1194:(EMA) issued an opinion requiring companies to take measures to limit the presence of nitrosamines in human medicines as far as possible and to ensure levels of these impurities do not exceed set limits. Nitrosamines are classified as probable human carcinogens (substances that could cause cancer). The limits for nitrosamines in medicines have been set using internationally agreed standards (ICH M7(R1)) based on lifetime exposure. Generally, people should not be exposed to a lifetime risk of cancer exceeding 1 in 100,000 from nitrosamines in their medicines. EU regulators first became aware of nitrosamines in medicines in mid-2018, and took regulatory actions, including recalling medicines and stopping the use of active substances from certain manufacturers. A subsequent CHMP review of
64:
386:
233:
73:
667:
672:
662:
771:
767:
42:
1280:
51:
2477:
2439:
2328:
2281:
937:
772:
2433:
FDA recommends using an LC-HRMS testing protocol to test samples of ranitidine. FDA's LC-HRMS testing method does not use elevated temperatures and has shown the presence of much lower levels of NDMA in ranitidine medicines than reported by the third-party laboratory. International regulators using
2430:
FDA observed the testing method used by a third-party laboratory uses higher temperatures. The higher temperatures generated very high levels of NDMA from ranitidine products because of the test procedure. FDA published the method for testing angiotensin II receptor blockers (ARBs) for nitrosamine
1387:
In August 2021, a class 2 medicines recall was issued for a batch of metformin hydrochloride 500 mg/5ml Oral
Solution from Rosemont Pharmaceuticals Limited, which was first distributed in December 2020, due to the identification of higher than acceptable levels of NDMA.
770:
1036:. The question is the level at which it is produced. In the U.S. state of California, the allowable level is 10 nanograms/liter. The Canadian province of Ontario set the standard at 9 ng/L. The potential problem is greater for recycled water that can contain
1327:. Huang was poisoned by his roommate Lin Senhao, who had placed NDMA into the water cooler in their dormitory. Lin claimed that he only did this as an April Fool's joke. He received a death sentence, and was executed in 2015.
1295:
In 1978, a teacher in Ulm, Germany, was sentenced to life in prison for trying to murder his wife by poisoning jam with NDMA and feeding it to her. Both the wife and the teacher later died from liver failure. That same year,
1383:
products from a number of manufacturers, resulting in recalls. In April 2020, ranitidine was withdrawn from the United States market, suspended in the
European Union, and suspended in Australia due to concerns about NDMA.
2584:
1308:. The incident resulted in the deaths of 30-year-old Duane Johnson and 11-month-old Chad Shelton. For his crime, Harper was sentenced to death, but committed suicide in prison before his execution could be carried out.
2266:
1167:" in rats. The induction of liver tumors in rats after chronic exposure to low doses is well documented. Its toxic effects on humans are inferred from animal experiments, but not well-established experimentally.
788:
2638:
2084:
2033:
680:
2313:
642:
2417:
2058:
1975:
1198:
blood-pressure medicines in 2019, led to new requirements for the manufacture of sartans, while its 2020 review of ranitidine recommended an EU-wide suspension of ranitidine medicines.
1050:
Contamination of drinking water with NDMA is of particular concern due to the minute concentrations at which it is harmful and the difficulty in detecting it at these concentrations.
1073:
NDMA is found at low levels in numerous items of human consumption, including cured meat, fish, beer, as well as during use of tobacco products and the inhalation of tobacco smoke.
2254:
1372:
for NDMA. The FDA announcement followed a recall of three versions of metformin in
Singapore, and the European Medicines Agency's request that manufacturers test for NDMA.
1779:"Dose and Time Relationships for Tumor Induction in the Liver and Esophagus of 4080 Inbred Rats by Chronic Ingestion of N-Nitrosodiethylamine or N-Nitrosodimethylamine"
773:
1699:
Andrzejewski, P.; Kasprzyk-Hordern, B.; Nawrocki, J. (2005). "The hazard of N-nitrosodimethylamine (NDMA) formation during water disinfection with strong oxidants".
2037:
2301:
2232:
1429:
1218:. The central nitrogen is bound to two methyl groups and the NO group with bond angles of 120°. The N-N and N-O distances are 1.32 and 1.26 Å, respectively.
