44:
241:
166:
35:
495:
500:
485:
490:
521:
524:
526:
631:
525:
739:
The
American chemist William Henry Rinkenbach (1894–1965) prepared EGDN by nitrating purified glycol obtained by fractioning the commercial product under pressure of 40mm Hg, and at a temperature of 120°. For this 20g of middle fraction of purified glycol was gradually added to mixture of 70g nitric
740:
acid and 130g sulfuric acid, maintaining the temperature at 23°. The resulting 49g of crude product was washed with 300ml of water to obtain 39.6g of purified product. The low yield so obtained could be improved by maintaining a lower temperature and using a different nitrating acid mixture.
982:
0%, OB to CO +21%; colorless volatile liquid when in pure state; yellowish liquid in crude state; sp gr 1.488 at 20/4° or 1.480 at 25°; n_D 1.4452 at 25° or 1.4472 at 20°; freezing point -22.75° (versus +13.1° for NG); frozen point given in is -22.3°; boiling point 199° at 760mm Hg (with
989:
by lead block compression (Hess crusher test) is 30.0 mm, versus 18.5 mm for NG and 16 mm for TNT (misleading, needs to give exact density and mass of explosive (25 or 50 g). Brisance by sand test, determined in mixtures with 40%
465:
747:
is carried out in exactly the same manner, with the same apparatus, and with the same mixed acids as nitration of glycerine. In the test nitration of anhydrous glycol (100g) with 625g of mixed acid
70:
Ethylene glycol dinitrate, Glycol dinitrate, Ethylene dinitrate, Ethylene nitrate, 1,2-Bis(nitrooxy)ethane, Nitroglycol (NGc), 1,2-Ethanediol dinitrate, Dinitroglycol, EGDN, Ethane-1,2-diyl dinitrate
1367:
736:
Other investigators preparing NGC before publication in 1926 of
Rinkenbach's work included: Champion (1871), Neff (1899) & Wieland & Sakellarios (1920), Dautriche, Hough & Oehme.
1002:
When ethylene glycol dinitrate is rapidly heated to 215 °C, it explodes; this is preceded by partial decomposition similar to that of nitroglycerin. EGDN has a slightly higher
1165:
571:
644:
813:
50% was used at 10-12°, the yield increased to 229g. In commercial nitration, the yields obtained from 100 kg anhydrous glycol and 625 kg of mixed acid containing
527:
846:
58% & water 1% were 222.2 kg of NGc at nitrating temp of 10-12° and only 218.3 kg at 29-30°. This means 90.6% of theory, as compared to 93.6% with NG.
1360:
535:
287:
2500:
1353:
549:
722:
123:
713:
Pure EGDN was first produced by the
Belgian chemist Louis Henry (1834–1913) in 1870 by dropping a small amount of ethylene glycol into a mixture of
1190:
2129:
2555:
542:
2702:
1814:
255:
1980:
2167:
1493:
1784:
1889:
2569:
2251:
2119:
651:
2697:
2687:
2657:
1819:
1643:
198:
494:
2505:
2316:
1789:
1529:
780:
60% at 10-12°, the yield was 222g and it dropped to 218g when the temp was raised to 29-30°. When 500g of mixed acid
219:
116:
2692:
2388:
2274:
2207:
2074:
1653:
595:
582:
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2137:
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730:
499:
484:
2677:
2586:
2197:
2114:
1846:
1658:
1534:
1114:
1061:
EGDN was used in manufacturing explosives to lower the freezing point of nitroglycerin, in order to produce
2486:
2393:
2142:
1874:
975:
Ethylene glycol dinitrate is a colorless volatile liquid when in pure state, but is yellowish when impure.
161:
2707:
2583:
2287:
2233:
2096:
2083:
1841:
1544:
2202:
1804:
1774:
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2510:
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2007:
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489:
477:
2147:
1851:
1799:
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1618:
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1206:
2432:
2029:
1769:
1638:
1628:
705:, and nitrogen gas, with no excess unreacted substances, without needing to react with anything else.
