324:
221:
1088:
35:
484:
800:
44:
584:
492:
464:
1560:
779:
that may be present. A variety of approaches to protection and deprotection of carbonyls including as dioxolanes are known. For example, consider the compound methyl cyclohexanone-4-carboxylate, where
1324:
Chang, Chih-Ching; Liao, Bei-Sih; Liu, Shiuh-Tzung (2007). "Deprotection of
Acetals and Ketals in a Colloidal Suspension Generated by Sodium Tetrakis(3,5-trifluoromethylphenyl)borate in Water".
3051:
1553:
1546:
597:
554:
3046:
729:
886:
2313:
1427:
806:
1302:
373:
1256:
1464:; Newbold, Amanda J.; Sanderson, William R. (1990). "Oxidation Reactions Using Urea–Hydrogen Peroxide; A Safe Alternative to Anhydrous Hydrogen Peroxide".
2622:
1122:
2682:
526:
1170:
1394:
Ziegler, Fredrick E.; Metcalf, Chester A.; Nangia, Ashwini; Schulte, Gayle (1993). "Structure and total synthesis of sporol and neosporol".
812:
can also be used for deprotection of acetal or ketal-protected carbonyl compounds. For example, deprotection of 2-phenyl-1,3-dioxolane to
2321:
2317:
1580:
1444:
1569:
1514:
1373:
1296:
1250:
753:
338:
1425:
Caster, Kenneth C.; Rao, A. Somasekar; Mohan, H. Rama; McGrath, Nicholas A.; Brichacek, Matthew (2012). "Trifluoroperacetic Acid".
2919:
796:, the reduction reaction carried out, and the protecting group removed by hydrolysis to produce 4-hydroxymethylcyclohexanone.
2462:
2371:
1940:
2457:
1904:
550:
1094:
A similar approach is used in the total synthesis of sporol, with the dioxolane ring later expanded to a dioxane system.
604:
3077:
3041:
728:
520:
271:
1282:
302:
784:
reduction will produce 4-hydroxymethylcyclohexanol. The ester functional group can be reduced without affecting the
3087:
2771:
2711:
1154:
1236:
2472:
2442:
1890:
949:
781:
228:
3015:
2763:
972:
934:
538:
1186:
483:
2332:
2239:
2094:
1013:
930:
216:
2795:
2309:
2041:
1722:
929:
of both compounds has been reported, and each includes a step in which a dioxolane system is formed using
178:
546:
3000:
2949:
2885:
2662:
2607:
2327:
2057:
2036:
1882:
1087:
620:
506:
476:
74:
2748:
1812:
2995:
2915:
2667:
2512:
1827:
1506:
1365:
1028:
62:
1807:
1533:
3072:
3010:
2672:
2557:
2367:
2169:
1151:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1069:
319:
104:
1742:
841:
534:
2935:
2860:
2743:
2738:
2652:
2497:
2452:
2274:
2154:
2149:
1925:
1900:
1862:
1802:
1717:
1594:
1572:
1288:
1242:
1137:
918:
562:
2647:
2642:
2352:
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1842:
1837:
1782:
1772:
1732:
1612:
2865:
2637:
2382:
2026:
1915:
1737:
1727:
1538:
910:
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3020:
2880:
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2487:
2437:
2294:
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2174:
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2109:
1767:
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2507:
2008:
1872:
1637:
1475:
1432:
1404:
1335:
1158:
922:
776:
772:
702:
675:
627:
558:
396:
799:
280:
198:
34:
2893:
2850:
2547:
2517:
2284:
2219:
2209:
2189:
1980:
1944:
1792:
1627:
926:
914:
889:
793:
722:
651:
647:
138:
323:
220:
114:
158:
2889:
2492:
2432:
2194:
1972:
1968:
1956:
1662:
768:
575:
43:
3066:
3005:
2845:
2831:
2827:
2819:
2767:
2427:
2422:
2289:
2224:
1707:
1622:
1126:
1073:
942:
706:
449:
439:
209:
17:
566:
2909:
2905:
2839:
2835:
2787:
2779:
2597:
2562:
2477:
2377:
2362:
2299:
2229:
2179:
2084:
2049:
2020:
2016:
2012:
2000:
1817:
1777:
1752:
1461:
813:
741:
714:
1436:
512:
260:
658:) at the 2-position with an oxygen atom. The corresponding saturated 6-membered C
3025:
2990:
2970:
2897:
2875:
2870:
2855:
2815:
2791:
2758:
2727:
2719:
2701:
2677:
2627:
2612:
2602:
2572:
2567:
2532:
2417:
2412:
2387:
2357:
2342:
2199:
2159:
2144:
2139:
2134:
2129:
2099:
2079:
2004:
1992:
1976:
1960:
1930:
1832:
1797:
1787:
1657:
1205:
1162:
941:
peracid, necessary in this case as the presence of water would lead to unwanted
1281:
Greene, Theodora W.; Wuts, Peter G. M. (1999). "1,3-Dioxanes, 1,3-Dioxolanes".