846:
1778:
1175:
950:
1155:
is 7 ng/L. As of July 2020, the EPA has not set a regulatory maximal contaminant level (MCL) for drinking water. At high doses, it is a "potent
2405:
2171:
1734:
George, J.; Rao, K. R.; Stern, R.; Chandrakasan, G. (2001). "Dimethylnitrosamine-induced liver injury in rats: the early deposition of collagen".
2456:
1979:
795:
1187:
2544:
Text was copied from this source which is copyright
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
2514:
Text was copied from this source which is copyright
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
2395:
Text was copied from this source which is copyright
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
2365:
Text was copied from this source which is copyright
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
2104:
Text was copied from this source which is copyright
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
1892:
Text was copied from this source which is copyright
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
1872:
1862:
Text was copied from this source which is copyright
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
1148:
2140:
1178:(42 U.S.C. 11002), and is subject to strict reporting requirements by facilities that produce, store, or use it in significant quantities.
425:
2585:"Class 2 Medicines Recall: Rosemont Pharmaceuticals Limited, Metformin Hydrochloride 500mg/5ml Oral Solution, PL 00427/0139, EL (21)A/20"
2085:"EMA reviewing medicines containing valsartan from Zhejiang Huahai following detection of an impurity: some being recalled across the EU"
1812:
1368:
was recalled around the world due to contamination with NDMA. In December 2019, the FDA began testing samples of the diabetes drug
2524:
945:
1933:
Mitch, William A.; Sedlak, David L. (2002). "Formation of N-Nitrosodimethylamine (NDMA) from Dimethylamine during Chlorination".
2345:
1808:
1171:
591:
1396:
A study has shown that NDMA perturbs arginine biosynthesis, mitochondrial genome maintenance, and DNA damage repair in yeast.
2375:
2607:
Ogbede, J.U., Giaever, G. & Nislow, C. A genome-wide portrait of pervasive drug contaminants. Sci Rep 11, 12487 (2021).
2059:"FDA Updates and Press Announcements on Angiotensin II Receptor Blocker (ARB) Recalls (Valsartan, Losartan, and Irbesartan)"
2005:
1842:
1501:
David L. Sedlak; Rula A. Deeb; Elisabeth L. Hawley; William A. Mitch; Timothy D. Durbin; Sam Mowbray; Steve Carr (2005).
1351:
1133:
2669:
2554:
1809:"40 CFR 355: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities"
1331:
1297:
400:
2222:
957:
284:
1226:
1081:
1487:
1292:
Several incidents in which NDMA was used intentionally to poison another person have garnered media attention.
623:
781:
1664:
Hecht, Stephen S. (1998). "Biochemistry, Biology, and Carcinogenicity of Tobacco-Specific N-Nitrosamines†".
2461:
2411:
2307:
2260:
2146:
2062:
724:
333:
228:
671:
41:
2431:
impurities. That method is not suitable for testing ranitidine because heating the sample generates NDMA.
364:
190:
666:
2494:
2434:
similar LC-MS testing methods have also shown the presence of low levels of NDMA in ranitidine samples.
1268:
The mechanism of its carcinogenicity involves metabolic activation steps resulting in the formation of
870:
857:
1503:"Sources and Fate of Nitrosodimethylamine and Its Precursors in Municipal Wastewater Treatment Plants"
742:
2529:
2499:
2380:
2350:
2089:
1877:
1847:
1191:
240:
1641:
1627:; Sedlak, D. L. (2003). "N-Nitrosodimethylamine (NDMA) as a Drinking Water Contaminant: A Review".
381:
278:
2255:"Statement alerting patients and health care professionals of NDMA found in samples of ranitidine"
150:
1636:
1500:
2664:
2659:
1215:
913:
694:
654:
542:
25:
1488:"Nitrosamines - Drinking Water Issues | California State Water Resources Control Board"
712:
2633:
Method Development for the Determination of N-Nitrosodimethylamine (NDMA) in Drinking Water
2632:
1942:
1743:
1708:
1578:
1514:
1312:
661:
342:
91:
1452:-nitrosamines in the Diet: Occurrence, Formation, Mechanisms and Carcinogenic Potential".
