Pentaerythritol tetranitrate (T3D0265)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (10)XML
Targets (10)
Record Information
Version2.0
Creation Date2009-03-06 18:58:24 UTC
Update Date2014-12-24 20:21:26 UTC
Accession NumberT3D0265
Identification
Common NamePentaerythritol tetranitrate
ClassSmall Molecule
DescriptionPentaerythritol 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.
Compound Type
  • Explosive Agent
  • Household Toxin
  • Industrial/Workplace Toxin
  • Nitrate
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1,3-Dinitrato-2,2-bis(nitratomethyl)propane
1-3 Propanediol,2,2-bis(nitroxy)methyl-dinitrate ester
2,2-Bis((nitrooxy)methyl)-1,3-propanediol dinitrate
2,2-Bis((nitrooxy)methyl)-1,3-propanediol dinitrate (ester)
2,2-Bis((nitrooxy)methyl)-1,3-propanediol dinitrate ester
2,2-Bis(Hydroxymethyl)-1,3-propanediol tetranitrate
2,2-Bisdihydroxymethyl-1,3-propanediol tetranitrate
2,2-Bis[(nitrooxy)methyl]-1,3-propanediol dinitrate (ester)
3-(Nitrooxy)-2,2-bis[(nitrooxy)methyl]propyl nitrate
Angicap
Angitet
Antora
Arcotrate
Baritrate
Cardiacap
CHOT
Corpent
Delt rate-20
Deltrate 20
Deltrate-20
Dilcoran
Dilcoran 80
Dilcoran-80
Dipentrate
Duotrate
El petn
Erinit
Erynitum
Extex
Hasethrol
Kaytrate
Lentrat
Lowetrate
LX 16 (explosive)
Martrate 45
Martrate-45
Metranil
Mikardol
Miltrate
Mixture name
Mycardol
Myotrate 10
Neo-corovas
Neopentanetetrayl nitrate
Nexol-e
Nicochloran
Niperyt
Niperyth
Nirason
Nitrin
Nitrinal
Nitrine
Nitrinol
Nitro-riletten
Nitrodex
Nitrolong
Nitropent
Nitropenta
Nitropenta 7W
Nitropentaerythrite
Nitropentaerythritol
Nitropenton
Nitrotalans
Omnitox
Ovadziak
P.E.T.N.
Pen-tetra
Pencard
PENT
Penta
Pentaerithrityl tetranitrate
Pentaerythrite tetranitrate
Pentaerythritol nitrate
Pentaerythritol tetran
Pentaerythritol tetranitrate with D-lactose monohydrate
Pentaerythritol tetranitrate, diluted
Pentaerythritol tetranitric acid
Pentaerythrityl tetranitrate
Pentaerythritylium tetranitricum
Pentafilin
Pentafin
Pentalog
Pentanitrine
Pentanitrol
Pentanitrolum
Pentarit
Pentestan-80
Pentetrate unicelles
Penthrit
Penthrite
Pentitrate
Pentral 80
Pentran
Pentrate
Pentrinat
Pentriol
Pentrite
Pentritol
Pentritol tempules
Pentryate
Pentryate 80
Pergitral
Peridex
Peridex-la
Peritrate
Perityl
PET
PETN
Petn, NF
Prevangor
Quintrate
Rythritol
Subicard
Tanipent
TEN
Tentrate-20
Terpate
Tetranitrate, pentaerythritol
Tetranitropentaerythritol
Tetrasule
Tetrate
Tranite d-lay
Vanguard brand of pentaerythritol tetranitrate
Vasitol
Vaso-80
Vaso-80 unicelies
Vaso-80 Unicelles
Vasodiatol
Vasolat
Chemical FormulaC5H8N4O12
Average Molecular Mass316.137 g/mol
Monoisotopic Mass316.014 g/mol
CAS Registry Number1978-11-05
IUPAC Name3-(nitrooxy)-2,2-bis[(nitrooxy)methyl]propyl nitrate
Traditional Namepentaerythritol tetranitrate
SMILES[O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O
InChI IdentifierInChI=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 KeyInChIKey=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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganic oxoanionic compounds
Sub ClassOrganic nitrates
Direct ParentAlkyl 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 FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point140.5°C
Boiling PointNot Available
Solubility0.043 mg/mL at 25°C [RINKENBACK,WH (1965)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP1.62ALOGPS
logP0.96ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area220.2 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity58.5 m³·mol⁻¹ChemAxon
Polarizability22.47 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-0009000000-9271f398a2613e45f1c42021-09-24View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-68a44f733aacfc2a316d2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0009000000-185ffab1386913b390162016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066s-3039000000-22fcdf0636286b159cca2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-eda307067ca65e9d68b02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1009000000-d1a266dd956e911a5f342016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-8159000000-d0a1089c0acf2a27da5c2016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-004j-9000000000-14fe59ae096adb8f0c172014-09-20View Spectrum