2985:
2965:
2930:
2823:
2811:
2799:
2706:
2695:
2691:
2632:
2527:
2522:
2502:
2407:
2279:
2234:
2214:
2164:
2119:
2069:
2065:
2053:
1984:
1964:
1952:
1910:
1867:
1857:
1852:
1847:
1822:
1757:
1697:
1642:
1617:
1602:
687:
530:
419:
189:
2803:
2783:
2753:
2723:
2715:
2617:
2577:
2537:
2482:
2402:
2347:
2304:
2249:
2124:
2114:
2089:
2045:
1996:
1988:
1948:
1935:
1762:
1712:
1667:
1652:
938:
542:
291:
1339:
2979:
2925:
2901:
2657:
2587:
2447:
2184:
2104:
2073:
2031:
1920:
1479:
1081:
710:
16:
This article is about 1,3-dioxolane. For the other dioxolane isomer, see
1408:
1356:
Pirrung, Michael C.; Morehead, Andrew T.; Young, Bruce G., eds. (2000).
2975:
2955:
2807:
2582:
2467:
2269:
2264:
2259:
2254:
1702:
1466:
1326:
1103:
1077:
756:
683:
679:
667:
429:
247:
229:
1086:
775:
so that they do not undergo reactions during transformations of other
2244:
1895:
851:
785:
718:
671:
623:
169:
858:
752:-2-methyl-4-trimethylammoniummethyl-1,3-dioxolane iodide which is a
574:
Except where otherwise noted, data are given for materials in their
1235:
Greene, Theodora W.; Wuts, Peter G. M. (1999). "Dimethyl acetals".
2397:
2392:
1607:
1206:"2-Cyclohexyloxyethanol (involves acetalisation of cyclohexanone)"
1080:, which then undergoes a ring-expansion reaction with a proximate
831:
789:
149:
137:
127:
674:
1,2-dioxolane (wherein the two oxygen centers are adjacent) is a
1043:
937:
method. This method involves no water, so it gives a completely
2683:
1542:
705:
containing the dioxolane ring. Dioxolanes can be prepared by
798:
727:
307:
42:
33:
1072:
with trifluoroperacetic acid is used to convert a suitable
1581:
1364:. The Total Synthesis of Natural Products. Vol. 11.
870:
792:. The ketal is produced by acid catalysed reaction with
816:
can be achieved in water in five minutes at 30 °C.
592:
2473:
Octatropine methylbromide (anisotropine methylbromide)
1428:
e-EROS Encyclopedia of
Reagents for Organic Synthesis
844:
2948:
1881:
1593:
1579:
1503:Name Reactions of Functional Group Transformations
880:
2663:Scopolamine butylbromide (hyoscine butylbromide)
1138:formal glycol - PubChem Public Chemical Database
259:
2688:Tooltip Selective serotonin reuptake inhibitors
1284:Greene's Protective Groups in Organic Synthesis
1238:Greene's Protective Groups in Organic Synthesis
113:
3052:Acetylcholine metabolism/transport modulators
1554:
1362:Part B: Bicyclic and Tricyclic Sesquiterpenes
1084:functional group to form the dioxolane ring.