210:
8:
116:
1946:
1747:
1712:
1582:
1518:
385:
232:
170:
126:
63:
1624:
1622:
1602:
1590:
1548:
1532:
1029:
1755:
1958:
1790:
1759:
1681:
1594:
1540:
1469:
1465:
1222:
2001:
1606:
1221:
NDMA forms from a variety of dimethylamine-containing compounds, e.g. hydrolysis of
72:
2608:
1950:
1915:
1751:
1716:
1673:
1646:
1586:
1552:
1522:
1461:
1316:
1273:
988:
746:
566:
531:
448:
1343:
1125:
2302:"Questions and Answers: NDMA impurities in ranitidine (commonly known as Zantac)"
1269:
1062:
1025:
1003:. It is a volatile yellow oil. NDMA has attracted wide attention as being highly
306:
2197:
1720:
1698:
1355:
1137:
2612:
2010:
1650:
1152:
1061:
range breaks the N–N bond. Thus, it can be used to degrade NDMA. Additionally,
1033:
928:
555:
2627:
1425:
831:
730:
2653:
2481:
2443:
2332:
2285:
2227:
1991:
Karsten Strey: "Die Welt der Gifte", Lehmanns, 2. Edition p. 193 (in German).
1919:
1733:
1598:
1347:
1237:
1129:
1037:
908:
716:
520:
221:
1569:
Najm, I.; Trussell, R. R. (2001). "NDMA Formation in Water and Wastewater".
1527:
1513:(1, Emerging Micropollutants in Treatment Systems (Jan.–Feb. 2005)): 32–39.
1502:
2115:
1962:
1763:
1544:
1233:
1041:
2457:"FDA Requests Removal of All Ranitidine Products (Zantac) from the Market"
1794:
1685:
1473:
794:
1156:
1054:
1004:
1000:
807:
1536:
780:
1380:
1365:
1008:
787:
479:
241:
201:
1954:
1677:
1151:(EPA) determined that the maximal admissible concentration of NDMA in
2562:
2346:"EMA to provide guidance on avoiding nitrosamines in human medicines"
1776:
1369:
1361:
1160:
1058:
353:
2406:"FDA updates and press announcements on NDMA in Zantac (ranitidine)"
1116:
Groundwater near rocket launch sites often has high levels of NDMA.
1040:. Further, NDMA can form or be leached during treatment of water by
927:
Except where otherwise noted, data are given for materials in their
1320:
1305:
753:
267:
1423:
149:
2480:
This article incorporates text from this source, which is in the
2442:
This article incorporates text from this source, which is in the
2331:
This article incorporates text from this source, which is in the
2284:
This article incorporates text from this source, which is in the
510:
293:
2376:"EMA to review ranitidine medicines following detection of NDMA"
1843:"EMA finalises opinion on presence of nitrosamines in medicines"
1623:
Mitch, W. A.; Sharp, J. O.; Trussell, R. R.; Valentine, R. L.;
1195:
734:
181:
2172:"Diabetes Drugs Latest to Be Targeted for Carcinogen Scrutiny"
1283:
Metabolic activation of NDMA relevant to its cancer-causation.
1232:
In the laboratory, NDMA can be synthesised by the reaction of
50:
1324:
1301:
1279:
1164:
1044:
317:
161:
139:
1174:
in the United States, as defined in Section 302 of the U.S.
369:
1364:
were recalled because of contamination with NDMA. In 2019,
999:
NNO. It is one of the simplest members of a large class of
883:
500:
258:
21:
17:
2141:"FDA Updates and Press Announcements on NDMA in Metformin"
1902:
Krebs, Bernt; Mandt, Jürgen (1975). "Kristallstruktur des
1084:, a rocket fuel, is a highly effective precursor to NDMA:
738:
1568:
2198:"FDA Investigating Metformin for Possible Carcinogen"
1430:
National Institute for Occupational Safety and Health
2116:"Sale of heartburn drug suspended over cancer fears"
1837:
1835:
1833:
1831:
1829:
1777:
Peto, R.; Gray, R.; Brantom, P.; Grasso, P. (1991).
