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265:
62:
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53:
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1062:
and can also be produced by metabolism of its esters found in food. It has a characteristic odor like rancid butter (4-carbon organic compounds take the root, butyl, which is in turn from butyric which is in turn from the Latin word for butter and the Greek, βούτυρον) but
702:
640:
602:
1626:
Matsumoto-Oda, Akiko; Oda, Ryo; Hayashi, Yukako; Murakami, Hiroshi; Maeda, Norihiko; Kumazaki, Kiyonori; Shimizu, Keiko; Matsuzawa, Tetsuro (2003). "Vaginal Fatty Acids
Produced by Chimpanzees during Menstrual Cycles".
744:
1077:
Isobutyric acid, along with several other short-chain fatty acids collectively known as "copulins," is found abundantly in human vaginal secretions. Levels of isobutyric acid fluctuate throughout the
1304:
1687:
698:
1042:
are present naturally in a wide variety of foods and, at varying concentrations, can impart a range of flavors. The compound's safety as a food additive was reviewed by an
2845:
2611:
1167:
729:
475:
2834:
1308:
1253:
1680:
751:
694:
842:
Isobutyric acid is a colorless liquid with a somewhat unpleasant odor. It is soluble in water and organic solvents. It is found naturally in
686:
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1673:
2298:
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440:
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680:
373:
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404:
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2468:
1135:
566:
2302:
272:
1577:"Effect of Copulins on Rating of Female Attractiveness, Mate-Guarding, and Self-Perceived Sexual Desirability"
2472:
1002:
derivatives. Its acid chloride is commonly used as the intermediate to obtain the others. When heated with a
621:
2867:
1776:
1750:
1707:
585:
1217:
626:
260:
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832:
2256:
202:
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2686:
2643:
2290:
2261:
2211:
2117:
1713:
934:
Isobutyric acid can also be manufactured commercially using engineered bacteria with a sugar feedstock.
654:
631:
614:
144:
2147:
2142:
1329:
I. Pierre and E. Puchot (1873). "New
Studies on Valerianic Acid and its Preparation on a Large Scale".
2281:
2784:
2484:
2029:
1995:
1484:
963:
80:
1962:
2464:
2246:
1983:
1868:
1132:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
421:
110:
2448:
2444:
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2432:
2741:
2736:
2726:
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1884:
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162:
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2202:
2055:
1872:
1828:
1526:
Lucas, Kerry A.; Filley, Jessica R.; Erb, Jeremy M.; Graybill, Eric R.; Hawes, John W. (2007).
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820:
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672:
31:
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2510:
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2009:
1968:
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1876:
1848:
1242:
999:
967:
899:
556:
546:
253:
2544:
2488:
2480:
2436:
2404:
2014:
1991:
1561:
1512:
1003:
828:
35:
1740:
1050:
panel, who concluded that there were no concerns at the likely levels of intake.
346:
2789:
2706:
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2172:
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2109:
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1987:
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1910:
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291:
213:
52:
1648:
1602:
1593:
1280:
2774:
2731:
2716:
2711:
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2526:
2522:
2415:
2346:
2286:
2226:
2221:
2187:
2097:
2093:
2034:
2024:
2003:
1949:
1853:
1820:
1082:
955:
888:
393:
1656:
1553:
1544:
1527:
660:
17:
1504:
1426:
668:
2769:
2555:
2540:
2530:
2518:
2387:
2377:
2363:
2177:
2043:
2019:
1978:
1843:
750:
743:
736:
709:
233:
1528:"Peroxisomal Metabolism of Propionic Acid and Isobutyric Acid in Plants"
1475:
Amoore, J. E. (1967). "Specific
Anosmia: A Clue to the Olfactory Code".
242:
2666:
2498:
2167:
2113:
2051:
1954:
1858:
1804:
1796:
1781:
1760:
1755:
1257:. Vol. 4 (11th ed.). Cambridge University Press. p. 892.
1064:
1007:
853:
536:
333:
273:
1640:
1496:
2494:
1812:
1768:
1039:
951:
858:
824:
809:
193:
774:
Except where otherwise noted, data are given for materials in their
664:
1271:
Riemenschneider, Wilhelm; Bolt, Hermann (2000). "Esters, Organic".
1246:
321:
2127:
991:
987:
864:
843:
357:
173:
143:
133:
2587:
2459:
2132:
312:
1669:
2073:
1451:
1407:"Safety evaluation of certain food additives and contaminants"
1047:
1043:
409:
60:
51:
1348:
Jenkins, P. R. (1985). "Carboxylic acids and derivatives".
