315:
208:
50:
41:
481:
782:
The effects of TMAO on the backbone and charged residues of peptides are found to stabilize compact conformations, whereas effects of TMAO on nonpolar residues lead to peptide swelling. This suggests competing mechanisms of TMAO on proteins, which accounts for hydrophobic swelling, backbone collapse,
604:
found in molluscs, crustaceans, and all marine fishes and bony fishes. It is a protein stabilizer that serves to counteract the protein-destabilizing effects of pressure. In general, the bodies of animals living at great depths are adapted to high pressure environments by having pressure-resistant
1337:
Yang JJ, Shu XO, Herrington DM, Moore SC, Meyer KA, Ose J, Menni C, Palmer ND, Eliassen H, Harada S, Tzoulaki I, Zhu H, Albanes D, Wang TJ, Zheng W, Cai H, Ulrich CM, Guasch-Ferré M, Karaman I, Fornage M, Cai Q, Matthews CE, Wagenknecht LE, Elliott P, Gerszten RE, Yu D. (2021).
813:). Those suffering from trimethylaminuria are unable to convert choline-derived trimethylamine into trimethylamine oxide. Trimethylamine then accumulates and is released in the person's sweat, urine, and breath, giving off a strong fishy odor.
605:
biomolecules and small organic molecules present in their cells, known as piezolytes, of which TMAO is the most abundant. These piezolytes give the proteins the flexibility they need to function properly under great pressure.
870:
Exposure limit guidelines with a detailed description of toxicity are available such as "Recommendation from the
Scientific Committee on Occupational Exposure Limits" by the European Union Commission.
1833:
Guasti L, Galliazzo S, Molaro M, Visconti E, Pennella B, Gaudio GV, Lupi A, Grandi AM, Squizzato A. (2021). "TMAO as a biomarker of cardiovascular events: a systematic review and meta-analysis".
555:
and thus killing the animal. The concentration of TMAO increases with the depth at which the animal lives; TMAO is found in high concentrations in the deepest-living described fish species,
1890:
Zhang H, Yao G. (2023). "Significant correlation between the gut microbiota-derived metabolite trimethylamine-N-oxide and the risk of stroke: evidence based on 23 observational studies".
494:
1998:"Relationship between trimethylamine N-oxide and the risk of hypertension in patients with cardiovascular disease: A meta-analysis and dose-response relationship analysis"
2045:
1982:
1876:
1512:
1449:
1397:
1204:
1141:
1078:
1576:
Zou, Q., Bennion BJ, Daggett V, Murphy KP (2002). "The
Molecular Mechanism of Stabilization of Proteins by TMAO and Its Ability to Counteract the Effects of Urea".
1414:
Lombardo M, Aulisa G, Marcon D, Rizzo G. (2022). "The
Influence of Animal- or Plant-Based Diets on Blood and Urine Trimethylamine-N-Oxide (TMAO) Levels in Humans".
2059:
Directorate-General for
Employment SA, Scientific Committee on Occupational Exposure Limits, Nielsen GD, Pospischil E, Johanson G, Klein CL, et al. (2017).
1092:
Li D, Lu Y, Yuan S, Cai X, He Y, Chen J, Wu Q, He D, Fang A, Bo Y, Song P, Bogaert D, Tsilidis K, Larsson SC, Yu H, Zhu H, Theodoratou E, Zhu Y, Li X. (2022).
364:
1155:
Dean YE, Rouzan SS, Loayza
Pintado JJ, Talat NE, Mohamed ARH, Verma S, Anwar Kamdi Z, Gir D, Helmy A, Helmy Z, Afzal A, Mady T, Hazimeh Y, Aiash H. (2023).
1315:
1787:
Zschocke J, Kohlmueller D, Quak E, Meissner T, Hoffmann GF, Mayatepek E (1999). "Mild trimethylaminuria caused by common variants in FMO3 gene".
2125:
1157:"Serum trimethylamine N-oxide levels among coronary artery disease and acute coronary syndrome patients: a systematic review and meta-analysis"
1039:"Gut microbe-generated metabolite trimethylamine-N-oxide as cardiovascular risk biomarker: a systematic review and dose-response meta-analysis"
1699:
Su Z, Mahmoudinobar F, Dias CL (2017). "Effects of
Trimethylamine-N-oxide on the Conformation of Peptides and its Implications for Proteins".