1448:
Tricker, A.R.; Preussmann, R. (1991). "Carcinogenic
1330:
In 2018, NDMA was used in an attempted poisoning at
2398:
1360:In 2018, and then again in 2019, various brands of
1176:Emergency Planning and Community Right-to-Know Act
2639:"Nitrosamine impurities in medications: Guidance"
1826:
1447:
1024:Of more general concern, NDMA can be produced by
2651:
2487:
1315:, Huang Yang, a postgraduate medical student at
700:
305:
1976:Ein teuflischer Plan: Tod aus dem Marmeladeglas
1692:
1571:Journal of the American Water Works Association
1391:
1225:. Dimethylamine is susceptible to oxidation to
769:
125:
2517:
2495:"Suspension of ranitidine medicines in the EU"
2449:
2296:
2294:
1801:
1352:Angiotensin II receptor blocker § recalls
1188:Committee for Medicinal Products for Human Use
1134:Angiotensin II receptor blocker § recalls
708:
704:
1149:United States Environmental Protection Agency
2628:CDC - NIOSH Pocket Guide to Chemical Hazards
2223:"Health Canada assessing NDMA in ranitidine"
2215:
2006:"The Prognosis for this Patient is Horrible"
1994:
1214:O core of NDMA is planar, as established by
2291:
2247:
1932:
1618:
1616:
1298:Steven Roy Harper spiked lemonade with NDMA
812:61.0 °C (141.8 °F; 334.1 K)
525:153.1 °C; 307.5 °F; 426.2 K
2525:"Ranitidine-containing medicinal products"
2195:
1901:
1564:
1562:
384:
231:
209:
2113:
1727:
1640:
1526:
1443:
1441:
1439:
341:
2169:
1613:
1424:NIOSH Pocket Guide to Chemical Hazards.
1379:-nitrosodimethylamine was discovered in
1278:
2000:
1559:
380:
283:
2652:
2559:Therapeutic Goods Administration (TGA)
2269:from the original on 26 September 2019
2235:from the original on 26 September 2019
1935:Environmental Science & Technology
1436:
1419:
1417:
1415:
1413:
1411:
1409:
222:
1663:
1337:
412:Key: UMFJAHHVKNCGLG-UHFFFAOYSA-N
189:
169:
2420:from the original on 29 October 2019
2368:
2338:
2316:from the original on 24 October 2019
1770:
1657:
1494:
1454:Mutation Research/Genetic Toxicology
2170:Lauerman, John (December 4, 2019).
2094:(Press release). September 17, 2018
1406:
1319:, was the victim of a poisoning in
1065:removes approximately 50% of NDMA.
296:
266:
13:
2385:(Press release). 13 September 2019
2355:(Press release). 13 September 2019
1591:10.1002/j.1551-8833.2001.tb09129.x
765:
637:Known carcinogen, extremely toxic
409:InChI=1S/C2H6N2O/c1-4(2)3-5/h1-2H3
71:
62:
14:
2681:
2621:
2462:U.S. Food and Drug Administration
1629:Environmental Engineering Science
1181:
1057:radiation in the 200 to 260
1019:
2475:
2437:
2326:
2279:
2114:BBC Staff (September 29, 2019).
1142:
935:
670:
665:
660:
466:
460:
49:
40:
2601:
2577:
2547:
2196:Koenig, D. (December 6, 2019).
2189:
2163:
2133:
2107:
2077:
2051:
2026:
1985:
1969:
1926:
1895:
1865:
1666:Chemical Research in Toxicology
1227:unsymmetrical dimethylhydrazine
1082:Unsymmetrical dimethylhydrazine
931:(at 25 °C , 100 kPa).
2561:. 2 April 2020. Archived from
2504:(Press release). 30 April 2020
1480:
1300:at the Johnson family home in
1287:
1229:, which air-oxidizes to NDMA.
1076:
624:Occupational safety and health
472:
454:
1:
2465:(Press release). 1 April 2020
1756:10.1016/S0300-483X(00)00352-8
1399:
1172:extremely hazardous substance
1119:
1068:
1014:
851:(US health exposure limits):
2412:Food and Drug Administration
2308:Food and Drug Administration
2261:Food and Drug Administration
2147:Food and Drug Administration
2063:Food and Drug Administration
1852:(Press release). 9 July 2020
1466:10.1016/0165-1218(91)90123-4
1392:Effect on biological systems
1344:Ranitidine § impurities
1201:
1126:Ranitidine § impurities
7:
1721:10.1016/j.desal.2004.11.009
1356:Metformin § impurities
1138:Metformin § impurities
820:or concentration (LD, LC):
58:
10:
2686:
2613:10.1038/s41598-021-91792-1
1813:Government Printing Office
1651:10.1089/109287503768335896
1507:Water Environment Research
1341:
1123:
1053:Relatively high levels of
864:OSHA-Regulated Carcinogen
15:
2670:IARC Group 2A carcinogens
2530:European Medicines Agency
2500:European Medicines Agency
2381:European Medicines Agency
2351:European Medicines Agency
2090:European Medicines Agency
2034:"15 days log in hospital"
1878:European Medicines Agency
1848:European Medicines Agency
1192:European Medicines Agency
925:
894:
845:
816:
641:
621:
616:
584:
441:
421:
396:
109:
90:
85:
57:
48:
39:
1920:10.1002/cber.19751080419
1906:-Nitrosodimethylamins".