835:. Deprotonation or esterification gives derivatives called
986:
The acid reacts as a typical carboxylic acid: it can form
30:"Valerianic acid" redirects here. Not to be confused with
721:
2598:
1058:
In humans, isobutyric acid is a minor product of the
1575:
Williams, Megan N.; Jacobson, Amy (April 22, 2016).
1085:
status. Similar cycles are observed in chimpanzees.
879:
Isobutyric acid is manufactured by the oxidation of
2755:
2642:
2625:
2596:
1723:
1706:
1405:FAO/WHO Expert Committee on food additives (1998).
1081:, and it is hypothesized to act as an indicator of
300:
1067:for it has been reported in about 2.5% of people.
970:. In the presence of proton donors, the action of
27:Carboxylic acid with chemical formula (CH3)2CHCO2H
1456:"Specifications for flavourings: isobutyric acid"
161:
345:
1074:of isobutyric acid in plants has been studied.
725:
119:
1273:Ullmann's Encyclopedia of Industrial Chemistry
449:InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)
2757:
2644:
1681:
1305:"Biological pathways to produce methacrylate"
894:It can also be prepared by the high pressure
459:InChI=1/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)
8:
1166:: CS1 maint: DOI inactive as of June 2024 (
2639:
1720:
1688:
1674:
1666:
424:
263:
221:
40:
1610:
1592:
1587:(2). SAGE Publications: 147470491664332.
1543:
1266:
1264:
381:
2846:Ionotropic glutamate receptor modulators
1725:
1237:
1235:
1233:
1105:
480:
445:
420:
241:
1159:
561:155 °C (311 °F; 428 K)
551:−47 °C (−53 °F; 226 K)
254:
2603:Tooltip N-Methyl-D-aspartate receptor
768:55 °C (131 °F; 328 K)
452:Key: KQNPFQTWMSNSAP-UHFFFAOYSA-N
201:
181:
7:
2295:4-hydroxyquinoline-3-carboxylic acid
2153:4-Phenyl-4-formyl-N-methylpiperidine
942:Many routes are known including the
2118:trichloroethane (methyl chloroform)
462:Key: KQNPFQTWMSNSAP-UHFFFAOYAB
336:
320:
2722:Pesampator (BIIB-104, PF-04958242)
25:
1181:Bjerrum, J.; et al. (1958).
1038:Isobutyric acid and its volatile
1427:"Metabocard for isobutyric acid"
1352:. Vol. 7. pp. 96–160.
630:
625:
620:
510:
1532:Journal of Biological Chemistry
778:(at 25 °C , 100 kPa).
1136:The Royal Society of Chemistry
883:, which is a byproduct of the
516:
504:
1:
2821:Receptor/signaling modulators
2762:Tooltip Glycine transporter 2
2672:Bitopertin (RG1678/RO4917838)
2649:Tooltip Glycine transporter 1
1350:General and Synthetic Methods
2873:Glycine receptor antagonists
2839:receptor positive modulators
1218:"NFPA Hazard Classification"
1018:-hydroxyisobutyric acid, (CH
978:also gives isobutyric acid.
1358:10.1039/9781847556196-00096
1185:. London: Chemical Society.
1144:10.1039/9781849733069-FP001
1095:Sucrose acetate isobutyrate
1006:solution it is oxidized to
47:
2889:
1877:chlorobutanol (chloretone)
1635:(2). S. Karger AG: 75–79.
29:
2812:
1992:pregnenolone (eltanolone)
1969:Glutamic acid (glutamate)
1431:Human Metabolome Database
808:with structural formula (
772:
601:
596:
531:88.11 g/mol
491:
471:
436:
103:
91:
79:
74:
46:
2828:GABA receptor modulators
1730:Tooltip Glycine receptor
1594:10.1177/1474704916643328
1281:10.1002/14356007.a09_565
831:. It is classified as a
681:Precautionary statements
2473:3β-androsterone sulfate
2469:3α-androsterone sulfate
1581:Evolutionary Psychology
1386:The Good Scents Company
1254:Encyclopædia Britannica
1146:(inactive 2024-06-22).