2078:
1094:"Gut microbiota-derived metabolite trimethylamine-N-oxide and multiple health outcomes: an umbrella review and updated meta-analysis"
806:
329:
1935:"The Gut Microbial Metabolite Trimethylamine N-Oxide and Hypertension Risk: A Systematic Review and Dose-Response Meta-analysis"
1340:"Circulating trimethylamine N-oxide in association with diet and cardiometabolic biomarkers: an international pooled analysis"
501:
1037:
Schiattarella GG, Sannino A, Toscano E, Giugliano G, Gargiulo G, Franzone A, Trimarco B, Esposito G, Perrino C. (2017).
947:"Pseudoliparis swirei sp. nov.: A newly-discovered hadal snailfish (Scorpaeniformes: Liparidae) from the Mariana Trench"
260:
293:
1220:"Organic osmolytes as compatible, metabolic, and counteracting cytoprotectants in high osmolarity and other stresses"
588:. High TMAO concentrations are associated with an increased risk of all-cause mortality and cardiovascular disease.
145:
2135:
2120:
827:
2110:
720:
716:
545:
1311:
203:
2062:
SCOEL/REC/179 trimethylamine: recommendation from the
Scientific Committee on Occupational Exposure Limits
551:
TMAO is found in the tissues of marine crustaceans and marine fish, where it prevents water pressure from
2105:
2039:
1976:
1870:
1506:
1443:
1391:
1198:
1135:
1072:
843:
2130:
1708:
1653:
914:
903:"Fishes of the hadal zone including new species, in situ observations and depth records of Liparidae"
770:
It is used in certain oxidation reactions, e.g. the conversion of alkyl iodides to the corresponding
557:
552:
62:
310:
625:
99:
49:
2115:
1915:
1858:
1812:
641:
2074:
2027:
1964:
1907:
1850:
1804:
1769:
1724:
1681:
1618:
1594:
1578:
1494:
1431:
1379:
1293:
1242:
1186:
1123:
1060:
1014:
968:
901:
Linley, T.D., M.E. Gerringer, P.H. Yancey, J.C. Drazen, C.L. Weinstock, A.J. Jamieson (2016).
802:
797:
693:
653:
2066:
2017:
2009:
1954:
1946:
1899:
1842:
1796:
1759:
1716:
1671:
1661:
1586:
1558:
1533:
1484:
1476:
1423:
1369:
1359:
1351:
1283:
1273:
1232:
1176:
1168:
1113:
1105:
1050:
1004:
958:
922:
783:
and stabilization of charge-charge interactions. These mechanisms are observed in Trp cage.
637:
581:
525:
444:
387:
1549:
Soderquist, J. A., Anderson, C. L. (1986). "Crystalline anhydrous trimethylamine N-oxide".
1465:"The dietary source of trimethylamine N-oxide and clinical outcomes: an unexpected liaison"
276:
269:
116:
1464:
879:
705:
185:
109:
945:
Gerringer, M.E., T.D. Linley, P.H. Yancey, A.J. Jamieson, E. Goetze, J.C. Drazen (2016).
2022:
1997:
1712:
1657:
1489:
1181:
1156:
918:
314:
207:
165:
1959:
1934:
1676:
1641:
1374:
1339:
1288:
1261:
1118:
1093:
996:
831:
763:
This reaction is used to decomplex organic ligands from metals, e.g. from (diene)Fe(CO)
609:
569:
562:
472:
1800:
1562:
1009:
2099:
1919:
1862:
1224:
987:
728:
433:
196:
17:
1816:
1720:
859:
633:
1742:
Treacy, E.P., Akerman BR, Chow LM, Youil R, Bibeau C, Lin J, et al. (1998).
1172:
249:
2013:
1613:
585:
537:
40:
1903:
1846:
1646:
Proceedings of the
National Academy of Sciences of the United States of America
1427:
1055:
1038:
1950:
963:
946:
927:
902:
858:
High circulating TMAO concentrations are associated with an increased risk of
842:
High circulating TMAO concentrations are associated with an increased risk of
573:
438:
220 to 222 °C (428 to 432 °F; 493 to 495 K) (dihydrate: 96 °C)
415:
176:
1537:
548:. Both the anhydrous and hydrated materials are white, water-soluble solids.