1873:"Nitrosamine impurities"
1789:(23 Part 2): 6452–6469.
1348:Valsartan § recalls
1130:Valsartan § recalls
725:Precautionary statements
16:Not to be confused with
2065:(FDA). November 7, 2019
1528:10.2175/106143005X41591
1170:It is classified as an
1011:in laboratory animals.
1811:(2/14/2024 ed.).
1284:
776:
505:faint, characteristic
103:-Dimethylnitrous amide
76:
67:
35:-Nitrosodimethylamine
2265:. 13 September 2019.
2231:. 13 September 2019.
1334:in Kingston, Canada.
1282:
1216:X-ray crystallography
973:-Nitrosodimethylamine
775:
537:290 mg/ml (at 20 °C)
75:
66:
26:N-Nitrosodiethylamine
2004:(January 25, 1982).
1313:Fudan poisoning case
991:with the formula (CH
917:-Nitrosodiethylamine
758:(fire diamond)
92:Preferred IUPAC name
2416:. 28 October 2019.
2312:. 11 October 2019.
1978:(archived from the
1947:2002EnST...36..588M
1748:2001Toxgy.156..129G
1713:2005Desal.176...37A
1583:2001JAWWA..93b..92N
1519:2005WaEnR..77...32S
1375:In September 2019,
981:dimethylnitrosamine
532:Solubility in water
487: g·mol
285:Dimethylnitrosamine
36:
2176:Bloomberg Business
1908:Chemische Berichte
1338:Drug contamination
1332:Queen's University
1285:
1186:In July 2020, the
958:Infobox references
895:Related compounds
886:(Immediate danger)
777:
560:700 Pa (at 20 °C)
77:
68:
31:
2565:on 29 August 2021
1955:10.1021/es010684q
1882:. 23 October 2019
1678:10.1021/tx980005y
1625:Alvarez-Cohen, L.
1223:dimethylformamide
979:), also known as
966:Chemical compound
964:
963:
901:Related compounds
841:
695:Hazard statements
365:CompTox Dashboard
151:Interactive image
81:
80:
2677:
2646:
2615:
2605:
2599:
2598:
2596:
2595:
2581:
2575:
2574:
2572:
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2551:
2545:
2543:
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2539:
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2515:
2513:
2511:
2509:
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2485:
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2478:
2474:
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2453:
2447:
2441:
2440:
2436:
2427:
2425:
2402:
2396:
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2392:
2390:
2372:
2366:
2364:
2362:
2360:
2342:
2336:
2330:
2329:
2325:
2323:
2321:
2298:
2289:
2283:
2282:
2278:
2276:
2274:
2251:
2245:
2244:
2242:
2240:
2219:
2213:
2212:
2210:
2208:
2193:
2187:
2186:
2184:
2182:
2167:
2161:
2160:
2158:
2156:
2137:
2131:
2130:
2128:
2126:
2111:
2105:
2103:
2101:
2099:
2081:
2075:
2074:
2072:
2070:
2055:
2049:
2048:
2046:
2045:
2036:. Archived from
2030:
2024:
2023:
2021:
2019:
2014:. pp. 57–71
1998:
1992:
1989:
1983:
1973:
1967:
1966:
1930:
1924:
1923:
1914:(4): 1130–1137.
1899:
1893:
1891:
1889:
1887:
1869:
1863:
1861:
1859:
1857:
1839:
1824:
1823:
1821:
1819:
1805:
1799:
1798:
1774:
1768:
1767:
1742:(2–3): 129–138.
