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in any desired direction. Absent a driving force, thionitrosos form out of nitrosamines, which form out of nitrite esters, which form out of nitrous acid.
1761:
1363:
1333:
1751:
1353:
754:
Wang, P. G.; Xian, M.; Tang, X.; Wu, X.; Wen, Z.; Cai, T.; Janczuk, A. J. (2002). "Nitric Oxide Donors: Chemical
Activities and Biological Applications".
684:, pp. 27–28, 209. Williams refers to Traube products as "Drago complexes"; note the typo on p. 27, which should refer to "2:1 complexes".
155:
functionality. The synonymy arises because the R-NO functionality can be interpreted two different ways, depending on the physico-chemical environment:
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2009:
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Mannick, Joan B.; Schonhoff, Christopher M. (7 July 2009). "Review: NO Means No and Yes: Regulation of Cell
Signaling by Protein Nitrosylation".
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2014:
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434:, so that the initial nitroso product (from the first addition) is reduced to a disulfonyl hydroxylamine. A variant on this process with
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nitrosate primary amines during the acid environment of the stomach, and the resulting diazonium ions alkylate DNA, leading to cancer.
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364:, proton release to the solvent is typically rate-limiting, and the reaction can be suppressed in superacidic conditions.
209:
72:
1688:
361:
2114:
738:
580:
Hayton, T. W.; Legzdins, P.; Sharp, W. B. (2002). "Coordination and
Organometallic Chemistry of Metal-NO Complexes".
344:
can substitute directly onto an aromatic ring, but the ring must be substantially activated, because NO is about 14
1343:
548:
If the amine is secondary, then the product is stable, but primary amines decompose in acid to the corresponding
2128:
837:
López-Rodríguez, Rocío; McManus, James A.; Murphy, Natasha S.; Ott, Martin A.; Burns, Michael J. (2020-09-18).
61:
460:
than the sulfur atom. The formation of an alkyl nitrite from an alcohol and nitrous acid is a common example:
278:
Some form of Lewis acid also enhances the electrophilicity of NO carriers, but the acid need not be Brønsted:
439:
2216:
1202:
552:, and then attack any nearby nucleophile. Nitrosation of a primary amine is thus sometimes referred to as
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transfer is catalyzed by a strong nucleophile, such as (in increasing order of efficacy)
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Although such cations have not been isolated, nitrosating reagents likely coordinate to
371:
typically oxidizes the initially-nitroso product to a nitro compound or diazonium salt.
1310:
1267:
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866:
640:
549:
243:
solution. Nitrous acid is unstable, and high yields require a rapid reaction rate; NO
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597:
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NO. It commonly occurs to a metal (e.g. iron) or a thiol, leading to nitrosyl iron
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There are multiple chemical mechanisms by which this can be achieved, including
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The stable secondary nitrosamines are carcinogens in rodents. The compounds
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cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)
456:-nitroso compounds, but are less reactive because the oxygen atom is less
2200:
1971:
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1123:
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839:"Pathways for N -Nitroso Compound Formation: Secondary Amines and Beyond"
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notwithstanding. But atmospheric oxygen can oxidize nitric oxide to
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may react similarly, but it is unclear if they release NO or NO.
260:
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220:
136:
Nitrosylation results in a molecule "R" adducted with the group N=O
2100:
1966:
1479:
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1423:
1242:
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1083:
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are two names for the process of converting organic compounds or
818:
282:, for example, nitrosates best in neutral-to-basic conditions.
27:
Process of converting organic compounds into nitroso derivatives
2196:
2092:
1986:
1549:
836:
663:
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271:) can also nitrosate under such conditions; and the equilibria
197:
806:
579:
511:
500:
390:
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2001:
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782:
877:
702:
958:
Nitroxyl anion (NO; oxonitrate(1-), hyponitrite anion)
934:
1449:
Methylamine hexamethylene methylamine/NO (MAHMA/NO)
651:
722:
440:Raschig's hydroxylamine production technique
223:thiols in proteins, which is an important part of
1263:Amyl nitrite (isoamyl nitrite, isopentyl nitrite)
305:ions catalyze disproportionation into NO and NO.
