24:
250:
175:
689:
427:
649:
422:
2935:
604:. Poisonings related to these mushrooms have occurred predominately in Europe where mushroom foraging was common, though cases of orellanine poisoning have been reported in North America and Australia as well. There are several reported cases of people ingesting orellanine-containing mushrooms after mistaking them for
820:
orellanine is the long latency; the first symptoms usually do not appear until 2–4 to 14 days after ingestion. The latent period decreases with the quantity of mushrooms consumed. The first symptoms of orellanine poisoning are similar to the common
723:
Orellanine displays a wide spectrum of toxin effects in plants, animals, and microorganisms. Although the mechanism of toxicity of orellanine is not yet fully understood, it likely targets cellular processes found in both
875:, if needed. Complete recovery of renal function is recovered in only 30% of poisoned patients. There are reports of cases where treatment using corticosteroids and antioxidants led to improved clinical outcomes.
435:
402:
633:
The first successful synthesis of orellanine was reported in 1985. The total synthesis of orellanine starting with the bromination of 3-hydroxypyridine was reported a year later in 1986.
782:. Like orellanine, paraquat and diquat are toxic not only to plants, but also to humans and livestock. Bipyridine compounds with charged nitrogen atoms disrupt important
630:
The chemical structure of orellanine was first deduced by
Antkowiak and Gessner in 1979, who identified it as 3,3',4,4'-tetrahydroxy- 2,2'-bipyridine-1,1'-dioxide.
627:
and determine various physical and chemical properties of orellanine. He found that the toxicity of the mushroom was due to both delayed and acute kidney injury.
119:
641:
The first synthesis of orellanine was reported in 1985 by
Dehmlow and Schulz, and required ten steps starting from 3-aminopyridine. The following year, Tiecco
1580:
855:
of orellanine in mice is 12 to 20 mg per kg body weight; this is the dose which leads to death within two weeks. From cases of orellanine-related
1545:
2989:
794:
and sometimes passing the electrons along into other, often undesirable, redox reactions. The terminal products of these reactions can be harmful
289:
1174:
Gryzmala, S. (1962). "L'isolement de l'Orellanine poison du
Cortinarius orellanus Fries et l'Ă©tude de ses effets anatomo-pathologiques".
845:) and eventually decreased or nonexistent urine output and other symptoms of kidney failure occur. If left untreated death will follow.
2959:
2527:
1610:
1240:
Dehmlow, Eckehard V.; Schulz, Hans-Joachim (1985). "Synthesis of orellanine the lethal poison of a toadstool - ScienceDirect".
1570:
1737:
2984:
1866:
1858:
264:
1862:
1750:
1602:
615:
Orellanine was first isolated in 1962, when Stanisław
Grzymala extracted and isolated orellanine from the mushroom
23:
520:
1965:
1836:
2655:
2612:
383:
703:. In this crystal structure, the two pyridine rings are nearly perpendicular to each other, making orellanine
2117:
1761:
1756:
467:
207:
170:
228:
426:
1876:
1370:"Structure of an orellanine–trifluoroacetic acid complex: evidence of a very short O–H⋯O hydrogen bond"
768:
745:
1271:
1199:
571:, Poland, resulted in 11 deaths. Orellanine comes from a class of mushrooms that fall under the genus
485:
1270:
Tiecco, Marcello; Tingoli, Macro; Testaferri, Lorenzo; Chianelli, Donatella; Wenkert, Ernest (1986).
753:
245:
2166:
761:
596:
1950:
1938:
1742:
1731:
1073:
1072:
Dinis-Oliveira, Ricardo Jorge; Soares, Mariana; Rocha-Pereira, Carolina; Carvalho, FĂ©lix (2015).
795:
1984:
1922:
1680:
1998:
139:
2979:
2969:
2773:
2408:
1769:
757:
704:
700:
580:
449:
414:
36:
932:"Novel methods for identification and quantification of the mushroom nephrotoxin orellanine"
2974:
2012:
1960:
1595:
1495:
1440:
1381:
1321:
985:
931:
749:
645:
reported the total synthesis of orellanine in nine steps starting from 3-hydroxypyridine.