1731:
1725:
1724:
1696:
1690:
1689:
1661:
1655:
1654:
1644:
1620:
1611:
1610:
1566:
1557:
1556:
1530:
1498:
1492:
1491:
1484:
1478:
1477:
1460:(3–4): 277–289.
1445:
1434:
1433:
1421:
1317:Fudan University
1274:alkylating agent
989:organic compound
948:
942:
939:
938:
839:
797:
790:
783:
768:
748:
744:
740:
736:
732:
718:
714:
710:
706:
702:
674:
669:
664:
608:
585:Thermochemistry
567:Refractive index
486:
474:
468:
462:
456:
449:Chemical formula
389:
388:
373:
371:
345:
309:
298:
287:
270:
243:
235:
224:
213:
193:
173:
153:
129:
59:
53:
44:
37:
30:
2685:
2684:
2680:
2679:
2678:
2676:
2675:
2674:
2650:
2649:
2645:. 4 April 2022.
2637:
2624:
2619:
2618:
2606:
2602:
2593:
2591:
2583:
2582:
2578:
2568:
2566:
2553:
2552:
2548:
2537:
2535:
2534:. 30 April 2020
2523:
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2319:
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873:(Recommended)
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2665:Hepatotoxins
2660:Nitrosamines
2642:
2603:
2592:. Retrieved
2588:
2579:
2567:. Retrieved
2563:the original
2558:
2555:"Ranitidine"
2549:
2536:. Retrieved
2528:
2519:
2506:. Retrieved
2498:
2489:
2467:. Retrieved
2460:
2451:
2429:
2422:. Retrieved
2409:
2400:
2389:19 September
2387:. Retrieved
2379:
2370:
2359:19 September
2357:. Retrieved
2349:
2340:
2318:. Retrieved
2305:
2273:26 September
2271:. Retrieved
2258:
2249:
2239:26 September
2237:. Retrieved
2226:
2217:
2207:December 14,
2205:. Retrieved
2201:
2191:
2179:. Retrieved
2175:
2165:
2153:. Retrieved
2144:
2135:
2123:. Retrieved
2119:
2109:
2096:. Retrieved
2088:
2079:
2069:November 15,
2067:. Retrieved
2053:
2042:. Retrieved
2038:the original
2028:
2016:. Retrieved
2009:
1996:
1987:
1971:
1938:
1934:
1928:
1911:
1907:
1903:
1897:
1884:. Retrieved
1876:
1867:
1854:. Retrieved
1846:
1818:February 16,
1816:. Retrieved
1803:
1786:
1782:
1772:
1739:
1735:
1729:
1704:
1701:Desalination
1700:
1694:
1669:
1665:
1659:
1632:
1628:
1577:(2): 92–99.
1574:
1570:
1510:
1506:
1496:
1482:
1457:
1453:
1449:
1395:
1386:
1376:
1374:
1359:
1329:
1311:In the 2013
1310:
1294:
1291:
1267:
1234:nitrous acid
1231:
1220:
1205:
1185:
1169:
1146:
1115:
1080:
1072:
1052:
1049:
1030:chlorination
1023:
1007:and a known
1001:nitrosamines
984:
980:
976:
970:
969:
968:
914:
847:
817:
754:
686:
643:
633:Main hazards
622:
612:1.65 MJ/mol
601:
570:
544:
318:RTECS number
191:ChEMBL117311
110:Identifiers
100:
96:
32:
2125:December 3,
2098:December 3,
1288:As a poison
1157:hepatotoxin
1100:+ 2 O → (CH
1077:Rocket fuel
1005:hepatotoxic
840:(oral, rat)
838:37.0 mg/kg
832:median dose
818:Lethal dose
808:Flash point
681:Signal word
627:(OHS/OSH):
515:1.005 g/mL
495:Yellow oil
492:Appearance
442:Properties
229:100.000.500
171:CHEBI:35807
2654:Categories
2594:2021-08-27
2424:28 October
2320:23 October
2181:January 5,
2044:2013-04-30
1736:Toxicology
1400:References
1381:ranitidine
1366:ranitidine
1342:See also:
1244:HONO + (CH
1124:See also:
1120:Regulation
1069:Cured meat
1015:Occurrence
1009:carcinogen
655:Pictograms
594:combustion
480:Molar mass
343:M43H21IO8R
202:ChemSpider
138:3D model (
117:CAS Number
1637:CiteSeerX
1599:0003-150X
1370:metformin
1362:valsartan
1202:Chemistry
987:), is an
743:P301+P310
646:labelling
354:UN number
325:IQ0525000
250:200-549-8
242:EC Number
2418:Archived
2314:Archived
2267:Archived
2233:Archived
2202:Medscape
2120:BBC News
1980:original
1963:11878371
1764:11164615
1607:93202942
1545:15765933
1537:25045835
1432:(NIOSH).