159:Nitrosylation interprets the process as adding a
2228:
614:
1124:Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)
167:(e.g., in nitrosylated heme = nitrosylheme) or
263:. Indeed, (meta)stable nitrosation products (
1540:N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide
1099:Ethylene glycol dinitrate (EGDN; nitroglycol)
920:
151:derivatives, i.e., compounds containing the
62:introducing citations to additional sources
503:. Typically, this reaction occurs when the
409:They are liable to disproportionate to the
374:
927:
913:
843:Organic Process Research & Development
1283:Isobutyl nitrite (2-methylpropyl nitrite)
1193:Nitroglycerin (glyceryl trinitrate (GTN))
308:
883:
824:
812:
800:
788:
720:
708:
681:
669:
657:
476:
235:Nitrosation is typically performed with
131:
52:Relevant discussion may be found on the
1359:S-Nitrosocysteine (SNC, CysNO, SNO-Cys)
1349:S-Nitroso-N-valerylpenicillamine (SNVP)
301:, which does nitrosate. Alternatively
14:
2229:
1344:S-Nitroso-N-acetylpenicillamine (SNAP)
1218:Sodium trioxodinitrate (Angeli's salt)
174:Nitrosation interprets it as adding a
908:
721:Williams, D. L. H. (1988).
693:
422:sulfides with no hydrogen substituent
2179:non-selective PDE inhibitors (e.g.,
963:Nitric oxide (NO; nitrogen monoxide)
230:
181:. It commonly occurs with amines (–
29:
1203:Pentaerithrityl tetranitrate (PETN)
1089:Diethylene glycol dinitrate (DEGDN)
698:(8th ed.). Wiley. p. 634.
362:electrophilic aromatic substitution
24:
2108:Indirect/downstream NO modulators:
1876:Asymmetric dimethylarginine (ADMA)
985:
203:
25:
2258:
1906:Nitroarginine methyl ester (NAME)
1369:S-Nitrosoglutathione (GSNO, SNOG)
1339:S-Nitroso-N-acetylcysteine (SNAC)
1213:Propylene glycol dinitrate (PGDN)
968:Nitrosonium (NO; nitrosyl cation)
893:
239:, formed from acidification of a
430:and sulfinic acids add twice to
45:relies largely or entirely on a
34:
1434:Diethylenetriamine/NO (DETA/NO)
830:
694:Smith, Michael B. (2020).
73:"Nitrosation and nitrosylation"
1634:N-(1-Iminoethyl)-L-ornithine (
747:
714:
687:
675:
608:
573:
13:
1:
2217:Receptor/signaling modulators
1886:Guanidinoethyldisulfide (GED)
1104:Isosorbide mononitrate (ISMN)
1094:Erythritol tetranitrate (ETN)
566:
141:Nitrosation and nitrosylation
1354:S-Nitrosocaptopril (SNO-Cap)
1183:Nitroflurbiprofen (HCT-1026)
1178:Nitroatorvastatin (NCX-6560)
629:10.1080/10715760310001629065
514:attacks the nitrogen of the
472:
320:, are typically prepared by
7:
1829:Aminoguanidine (pimagedine)
1722:Aminoguanidine (pimagedine)
1619:Aminoguanidine (pimagedine)
1383:N-Nitroso compounds (e.g.,
1198:Nitropravastatin (NCX-6550)
1109:Isosorbide dinitrate (ISDN)
495:arise from the reaction of
219:, the conjugation of NO to
10:
2263:
2115:AT-II receptor antagonists
1860:Nitroarginine (NNA, NOARG)
1697:1-Amino-2-hydroxyguanidine
1669:Nitroarginine (NNA, NOARG)
1416:Sodium nitroprusside (SNP)
385:are typically prepared by
124:
2210:
2027:
2000:
1938:
1868:
1819:
1687:
1574:
1565:
1548:
1065:
976:
948:
696:March's Organic Chemistry
452:compounds are similar to
1594:3-Chloro-5-nitroindazole
1429:Diethylamine/NO (DEA/NO)
1401:Metal nitrosyl complexes
1329:S-Nitrosoalbumin (SNALB)
1023:Cinaciguat (BAY 58-2667)
855:10.1021/acs.oprd.0c00323
827:, pp. 150–151, 177.