Toxicity Profile
Route of ExposureOral (6) ; Dermal (6) ; inhalation (6)
Mechanism of ToxicityNitrate'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, 5)
MetabolismIntake 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. (4)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (2)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNitrate and nitrite poisoning causes methemoglobinemia. Nitrites may cause pregnancy complications and developmental effects. They may also be carcinogenic. (4)
SymptomsNitrate 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. (4)
TreatmentMethemoglobinemia 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. (5)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID6518
ChEMBL IDCHEMBL466659
ChemSpider IDNot Available
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID25520
BioCyc IDNot Available
CTD IDNot Available
Stitch IDPentaerythritol tetranitrate
PDB IDNot Available
ACToR ID1133
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0265.pdf
General References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  3. International Programme on Chemical Safety (IPCS) INCHEM (1989). Poison Information Monograph for Endosulfan. [Link]
  4. ATSDR - Agency for Toxic Substances and Disease Registry (2007). Case Studies in Environmental Medicine. Nitrate/Nitrite Toxicity. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  5. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
  6. Wikipedia. Fentin acetate. Last Updated 30 March 2009. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

Target Details
1. Hemoglobin subunit alpha
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBA1
Uniprot ID:
P69905
Molecular Weight:
15257.405 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
2. Hemoglobin subunit beta
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an endogenous inhibitor of enkephalin-degrading enzymes such as DPP3, and as a selective antagonist of the P2RX3 receptor which is involved in pain signaling, these properties implicate it as a regulator of pain and inflammation.
Gene Name:
HBB
Uniprot ID:
P68871
Molecular Weight:
15998.34 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
3. Hemoglobin subunit delta
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBD
Uniprot ID:
P02042
Molecular Weight:
16055.41 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
4. Hemoglobin subunit epsilon
General Function:
Oxygen transporter activity
Specific Function:
The epsilon chain is a beta-type chain of early mammalian embryonic hemoglobin.
Gene Name:
HBE1
Uniprot ID:
P02100
Molecular Weight:
16202.71 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
5. Hemoglobin subunit gamma-1
General Function:
Oxygen transporter activity
Specific Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Gene Name:
HBG1
Uniprot ID:
P69891
Molecular Weight:
16140.37 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
6. Hemoglobin subunit gamma-2
General Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Specific Function:
Heme binding
Gene Name:
HBG2
Uniprot ID:
P69892
Molecular Weight:
16126.35 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
7. Hemoglobin subunit mu
General Function:
Oxygen transporter activity
Specific Function:
Not Available
Gene Name:
HBM
Uniprot ID:
Q6B0K9
Molecular Weight:
15617.97 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
8. Hemoglobin subunit theta-1
General Function:
Oxygen transporter activity
Specific Function:
Not Available
Gene Name:
HBQ1
Uniprot ID:
P09105
Molecular Weight:
15507.575 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
9. Hemoglobin subunit zeta
General Function:
Oxygen transporter activity
Specific Function:
The zeta chain is an alpha-type chain of mammalian embryonic hemoglobin.
Gene Name:
HBZ
Uniprot ID:
P02008
Molecular Weight:
15636.845 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
10. Estrogen receptor
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC502.31 uMACEA_T47D_80hr_PositiveACEA Biosciences
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]