43:
2044:
2039:
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1809:
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56:
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991:
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2246:
2177:
1925:
1904:
1209:(Investigations of ether derivatives of polybasic alcohols and polyprotic acids (fourth part)),
2331:
2064:
1458:
1438:
2366:
2361:
1975:
1970:
1894:
1728:
1589:
1584:
1579:
1574:
1418:
1314:
1207:"Untersuchungen über die Aetherderivate der mehratomigen Alkohole und Säuren (Vierter Theil.)"
1186:
1070:
1014:
427:
2356:
2351:
2341:
2321:
2054:
1569:
1313:. American Chemical Society Monograph. Vol. 114. Reinhold. pp. 65–7, 130–134, 312.
2402:
1996:
1965:
1879:
1830:
1723:
1674:
1554:
1270:
1240:
697:, meaning that its ideal exothermic decomposition would completely convert it to low energy
453:
401:
315:
2152:
1764:
207:
143:
34:
2590:
2261:
2049:
1884:
1648:
682:
92:
240:
165:
2610:
2269:
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2059:
1759:
1746:
1733:
1379:
1109:
891:
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686:
622:
412:
1180:
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2109:
1738:
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718:
390:
380:
154:
1345:
2628:
2604:
1935:
1703:
1403:
1390:
1376:
1335:
187:
2641:
2412:
2336:
1945:
1940:
1825:
1666:
1564:
1408:
1097:
714:
561:
994:, gave for NGc mixtures slightly higher results then with those containing NG.
2614:
2594:
2528:
2182:
1599:
1594:
1483:
1463:
1340:
1161:
342:
134:
1318:
1244:
2600:
2559:
2422:
2417:
1478:
1129:
690:
679:
17:
2634:
cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)
2621:
2577:
2563:
2478:
2380:
2069:
1960:
1507:
1398:
1062:
1003:
726:
548:
541:
534:
507:
1274:
689:
in both manufacture and properties, though it is more volatile and less
2541:
2407:
1920:
1915:
1864:
1683:
1678:
1604:
1524:
1513:
1066:
370:
174:
2637:
2533:
2427:
1990:
1090:
1074:
1228:
621:
Except where otherwise noted, data are given for materials in their
1082:
1065:
for use in colder weather. Due to its volatility it was used as a
702:
122:
115:
105:
2515:
2442:
2016:
1261:
Rinkenbach, W. H. (1926). "The
Properties of Glycol Dinitrate".
1089:
owing to the lack of secondary hydroxyl groups in the precursor
608:
360:
1349:
1096:
Like other organic nitrates, ethylene glycol dinitrate is a
224:
955:
from ethylene through chlorohydrin & ethylene oxide.
519:
1289:"Ueber eine Verbindung des Aethylens mit Salpetersäure"
639:
1399:
Nitroxyl anion (NO; oxonitrate(1-), hyponitrite anion)
1166:
National
Institute for Occupational Safety and Health
678:, is a colorless, oily, explosive liquid obtained by
693:. Unlike nitroglycerine, the chemical has a perfect
2468:
2441:
2379:
2309:
2260:
2128:
2015:
2006:
1989:
1890:
Methylamine hexamethylene methylamine/NO (MAHMA/NO)
1506:
1426:
1417:
1389:
1704:Amyl nitrite (isoamyl nitrite, isopentyl nitrite)
1009:Ethylene glycol dinitrate reacts violently with
186:
1565:Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)
523:
91:
1293:Berichte der deutschen chemischen Gesellschaft
1291:(On a compound of ethylene with nitric acid),
1233:Berichte der Deutschen Chemischen Gesellschaft
1211:Berichte der deutschen chemischen Gesellschaft
939:Direct Production of NGc from Gaseous Ethylene
264:InChI=1S/C2H4N2O6/c5-3(6)9-1-2-10-4(7)8/h1-2H2
1981:N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide
1540:Ethylene glycol dinitrate (EGDN; nitroglycol)
1361:
1256:
1254:
274:InChI=1/C2H4N2O6/c5-3(6)9-1-2-10-4(7)8/h1-2H2
8:
1341:CDC - NIOSH Pocket Guide to Chemical Hazards
395:197.5 °C (387.5 °F; 470.6 K)
1179:Meyer, M.; Köhler, J.; Homburg, A. (2007).