672:, pp. 202, 206–207.
375:Of chalcogen heteroatoms
348:less electrophilic than
200:and chemical synthesis.
125:Not to be confused with
2186:PDE9 inhibitors (e.g.,
1674:Pentamidine isethionate
1584:3-Bromo-7-nitroindazole
1471:Heterocyclic compounds:
995:Activators/stimulators:
210:biological functions of
171:-nitrosothiols (RSNOs).
2143:L-Type calcium channel
815:, pp. 186, 191–2.
485:
309:On the carbon skeleton
137:
1747:Cindunistat (SD-6010)
1702:2-Ethylaminoguanidine
1459:Spermine/NO (SPER/NO)
1256:O-Nitroso compounds (
900:Nitrosation of Amines
617:Free Radical Research
480:
464:ROH + HONO → RONO + H
401:RSH + HONO → RSNO + H
295:Traube-type reactions
293:is a poor nitrosant,
135:
2133:receptor antagonists
1806:Ronopterin (VAS-203)
1505:Molsidomine (SIN-10)
1426:(diazeniumdiolates):
1406:Roussin's black salt
1119:Mannitol hexanitrate
731:Cambridge University
58:improve this article
1500:Linsidomine (SIN-1)
1397:Nitrosyl compounds:
1364:S-Nitrosodiclofenac
1334:S-Nitrosated AR545C
1319:S-Nitroso compounds
803:, pp. 182–183.
791:, pp. 174–175.
733:. pp. 59, 61.
2237:Chemical reactions
1411:Roussin's red salt
1268:Cyclohexyl nitrite
1159:Nipradilol (K-351)
486:
332:RNHOH + → RNO + H
138:
2247:Organic reactions
2224:
2223:
2049:
2040:
2023:
2022:
1956:
1934:
1933:
1854:
1850:
1841:
1837:
1834:N-(1-Iminoethyl)-
1800:
1796:
1787:
1783:
1780:N-(1-Iminoethyl)-
1774:
1770:
1767:N-(1-Iminoethyl)-
1707:2-Iminopiperidine
1663:
1659:
1650:
1646:
1637:
1559:
1288:Isopropyl nitrite
1234:Nitroso compounds
1076:
1061:
1060:
886:, pp. 81–83.
768:10.1021/cr000040l
729:. Cambridge, UK:
711:, pp. 63–70.
594:10.1021/cr000074t
360:. Unusually for
314:Nitroso compounds
231:Organic synthesis
123:
122:
108:
16:(Redirected from
2254:
2150:dihydropyridines
2050:-arginine (NOHA)
2047:
2038:
1992:alpha aminoacids
1962:chlorogenic acid
1957:-arginine (NOHA)
1954:
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1839:
1835:
1798:
1794:
1785:
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1772:
1768:
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1648:
1644:
1635:
1589:3-Chloroindazole
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1563:
1562:
1553:
1251:
1250:
1188:Nitrofluvastatin
1172:
1171:
1114:Itramin tosilate
1070:
983:
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929:
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915:
906:
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887:
881:
875:
874:
849:(9): 1558–1585.
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798:
792:
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779:
762:(4): 1091–1134.
756:Chemical Reviews
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550:diazonium cation
358:
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299:nitrogen dioxide
188:), leading to a
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180:
166:
161:nitrosyl radical
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2170:PDE5 inhibitors
2132:
2096:
2083:
2019:
1996:
1930:
1864:
1815:
1683:
1609:7-Nitroindazole
1604:6-Nitroindazole
1599:5-Nitroindazole
1552:
1544:
1321:(thionitrites):
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1246:
1245:
1244:
1208:Propatylnitrate
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561:are believed to
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510:of a secondary
501:amino compounds
481:Nitrosation of
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467:
415:nitrogen oxides
404:
377:
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351:
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311:
284:Roussin's salts
233:
225:cell signalling
217:S-nitrosylation
206:
204:In biochemistry
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182:
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176:nitrosonium ion
164:
152:
145:metal complexes
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2111:ACE inhibitors
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1314:-Butyl nitrite
1308:
1306:Pentyl nitrite
1303:
1301:-Butyl nitrite
1295:
1293:Methyl nitrite
1290:
1285:
1280:
1275:
1270:
1265:
1258:alkyl nitrites
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894:External links
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588:(1): 935–991.
