1607-17-6

Basic information

• Product Name: pentrinitrol
• Synonyms: pentrinitrol;pentaerythritol trinitrate;3-Nitrooxy-2,2-bis(nitrooxymethyl)-1-propanol;Nitric acid 2,2-bis[(nitrooxy)methyl]-3-hydroxypropyl ester;Petrin;W-2197;[2-(hydroxymethyl)-3-nitrooxy-2-(nitrooxymethyl)propyl] nitrate;nitric acid [2-methylol-3-nitrooxy-2-(nitrooxymethyl)propyl] ester
• CAS NO: 1607-17-6
• Molecular Formula: C₅H₉N₃O₁₀
• Molecular Weight: 271.14
• EINECS: 216-529-7
• Mol File: 1607-17-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 32°
• Boiling Point: 278.7°Cat760mmHg
• Flash Point: 122.3°C
• Appearance: /
• Density: d420 1.554
• Vapor Pressure: 0.000513mmHg at 25°C
• Refractive Index: nD20 1.4941
• PKA: 14.07±0.10(Predicted)
• CAS DataBase Reference: pentrinitrol(CAS DataBase Reference)
• NIST Chemistry Reference: pentrinitrol(1607-17-6)
• EPA Substance Registry System: pentrinitrol(1607-17-6)

Safety Data

• RIDADR: 0473
• HazardClass: 1.1A
• PackingGroup: II
• Hazardous Substances Data: 1607-17-6(Hazardous Substances Data)

Usage

Uses

Vasodilator (coronary).

Brand name

Petrin (Parke-Davis).

Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating vapors.

InChI:InChI=1/C5H9N3O10/c9-1-5(2-16-6(10)11,3-17-7(12)13)4-18-8(14)15/h9H,1-4H2

Upstream product

• 78-11-5 Pentaerythritol tetranitrate 
• 92303-24-7 pentaerythrityl trinitrate acetate 
• 99-05-8 meta-aminobenzoic acid 
• 150-13-0 4-amino-benzoic acid 
• 121-47-1 3-aminobenzenesulfonic acid 
• 121-57-3 4-aminobenzene sulfonic acid 
• 115-77-5 Pentaerythritol 
• 260268-26-6 2,2-dimethyl-1-nitrooxy-2,2-bis(nitrooxymethyl)-4-oxa-5,5-diphenyl-5-silaheptane 
• 1522-92-5 2,2-bis(bromomethyl)-3-bromo-propan-1-ol 

Downstream Products

• 1607-00-7 pentaerythrityl mononitrate 
• 1607-01-8 2,2-bis(hydroxymethyl)propane-1,3-diol dinitrate 
• 1538580-28-7 (Z)-3-(nitrooxy)-2,2-bis((nitrooxy)methyl)propyl 2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetate 
• 1538580-33-4 (Z)-3-(nitrooxy)-2,2-bis((nitrooxy)methyl)propyl 5-fluoro-2-methyl-1-(4-(methylthio)benzylidene)-1H-inden-3-ylacetate 
• 1538580-38-9 (Z)-3-(nitrooxy)-2,2-bis((nitrooxy)methyl)propyl 2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetate 

Relevant articles and documents

Synthesis and biological evaluation of nitric oxide-donating analogues of sulindac for prostate cancer treatment

A series of analogues of the non-steroidal anti-inflammatory drug (NSAID) sulindac 1 were synthesised tethered to nitric oxide (NO) donating functional groups. Sulindac shows antiproliterative effects against immortal PC3 cell lines. It was previously demonstrated that the effect can be enhanced when tethered to NO releasing groups such as nitrate esters, furoxans and sydnonimines. To explore this approach further, a total of fifty-six sulindac-NO analogues were prepared and they were evaluated as NO-releasing cytotoxic agents against prostate cancer (PCa) cell lines. Compounds 1k and 1n exhibited significant cytotoxic with IC50 values of 6.1 ± 4.1 and 12.1 ± 3.2 μM, respectively, coupled with observed nitric oxide release.

Nitrostated and nitrosylated prostaglandins, compositions and methods of use

The present invention describes novel nitrosated and/or nitrosylated prostaglandins, and novel compositions comprising at least one nitrosated and/or nitrosylated prostaglandin, and, optionally, at least one compound that donates, transfers or releases nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor, stimulates endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase, and/or at least one vasoactive agent. The present invention also provides novel compositions comprising at least one prostaglandin and at least one S-nitrosothiol compound, and, optionally, at least one vasoactive agent. The prostaglandin is preferably a prostaglandin E1 compound, more preferably alprostadil, and the S-nitrosothiol compound is preferably S-nitrosoglutathione. The present invention also provides methods for treating or preventing sexual dysfunctions in males and females, for enhancing sexual responses in males and females, and for treating or preventing cerebrovascular disorders, cardiovascular disorders, benign prostatic hyperplasia (BPH), glaucoma, peptic ulcers or for inducing abortions. The compounds and/or compositions of the present invention can also be provided in the form of a pharmaceutical kit.

Pentaerythritol derivatives, their production and use and intermediates for their synthesis

The invention describes novel compounds derived from pentaerythritol of general formula I, XIV, XVI, XIX and XXII, the substituents being as defined in the description, which can be used as pharmaceutical active substances, especially for the treatment of cardiovascular diseases.