ContaminantDB: Pentaerythritol tetranitrate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (10)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:24 UTC

Update Date

2026-05-14 18:18:10 UTC

Accession Number

CHEM000228

Identification

Common Name

Pentaerythritol tetranitrate

Class

Small Molecule

Description

Pentaerythritol tetranitrate (PETN), also known as PENT, PENTA, TEN, corpent, penthrite is the nitrate ester of pentaerythritol, and is structurally very similar to nitroglycerin. PETN is best known as an explosive. It is one of the most powerful high explosives known. PETN mixed with a plasticizer forms a plastic explosive. It is also used as a vasodilator drug to treat certain heart conditions, such as for management of angina. PETN works by releasing the signaling gas nitric oxide in the body. The heart medicine Lentonitrat is nearly pure PETN. Monitoring of oral usage of the drug by patients can be performed by determination of plasma levels of several of its hydrolysis products, pentaerythritol dinitrate, pentaerythritol mononitrate and pentaerythritol, in plasma using gas chromatography-mass spectrometry.

Contaminant Sources

EAFUS Chemicals
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Explosive Agent
Household Toxin
Industrial/Workplace Toxin
Nitrate
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,3-Dinitrato-2,2-bis(nitratomethyl)propane	ChEBI
2,2-Bis((nitrooxy)methyl)-1,3-propanediol dinitrate	ChEBI
2,2-Bis((nitrooxy)methyl)-1,3-propanediol dinitrate ester	ChEBI
2,2-Bis(hydroxymethyl)-1,3-propanediol tetranitrate	ChEBI
3-(Nitrooxy)-2,2-bis[(nitrooxy)methyl]propyl nitrate	ChEBI
Corpent	ChEBI
Neopentanetetrayl nitrate	ChEBI
Nitropenta	ChEBI
Nitropentaerythrite	ChEBI
Nitropentaerythritol	ChEBI
PENT	ChEBI
Pentaerithrityl tetranitrate	ChEBI
Pentaerithrityli tetranitras	ChEBI
Pentaerythritylium tetranitricum	ChEBI
Penthrite	ChEBI
PETN	ChEBI
TEN	ChEBI
Tetranitrate de pentaerithrityle	ChEBI
Tetranitrato de pentaeritritilo	ChEBI
Tetranitropentaerythritol	ChEBI
Pentritol tempules	Kegg
2,2-Bis((nitrooxy)methyl)-1,3-propanediol dinitric acid	Generator
2,2-Bis((nitrooxy)methyl)-1,3-propanediol dinitric acid ester	Generator
2,2-Bis(hydroxymethyl)-1,3-propanediol tetranitric acid	Generator
3-(Nitrooxy)-2,2-bis[(nitrooxy)methyl]propyl nitric acid	Generator
Neopentanetetrayl nitric acid	Generator
Pentaerithrityl tetranitric acid	Generator
Tetranitric acid de pentaerithrityle	Generator
Pentaerythritol tetranitric acid	Generator
Erinit	MeSH
Parke davis brand OF pentaerythritol tetranitrate	MeSH
Tetranitrate, pentaerythritol	MeSH
Alpharma brand OF pentaerythritol tetranitrate	MeSH
Dilcoran	MeSH
Nirason	MeSH
Ravensberg brand OF pentaerythritol tetranitrate	MeSH
Tetrate	MeSH
Vanguard brand OF pentaerythritol tetranitrate	MeSH
dexo Brand OF pentaerythritol tetranitrate	MeSH
Nitrodex	MeSH
Pentalog	MeSH
Peritrate	MeSH

Chemical Formula

C₅H₈N₄O₁₂

Average Molecular Mass

316.137 g/mol

Monoisotopic Mass

316.014 g/mol

CAS Registry Number

1978-11-05

IUPAC Name

3-(nitrooxy)-2,2-bis[(nitrooxy)methyl]propyl nitrate

Traditional Name

pentaerythritol tetranitrate

SMILES

[O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O

InChI Identifier

InChI=1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2

InChI Key

TZRXHJWUDPFEEY-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alkyl nitrates. These are organic compounds containing a nitrate that is O-linked to an alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organic oxoanionic compounds

Sub Class

Organic nitrates

Direct Parent

Alkyl nitrates

Alternative Parents

Substituents

Alkyl nitrate
Organic nitro compound
Organic nitric acid or derivatives
Organic 1,3-dipolar compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

pentaerythritol nitrate (CHEBI:25879 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

vasodilator agent

Biological Roles

Not Available

Chemical Roles

explosive

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	140.5°C
Boiling Point	Not Available
Solubility	0.043 mg/mL at 25°C [RINKENBACK,WH (1965)]

Predicted Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	1.62	ALOGPS
logP	0.96	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	220.2 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	58.5 m³·mol⁻¹	ChemAxon
Polarizability	22.47 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0009000000-9271f398a2613e45f1c4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-68a44f733aacfc2a316d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0009000000-185ffab1386913b39016	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066s-3039000000-22fcdf0636286b159cca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-eda307067ca65e9d68b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1009000000-d1a266dd956e911a5f34	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-016r-8159000000-d0a1089c0acf2a27da5c	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004j-9000000000-14fe59ae096adb8f0c17	Spectrum

Toxicity Profile

Route of Exposure

Oral (4) ; Dermal (4) ; inhalation (4)

Mechanism of Toxicity

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. (1, 6)

Metabolism

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. (5)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity (not listed by IARC). (2)

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Nitrate and nitrite poisoning causes methemoglobinemia. Nitrites may cause pregnancy complications and developmental effects. They may also be carcinogenic. (5)

Symptoms

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. (5)

Treatment

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. (6)

Concentrations

Not Available

External Links

DrugBank ID

DB06154

HMDB ID

HMDB0256253

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Pentaerythritol_tetranitrate

Chemspider ID

6271

ChEBI ID

25879

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Pentaerythritol tetranitrate (CHEM000228)

Structure for CHEM000228: Pentaerythritol tetranitrate