586:
567:
Orellanine first came to people's attention in 1952 when a mass poisoning of 102 people in
421:
216:
151:
95:
929:
8:
2938:
609:
85:
1499:
1444:
1385:
1325:
989:
489:
249:
174:
2964:
2876:
2046:
2004:
1881:
1712:
1527:
1464:
1416:
1345:
1156:
1101:
1017:
856:
849:
1291:
1253:
1215:
947:
2921:
note: some toxins are produced by lower species and pass through intermediate species
2881:
2825:
2112:
1519:
1511:
1456:
1397:
1337:
1219:
1148:
1140:
1093:
1009:
1001:
951:
930:
Oubrahim H.; Richard J.-M.; Cantin-Esnault D.; Seigle-Murandi F.; Trecourt F (1997).
1531:
1468:
1349:
1160:
1021:
2820:
2638:
2244:
2160:
2102:
1908:
1503:
1448:
1389:
1329:
1287:
1249:
1211:
1132:
1105:
1085:
993:
943:
810:
809:, the latter of which are harmful to cells. It is thought that orellanine produces
682:
674:
552:
312:
1552:
760:. In addition, orellanine has also been shown to interfere with the production of
699:
The chemical structure of synthetically produced orellanine has been confirmed by
196:
2903:
2808:
2403:
2058:
1955:
1800:
1775:
1660:
1588:
708:
707:. However, samples of orellanine extracted from mushrooms are optically inactive
692:
605:
481:
1369:
273:
InChI=1S/C10H8N2O6/c13-5-1-3-11(17)7(9(5)15)8-10(16)6(14)2-4-12(8)18/h1-4,13-16H
2845:
2393:
2333:
2156:
2148:
1895:
1849:
1618:
884:
871:
against orellanine poisoning. Treatment consists mainly of supportive care and
838:
620:
548:
514:
1484:"Nephrotoxicity of orellanine, a toxin from the mushroomCortinarius orellanus"
1393:
473:
2953:
2835:
2778:
2532:
2495:
2443:
2388:
2373:
2249:
2209:
2152:
1946:
1795:
1718:
1515:
1401:
1341:
1223:
1144:
1089:
1005:
688:
648:
163:
2898:
2888:
2871:
2840:
2788:
2752:
2711:
2665:
2602:
2505:
2428:
2363:
2198:
2194:
2190:
2176:
1990:
1826:
1623:
1152:
1120:
1097:
872:
859:
in humans it seems that the lethal dose for humans is considerably lower.
712:
1523:
1460:
1013:
955:
2861:
2815:
2803:
2660:
2607:
2557:
2463:
2458:
2448:
2413:
2398:
2264:
1975:
1932:
1903:
1723:
1701:
1638:
1628:
1071:
906:
901:
817:
733:
573:
493:
1121:"Deliberate ingestion of "magic" mushrooms may also cause renal failure"
2893:
2830:
2747:
2725:
2670:
2633:
2577:
2547:
2537:
2478:
2468:
2453:
2438:
2433:
2418:
2338:
2323:
2239:
2229:
2214:
2181:
1871:
1831:
1648:
1643:
1507:
1452:
1333:
1308:
Kubicki, Maciej; Borowiak, Teresa; Antkowiak, Wiesław Z. (1991-08-01).
997:
803:
725:
346:
130:
1546:
Orellanine: From Fungal Origin to a
Potential Future Cancer Treatment.
1136:
2798:
2793:
2783:
2763:
2706:
2696:
2691:
2650:
2562:
2378:
2358:
2348:
2308:
2303:
2283:
2254:
2204:
2186:
2139:
2131:
2038:
2022:
1633:
1483:
1482:
Richard, Jean-Michel; Louis, Josette; Cantin, Danielle (1988-03-01).