442:36 kp = 353 N pistil load no reaction
385:−22.0 °C (−7.6 °F; 251.2 K)
2012:
2003:
1423:
1368:
1354:
1346:
1336:WebBook page for ethylene glycol dinitrate
729:, but this was actually contaminated with
239:
164:
142:
26:
1724:Isobutyl nitrite (2-methylpropyl nitrite)
1634:Nitroglycerin (glyceryl trinitrate (GTN))
1309:Curme, G. O.; Johnston, F., eds. (1952).
721:cooled to 0 °C. The previous year,
206:
1185:(6th ed.). WILEY-VCH. p. 227.
1160:NIOSH Pocket Guide to Chemical Hazards.
1800:S-Nitrosocysteine (SNC, CysNO, SNO-Cys)
1790:S-Nitroso-N-valerylpenicillamine (SNVP)
1141:
978:Molar weight 152.07, N 18.42%, OB to CO
953:Preparation of NGc by method of Messing
355:Oily, colorless to light yellow liquid
292:
260:
235:
1785:S-Nitroso-N-acetylpenicillamine (SNAP)
1659:Sodium trioxodinitrate (Angeli's salt)
1155:
1153:
1151:
1149:
1147:
1145:
1085:. It is considerably more stable than
946:Preparation of NGc from Ethylene Oxide
725:had produced EGDN by the nitration of
155:
1231:[The nitration of ethylene].
1227:Wieland, H.; Sakellarios, E. (1920).
1081:, until 1995 when it was replaced by
566:215 °C; 419 °F; 488 K
267:Key: UQXKXGWGFRWILX-UHFFFAOYSA-N
7:
2620:non-selective PDE inhibitors (e.g.,
1404:Nitric oxide (NO; nitrogen monoxide)
1263:Industrial and Engineering Chemistry
1644:Pentaerithrityl tetranitrate (PETN)
1530:Diethylene glycol dinitrate (DEGDN)
960:Preparation of NGc by duPont method
177:
2549:Indirect/downstream NO modulators:
2317:Asymmetric dimethylarginine (ADMA)
25:
2347:Nitroarginine methyl ester (NAME)
1810:S-Nitrosoglutathione (GSNO, SNOG)
1780:S-Nitroso-N-acetylcysteine (SNAC)
1654:Propylene glycol dinitrate (PGDN)
1409:Nitrosonium (NO; nitrosyl cation)
629:
498:
493:
488:
483:
42:
33:
1875:Diethylenetriamine/NO (DETA/NO)
1013:, yielding ethylene glycol and
625:(at 25 °C , 100 kPa).
2075:N-(1-Iminoethyl)-L-ornithine (
1:
2658:Receptor/signaling modulators
2327:Guanidinoethyldisulfide (GED)
1545:Isosorbide mononitrate (ISMN)
1535:Erythritol tetranitrate (ETN)
1229:"Die Nitrierung des Äthylens"
576:(US health exposure limits):
1795:S-Nitrosocaptopril (SNO-Cap)
1624:Nitroflurbiprofen (HCT-1026)
1619:Nitroatorvastatin (NCX-6560)
2270:Aminoguanidine (pimagedine)
2163:Aminoguanidine (pimagedine)
2060:Aminoguanidine (pimagedine)
1824:N-Nitroso compounds (e.g.,
1639:Nitropravastatin (NCX-6550)
1550:Isosorbide dinitrate (ISDN)
890:or through the reaction of
2724:
2556:AT-II receptor antagonists
2301:Nitroarginine (NNA, NOARG)
2138:1-Amino-2-hydroxyguanidine
2110:Nitroarginine (NNA, NOARG)
1857:Sodium nitroprusside (SNP)
745:Direct Nitration of Glycol
28:Ethylene glycol dinitrate
2651:
1077:, to allow more reliable
664:Ethylene glycol dinitrate
619:
570:
464:
459:
421:
417:0.05 mmHg (@ 20 °C)
347:152.1 g/mol
308:
283:
251:
75:
67:
61:Ethane-1,2-diyl dinitrate
55:
50:
41:
32:
2703:Sugar alcohol explosives
2035:3-Chloro-5-nitroindazole
1870:Diethylamine/NO (DEA/NO)
1842:Metal nitrosyl complexes
1770:S-Nitrosoalbumin (SNALB)
1464:Cinaciguat (BAY 58-2667)
1245:10.1002/cber.19200530211
432:0.02 kp m = 0.2 Nm
2627:PDE9 inhibitors (e.g.,
2115:Pentamidine isethionate
2025:3-Bromo-7-nitroindazole
1912:Heterocyclic compounds:
1436:Activators/stimulators:
1115:Erythritol tetranitrate
731:beta-nitroethyl nitrate
2584:L-Type calcium channel
709:History and production
530:
2188:Cindunistat (SD-6010)
2143:2-Ethylaminoguanidine
1900:Spermine/NO (SPER/NO)
1697:O-Nitroso compounds (
1083:dimethyldinitrobutane
529:
2574:receptor antagonists
2247:Ronopterin (VAS-203)
1946:Molsidomine (SIN-10)
1867:(diazeniumdiolates):
1847:Roussin's black salt
1560:Mannitol hexanitrate
1125:Mannitol hexanitrate
1120:Xylitol pentanitrate
1006:than nitroglycerin.