586:Magnetic susceptibility
2717:ORG-25935 (SCH-900435)
1906:Alkylbenzene sulfonate
1545:10.1074/jbc.m701028200
1012:potassium permanganate
833:short-chain fatty acid
798:2-methylpropanoic acid
732:
96:2-Methylpropionic acid
85:2-Methylpropanoic acid
65:
56:
2790:Opiranserin (VVZ-149)
2090:diethyl ether (ether)
1138:. 2014. p. 748.
856:, and in the root of
731:
64:
55:
2485:pregnenolone sulfate
2465:Neuroactive steroids
2423:constituents (e.g.,
2383:Cyanotriphenylborate
2344:Negative modulators:
2267:N,N-Dimethylmuscimol
2193:Cyanotriphenylborate
2030:Tetrahydrocannabinol
1996:pregnenolone acetate
1984:Neuroactive steroids
1957:constituents (e.g.,
1866:Positive modulators:
1248:"Butyric Acid"
964:potassium dichromate
714:(fire diamond)
81:Preferred IUPAC name
2477:deoxycorticosterone
2257:N-Methylbicuculline
1629:Folia Primatologica
1538:(34): 24980–24989.
1489:1967Natur.214.1095A
1483:(5093): 1095–1098.
1183:Stability Constants
966:in the presence of
703:P305+P351+P338+P310
541:0.9697 g/cm (0 °C)
43:
2687:Glycyldodecylamide
2291:4-hydroxyquinoline
2262:N-Methylstrychnine
938:Laboratory methods
902:) from propylene:
896:hydrocarboxylation
863:, and as an ethyl
782:Infobox references
733:
66:
57:
41:
2855:
2854:
2808:
2807:
2780:Ethanol (alcohol)
2682:Ethanol (alcohol)
2636:
2621:
2620:
2242:Isonipecotic acid
2148:2-Nitrostrychnine
2143:2-Aminostrychnine
2122:trichloroethylene
1924:sodium thiopental
1881:ethanol (alcohol)
1823:
1815:
1807:
1799:
1771:
1763:
1717:
1641:10.1159/000070000
1497:10.1038/2141095a0
1382:"Isobutyric acid"
1367:978-0-85186-884-4
1198:"Isobutyric acid"
1153:978-0-85404-182-4
849:Ceratonia siliqua
790:Chemical compound
788:
787:
655:Hazard statements
592:-56.06x10 cm/mol
405:CompTox Dashboard
145:Interactive image
70:
69:
16:(Redirected from
2880:
2763:
2759:
2650:
2646:
2640:
2630:
2604:
2600:
2503:dextromethorphan
2393:Dihydropyridines
2332:Thiocolchicoside
2282:Pseudostrychnine
2222:Gaboxadol (THIP)
2216:anandamide (AEA)
2208:Endocannabinoids
1940:Dihydropyridines
1900:trifluoroethanol
1896:trichloroethanol
1821:
1813:
1805:
1797:
1769:
1761:
1731:
1727:
1721:
1711:
1697:Glycine receptor
1690:
1683:
1676:
1667:
1661:
1660:
1623:
1617:
1616:
1614:
1596:
1572:
1566:
1565:
1547:
1523:
1517:
1516:
1472:
1466:
1465:
1463:
1462:
1448:
1442:
1441:
1439:
1438:
1423:
1417:
1416:
1414:
1413:
1402:
1396:
1395:
1393:
1392:
1378:
1372:
1371:
1345:
1339:
1338:
1326:
1320:
1319:
1317:
1316:
1307:. Archived from
1301:
1295:
1294:
1268:
1259:
1258:
1250:
1239:
1228:
1227:
1225:
1224:
1214:
1208:
1207:
1205:
1204:
1193:
1187:
1186:
1178:
1172:
1171:
1165:
1157:
1130:"Front Matter".