1309:
974:"Mushroom poisoning caused by species of the genus Cortinarius fries"
973:
830:
822:
791:
787:
772:
729:
540:
513:
Except where otherwise noted, data are given for materials in their
2701:
2681:
2592:
2587:
2552:
2542:
2517:
2473:
2423:
2368:
2343:
2328:
2293:
2288:
2219:
2171:
2144:
2090:
2018:
1671:
896:
868:
799:
775:
678:
544:
1374:
505:
118:
2856:
2318:
2313:
2298:
2259:
2234:
2071:
2051:
1691:
842:
834:
695:
of orellanine. The more stable (oxide) form is shown on the left.
477:
183:
1269:
2623:
2597:
2567:
2383:
2085:
2066:
1814:
911:
826:
779:
556:
1556:
1119:
Deutsch, Christopher J.; Swallow, Daniel (24 September 2012).
2572:
2488:
2483:
2353:
2274:
1613:
1368:
Cohen-Addad, C.; Richard, J.-M.; Guitel, J.-C. (1987-03-15).
783:
568:
108:
887:
as a potential treatment for various forms of renal cancer.
841:(immense thirst, frequent urination, pain on and around the
233:
2737:
2645:
806:
367:
1272:"Total synthesis of orellanine : The lethal toxin of
2582:
741:
737:
1367:
1307:
837:, etc.), these symptoms are followed by early stages of
732:. Orellanine has been found to inhibit the synthesis of
1414:
1314:
1198:
Antkowiak, Wieław Z.; Gessner, Wiesł P. (1979-01-01).
652:
The nine-step total synthesis of orellanine (compound
459:
1421:. I. Chemical characterization of the main toxin of
1481:
1575:Pacific Northwest Fungi, Featured Fungus Number 4
1074:"Human and experimental toxicology of orellanine"
971:
2951:
1197:
972:Schumacher, Trond; Høiland, Klaus (1983-06-01).
816:In humans, a characteristic of poisoning by the
455:
195:
1429:(Kuhn & Romagn) and acute toxicity in mice"
94:
1415:Prast, Helmut; Werner; Pfaller; Moser (1988).
1118:
501:
1596:
1239:
1679:
1538:
1176:Bulletin de la Société Mycologique de France
813:in a similar manner to paraquat and diquat.
619:. Grzymala was also able to demonstrate the
397:Highly toxic with delayed onset of toxicity
1200:"The structures of orellanine and orelline"
555:compound somewhat related to the herbicide
543:found in a group of mushrooms known as the
1603:
1589:
771:, and chemically resembles the bipyridine
681:, with the more stable tautomer being the
497:
248:
173:
150:
138:
2528:Androctonus australis hector insect toxin
1310:"Crystal structure of orellanine hydrate"
1235:
1233:
215:
73:2,2-Bipyridine-3,3-4,4-tetrol-1,1-dioxide
1265:
1263:
1173:
1067:
1065:
1063:
1061:
1059:
1057:
1055:
1053:
1051:
687:
647:
2990:Drugs with unknown mechanisms of action
1049:
1047:
1045:
1043:
1041:
1039:
1037:
1035:
1033:
1031:
244:
2952:
1544:Lyons MJ, Ehrhardt C, Walsh JJ (2023)
1230:
362:Colorless to white crystalline powder
164:
1584:
1363:
1361:
1359:
1260:
276:Key: JEWWXPOUSBVQKG-UHFFFAOYSA-N
1303:
1301:
1193:
1191:
1189:
1028:
967:
965:
1078:Human & Experimental Toxicology
656:) from 3-hydroxypyridine (compound
186:
13:
1882:Staphylococcal Enterotoxin B (SEB)
1417:"Toxic properties of the mushroom
1356:
578:and has been found in the species
14:
3001:
2960:Mycotoxins found in Basidiomycota
1564:
1298:
1186:
962:
769:positively charged nitrogen atoms
2934:
2933:
1553:DOI:10.1021/acs.jnatprod.2c01068
767:Orellanine is a bipyridine with
425:
420:
330:
324:
22:
1966:Extracellular adenylate cyclase
1475:
1408:
715:during the extraction process.
