, which can result in a headache, weakness, dizziness, and the activation of compensatory sympathetic reflexes, including tachycardia and peripheral arteriolar vasoconstriction. Smooth muscles in the bronchi, biliary tract, gastrointestinal tract, ureters, and uterus also can be relaxed by nitrovasodilators. PETN seems to be unique among the long-acting nitrovasodilators in that patients do not demonstrate tolerance to treatment, which results in sustained vasodilation in humans with continuous PETN treatment. Important to note is that this drug is devoid of induction of oxidative stress and related side-effects such as endothelial dysfunction or tolerance to nitrates. Some of these effects are related to special pharmacokinetics of PETN, but upon chronic administration, PETN also induces antioxidative pathways at the genomic level, resulting in increased expression of heme _oxygenase-1 (HO-1)_ _and ferritin_, both possessing highly protective properties. There is good experimental evidence that at least part of the beneficial profile of long-term treatment with this drug is based on the activation of the _heme oxygenase-1/ferritin_ system.

Pentaerythritol tetranitrate is the lipid soluble polyol ester of nitric acid belonging to the family of _nitro-vasodilators_. Pentaerythritol tetranitrate releases free nitric oxide (NO) after the denitration reaction, which triggers NO-dependent signaling transduction involving soluble _guanylate cyclase (sGC_). Nitric oxide binds reversibly to the ferrous-heme center of sGC, causing conformational change and activating the enzyme. This enzyme activation results in increased cellular concentrations of _cyclic guanosine monophosphate _(cGMP) within the vascular smooth muscle, resulting in vasodilation mediated by cGMP-dependent protein kinases. Additionally, this agent causes dose-dependent arterial and venous bed.

The nitrates reduce myocardial oxygen requirements through their effects on the systemic circulation. Their systemic actions include (1) a reduction in venous tone, which leads to pooling of blood in peripheral veins, decr venous return, and reduced ventricular volume and myocardial tension (preload); and (2) a decr in peripheral vascular resistance, which reduces arterial blood pressure and ventricular outflow resistance (afterload). /Nitrates/

Antianginal or cardiac load reducing agent: /Mechanism of action/ not specifically known but thought to cause a reduction of myocardial oxygen demand. This is attributed to a reduction in left ventricular preload and afterload because of venous (predominantly) and arterial dilation with a more efficient redistribution of blood flow within the myocardium. Antihypertensive: Peripheral vasodilation. /Nitrates (systemic)/

The basic mechanisms responsible for the vasodilatory and anti-ischemic action of organic nitrates involve bioactivation of, and nitric oxide (NO) release from, these compounds which have therefore been termed NO donors. The organic nitrate pentaerythritol tetranitrate (PETN) is known to possess antioxidant properties that are thought to be the underlying cause for its specific pharmacological profile. In contrast to other long-acting nitrates, PETN induces tolerance- free vasodilation in humans and was reported to prevent endothelial dysfunction as well as atherogenesis in cholesterol- fed rabbits. ... The active PETN metabolite PETriN stimulates protein expression of the antioxidant defense protein heme oxygenase-1 (HO-1). Additionally, PETriN enhanced the enzymatic activity of HO-1 measured as formation of the HO-1 metabolites bilirubin and carbon monoxide in lysates from endothelial cells. HO-1 induction subsequently led to a marked increase in protein expression of a second antioxidant protein, ferritin, via the HO-1-dependent release of free iron from endogenous heme sources. Pretreatment of endothelial cells with PETriN was followed by increased cellular resistance to oxidant injury mediated by hydrogen peroxide. Endothelial protection by PETriN was mimicked by exogenous bilirubin which led to an almost complete reversal of hydrogen peroxide-induced toxicity. Increased HO-1 and ferritin expression as well as endothelial protection occurred at micromolar concentrations of PETriN which are well within the range of plasma or tissue levels that can be expected during oral therapy. The capacity to protect the endothelium in vitro may translate into and explain the previously observed antiatherogenic actions of PETN in vivo. ... Moreover, in earlier investigations aimed at assessing the antiatherogenic potential of nitrates, PETN but not isosorbide nitrates prevented plaque formation and endothelial dysfunction in animal models of atherosclerosis. Thus, the ability to activate HO-1 induction and associated antioxidant pathways apparently distinguishes PETN from other long-acting nitrates and may explain their different patterns of action in vivo.