8:
1420:
1418:
3047:Nicotinic acetylcholine receptor modulators
2623:3-Quinuclidinyl thiochromane-4-carboxylate
1590:
1586:Tooltip Muscarinic acetylcholine receptors
1561:
1547:
1539:
322:
219:
197:
22:
1351:
1349:
1276:
1274:
869:
864:
859:
852:
846:
845:
843:
279:
1230:
1228:
1115:
444:−95 °C (−139 °F; 178 K)
378:
343:
318:
1389:
1387:
1385:
210:
1305:from the original on December 7, 2016
1259:from the original on December 3, 2016
1204:R. A. Daignault, E. L. Eliel (1973).
454:75 °C (167 °F; 348 K)
350:Key: SNQXJPARXFUULZ-UHFFFAOYSA-N
177:
157:
7:
1534:environmental and toxicological data
925:which has a 1,3-dioxane ring. The
360:Key: SNQXJPARXFUULZ-UHFFFAOYAS
347:InChI=1S/C3H6O2/c1-2-4-5-3-1/h1-3H2
250:
357:InChI=1/C3H6O2/c1-2-4-5-3-1/h1-3H2
14:
2285:Etybenzatropine (ethybenztropine)
1957:chlorphenamine (chlorpheniramine)
1941:Antihistamines (first-generation)
1718:Desmethylclozapine (norclozapine)
1570:Muscarinic acetylcholine receptor
754:muscarinic acetylcholine receptor
582:
482:
3006:Meclofenoxate (centrophenoxine)
2824:northiaden (desmethyldosulepin)
578:(at 25 °C , 100 kPa).
2463:N-Methyl-3-piperidyl benzilate
1155:The Royal Society of Chemistry
935:hydrogen peroxide – urea
917:that includes a 1,3-dioxolane
788:by protecting the ketone as a
1:
3042:Receptor/signaling modulators
2458:N-Ethyl-3-piperidyl benzilate
1437:10.1002/047084289X.rt254.pub2
1291:. pp. 308–322, 724–727.
1245:. pp. 297–304, 724–727.
881:{\displaystyle {\ce {->}}}
767:Organic compounds containing
678:. 1,3-dioxolane is used as a
2898:cyamemazine (cyamepromazine)
1068:In the case of neosporol, a
732:synthesis of dioxolane group
650:(THF) by replacement of the
2712:Tetracyclic antidepressants
2603:Profenamine (ethopropazine)
2225:Dicycloverine (dicyclomine)
1163:10.1039/9781849733069-FP001
29:
3109:
2861:Tripitamine (tripitramine)
2085:Benzatropine (benztropine)
1493:Hagen, Timothy J. (2007).
1220:, vol. 5, p. 303
15:
3034:
2764:Tricyclic antidepressants
2314:+beclometasone/formoterol
1891:3-Quinuclidinyl benzilate
933:(TFPAA), prepared by the
782:lithium aluminium hydride
572:
463:
458:
424:74.08 g/mol
389:
369:
334:
97:
85:
73:
61:
56:
28:
3016:Phosphatidylethanolamine
1191:pubchem.ncbi.nlm.nih.gov
888: PhCHO +
521:Precautionary statements
2240:Diphemanil metilsulfate
2095:Benzilylcholine mustard
2042:Atypical antipsychotics
1358:"10. Neosporol, Sporol"
931:trifluoroperacetic acid
694:As a class of compounds
2886:Typical antipsychotics
2658:Scopolamine (hyoscine)
2333:Hexahydrosiladifenidol
2310:Glycopyrronium bromide
1091:
921:, and is an isomer of
882:
875:
803:
733:
47:
38:
3001:Glycerophosphocholine
2804:dosulepin (dothiepin)
2608:Propantheline bromide
2483:Otenzepad (AF-DX 116)
2037:Atropine methonitrate
1507:John Wiley & Sons
1495:"Prilezhaev reaction"
1366:John Wiley & Sons
1340:10.1055/s-2007-968009
1157:. 2014. p. 145.
1090:
883:
847:
802:
731:
79:1,3-Dioxacyclopentane
75:Systematic IUPAC name
46:
37:
2996:Dimethylethanolamine
2916:Umeclidinium bromide
2796:desmethyldesipramine
2513:Oxyphenonium bromide
1723:Ethoxysebacylcholine
1509:. pp. 274–281.