896:dinitrogen pentoxide
685:. It is similar to
589:C 0.2 ppm (1 mg/m)
512:(fire diamond)
438:Friction sensitivity
57:Preferred IUPAC name
2698:Explosive detection
2688:Explosive chemicals
1941:Linsidomine (SIN-1)
1838:Nitrosyl compounds:
1805:S-Nitrosodiclofenac
1775:S-Nitrosated AR545C
1760:S-Nitroso compounds
1275:10.1021/ie50203a027
1087:glyceryl trinitrate
1079:explosive detection
1011:potassium hydroxide
998:Chemical properties
971:Physical properties
448:Detonation velocity
402:Solubility in water
29:
1852:Roussin's red salt
1709:Cyclohexyl nitrite
1600:Nipradilol (K-351)
1071:plastic explosives
652:Infobox references
611:(Immediate danger)
531:
295:O=N(=O)OCCON(=O)=O
27:
2693:Liquid explosives
2665:
2664:
2490:
2481:
2464:
2463:
2397:
2375:
2374:
2295:
2291:
2282:
2278:
2275:N-(1-Iminoethyl)-
2241:
2237:
2228:
2224:
2221:N-(1-Iminoethyl)-
2215:
2211:
2208:N-(1-Iminoethyl)-
2148:2-Iminopiperidine
2104:
2100:
2091:
2087:
2078:
2000:
1729:Isopropyl nitrite
1675:Nitroso compounds
1517:
1502:
1501:
1299: : 329–330.
1287:A. Kekulé (1869)
1269:(11): 1195–1197.
1217: : 529–533.
1192:978-3-527-31656-4
1067:detection taggant
1015:potassium nitrate
660:Chemical compound
658:
657:
428:Shock sensitivity
220:CompTox Dashboard
124:Interactive image
117:Interactive image
16:(Redirected from
2715:
2591:dihydropyridines
2491:-arginine (NOHA)
2488:
2479:
2433:alpha aminoacids
2403:chlorogenic acid
2398:-arginine (NOHA)
2395:
2293:
2289:
2280:
2276:
2239:
2235:
2226:
2222:
2213:
2209:
2102:
2098:
2089:
2085:
2076:
2030:3-Chloroindazole
2013:
2004:
1994:
1692:
1691:
1629:Nitrofluvastatin
1613:
1612:
1555:Itramin tosilate
1511:
1424:
1370:
1363:
1356:
1347:
1323:
1322:
1306:
1300:
1285:
1279:
1278:
1258:
1249:
1248:
1224:
1218:
1205:L. Henry (1870)
1203:
1197:
1196:
1176:
1170:
1169:
1157:
983:decomposition).