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529:+ 2 H → NO + H
526:
474:
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407:
406:
402:
383:-nitrosothiols
376:
373:
354:
340:In principle,
338:
337:
333:
326:hydroxylamines
318:nitrosobenzene
310:
307:
265:alkyl nitrites
241:sodium nitrite
232:
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184:
172:
121:
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114:September 2024
56:. Please help
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2010:Calmidazolium
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1300:
1296:
1294:
1291:
1289:
1286:
1284:
1281:
1279:
1278:Hexyl nitrite
1276:
1274:
1273:Ethyl nitrite
1271:
1269:
1266:
1264:
1261:
1259:
1253:
1241:
1239:
1235:
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884:Williams 1988
880:
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825:Williams 1988
821:
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789:Williams 1988
785:
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740:0-521-26796-X
736:
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709:Williams 1988
705:
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682:Williams 1988
678:
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670:Williams 1988
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517:
516:electrophilic
513:
509:
506:
502:
499:sources with
498:
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331:
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319:
315:
306:
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296:
292:
287:
285:
281:
280:nitroprusside
276:
274:
273:can be driven
270:
266:
262:
258:
254:
250:
246:
242:
238:
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226:
222:
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85:
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78:
75: –
74:
70:
69:Find sources:
63:
59:
55:
49:
48:
47:single source
43:This article
41:
37:
32:
31:
19:
2213:
2212:
2188:paraxanthine
2164:beta blocker
2107:
2056:
2034:
1838:-ornithine (
1771:-ornithine (
1516:
1495:Feprosidnine
1490:Sydnonimines
1488:
1473:
1470:
1422:
1399:
1396:
1385:nitrosamines
1382:
1317:
1311:
1298:
1255:
1232:
1082:
1049:
1028:GSK-2181236A
994:
936:Nitric oxide
879:
846:
842:
832:
820:
808:
796:
784:
759:
755:
749:
724:
716:
704:
695:
689:
677:
665:
653:
620:
616:
610:
585:
581:
575:
558:
547:
505:nucleophilic
493:Nitrosamines
488:
487:
458:nucleophilic
453:
445:
444:
432:nitrous acid
426:
419:
408:
395:nitrous acid
387:condensation
380:
378:
366:
339:
312:
291:nitric oxide
289:In general,
288:
277:
269:nitrosamines
237:nitrous acid
234:
213:nitric oxide
207:
195:
168:
140:
139:
111:
101:
94:
87:
80:
68:
44:
2201:simvastatin
2035:Precursors:
1972:epicatechin
1896:Indospicine
1851:-arginine (
1797:-arginine (
1732:AR-C 102222
1660:-arginine (
1647:-arginine (
1510:Sydnonimine
1243:Nitrite (NO
1226:Trolnitrate
1222:Tenitramine
1164:Nitrate (NO
1050:Inhibitors:
1033:Praliciguat
1013:BAY 60-4552
1008:BAY 41-8543
1003:BAY 41-2272
725:Nitrosation
554:deamination
540:NH + NO → R
519:nitrosonium
257:thiocyanate
190:nitrosamine
18:Nitrosation
2231:Categories
2174:sildenafil
2154:nifedipine
2057:Cofactors:
2046:N-Hydroxy-
1953:N-Hydroxy-
1742:Canavanine
1737:BYK-191023
1556:inhibitors
1485:REC15/2739
1464:V-PYRRO/NO
1154:Nicorandil
1043:Vericiguat
942:modulators
623:(1): 1–7.
