Pentaerythritol tetranitrate

For research use only. Not for therapeutic Use.

  • CAT Number: I034400
  • CAS Number: 78-11-5
  • Molecular Formula: C5H8N4O12
  • Molecular Weight: 316.14
  • Purity: 98%
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Pentaerythritol tetranitrate (PETN)(Cat No.:I034400)is a powerful organic nitrate compound used primarily as an explosive and in medical applications. It is known for its high explosive velocity and stability, making it valuable in military and industrial explosives, such as dynamite and detonators. In medicine, PETN is sometimes used as a vasodilator to treat conditions like angina, as it can help relax blood vessels and improve blood flow. PETN is chemically similar to nitroglycerin, but with greater stability, making it safer for handling in certain applications.


Catalog Number I034400
CAS Number 78-11-5
Synonyms

Pentaerythritol tetranitrate; HSDB6313; HSDB-6313; HSDB 6313

Molecular Formula C5H8N4O12
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name [3-nitrooxy-2,2-bis(nitrooxymethyl)propyl] nitrate
InChI 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
InChIKey TZRXHJWUDPFEEY-UHFFFAOYSA-N
SMILES C(C(CO[N+](=O)[O-])(CO[N+](=O)[O-])CO[N+](=O)[O-])O[N+](=O)[O-]
Reference

1: Friedrich EB, Böhm M. Pentaerythrityltetranitrat [Pentaerythritol tetranitrate]. Dtsch Med Wochenschr. 2006 Apr 7;131(14):749-50. German. doi: 10.1055/s-2006-933726. PMID: 16596492.
2: Schuhmacher S, Wenzel P, Schulz E, Oelze M, Mang C, Kamuf J, Gori T, Jansen T, Knorr M, Karbach S, Hortmann M, Mäthner F, Bhatnagar A, Förstermann U, Li H, Münzel T, Daiber A. Pentaerythritol tetranitrate improves angiotensin II-induced vascular dysfunction via induction of heme oxygenase-1. Hypertension. 2010 Apr;55(4):897-904. doi: 10.1161/HYPERTENSIONAHA.109.149542. Epub 2010 Feb 15. PMID: 20157049; PMCID: PMC3080599.
3: Klapötke TM, Krumm B, Unger CC. Energetic Metal and Nitrogen-Rich Salts of the Pentaerythritol Tetranitrate Analogue Pentaerythritol Tetranitrocarbamate. Inorg Chem. 2019 Feb 18;58(4):2881-2887. doi: 10.1021/acs.inorgchem.8b03540. Epub 2019 Jan 31. PMID: 30702272.
4: Üzer A, Yalçın U, Can Z, Erçağ E, Apak R. Indirect Determination of Pentaerythritol Tetranitrate (PETN) with a gold nanoparticles-based colorimetric sensor. Talanta. 2017 Dec 1;175:243-249. doi: 10.1016/j.talanta.2017.06.049. Epub 2017 Jun 20. PMID: 28841986.
5: Wu Z, Siuda D, Xia N, Reifenberg G, Daiber A, Münzel T, Förstermann U, Li H. Maternal treatment of spontaneously hypertensive rats with pentaerythritol tetranitrate reduces blood pressure in female offspring. Hypertension. 2015 Jan;65(1):232-7. doi: 10.1161/HYPERTENSIONAHA.114.04416. Epub 2014 Nov 10. PMID: 25385760.
6: Taefi Z, Ghasemi F, Hormozi-Nezhad MR. Selective colorimetric detection of pentaerythritol tetranitrate (PETN) using arginine-mediated aggregation of gold nanoparticles. Spectrochim Acta A Mol Biomol Spectrosc. 2020 Mar 5;228:117803. doi: 10.1016/j.saa.2019.117803. Epub 2019 Nov 16. PMID: 31761546.
7: Steven S, Oelze M, Brandt M, Ullmann E, Kröller-Schön S, Heeren T, Tran LP, Daub S, Dib M, Stalleicken D, Wenzel P, Münzel T, Daiber A. Pentaerythritol Tetranitrate In Vivo Treatment Improves Oxidative Stress and Vascular Dysfunction by Suppression of Endothelin-1 Signaling in Monocrotaline-Induced Pulmonary Hypertension. Oxid Med Cell Longev. 2017;2017:4353462. doi: 10.1155/2017/4353462. Epub 2017 Feb 28. PMID: 28337251; PMCID: PMC5350298.
8: Wang B, Huang W, Zhou J, Tang X, Chen Y, Peng C, Han B. Drug design based on pentaerythritol tetranitrate reductase: synthesis and antibacterial activity of Pogostone derivatives. Org Biomol Chem. 2017 Aug 9;15(31):6548-6556. doi: 10.1039/c7ob01429e. PMID: 28745773.
9: Brust H, van Asten A, Koeberg M, van der Heijden A, Kuijpers CJ, Schoenmakers P. Pentaerythritol tetranitrate (PETN) profiling in post-explosion residues to constitute evidence of crime-scene presence. Forensic Sci Int. 2013 Jul 10;230(1-3):37-45. doi: 10.1016/j.forsciint.2013.03.042. Epub 2013 Apr 23. PMID: 23622790.
10: Mullen M, Giordano BC. Part per quadrillion quantitation of pentaerythritol tetranitrate vapor using online sampling gas chromatography-mass spectrometry. J Chromatogr A. 2019 Oct 11;1603:407-411. doi: 10.1016/j.chroma.2019.05.029. Epub 2019 May 15. PMID: 31126591.

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