845:
844:
843:
835:
834:
824:
823:
822:
812:
811:
810:
802:
801:
791:
790:
789:
779:
778:
777:
769:
768:
758:
757:
756:
674:, also known as
642:
636:
633:
632:
551:
544:
537:
522:
502:
497:
492:
487:
316:Chemical formula
244:
243:
228:
226:
210:
190:
179:
168:
157:
146:
126:
119:
95:
46:
37:
30:
21:
2723:
2722:
2718:
2717:
2716:
2714:
2713:
2712:
2668:
2667:
2666:
2661:
2647:
2611:PDE5 inhibitors
2573:
2537:
2524:
2460:
2437:
2371:
2305:
2256:
2124:
2050:7-Nitroindazole
2045:6-Nitroindazole
2040:5-Nitroindazole
1993:
1985:
1762:(thionitrites):
1690:
1687:
1686:
1685:
1649:Propatylnitrate
1611:
1608:
1607:
1606:
1510:
1498:
1413:
1385:
1374:
1332:
1327:
1326:
1308:
1307:
1303:
1286:
1282:
1260:
1259:
1252:
1226:
1225:
1221:
1204:
1200:
1193:
1178:
1177:
1173:
1159:
1158:
1143:
1138:
1106:
1059:
1052:
1048:
1044:
1040:
1036:
1032:
1028:
1024:
1000:
981:
973:
968:
933:
929:
925:
921:
917:
913:
909:
905:
885:
881:
877:
873:
869:
865:
861:
857:
853:
842:
839:
838:
837:
833:
830:
829:
828:
826:
821:
818:
817:
816:
814:
809:
806:
805:
804:
800:
797:
796:
795:
793:
788:
785:
784:
783:
781:
776:
773:
772:
771:
767:
764:
763:
762:
760:
755:
752:
751:
750:
748:
711:
683:ethylene glycol
661:
654:
649:
648:
647: ?)
638:
634:
630:
626:
612:
599:
586:
556:
555:
554:
553:
546:
539:
532:
528:
520:
480:
422:Explosive data
404:
336:
332:
328:
324:
318:
304:
301:
296:
291:
290:
279:
276:
275:
269:
268:
265:
259:
258:
247:
229:
222:
213:
193:
180:
149:
129:
109:
98:
85:
71:
63:
62:
23:
22:
15:
12:
11:
5:
2721:
2719:
2711:
2710:
2705:
2700:
2695:
2690:
2685:
2680:
2678:Nitrate esters
2670:
2669:
2663:
2662:
2652:
2649:
2648:
2646:
2645:
2635:
2632:
2625:
2618:
2608:
2598:
2581:
2571:
2567:
2552:ACE inhibitors
2545:
2544:
2539:
2535:
2531:
2526:
2522:
2518:
2513:
2508:
2503:
2494:
2493:
2484:
2472:
2470:
2466:
2465:
2462:
2461:
2459:
2458:
2453:
2447:
2445:
2439:
2438:
2436:
2435:
2430:
2425:
2420:
2415:
2410:
2405:
2400:
2391:
2385:
2383:
2377:
2376:
2373:
2372:
2370:
2369:
2364:
2359:
2354:
2349:
2344:
2339:
2334:
2329:
2324:
2319:
2313:
2311:
2307:
2306:
2304:
2303:
2298:
2285:
2272:
2266:
2264:
2258:
2257:
2255:
2254:
2249:
2244:
2231:
2218:
2205:
2200:
2195:
2190:
2185:
2180:
2175:
2170:
2165:
2160:
2155:
2150:
2145:
2140:
2134:
2132:
2126:
2125:
2123:
2122:
2117:
2112:
2107:
2094:
2081:
2072:
2067:
2062:
2057:
2052:
2047:
2042:
2037:
2032:
2027:
2021:
2019:
2010:
2001:
1987:
1986:
1984:
1983:
1978:
1973:
1968:
1963:
1954:
1953:
1948:
1943:
1938:
1923:
1908:
1907:
1902:
1897:
1892:
1887:
1882:
1877:
1872:
1860:
1859:
1854:
1849:
1834:
1833:
1817:
1812:
1807:
1802:
1797:
1792:
1787:
1782:
1777:
1772:
1767:
1755:-Butyl nitrite
1749:
1747:Pentyl nitrite
1744:
1742:-Butyl nitrite
1736:
1734:Methyl nitrite
1731:
1726:
1721:
1716:
1711:
1706:
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1330:External links
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699:carbon dioxide
695:oxygen balance
687:nitroglycerine
666:, abbreviated
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623:standard state
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1719:Hexyl nitrite
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1714:Ethyl nitrite
1712:
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1128:
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1123:
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724:
723:August Kekulé
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605:
602:ST 0.1 mg/m
601:
598:(Recommended)
597:
593:
592:
588:
585:(Permissible)
584:
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391:Boiling point
389:
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381:Melting point
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359:
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237:DTXSID6027264
234:
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221:
217:
216:
209:
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185:
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182:
176:
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171:
167:
163:
160:
158:
156:ECHA InfoCard
153:
152:
145:
141:
140:
138:
136:
133:
132:
125:
121:
118:
114:
113:
111:
107:
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101:
94:
90:
89:
87:
84:
80:
79:
74:
66:
58:
54:
49:
45:
40:
36:
31:
19:
2683:Antianginals
2654:
2653:
2629:paraxanthine
2605:beta blocker
2548:
2497:
2475:
2279:-ornithine (
2212:-ornithine (
1957:
1936:Feprosidnine
1931:Sydnonimines
1929:
1914:
1911:
1863:
1840:
1837:
1826:nitrosamines
1823:
1758:
1752:
1739:
1696:
1673:
1539:
1523:
1490:
1469:GSK-2181236A
1435:
1377:Nitric oxide
1310:
1304:
1296:
1292:
1283:
1266:
1262:
1236:
1232:
1222:
1214:
1210:
1201:
1181:
1174:
1095:
1060:
1008:
1001:
986:
985:
977:
974:
959:
957:
952:
950:
945:
943:
938:
936:
889:
744:
742:
738:
735:
712:
675:
671:
667:
663:
662:
572:
508:
466:
375:1.4918 g/cm
76:Identifiers
68:Other names
2642:simvastatin
2476:Precursors:
2413:epicatechin
2337:Indospicine
2292:-arginine (
2238:-arginine (
2173:AR-C 102222
2101:-arginine (
2088:-arginine (
1951:Sydnonimine
1684:Nitrite (NO
1667:Trolnitrate
1663:Tenitramine
1605:Nitrate (NO
1491:Inhibitors:
1474:Praliciguat
1454:BAY 60-4552
1449:BAY 41-8543
1444:BAY 41-2272
1098:vasodilator
1037:+ 2 KOH → C
676:Nitroglycol
562:Flash point
352:Appearance
309:Properties
162:100.010.058
18:Nitroglycol
2672:Categories
2615:sildenafil
2595:nifedipine
2498:Cofactors:
2487:N-Hydroxy-
2394:N-Hydroxy-
2183:Canavanine
2178:BYK-191023
1997:inhibitors
1926:REC15/2739
1905:V-PYRRO/NO
1595:Nicorandil
1484:Vericiguat
1383:modulators
1182:Explosives
1136:References
992:kieselguhr
966:Properties
792:50% &
759:40% &
478:Pictograms
452:7300
343:Molar mass
208:9CZ6PE9E3J
135:ChemSpider
104:3D model (
83:CAS Number
2655:See also:
2601:Nebivolol
2560:captopril
2482:-Arginine
2423:norvaline
2418:ornithine
2332:GW-273629
2288:N-Methyl-
2234:N-Methyl-
2225:-lysine (
2097:N-Propyl-
2084:N-Methyl-
2065:ARL-17477
1958:Unsorted:
1508:NO donors
1479:Riociguat
1459:BI-703704
1439:Ataciguat
1380:signaling
1319:558186858
1130:RE factor
680:nitrating
469:labelling
365:odorless
2622:caffeine
2587:blockers
2578:bosentan
2564:losartan
2381:Arginase
2367:VAS-2381
2362:ONO-1714
2310:Unsorted
2070:Indazole
1976:FR146881
1971:FR144220
1961:Cimlanod
1916:Furoxans
1895:PROLI/NO
1865:NONOates
1815:SNO-t-PA
1679:nitrites
1590:NCX-4215
1585:NCX 4040
1580:NCX-4016
1575:NCX-2216
1525:Nitrates
1514:prodrugs
1168:(NIOSH).