517:(at 25 °C , 100 kPa).
1167:
1112:
923:
883:This compound is currently in
384:Occupational safety and health
336:
318:
1:
2118:Fibronectin binding protein A
1292:10.1016/S0040-4020(01)87367-1
1254:10.1016/S0040-4039(00)94981-5
1216:10.1016/S0040-4039(01)86882-9
948:10.1016/S0021-9673(96)00695-4
917:
155: (non-zwitterionic form)
862:
668:
636:
7:
1859:Staphylococcus aureus alpha
1837:Panton–Valentine leukocidin
890:
878:
829:, vomiting, stomach pains,
748:of several enzymes such as
718:
10:
3006:
1877:Toxic shock syndrome toxin
1427:Cortinarius speciosissimus
746:non-competitive inhibition
562:
297:1ccc(O)c(O)c1c2()ccc(O)c2O
2985:Experimental cancer drugs
2929:
2916:
2854:
2774:(+)-Allopumiliotoxin 267A
2761:
2735:
2724:
2679:
2621:
2515:
2504:
2273:
2130:
2101:
2037:
1974:
1921:
1894:
1847:
1822:
1813:
1786:
1699:
1690:
1670:
1659:
1394:10.1107/S0108270187095222
936:Journal of Chromatography
511:
401:
381:
376:
305:
285:
260:
78:
68:
35:
30:
21:
2167:beta-Nitropropionic acid
1090:10.1177/0960327115613845
790:, 'stealing' one or two
762:adenosine triphosphatase
610:hallucinogenic mushrooms
551:. Structurally, it is a
468:Precautionary statements
1951:Heat-labile enterotoxin
1942:heat-stable enterotoxin
796:reactive oxygen species
2060:Bacillus thuringiensis
1488:Archives of Toxicology
1433:Archives of Toxicology
978:Archives of Toxicology
696:
677:. Orellanine displays
665:
660:) described by Tiecco
1423:Cortinarius orellanus
1419:Cortinarius orellanus
1274:Cortinarius orellanus
758:leucyl aminopeptidase
754:Îł-glutamyltransferase
701:X-ray crystallography
691:
651:
1961:Pseudomonas exotoxin
1572:Cortinarius rubellus
750:alkaline phosphatase
1500:1988ArTox..62..242R
1445:1988ArTox..62...81P
1386:1987AcCrC..43..504C
1326:1991JCCry..21..401K
1242:Tetrahedron Letters
1204:Tetrahedron Letters
990:1983ArTox..53...87S
354: g·mol
18:
2877:Alpha-Bungarotoxin
2047:Lipopolysaccharide
2005:Pore-forming toxin
1551:86 (6):1620-1631.
1508:10.1007/BF00570151
1453:10.1007/bf00316263
1334:10.1007/BF01160652
998:10.1007/BF00302720
867:There is no known
857:mushroom poisoning
736:such as proteins,
697:
675:bipyridine N-oxide
666:
553:bipyridine N-oxide
547:within the family
521:Infobox references
16:
2947:
2946:
2912:
2911:
2882:Beta-Bungarotoxin
2826:Pumiliotoxin 251D
2720:
2719:
2126:
2125:
2113:Clumping factor A
2033:
2032:
1917:
1916:
1890:
1889:
1809:
1808:
1248:(40): 4903–4906.
1210:(21): 1931–1934.
1137:10.1136/bmj.e6388
529:Chemical compound
527:
526:
450:Hazard statements
229:CompTox Dashboard
120:Interactive image
48:-Tetrahydroxy-2,2
2997:
2937:
2936:
2865:
2821:Histrionicotoxin
2767:
2741:
2733:
2732:
2685:
2639:Alpha-latrotoxin
2627:
2521:
2513:
2512:
2245:Sterigmatocystin
2197:, Fumonisin B3,
2161:epsilon-amanitin
2080:B. thuringiensis
1909:Diphtheria toxin
1852:
1820:
1819:
1789:
1705:
1697:
1696:
1688:
1687:
1677:
1676:
1668:
1667:
1605:
1598:
1591:
1582:
1581:
1559:
1542:
1536:
1535:
1479:
1473:
1472:
1412:
1406:
1405:
1365:
1354:
1353:
1305:
1296:
1295:
1286:(5): 1475–1485.