2060:
1666:
2031:
1968:
1911:
1854:
1808:
1728:
1685:
1598:
1498:
1435:
1383:
1364:
1355:
1297:
1246:
1190:
1127:
1109:
1064:
1018:
972:
1773:
1764:
1743:
1480:
1278:
1933:
Ge X, Zheng L, Zhuang R, Yu P, Xu Z, Liu G, Xi X, Zhou X, Fan H. (2020).
771:
629:
601:
613:
577:
236:
1640:
Shea JE, Feinstein SC, Lapointe NE, Larini L, Levine ZA (2015-03-03).
1590:
1237:
1219:
847:
727:
NO is employed as a decarbonylation agent according to the following
456:
471:
Except where otherwise noted, data are given for materials in their
2070:
224:
463:
156:
144:
134:
1642:"Regulation and aggregation of intrinsically disordered peptides"
1463:
Evans M, Dai L, Avesani CM, Kublickiene K, Stenvinkel P. (2023).
709:
215:
692:
The dihydrate is dehydrated by azeotropic distillation from
298:
1262:"Trimethylamine N-Oxide: The good, the bad and the unknown"
1260:
Velasquez M, Ramezani A, Manal A, Raj D (8 November 2016).
540:. Although the anhydrous compound is known, trimethylamine
1744:"Mutations of the flavin-containing monooxygenase gene (
565:, at a recorded depth of 8,076 m (26,496 ft).
1996:
Han JM, Guo L, Chen XH, Xie Q, Song XY, Ma YL. (2024).
1312:"What does it take to live at the bottom of the ocean?"
907:
Deep Sea
Research Part I: Oceanographic Research Papers
489:
1748:) cause trimethylaminuria, a defect in detoxication"
830:are associated with an increased risk of all-cause
708:experiments to counteract the unfolding effects of
652:TMAO can be synthesized from TMA by treatment with
568:In animals, TMAO is a product of the oxidation of
805:is a rare defect in the production of the enzyme
576:of trimethyl quaternary ammonium compounds, like
1409:
1407:
248:
1032:
1030:
1028:
940:
938:
115:
108:
1530:Encyclopedia of Reagents for Organic Synthesis
311:DTXSID001030179 DTXSID8049678, DTXSID001030179
2065:. Publications Office of the European Union.
616:that is characteristic of degrading seafood.
8:
2044:: CS1 maint: multiple names: authors list (
1981:: CS1 maint: multiple names: authors list (
1875:: CS1 maint: multiple names: authors list (
1511:: CS1 maint: multiple names: authors list (
1448:: CS1 maint: multiple names: authors list (
1396:: CS1 maint: multiple names: authors list (
1203:: CS1 maint: multiple names: authors list (
1140:: CS1 maint: multiple names: authors list (
1077:: CS1 maint: multiple names: authors list (
896:
894:
1528:A. J. Pearson "Trimethylamine N-Oxide" in
1344:The American Journal of Clinical Nutrition
313:
206:
184:
28:
2021:
1958:
1763:
1675:
1665:
1532:, John Wiley & Sons, 2001: New York.
1488:
1373:
1363:
1287:
1277:
1236:
1180:
1117:
1054:
1008:
986:Baker, J.R., Chaykin, S. (1 April 1962).
962:
926:
624:TMAO levels increase with consumption of
275:
268:
1524:
1522:
890:
369:
334:
309:
2037:
1974:
1892:European Journal of Clinical Nutrition
1868:
1504:
1441:
1389:
1196:
1133:
1070:
197:
1828:
1826:
544:-oxide is usually encountered as the
341:Key: UYPYRKYUKCHHIB-UHFFFAOYSA-N
164:
7:
988:"The biosynthesis of trimethylamine-
351:Key: UYPYRKYUKCHHIB-UHFFFAOYAU
239:
223:
640:such as vegan, vegetarian and the
25:
807:flavin-containing monooxygenase 3
338:InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3
87:Trimethylamine oxide, TMAO, TMANO
1318:from the original on 13 May 2016
704:Trimethylamine oxide is used in
479:
405:
399:
348:InChI=1/C3H9NO/c1-4(2,3)5/h1-3H3
48:
39:
828:circulating TMAO concentrations
475:(at 25 °C , 100 kPa).