1127:
1121:
1117:, 11th Edition,
1110:
976:methacrylic acid
948:isobutyronitrile
885:hydroformylation
881:isobutyraldehyde
802:isobutanoic acid
796:, also known as
753:
746:
739:
724:
704:
700:
696:
692:
688:
674:
670:
666:
662:
634:
629:
624:
518:
512:
506:
499:Chemical formula
429:
428:
413:
411:
385:
349:
338:
324:
304:
275:
267:
256:
245:
225:
205:
185:
165:
147:
123:
98:Isobutanoic acid
48:
44:
42:Isobutyric acid
21:
2888:
2887:
2883:
2882:
2881:
2879:
2878:
2877:
2858:
2857:
2856:
2851:
2838:
2804:
2761:
2751:
2662:ALX-5407 (NFPS)
2648:
2629:
2617:
2602:
2592:
2352:Benzodiazepines
2237:Isobutyric acid
2078:chloral hydrate
1930:Chlormethiazole
1892:tribromoethanol
1888:-butanol (2M2P)
1729:
1710:
1702:
1694:
1664:
1625:
1624:
1620:
1574:
1573:
1569:
1525:
1524:
1520:
1474:
1473:
1469:
1460:
1458:
1450:
1449:
1445:
1436:
1434:
1425:
1424:
1420:
1411:
1409:
1404:
1403:
1399:
1390:
1388:
1380:
1379:
1375:
1368:
1347:
1346:
1342:
1331:Ann. Chim. Phys
1328:
1327:
1323:
1314:
1312:
1303:
1302:
1298:
1291:
1270:
1269:
1262:
1241:
1240:
1231:
1222:
1220:
1216:
1215:
1211:
1202:
1200:
1196:Sigma-Aldrich.
1195:
1194:
1190:
1180:
1179:
1175:
1158:
1154:
1129:
1128:
1124:
1111:
1107:
1103:
1091:
1079:menstrual cycle
1056:
1036:
1029:
1025:
1021:
1014:oxidizes it to
984:
940:
929:
925:
921:
917:
913:
909:
877:
818:
813:
806:carboxylic acid
794:Isobutyric acid
791:
784:
779:
758:
757:
756:
755:
748:
741:
734:
730:
722:
683:
657:
643:
617:
589:
575:
521:
515:
509:
501:
487:
484:
479:
478:
467:
464:
463:
460:
454:
453:
450:
444:
443:
432:
414:
407:
388:
368:
352:
339:
327:
307:
294:
285:
248:
228:
208:
188:
168:
150:
137:
126:
113:
99:
97:
95:
94:Isobutyric acid
87:
86:
39:
28:
23:
22:
15:
12:
11:
5:
2886:
2884:
2876:
2875:
2870:
2868:Alkanoic acids
2860:
2859:
2853:
2852:
2850:
2849:
2842:
2836:
2831:
2824:
2817:
2813:
2810:
2809:
2806:
2805:
2803:
2802:
2797:
2792:
2787:
2782:
2777:
2772:
2766:
2764:
2753:
2752:
2750:
2749:
2744:
2739:
2734:
2729:
2724:
2719:
2714:
2709:
2704:
2699:
2694:
2689:
2684:
2679:
2674:
2669:
2664:
2659:
2653:
2651:
2637:
2623:
2622:
2619:
2618:
2616:
2615:
2607:
2605:
2594:
2593:
2591:
2590:
2585:
2580:
2558:
2553:
2548:
2534:
2492:
2462:
2457:
2452:
2418:
2413:
2408:
2390:
2385:
2380:
2375:
2349:
2340:
2339:
2334:
2329:
2324:
2319:
2314:
2284:
2279:
2274:
2272:Nipecotic acid
2269:
2264:
2259:
2254:
2249:
2244:
2239:
2234:
2229:
2224:
2219:
2205:
2200:
2195:
2190:
2185:
2180:
2175:
2170:
2165:
2160:
2155:
2150:
2145:
2136:
2135:
2130:
2125:
2106:methoxyflurane
2067:
2037:
2032:
2027:
2022:
2017:
2012:
2007:
1981:
1976:
1971:
1966:
1963:ginsenoside-Rf
1952:
1947:
1937:
1932:
1927:
1913:
1908:
1903:
1862:
1861:
1856:
1851:
1846:
1841:
1839:Picolinic acid
1836:
1831:
1826:
1818:
1810:
1802:
1794:
1789:
1784:
1779:
1774:
1766:
1758:
1753:
1748:
1743:
1734:
1732:
1718:
1704:
1703:
1695:
1693:
1692:
1685:
1678:
1670:
1663:
1662:
1618:
1567:
1518:
1467:
1443:
1418:
1397:
1373:
1366:
1340:
1321:
1296:
1290:978-3527306732
1289:
1275:. p. 10.
1260:
1245:, ed. (1911).