Nitrates vary in their potential to induce the development of tolerance. During long-lasting nitrate therapy, except pentaerythritol tetranitrate (PETN), one can observe the development of reactive oxygen species (ROS) inside the muscular cell of a vessel wall, and these bind with nitric oxide (NO). This leads to decreased NO activity, thus, nitrate tolerance. PETN has no tendency to form ROS, and therefore during long-term PETN therapy, there is probably no tolerance or cross-tolerance, as during treatment with other nitrates.

The elimination half-life in plasma from male volunteers given an oral 100-mg dose of the tetranitrate was reported to be 4-5 hours.

The elimination half-life in plasma from male volunteers given an oral 100-mg dose of the tetranitrate was reported to be 4-5 hours for the dinitrate and 10-11 hours for the mononitrate of pentaerythritol.

Extensively metabolized in the liver. Metabolites: pentaerythritol trinitrate, pentaerythritol dinitrate, pentaerythritol mononitrate, & pentaerythritol (inactive)

Rapid de-esterfication of pentaerythritol tetranitrate after po dosing to humans resulted in measurable serum levels of pentaerythritol, pentaerythritol pentaerythritol mononitrate, and small amt of the dinitrate, but no unchanged drug. The kinetics of urinary excretion of pentaerythritol tetranitrate were first-order and dose-dependent. The ratio of mononitrate to pentaerythritol excreted in urine was 3:1 from a 40 mg dose and 1:1 from a 20 mg dose, suggesting a limited capacity for conversion of pentaerythritol mononitrate into pentaerythritol.

The main metabolites were found to be pentaerythritol and the mononitrate ester; unchanged drug was recovered from feces only, suggesting a partial hydrolysis mediated by the intestinal microflora to be necessary prior to absorption /in man/.

Pentaerythritol tetranitrate is metabolized primarily to ... pentaerythritol trinitrate (pertrinitrol) ... . The trinitrate, dinitrate, and mononitrate metabolites may undergo glucuronide conjugation. The plasma half-life of pentaerythritol trinitrate, which is therapeutically active, is about 10 min. The other metabolites are inactive.

Intake of some amount of nitrates and nitrites is a normal part of the nitrogen cycle in humans. In vivo conversion of nitrates to nitrites can occur in the gastrointestional tract under the right conditions, significantly enhancing nitrates' toxic potency. The major metabolic pathway for nitrate is conversion to nitrite, and then to ammonia. Nitrites, nitrates, and their metabolites are excreted in the urine. (L1137)

Mainly the urine.

The steady-state volume of distribution was 4.2 +/- 1.1 L/kg (n = 6) in rats given this drug by the intra-arterial route.

In a pharmacokinetic study of rats after intra-arterial administration of this drug, the clearance was measured to be 0.61 +/- 0.16 L/min/kg.

During the first 4 hr after ... /pentaerythritol tetranitrate/ admin /in humans/ ... there were significant blood levels of pentaerythritol dinitrate.

PETN is absorbed slowly from the gastrointestinal tract and lung but not appreciably through the skin.

The systemic absorption of meprobamate, diphenhydramine and pentaerythritol tetranitrate (PETN) has been demonstrated following oral administration of a formulation containing all three drug substances to human volunteers. A study undertaken in dogs has also been made of the pharmacokinetics of the major nitrated metabolite of PETN when the parent drug is administered with and without meprobamate and diphenhydramine. Pentaerythritol mononitrate shows a six-fold increase in both peak plasma concentrations and area under the 0-12 hour plasma concentration-time curve when PETN is co-administered with a combination of meprobamate, diphenhydramine and nicotinic acid. No such increase is apparent when either meprobamate or diphenhydramine is excluded from the dose. Further increases in pentaerythritol mononitrate plasma levels and AUC 0-12 hr are observed when all of the drugs are administered as the formulated coated tablet (VisanoCor).