1721:10.1103/physrevlett.119.108102
1161:Annals of Medicine and Surgery
408:
393:
1:
2126:Quaternary ammonium compounds
1801:10.1016/S0140-6736(99)80019-1
1563:10.1016/S0040-4039(00)84884-4
1010:10.1016/S0021-9258(18)60325-4
1173:10.1097/MS9.0000000000001426
778:Effects on protein stability
2014:10.1097/MD.0000000000036784
2152:
1904:10.1038/s41430-022-01104-7
1847:10.1007/s11739-020-02470-5
1628:, vol. 5, p. 872
1428:10.1007/s13668-021-00387-9
795:
536:NO. It is in the class of
964:10.11646/zootaxa.4358.1.7
928:10.1016/j.dsr.2016.05.003
612:(TMA), which is the main
561:, which was found in the
469:
380:
360:
325:
92:
84:
61:
56:
47:
38:
1752:Human Molecular Genetics
1538:10.1002/047084289X.rt268
1056:10.1093/eurheartj/ehx342
721:nucleophilic abstraction
717:organometallic chemistry
1951:10.1093/advances/nmz064
1701:Physical Review Letters
1667:10.1073/pnas.1418155112
1612:Volker Franzen (1973).
700:Laboratory applications
1043:European Heart Journal
838:Cardiovascular disease
632:, shellfish and total
628:protein such as eggs,
1279:10.3390/toxins8110326
844:cardiovascular events
74:-Dimethylmethanamine
2002:Medicine (Baltimore)
1356:10.1093/ajcn/nqaa430
1110:10.1093/ajcn/nqac074
558:Pseudoliparis swirei
528:with the formula (CH
63:Preferred IUPAC name
18:Trimethylamine oxide
1765:10.1093/hmg/7.5.839
1713:2017PhRvL.119j8102S
1658:2015PNAS..112.2758L
1481:10.1093/ckj/sfad095
1314:. BBC Earth. 2016.
1218:Yancey, P. (2005).
919:2016DSRI..114...99L
644:lower TMAO levels.
608:TMAO decomposes to
553:distorting proteins
445:Solubility in water
420:75.11
35:
866:Potential toxicity
642:Mediterranean diet
502:Infobox references
29:
2080:978-92-79-66627-8
1626:Collected Volumes
1619:Organic Syntheses
1591:10.1021/ja004206b
1579:J. Am. Chem. Soc.
1557:(34): 3961–3962.
1475:(11): 1804–1812.
1238:10.1242/jeb.01730
1231:(15): 2819–2830.
1167:(12): 6123–6133.
1049:(39): 2948–2956.
803:Trimethylaminuria
798:Trimethylaminuria
792:Trimethylaminuria
694:dimethylformamide
654:hydrogen peroxide
638:Plant-based diets
510:Chemical compound
508:
507:
294:CompTox Dashboard
146:Interactive image
16:(Redirected from
2143:
2136:Methyl compounds
2121:Oxidizing agents
2091:
2090:
2088:
2087:
2056:
2050:
2049:
2043:
2035:
2025:
1993:
1987:
1986:
1980:
1972:
1962:
1930:
1924:
1923:
1887:
1881:
1880:
1874:
1866:
1835:Intern Emerg Med
1830:
1821:
1820:
1784:
1778:
1777:
1767:
1739:
1733:
1732:
1696:
1690:
1689:
1679:
1669:
1652:(9): 2758–2763.
1637:
1631:
1629:
1622:
1609:
1603:
1602:
1585:(7): 1192–1202.
1573:
1567:
1566:
1551:Tetrahedron Lett
1546:
1540:
1526:
1517:
1516:
1510:
1502:
1492:
1460:
1454:
1453:
1447:
1439:
1411:
1402:
1401:
1395:
1387:
1377:
1367:
1350:(5): 1145–1156.