1267:
1258:
1257:
1237:
1228:
1227:
1195:
1184:
1183:
1171:
1165:
1164:
1116:
1110:
1109:
1084:(9): 1016–1029.
1069:
1026:
1025:
969:
960:
959:
927:
811:oxidative stress
711:, likely due to
709:racemic mixtures
683:pyridine N-oxide
673:Orellanine is a
507:
503:
499:
495:
491:
487:
483:
479:
475:
461:
457:
429:
424:
353:
338:
332:
326:
320:
313:Chemical formula
253:
252:
237:
235:
219:
199:
188:
177:
166:
154:
142:
122:
98:
61:
51:
47:
43:
26:
19:
15:
3005:
3004:
3000:
2999:
2998:
2996:
2995:
2994:
2950:
2949:
2948:
2943:
2925:
2908:
2904:Cardiotoxin III
2860:
2855:
2850:
2762:
2757:
2736:
2728:
2716:
2680:
2675:
2622:
2617:
2516:
2508:
2500:
2404:Resiniferatoxin
2269:
2122:
2104:
2097:
2062:delta endotoxin
2029:
1970:
1956:Pertussis toxin
1924:
1913:
1886:
1848:
1843:
1805:
1801:Listeriolysin O
1787:
1782:
1700:
1682:
1662:
1655:
1609:
1567:
1562:
1543:
1539:
1480:
1476:
1413:
1409:
1366:
1357:
1306:
1299:
1276:fries mushroom"
1268:
1261:
1238:
1231:
1196:
1187:
1172:
1168:
1117:
1113:
1070:
1029:
970:
963:
928:
924:
920:
893:
885:clinical trials
881:
865:
853:
721:
693:Tautomerization
671:
639:
565:
530:
523:
518:
470:
452:
438:
417:
394:
351:
341:
335:
329:
323:
315:
301:
298:
293:
292:
281:
278:
277:
274:
268:
267:
256:
238:
231:
222:
202:
189:
158:
125:
112:
101:
88:
74:
72:
64:
59:
49:
45:
41:
12:
11:
5:
3003:
2993:
2992:
2987:
2982:
2977:
2972:
2967:
2962:
2945:
2944:
2942:
2941:
2930:
2927:
2926:
2924:
2923:
2917:
2914:
2913:
2910:
2909:
2907:
2906:
2901:
2896:
2891:
2886:
2885:
2884:
2879:
2868:
2866:
2852:
2851:
2849:
2848:
2846:Zetekitoxin AB
2843:
2838:
2833:
2828:
2823:
2818:
2813:
2812:
2811:
2806:
2801:
2796:
2791:
2781:
2776:
2770:
2768:
2759:
2758:
2756:
2755:
2750:
2744:
2742:
2730:
2722:
2721:
2718:
2717:
2715:
2714:
2709:
2704:
2699:
2694:
2688:
2686:
2677:
2676:
2674:
2673:
2668:
2663:
2658:
2653:
2648:
2643:
2642:
2641:
2630:
2628:
2619:
2618:
2616:
2615:
2610:
2605:
2600:
2595:
2590:
2585:
2580:
2575:
2570:
2565:
2560:
2555:
2550:
2545:
2540:
2535:
2530:
2524:
2522:
2510:
2502:
2501:
2499:
2498:
2493:
2492:
2491:
2486:
2476:
2471:
2466:
2461:
2456:
2451:
2446:
2441:
2436:
2431:
2426:
2421:
2416:
2411:
2406:
2401:
2396:
2394:Pseudaconitine
2391:
2386:
2381:
2376:
2371:
2366:
2361:
2356:
2351:
2346:
2341:
2336:
2334:Djenkolic acid
2331:
2326:
2321:
2316:
2311:
2306:
2301:
2296:
2291:
2286:
2280:
2278:
2271:
2270:
2268:
2267:
2262:
2257:
2252:
2247:
2242:
2237:
2232:
2227:
2222:
2217:
2212:
2207:
2202:
2184:
2179:
2174:
2169:
2164:
2157:gamma-amanitin
2149:alpha-amanitin
2142:
2136:
2134:
2128:
2127:
2124:
2123:
2121:
2120:
2115:
2109:
2107:
2099:
2098:
2096:
2095:
2094:
2093:
2088:
2076:
2075:
2074:
2069:
2056:
2055:
2054:
2043:
2041:
2035:
2034:
2031:
2030:
2028:
2027:
2026:
2025:
2009:
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165:ECHA InfoCard
162:
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67:
62:
55:
38:
34:
29:
25:
20:
2980:Nephrotoxins
2970:Amine oxides
2920:
2899:Calcicludine
2889:Calciseptine
2872:Bungarotoxin
2841:Tarichatoxin
2789:Arenobufagin
2753:Tetrodotoxin
2712:Tetrodotoxin
2666:Vanillotoxin
2603:Phaiodotoxin
2506:Invertebrate
2429:Solasodamine
2364:Lotaustralin
2224:
2199:Fumonisin B4
2195:Fumonisin B2
2191:Fumonisin B1
2177:Cytochalasin
2079:
2059:
2011:
1997:
1991:Superantigen
1983:
1939:
1827:Streptolysin
1768:
1749:
1730:
1711:
1576:
1571:
1548:
1540:
1491:
1487:
1477:
1439:(1): 81–88.
1436:
1432:
1426:
1425:(Fries) and
1422:
1418:
1410:
1377:
1373:
1317:
1313:
1283:
1279:
1273:
1245:
1241:
1207:
1203:
1179:
1175:
1169:
1128:
1124:
1114:
1081:
1077:
981:
977:
939:
935:
925:
882:
873:hemodialysis
866:
847:
815:
766:
734:biomolecules
722:
713:racemization
698:
672:
661:
657:
653:
642:
640:
632:
629:
625:C. orellanus
624:
617:C. orellanus
616:
614:
602:bruneofulvus
601:
595:
591:
585:
581:C. orellanus
579:
572:
566:
536:
532:
531:
441:
403:
393:Main hazards
382:
147:-oxide form)
144:
79:Identifiers
69:Other names
57:
53:
52:-bipyridine-
2975:Bipyridines
2862:Snake venom
2816:Epibatidine
2804:Cinobufagin
2661:Stromatoxin
2608:Imperatoxin
2558:Scyllatoxin
2464:Tagetitoxin
2459:Swainsonine
2449:Solauricine
2414:Solamargine
2409:Scopolamine
2399:Retronecine
2265:Zearalenone
1933:Shiga toxin
1904:Cord factor
1743:Enterotoxin
1738:Alpha toxin
1732:perfringens
1724:Tetanolysin
1702:Clostridium
1639:hepatotoxin
1629:enterotoxin
1619:cardiotoxin
1280:Tetrahedron
907:Nephrotoxin
902:Cortinarius
818:nephrotoxin
726:prokaryotes
679:tautomerism
597:rainerensis
574:Cortinarius
436:Signal word
387:(OHS/OSH):
359:Appearance
306:Properties
171:100.232.424
17:Orellanine
2954:Categories
2894:Taicatoxin
2831:Samandarin
2784:Bufotoxins
2748:Ciguatoxin
2726:Vertebrate
2671:Huwentoxin
2651:Cupiennins
2634:Latrotoxin
2578:Kaliotoxin
2548:Margatoxin
2538:Maurotoxin
2479:Toxalbumin
2469:Tinyatoxin
2454:Strychnine
2439:Solasonine
2434:Solasodine
2419:Solanidine
2339:Falcarinol
2324:Delphinine
2240:Phalloidin
2230:Ochratoxin
2225:Orellanine
2215:Lolitrem B
2182:Ergotamine
2132:Mycotoxins
1976:Mechanisms
1935:/Verotoxin
1872:Exfoliatin
1832:Leukocidin
1649:phototoxin
1644:neurotoxin
1549:J Nat Prod
1182:: 394–404.