1243:Chisholm, Hugh
1229:
1209:
1188:
1173:
1152:
1122:
1104:
1102:
1099:
1098:
1097:
1090:
1087:
1060:gut microbiome
1055:
1052:
1035:
1032:
1027:
1023:
1019:
983:
980:
972:sodium amalgam
939:
936:
932:
931:
927:
923:
919:
915:
911:
907:
876:
873:
816:
811:
789:
786:
785:
780:
776:standard state
773:
770:
769:
766:
760:
759:
749:
742:
735:
720:
719:
718:
717:
715:
706:
705:
699:P303+P361+P353
695:P301+P312+P330
684:
679:
676:
675:
658:
653:
650:
649:
644:
639:
636:
635:
618:
613:
610:
609:
599:
598:
594:
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590:
584:
581:
580:
577:
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563:
562:
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553:
552:
549:
543:
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539:
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532:
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482:
474:
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468:
466:
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455:
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447:
439:
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431:
430:
417:
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403:
400:
399:
396:
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378:
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370:
369:
367:
366:
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354:
353:
351:
350:
342:
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332:
329:
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317:
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309:
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306:
305:
297:
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279:
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269:
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258:
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218:
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210:
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198:
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178:
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158:
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131:
128:
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116:
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109:
106:
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101:
100:
93:
89:
88:
84:
83:
77:
76:
72:
71:
68:
67:
58:
32:Valerenic acid
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2885:
2874:
2871:
2869:
2866:
2865:
2863:
2848:
2847:
2843:
2841:
2840:
2832:
2830:
2829:
2825:
2823:
2822:
2818:
2815:
2814:
2811:
2801:
2798:
2796:
2793:
2791:
2788:
2786:
2783:
2781:
2778:
2776:
2773:
2771:
2768:
2767:
2765:
2760:
2754:
2748:
2745:
2743:
2740:
2738:
2735:
2733:
2730:
2728:
2725:
2723:
2720:
2718:
2715:
2713:
2710:
2708:
2705:
2703:
2700:
2698:
2695:
2693:
2690:
2688:
2685:
2683:
2680:
2678:
2675:
2673:
2670:
2668:
2665:
2663:
2660:
2658:
2655:
2654:
2652:
2647:
2641:
2638:
2634:
2628:
2624:
2613:
2609:
2608:
2606:
2601:
2595:
2589:
2586:
2584:
2581:
2578:
2574:
2570:
2566:
2562:
2559:
2557:
2554:
2552:
2549:
2546:
2542:
2538:
2535:
2532:
2528:
2524:
2520:
2516:
2512:
2511:levomethadone
2508:
2504:
2500:
2496:
2493:
2490:
2486:
2482:
2478:
2474:
2470:
2466:
2463:
2461:
2458:
2456:
2453:
2450:
2446:
2442:
2438:
2434:
2430:
2426:
2422:
2419:
2417:
2414:
2412:
2409:
2406:
2402:
2398:
2394:
2391:
2389:
2386:
2384:
2381:
2379:
2376:
2373:
2369:
2368:flunitrazepam
2365:
2361:
2357:
2353:
2350:
2348:
2345:
2342:
2341:
2338:
2335:
2333:
2330:
2328:
2325:
2323:
2320:
2318:
2315:
2312:
2308:
2304:
2300:
2296:
2292:
2288:
2285:
2283:
2280:
2278:
2275:
2273:
2270:
2268:
2265:
2263:
2260:
2258:
2255:
2253:
2250:
2248:
2247:Isostrychnine
2245:
2243:
2240:
2238:
2235:
2233:
2230:
2228:
2225:
2223:
2220:
2217:
2213:
2209:
2206:
2204:
2201:
2199:
2196:
2194:
2191:
2189:
2186:
2184:
2181:
2179:
2176:
2174:
2171:
2169:
2166:
2164:
2161:
2159:
2156:
2154:
2151:
2149:
2146:
2144:
2141:
2138:
2137:
2134:
2131:
2129:
2126:
2123:
2119:
2115:
2111:
2107:
2103:
2099:
2095:
2091:
2087:
2083:
2079:
2075:
2071:
2068:
2065:
2061:
2057:
2053:
2049:
2045:
2041:
2038:
2036:
2033:
2031:
2028:
2026:
2023:
2021:
2018:
2016:
2013:
2011:
2010:Nitrous oxide
2008:
2005:
2001:
1997:
1993:
1989:
1985:
1982:
1980:
1977:
1975:
1972:
1970:
1967:
1964:
1960:
1956:
1953:
1951:
1948:
1945:
1941:
1938:
1936:
1933:
1931:
1928:
1925:
1921:
1920:pentobarbital
1917:
1914:
1912:
1909:
1907:
1904:
1901:
1897:
1893:
1889:
1887:
1882:
1878:
1874:
1870:
1867:
1864:
1863:
1860:
1857:
1855:
1852:
1850:
1849:Quisqualamine
1847:
1845:
1842:
1840:
1837:
1835:
1832:
1830:
1827:
1825:
1819:
1817:
1811:
1809:
1803:
1801:
1795:
1793:
1790:
1788:
1785:
1783:
1780:
1778:
1775:
1773:
1767:
1765:
1759:
1757:
1754:
1752:
1749:
1747:
1744:
1742:
1739:
1736:
1735:
1733:
1728:
1722:
1719:
1715:
1709:
1705:
1701:
1698:
1691:
1686:
1684:
1679:
1677:
1672:
1671:
1668:
1658:
1654:
1650:
1646:
1642:
1638:
1634:
1630:
1622:
1619:
1613:
1608:
1604:
1600:
1595:
1590:
1586:
1582:
1578:
1571:
1568:
1563:
1559:
1555:
1551:
1546:
1541:
1537:
1533:
1529:
1522:
1519:
1514:
1510:
1506:
1502:
1498:
1494:
1490:
1486:
1482:
1478:
1471:
1468:
1457:
1453:
1447:
1444:
1432:
1428:
1422:
1419:
1408:
1401:
1398:
1387:
1383:
1377:
1374:
1369:
1363:
1359:
1355:
1351:
1344:
1341:
1336:
1332:
1325:
1322:
1311:on 2012-05-02
1310:
1306:
1300:
1297:
1292:
1286:
1282:
1278:
1274:
1267:
1265:
1261:
1256:
1255:
1249:
1244:
1238:
1236:
1234:
1230:
1219:
1213:
1210:
1199:
1192:
1189:
1184:
1177:
1174:
1169:
1163:
1155:
1149:
1145:
1141:
1137:
1134:. Cambridge:
1133:
1126:
1123:
1120:
1116:
1115:
1109:
1106:
1100:
1096:
1093:
1092:
1088:
1086:
1084:
1080:
1075:
1073:
1068:
1066:
1061:
1053:
1051:
1049:
1045:
1041:
1033:
1031:
1017:
1013:
1009:
1005:
1001:
997:
993:
989:
981:
979:
977:
973:
969:
968:sulfuric acid
965:
961:
957:
953:
949:
945:
937:
935:
905:
904:
903:
901:
900:Koch reaction
897:
892:
890:
886:
882:
874:
872:
870:
866:
862:
860:
855:
851:
850:
845:
840:
838:
834:
830:
826:
822:
814:
807:
803:
799:
795:
783:
777:
771:
767:
765:
762:
761:
754:
747:
740:
716:
713:
712:
708:
707:
685:
682:
678:
677:
659:
656:
652:
651:
648:
645:
642:
638:
637:
633:
628:
623:
619:
616:
612:
611:
607:
605:
600:
595:
591:
587:
583:
582:
578:
572:
568:
565:
564:
560:
558:
557:Boiling point
555:
554:
550:
548:
547:Melting point
545:
544:
540:
538:
535:
534:
530:
528:
525:
524:
503:
500:
496:
495:
490:
481:
477:
470:
456:
446:
442:
435:
427:
423:
422:DTXSID4021636
419:
418:
416:
406:
402:
401:
397:
395:
392:
391:
384:
380:
379:
377:
375:
372:
371:
364:
363:
361:
359:
356:
355:
348:
344:
343:
341:
335:
331:
330:
323:
319:
318:
316:
314:
311:
310:
303:
299:
298:
296:
293:
289:
288:
281:
280:
278:
276:
271:
270:
266:
262:
259:
257:
255:ECHA InfoCard
252:
251:
244:
240:
239:
237:
235:
232:
231:
224:
220:
219:
217:
215:
212:
211:
204:
200:
199:
197:
195:
192:
191:
184:
180:
179:
177:
175:
172:
171:
164:
160:
159:
157:
154:
153:
146:
142:
141:
139:
135:
130:
129:
122:
118:
117:
115:
112:
108:
107:
102:
90:
82:
78:
73:
63:
59:
54:
50:
49:
45:
37:
33:
19:
2844:
2833:
2826:
2819:
2545:picrotoxinin
2489:progesterone
2481:DHEA sulfate
2449:ginkgolide M
2445:ginkgolide J
2441:ginkgolide C
2437:ginkgolide B
2433:ginkgolide A
2405:nitrendipine
2343:
2236:
2140:Antagonists:
2139:
2015:Penicillin G
1959:ginsenosides
1916:Barbiturates
1885:
1865:
1746:β-ABA (BABA)
1737:
1632:
1628:
1621:
1584:
1580:
1570:
1535:
1531:
1521:
1480:
1476:
1470:
1459:. Retrieved
1446:
1435:. Retrieved
1433:. 2020-03-26
1430:
1421:
1410:. Retrieved
1400:
1389:. Retrieved
1385:
1376:
1349:
1343:
1334:
1330:
1324:
1313:. Retrieved
1309:the original
1299:
1272:
1252:
1221:. Retrieved
1212:
1201:. Retrieved
1191:
1182:
1176:
1131:
1125:
1118:
1112:
1108:
1076:
1069:
1057:
1037:
1015:
1004:chromic acid
985:
941:
933:
893:
878:
857:
847:
841:
837:isobutyrates
836:
829:butyric acid
801:
797:
793:
792:
710:
646:
603:
570:
358:RTECS number
203:ChEMBL108778
104:Identifiers
92:Other names
36:Valeric acid
2742:SSR-504,734
2737:SSR-103,800
2727:PF-03463275
2707:Mardepodect
2627:Transporter
2573:tropisetron
2515:levorphanol
2507:dextrorphan
2429:ginkgolides
2397:nicardipine
2252:Laudanosine
2173:Cacotheline
2163:Bicuculline
2110:sevoflurane
2060:tropisetron
1944:nicardipine
1787:Hypotaurine
1114:Merck Index
1010:. Alkaline
918:O → (CH
914:+ CO + H
823:. It is an
764:Flash point
641:Signal word
492:Properties
483:O=C(O)C(C)C
261:100.001.087
183:CHEBI:16135
18:Isobutyrate
2862:Categories
2747:Tilapertin
2702:LY-2365109
2697:Iclepertin
2692:GSK1018921
2577:zatosetron
2565:bemesetron
2537:Picrotoxin
2455:Imipramine
2425:bilobalide
2411:Furosemide
2401:nifedipine
2372:flurazepam
2360:clonazepam
2356:bromazepam
2327:Strychnine
2322:Sinomenine
2287:Quinolines
2277:Pitrazepin
2198:Dendrobine
2183:Colchicine
2102:isoflurane
2086:desflurane
2082:chloroform
2064:zatosetron
2048:bemesetron
2000:minaxolone
1988:alfaxolone
1974:Ivermectin
1911:Anandamide
1834:Milacemide
1824:-Threonine
1792:Ivermectin
1700:modulators
1461:2020-10-03
1437:2020-09-30
1412:2020-09-30
1391:2020-10-03
1315:2011-10-07
1223:2020-10-03
1203:2020-10-03
1101:References
1072:metabolism
960:isobutanol
944:hydrolysis
875:Production
869:croton oil
615:Pictograms
527:Molar mass
383:8LL210O1U0
292:IUPHAR/BPS
214:ChemSpider
132:3D model (
111:CAS Number
2795:ORG-25543
2775:Amoxapine
2732:Sarcosine
2712:ORG-24598
2677:CP-802079
2583:Verapamil
2569:LY-278584
2561:Tropeines
2527:pethidine
2523:oripavine
2416:Genistein
2347:Amiloride
2227:Gelsemine
2203:Diaboline
2188:Colubrine
2098:halothane
2094:enflurane
2070:Volatiles
2056:LY-278584
2040:Tropeines
2035:Triclofos
2025:Tamoxifen
2004:ORG-20599
1950:Etomidate
1873:brometone
1854:Sarcosine
1829:MDL-27531
1741:β-Alanine
1738:Agonists:
1649:0015-5713
1603:1474-7049
1162:cite book
1083:ovulatory
996:anhydride
982:Reactions
956:oxidation
889:propylene
606:labelling
394:UN number
365:NQ4375000
282:201-195-7
274:EC Number
2816:See also
2770:ALX-1393
2633:blockers
2614:instead.
2556:Riluzole
2541:picrotin
2531:thebaine
2519:morphine
2388:Daidzein
2378:Corymine
2364:diazepam
2299:5,7-CIQA
2232:iso-THAZ
2178:Caffeine
2044:atropine
2020:Propofol
1979:Ketamine
1869:Alcohols
1844:Propofol
1808:-Proline
1800:-Alanine
1764:-Alanine
1708:Receptor
1657:12778908
1612:10426864
1554:17580301
1454:(1998).