1321:Shanghai
1306:Nebraska
1252:NH → (CH
1161:fibrosis
755:NFPA 704
617:Hazards
433:CN(C)N=O
2569:19 July
2469:1 April
2155:11 July
2061:. U.S.
1943:Bibcode
1886:11 July
1856:11 July
1795:1933907
1744:Bibcode
1709:Bibcode
1686:9625726
1579:Bibcode
1553:9690388
1515:Bibcode
1474:2017213
1426:"#0461"
1260:NNO + H
1163:of the
1108:NNO + H
951:what is
949: (
550:−0.496
511:Density
294:PubChem
127:62-75-9
2589:GOV.UK
2508:2 June
2018:2 July
1961:
1793:
1762:
1684:
1639:
1605:
1597:
1551:
1543:
1535:
1472:
1354:, and
1196:sartan
1136:, and
1045:resins
946:verify
943:
687:Danger
580:1.437
485:74.083
426:SMILES
268:C14704
182:ChEMBL
86:Names
2538:6 May
2532:(EMA)
2502:(EMA)
2414:(FDA)
2410:U.S.
2383:(EMA)
2353:(EMA)
2310:(FDA)
2306:U.S.
2263:(FDA)
2259:U.S.
2149:(FDA)
2145:U.S.
2092:(EMA)
1880:(EMA)
1850:(EMA)
1603:S2CID
1549:S2CID
1533:JSTOR
1325:China
1302:Omaha
1272:, an
1236:with
1206:The C
1165:liver
848:NIOSH
401:InChI
358:3382
162:ChEBI
140:JSmol
24:, or
2571:2020
2540:2020
2510:2020
2471:2020
2426:2019
2391:2019
2361:2019
2322:2019
2275:2019
2241:2019
2209:2019
2183:2020
2157:2020
2127:2019
2100:2019
2071:2019
2020:2021
1959:PMID
1888:2020
1858:2020
1820:2024
1791:PMID
1760:PMID
1682:PMID
1595:ISSN
1541:PMID
1470:PMID
1147:The
977:NDMA
890:Ca
884:IDLH
747:P310
739:P284
735:P273
731:P260
717:H411
713:H372
709:H350
705:H330
701:H301
543:log
501:Odor
334:UNII
307:6124
279:MeSH
259:KEGG
211:5894
22:NMDA
18:MDMA
2609:doi
1951:doi
1916:doi
1912:108
1752:doi
1740:156
1717:doi
1705:176
1674:doi
1647:doi
1587:doi
1523:doi
1462:doi
1458:259
1096:NNH
1088:(CH
1032:or
1028:by
985:DMN
877:Ca
871:REL
858:PEL
644:GHS
605:298
370:EPA
297:CID
2656::
2641:.
2587:.
2557:.
2527:.
2497:.
2459:.
2428:.
2408:.
2378:.
2348:.
2304:.
2293:^
2257:.
2225:.
2200:.
2174:.
2143:.
2118:.
2087:.
2008:.
1957:.
1949:.
1939:36
1937:.
1910:.
1875:.
1845:.
1828:^
1787:51
1785:.
1781:.
1758:.
1750:.
1738:.
1715:.
1703:.
1680:.
1670:11
1668:.
1645:.
1633:20
1631:.
1615:^
1601:.
1593:.
1585:.
1575:93
1573:.
1561:^
1547:.
1539:.
1531:.
1521:.
1511:77
1509:.
1505:.
1468:.
1456:.
1438:^
1428:.
1408:^
1350:,
1346:,
1323:,
1304:,
1276:.
1240::
1132:,
1128:,
1059:nm
1055:UV
1047:.
828:50
826:LD
745:,
741:,
737:,
733:,
715:,
711:,
707:,
703:,
648::
597:(Δ
20:,
2611::
2597:.
2573:.
2542:.
2512:.
2484:.
2473:.
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