918:References
804:superoxide
773:herbicides
730:eukaryotes
533:Orellanine
415:Pictograms
347:Molar mass
217:082U1GSX3D
131:ChemSpider
107:3D model (
96:37338-80-0
86:CAS Number
71:Orellanin,
37:IUPAC name
2965:Alkaloids
2799:Bufotenin
2794:Bufotalin
2764:Amphibian
2707:Saxitoxin
2697:Eledoisin
2692:Conotoxin
2563:Hefutoxin
2379:Oleandrin
2359:Linamarin
2349:Helenalin
2309:Cicutoxin
2304:Chaconine
2284:Amygdalin
2255:Vomitoxin
2205:Gliotoxin
2187:Fumonisin
2140:Aflatoxin
2103:Virulence
2039:Endotoxin
1770:botulinum
1751:difficile
1661:Bacterial
1634:hemotoxin
1624:cytotoxin
1516:1432-0738
1402:0108-2701
1342:1572-8854
1224:0040-4039
1145:1756-1833
1131:: e6388.
1006:1432-0738
863:Treatment
831:headaches
792:electrons
788:organisms
669:Structure
637:Synthesis
541:mycotoxin
537:orellanin
490:P307+P311
486:P301+P310
406:labelling
372:Odorless
2939:Category
2702:Onchidal
2682:Mollusca
2593:Bestoxin
2588:Birtoxin
2553:Slotoxin
2543:Agitoxin
2518:Scorpion
2474:Tomatine
2424:Solanine
2369:Mimosine
2344:Gossypol
2329:Divicine
2294:Antiarin
2289:Anisatin
2220:Muscimol
2172:Citrinin
2145:Amatoxin
2091:Cry34Ab1
2019:AB toxin
2013:type III
1925:negative
1683:positive
1672:Exotoxin
1557:37308446
1532:36515278
1469:24495871
1350:94292766
1161:32430024
1153:23008206
1098:26553321
1022:29016554
891:See also
879:Research
869:antidote
800:peroxide
798:such as
776:paraquat
719:Toxicity
664:in 1986.
587:rubellus
545:Orellani
377:Hazards
140:10266115
63:-dioxide
2857:Reptile
2319:Daphnin
2314:Coniine
2299:Brucine
2260:Zeranol
2235:Patulin
2082:toxins
2072:Cry3Bb1
2052:Lipid A
1999:type II
1940:E. coli
1692:Bacilli
1524:3196164
1496:Bibcode
1461:3190463
1441:Bibcode
1382:Bibcode
1322:Bibcode
1106:7230959
1014:6349583
986:Bibcode
956:9181972
843:kidneys
835:myalgia
592:henrici
563:History
352:252.182
184:PubChem
143: (
2729:toxins
2624:Spider
2598:BmKAEP
2568:HgeTx1
2509:toxins
2384:Persin
2277:toxins
2105:factor
2086:Cry6Aa
2078:Other
2067:Cry1Ac
1985:type I
1788:Other:
1713:tetani
1663:toxins
1614:Toxins
1555:PMID:
1530:
1522:
1514:
1467:
1459:
1400:
1348:
1340:
1222:
1159:
1151:
1143:
1104:
1096:
1020:
1012:
1004:
954:
912:Diquat
827:nausea
780:diquat
756:, and
740:, and
705:chiral
662:et al.
643:et al.
606:edible
557:diquat
442:Danger
290:SMILES
31:Names
2656:PhTx3
2573:HsTx1
2496:Tutin
2489:Ricin
2484:Abrin
2354:Ledol
2275:Plant
1867:delta
1815:Cocci
1776:Botox
1528:S2CID
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