1334:
1328:
1327:
1325:
1323:
1308:
1302:
1301:
1291:
1281:
1257:
1251:
1250:
1240:
1215:
1209:
1208:
1202:
1194:
1184:
1152:
1146:
1145:
1139:
1131:
1121:
1089:
1083:
1082:
1076:
1068:
1058:
1034:
1023:
1022:
1012:
983:
977:
976:
966:
942:
933:
932:
930:
898:
745:NO + L → M(CO)
582:trimethylglycine
526:organic compound
492:
486:
483:
482:
428:colorless solid
410:
407:
401:
395:
388:Chemical formula
318:
317:
302:
300:
279:
272:
252:
241:
227:
210:
199:
188:
168:
148:
119:
112:
52:
43:
36:
21:
2151:
2150:
2146:
2145:
2144:
2142:
2141:
2140:
2111:Lipid disorders
2096:
2095:
2094:
2085:
2083:
2081:
2058:
2057:
2053:
2036:
1995:
1994:
1990:
1973:
1932:
1931:
1927:
1889:
1888:
1884:
1867:
1832:
1831:
1824:
1795:(9181): 834–5.
1786:
1785:
1781:
1741:
1740:
1736:
1698:
1697:
1693:
1639:
1638:
1634:
1624:
1611:
1610:
1606:
1575:
1574:
1570:
1548:
1547:
1543:
1527:
1520:
1503:
1462:
1461:
1457:
1440:
1413:
1412:
1405:
1388:
1336:
1335:
1331:
1321:
1319:
1310:
1309:
1305:
1259:
1258:
1254:
1217:
1216:
1212:
1195:
1154:
1153:
1149:
1132:
1091:
1090:
1086:
1069:
1036:
1035:
1026:
985:
984:
980:
944:
943:
936:
900:
899:
892:
888:
880:Greenland shark
876:
868:
856:
850:in particular.
840:
824:
819:
800:
794:
789:
780:
766:
759:
755:
751:
744:
740:
726:
706:protein folding
702:
687:
683:
679:
675:
671:
667:
663:
650:
622:
596:Trimethylamine
594:
535:
531:
514:Trimethylamine
511:
504:
499:
498:
497: ?)
488:
484:
480:
476:
459:
447:
404:
398:
390:
376:
373:
368:
367:
356:
353:
352:
349:
343:
342:
339:
333:
332:
321:
303:
296:
287:
255:
242:
230:
191:
171:
151:
138:
127:
102:
88:
80:
79:
30:Trimethylamine
23:
22:
15:
12:
11:
5:
2149:
2147:
2139:
2138:
2133:
2128:
2123:
2118:
2113:
2108:
2098:
2097:
2093:
2092:
2079:
2071:10.2767/440659
2051:
1988:
1925:
1898:(7): 731–740.
1882:
1841:(1): 201–207.
1822:
1779:
1734:
1707:(10): 108102.
1691:
1632:
1604:
1568:
1541:
1518:
1455:
1403:
1329:
1303:
1252:
1210:
1147:
1104:(1): 230–243.
1098:Am J Clin Nutr
1084:
1024:
1003:(4): 1309–13.
997:J. Biol. Chem.
978:
957:(1): 161–177.
934:
889:
887:
884:
883:
882:
875:
872:
867:
864:
855:
852:
839:
836:
823:
820:
818:
817:Health effects
815:
796:Main article:
793:
790:
788:
785:
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776:
764:
761:
760:
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746:
742:
736:
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698:
690:
689:
685:
681:
677:
673:
669:
665:
661:
649:
646:
621:
618:
610:trimethylamine
593:
592:Marine animals
590:
570:trimethylamine
563:Mariana Trench
533:
529:
509:
506:
505:
500:
478:
477:
473:standard state
470:
467:
466:
460:
455:
452:
451:
448:
443:
440:
439:
436:
430:
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193:
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159:
153:
152:
150:
149:
141:
139:
132:
129:
128:
126:
125:
113:
105:
103:
98:
95:
94:
90:
89:
86:
82:
81:
66:
65:
59:
58:
54:
53:
45:
44:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2148:
2137:
2134:
2132:
2129:
2127:
2124:
2122:
2119:
2117:
2114:
2112:
2109:
2107:
2104:
2103:
2101:
2082:
2076:
2072:
2068:
2064:
2063:
2055:
2052:
2047:
2041:
2033:
2029:
2024:
2019:
2015:
2011:
2008:(1): e36784.
2007:
2003:
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425:Appearance
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204:100.013.341
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886:References
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416:Molar mass
277:C73WZ0186W
270:FLD0K1SJ1A
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100:CAS Number
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822:Mortality
787:Disorders
648:Chemistry
546:dihydrate
282:dihydrate
122:dihydrate
110:1184-78-7
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1939:Adv Nutr
1912:35468932
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