1104:See also
1069:in some
1063:dynamite
1004:brisance
987:Brisance
727:ethylene
615:75 mg/m
509:NFPA 704
460:Hazards
93:628-96-6
2640:(e.g.,
2638:Statins
2613:(e.g.,
2589:(e.g.,
2576:(e.g.,
2558:(e.g.,
2408:ginseng
2357:NXN-462
2352:NCX-456
2342:KD-7040
2322:CKD-712
2055:A-84643
1921:Furoxan
1820:SNO-vWF
1570:NCX-466
1419:Targets
1311:Glycols
1162:"#0273"
1073:, e.g.
1049:+ 2 KNO
862:+ 2 HNO
691:viscous
645:what is
643: (
371:Density
337:
175:PubChem
2469:Others
2428:lysine
1991:Enzyme
1966:FK-409
1880:GLO/NO
1831:SIN-1A
1317:
1189:
1091:polyol
1075:Semtex
715:nitric
640:verify
637:
407:5 g/l
288:SMILES
51:Names
2501:NADPH
2296:-NMA)
2283:-NIO)
2242:-NMA)
2229:-NIL)
2216:-NIO)
2158:AEITU
2153:1400W
2105:-NPA)
2092:-NMA)
2079:-NIO)
1765:LA810
1391:Forms
1057:Other
910:O + N
882:+ 2 H
825:41%,
703:water
573:NIOSH
256:InChI
188:40818
144:37281
106:JSmol
2516:Heme
2443:CAMK
2262:eNOS
2252:TRIM
2203:MITU
2198:IPTU
2193:EITU
2130:iNOS
2120:TRIM
2017:nNOS
1885:JS-K
1753:tert
1315:OCLC
1187:ISBN
1045:(OH)
1029:(ONO
926:(ONO
894:and
874:(ONO
858:(OH)
717:and
670:and
668:EGDN
609:IDLH
361:Odor
199:UNII
2529:CaM
2511:FMN
2506:FAD
2456:W-7
2389:ABH
2168:AMT
2008:NOS
1494:ODQ
1428:sGC
1271:doi
1241:doi
958:5)
951:4)
944:3)
937:2)
918:→ C
866:→ C
815:HNO
782:HNO
749:HNO
743:1)
672:NGC
596:REL
583:PEL
467:GHS
454:m/s
225:EPA
178:CID
2674::
2593::
2570:ET
2562:,
2542:Ca
2521:BH
1928:;
1828:):
1822:;
1757:;
1701:):
1695:;
1295:,
1267:18
1265:.
1253:^
1237:53
1235:.
1213:,
1164:.
1144:^
1100:.
1093:.
1017::
962:.
948:.
941:.
898::
836:SO
803:SO
770:SO
733:.
701:,
471::
2644:)
2631:)
2624:)
2617:)
2607:)
2603:(
2597:)
2580:)
2572:B
2566:)
2554:/
2536:2
2534:O
2523:4
2489:L
2480:L
2396:L
2294:L
2290:L
2281:L
2277:L
2240:L
2236:L
2227:L
2223:L
2214:L
2210:L
2103:L
2099:L
2090:L
2086:L
2077:L
1999:)
1995:(
1933::
1918::
1844::
1740:n
1693:)
1689:2
1681::
1677:/
1614:)
1610:3
1527::
1516:)
1512:(
1369:e
1362:t
1355:v
1321:.
1297:2
1277:.
1273::
1247:.
1243::
1215:3
1195:.
1051:3
1047:2
1043:2
1041:H
1039:2
1035:2
1033:)
1031:2
1027:2
1025:H
1023:2
1021:C
980:2
932:2
930:)
928:2
924:4
922:H
920:2
916:5
914:O
912:2
908:4
906:H
904:2
902:C
886:O
884:2
880:2
878:)
876:2
872:4
870:H
868:2
864:3
860:2
856:4
854:H
852:2
850:C
841:4
832:2
827:H
820:3
808:4
799:2
794:H
787:3
775:4
766:2
761:H
754:3
635:N
550:4
543:1
536:2
335:6
333:O
331:2
329:N
327:4
325:H
323:2
321:C
227:)
223:(
108:)
20:)
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