Used to manufacture detonating fuses (Primacord), blasting caps, and pharmaceuticals (vasodilators) [HSDB]

Mainly in the manufacture of detonating fuse (Primacord), a waterproof textile filled with powdered PETN.

Demolition explosive; blasting caps

...A component (mixed with hexahydro-1,2,5-trinitro-1,3,4-triazine) in "plastic" explosives such as Semtex.

Therapeutic Category: Vasodilator (coronary)

Prophylactic anginal attacks

2023: 9,214,345 lb

1,3-Propanediol, 2,2-bis[(nitrooxy)methyl]-, dinitrate (ester) is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).[EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program. 1,3-Propanediol, 2,2-bis

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5863]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,3-Propanediol, 2,2-bis[(nitrooxy)methyl]-, 1,3-dinitrate. Aggreated National Production Volume: 1 to <10 milliom lbs.[US EPA; Non-Confidential 2006 Inventory Update Reporting. National Chemical Information. 1,3-Propanediol, 2,2-bis

1,3-Propanediol, 2,2-bis[(nitrooxy)methyl]-, dinitrate (ester) is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).[EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program. 1,3-Propanediol, 2,2-bis

For more U.S. Production (Complete) data for Pentaerythritol tetranitrate (6 total), please visit the HSDB record page.

The nitration of pentaerythritol is practically complete in a few seconds and is conducted continuously. Pentaerythritol and HNO3 (ca. 1 : 5.5) are fed into a well-stirred, jacketed reactor, with overflow in cascade into a second reactor of the same design. The temperature is maintained below 30 °C. PETN precipitates and may be isolated in one of two ways: 1. In a third reactor the reaction mixture is diluted with water to 55 wt % acid and filtered. The PETN is washed with water. 2. The reaction mixture is filtered immediately and then the 82 wt % spent nitric acid is concentrated, a cheaper process but less safe. Washed PETN is stable. It can be recrystallized by dilution of a hot acetone solution with water, which removes traces of acid and some organic impurities, and crystals of desirable size and flow properties for continuous feed purposes are obtained.

The commercially important explosive pentaerythritol tetranitrate is produced by direct reaction of pentaerythritol in nitric or nitric-sulfuric acid media.

Pentaerythritol tetranitrate (PETN) is prepared either in batches or by continuously nitrating pentaerythritol (tetramethylolmethane), which is manufactured from formaldehyde and acetaldehyde.

Semtex and C4 (RDX/PETN plus a plasticizer)

For medicinal purposes it is diluted with an inert ingredient, usually lactose, to prevent accidental explosions.

Available in ... 20 and 40 mg tablets for sublingual use and in 30, 45, 60 ... mg sustained-release capsules.

Explosives Manufacturing

1,3-Propanediol, 2,2-bis[(nitrooxy)methyl]-, 1,3-dinitrate: ACTIVE

Alkyl mercury compounds have been used as seed disinfectants and for fungicides. They have also been used in organic synthesis. /Mercury alkyl compounds/

The types of explosives of which the public are most aware are the molecular high-explosives, which include trinitro-1,3,5-triazacyclohexane (RDX), 1,3,5,7-tetranitro-1,3,5,7-tetraza-cyclooctane (HMX), pentaerythritoltetranitrate (PETN), Semtex and C4 (RDX/PETN plus a plasticizer), trinitrotoluene (TNT) and its variants, nitroglycerin (NG), nitrocellulose (NC), 2,4,6-trinitro-phenylmethylnitramine (tetryl), and ethylene glycol dinitrate (EGDN). Developed as high-grade military explosives or for use in various industrial and commercial settings, their supply is highly restricted.

SEMTEX 1A is a plastic explosive for special use on the basis of an inexplosive plasticizer with penthrite as an active component. The explosives contain a marking substance for pre-explosive detection. SEMTEX 1H is a plastic explosive for special use on the basis of an inexplosive plasticizer with penthrite and hexogene as active components. SEMTEX 10 is a plastic explosive for special use on the basis of an inexplosive plasticizer with penthrite as an active component. They are used primarily for destruction works, underwater blasting works (up to 100 m), and special blasting works.

Pentaerythritol tetranitrate (PETN) is a military munitions pollutant.