1089:See also
1026:C(OH)-CO
1000:chloride
954:and the
711:NFPA 704
597:Hazards
588:(χ)
234:DrugBank
2800:VVZ-368
2667:ASP2535
2563:(e.g.,
2539:(i.e.,
2499:codeine
2497:(e.g.,
2495:Opioids
2467:(e.g.,
2431:(e.g.,
2395:(e.g.,
2354:(e.g.,
2317:RU-5135
2289:(e.g.,
2210:(e.g.,
2168:Brucine
2114:toluene
2076:(e.g.,
2052:cocaine
2042:(e.g.,
1986:(e.g.,
1961:(e.g.,
1955:Ginseng
1942:(e.g.,
1935:D12-116
1918:(e.g.,
1871:(e.g.,
1859:Taurine
1816:-Serine
1782:Glycine
1772:-Serine
1756:Caesium
1714:ligands
1562:7143228
1513:4222453
1505:4861233
1485:Bibcode
1065:anosmia
1054:Biology
1008:acetone
952:alkalis
854:vanilla
804:, is a
567:Acidity
537:Density
334:PubChem
243:DB02531
121:79-31-2
2421:Ginkgo
2311:7-TFQA
2158:αEMBTL
1751:β-AIBA
1655:
1647:
1609:
1601:
1560:
1552:
1511:
1503:
1477:Nature
1364:
1337:: 366.
1287:
1150:
1040:esters
998:, and
861:dulcis
859:Arnica
852:), in
844:carobs
825:isomer
647:Danger
476:SMILES
322:C02632
194:ChEMBL
163:B00469
155:3DMet
75:Names
2785:NAGly
2758:GlyT2
2657:ACPPB
2645:GlyT1
2599:NMDAR
2337:Tutin
2307:7-TFQ
2303:7-CIQ
2128:Xenon
2074:gases
1558:S2CID
1509:S2CID
992:ester
988:amide
962:with
950:with
910:CH=CH
865:ester
579:4.86
441:InChI
398:2529
174:ChEBI
134:JSmol
2835:GABA
2612:here
2610:See
2588:Zinc
2551:PMBA
2543:and
2460:NBQX
2212:2-AG
2133:Zinc
1886:tert
1777:GABA
1726:GlyR
1653:PMID
1645:ISSN
1599:ISSN
1550:PMID
1501:PMID
1362:ISBN
1285:ISBN
1168:link
1148:ISBN
1119:5039
1070:The
1046:and
1034:Uses
926:CHCO
821:COOH
691:P280
687:P210
673:H314
669:H311
665:H302
661:H226
374:UNII
347:6590
313:KEGG
302:1060
223:6341
1637:doi
1607:PMC
1589:doi
1540:doi
1536:282
1493:doi
1481:214
1452:FAO
1354:doi
1277:doi
1140:doi
1048:WHO
1044:FAO
1030:H.
974:on
958:of
946:of
887:of
867:in
827:of
800:or
604:GHS
410:EPA
337:CID
34:or
2864::
2575:,
2571:,
2567:,
2529:,
2525:,
2521:,
2517:,
2513:,
2509:,
2505:,
2501:,
2487:,
2483:,
2479:,
2475:,
2471:,
2451:))
2447:,
2443:,
2439:,
2435:,
2427:,
2403:,
2399:,
2370:,
2366:,
2362:,
2358:,
2309:,
2305:,
2301:,
2297:,
2293:,
2214:,
2120:,
2116:,
2112:,
2108:,
2104:,
2100:,
2096:,
2092:,
2088:,
2084:,
2080:,
2062:,
2058:,
2054:,
2050:,
2046:,
2002:,
1998:,
1994:,
1990:,
1965:))
1922:,
1898:,
1894:,
1890:,
1883:,
1879:,
1875:,
1651:.
1643:.
1633:74
1631:.
1605:.
1597:.
1585:14
1583:.
1579:.
1556:.
1548:.
1534:.
1530:.
1507:.
1499:.
1491:.
1479:.
1429:.
1384:.
1360:.
1335:28
1333:.
1283:.
1263:^
1251:.
1232:^
1164:}}
1160:{{
994:,
990:,
906:CH
891:.
871:.
839:.
819:CH
810:CH
701:,
697:,
693:,
689:,
671:,
667:,
663:,
608::
576:)
569:(p
2837:A
2635:)
2631:(
2579:)
2547:)
2533:)
2491:)
2407:)
2374:)
2313:)
2218:)
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