567:References
428:Sulfinates
316:, such as
84:newspapers
2214:See also:
2160:Nebivolol
2119:captopril
2041:-Arginine
1982:norvaline
1977:ornithine
1891:GW-273629
1847:N-Methyl-
1793:N-Methyl-
1784:-lysine (
1656:N-Propyl-
1643:N-Methyl-
1624:ARL-17477
1517:Unsorted:
1067:NO donors
1038:Riociguat
1018:BI-703704
998:Ataciguat
939:signaling
871:225483602
863:1083-6160
582:Chem. Rev
473:Of amines
436:bisulfite
411:disulfide
322:oxidation
127:Nitration
54:talk page
2181:caffeine
2146:blockers
2137:bosentan
2123:losartan
1940:Arginase
1926:VAS-2381
1921:ONO-1714
1869:Unsorted
1629:Indazole
1535:FR146881
1530:FR144220
1520:Cimlanod
1475:Furoxans
1454:PROLI/NO
1424:NONOates
1374:SNO-t-PA
1238:nitrites
1149:NCX-4215
1144:NCX 4040
1139:NCX-4016
1134:NCX-2216
1084:Nitrates
1073:prodrugs
776:11942788
645:21787778
637:15061648
602:11942784
544:N-NO + H
508:nitrogen
261:thiourea
249:chloride
221:cysteine
215:include
2199:(e.g.,
2197:Statins
2172:(e.g.,
2148:(e.g.,
2135:(e.g.,
2117:(e.g.,
1967:ginseng
1916:NXN-462
1911:NCX-456
1901:KD-7040
1881:CKD-712
1614:A-84643
1480:Furoxan
1379:SNO-vWF
1129:NCX-466
978:Targets
497:nitrite
483:aniline
450:Nitroso
367:Excess
253:bromide
245:synthon
198:enzymes
149:nitroso
98:scholar
2028:Others
1987:lysine
1550:Enzyme
1525:FK-409
1439:GLO/NO
1390:SIN-1A
869:
861:
774:
737:
643:
635:
600:
521:ion:
303:cupric
100:
93:
86:
79:
71:
2060:NADPH
1855:-NMA)
1842:-NIO)
1801:-NMA)
1788:-NIL)
1775:-NIO)
1717:AEITU
1712:1400W
1664:-NPA)
1651:-NMA)
1638:-NIO)
1324:LA810
950:Forms
867:S2CID
641:S2CID
512:amine
391:thiol
389:of a
259:, or
165:Fe−NO
147:into
105:JSTOR
91:books
2075:Heme
2002:CAMK
1821:eNOS
1811:TRIM
1762:MITU
1757:IPTU
1752:EITU
1689:iNOS
1679:TRIM
1576:nNOS
1444:JS-K
1312:tert
859:ISSN
772:PMID
735:ISBN
633:PMID
598:PMID
413:and
393:and
208:The
153:R−NO
77:news
2088:CaM
2070:FMN
2065:FAD
2015:W-7
1948:ABH
1727:AMT
1567:NOS
1053:ODQ
987:sGC
851:doi
764:doi
760:102
625:doi
590:doi
586:102
438:is
346:bel
324:of
267:or
60:by
2233::
2152::
2129:ET
2121:,
2101:Ca
2080:BH
1487:;
1387:):
1381:;
1316:;
1260:):
1254:;
865:.
857:.
847:24
845:.
841:.
770:.
758:.
639:.
631:.
621:38
619:.
596:.
584:.
556:.
525:NO
442:.
424:.
417:.
397::
369:NO
350:NO
342:NO
328::
255:,
251:,
227:.
183:NH
179:NO
2203:)
2190:)
2183:)
2176:)
2166:)
2162:(
2156:)
2139:)
2131:B
2125:)
2113:/
2095:2
2093:O
2082:4
2048:L
2039:L
1955:L
1853:L
1849:L
1840:L
1836:L
1799:L
1795:L
1786:L
1782:L
1773:L
1769:L
1662:L
1658:L
1649:L
1645:L
1636:L
1558:)
1554:(
1492::
1477::
1403::
1299:n
1252:)
1248:2
1240::
1236:/
1173:)
1169:3
1086::
1075:)
1071:(
928:e
921:t
914:v
873:.
853::
778:.
766::
743:.
660:.
647:.
627::
604:.
592::
542:2
538:2
536:R
533:O
531:2
527:2
491:-
489:N
468:O
466:2
454:S
448:-
446:O
405:O
403:2
381:S
355:2
336:O
334:2
192:.
185:2
169:S
129:.
116:)
112:(
102:·
95:·
88:·
81:·
64:.
50:.
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