1480:10.1055/s-1990-21156
1368:. pp. 222–224.
842:
63:Preferred IUPAC name
3078:Muscarinic agonists
3011:Phosphatidylcholine
2673:Sofpironium bromide
2558:Pipenzolate bromide
2368:Ipratropium bromide
2170:Cimetropium bromide
1497:. In Li, Jie Jack;
1409:10.1021/ja00060a006
1070:Prilezhaev reaction
874:
872:
857:
646:. It is related to
25:
2744:Tiotropium bromide
2739:Timepidium bromide
2498:Oxitropium bromide
2453:Muscarinic toxin 7
2328:Hexahydrodifenidol
2275:Emepronium bromide
1926:Ambutonium bromide
1901:Aclidinium bromide
1289:Wiley-Interscience
1243:Wiley-Interscience
1092:
878:
860:
854:30 °C / 5 min
804:
740:-Dioxolane is the
734:
605:Infobox references
48:
39:
23:
3088:Protecting groups
3060:
3059:
3021:Phosphorylcholine
2959:
2944:
2943:
2881:Trospium chloride
2776:amitriptylinoxide
2749:Tiquizium bromide
2593:Prifinium bromide
2488:Otilonium bromide
2443:Methylscopolamine
2438:Methylhomatropine
2295:Fentonium bromide
2175:Clidinium bromide
1460:Cooper, Mark S.;
1397:J. Am. Chem. Soc.
1218:Collected Volumes
1211:Organic Syntheses
1172:978-0-85404-182-4
863:
855:
777:functional groups
763:Protecting groups
747:
703:organic compounds
666:rings are called
613:Chemical compound
611:
610:
507:Hazard statements
303:CompTox Dashboard
139:Interactive image
52:
51:
3100:
2953:
2734:Tiemonium iodide
2689:
2685:
2553:Phenyltoloxamine
2508:Oxyphencyclimine
2009:phenyltoloxamine
1813:Suberyldicholine
1591:
1587:
1583:
1563:
1556:
1549:
1540:
1521:
1520:
1490:
1484:
1483:
1457:
1451:
1450:
1422:
1413:
1412:
1403:(7): 2581–2589.
1391:
1380:
1379:
1353:
1344:
1343:
1321:
1315:
1314:
1312:
1310:
1287:(3rd ed.).
1278:
1269:
1268:
1266:
1264:
1241:(3rd ed.).
1232:
1223:
1221:
1214:
1201:
1195:
1194:
1183:
1177:
1176:
1149:"Front Matter".
1146:
1140:
1135:
1129:
1120:
1076:precursor to an
1063:
1062:
1061:
1053:
1052:
1042: +
1040:
1038:
1037:
1027: +
1025:
1023:
1022:
1012: →
1010:
1009:
1008:
1000:
999:
991:
990:
982:
981:
971: +
969:
968:
967:
959:
958:
906:Natural products
887:
885:
884:
879:
877:
876:
873:
871:
868:
861:
856:
853:
830: +
745:
628:chemical formula
595:
589:
586:
585:
568:
564:
560:
556:
552:
548:
544:
540:
536:
532:
528:
514:
486:
397:Chemical formula
327:
326:
311:
309:
283:
263:
252:
231:
223:
212:
201:
181:
161:
141:
117:
30:
26:
3108:
3107:
3103:
3102:
3101:
3099:
3098:
3097:
3063:
3062:
3061:
3056:
3030:
2952:
2940:
2894:chlorprothixene
2851:Trihexyphenidyl
2687:
2668:Silahexacyclium
2548:Phenglutarimide
2210:Desfesoterodine
2190:Cyclobenzaprine
1981:diphenhydramine
1945:brompheniramine
1877:
1828:Thiopilocarpine
1585:
1575:
1567:
1530:
1525:
1524:
1517:
1492:
1491:
1487:
1459:
1458:
1454:
1447:
1424:
1423:
1416:
1393:
1392:
1383:
1376:
1355:
1354:
1347:
1323:
1322:
1318:
1308:
1306:
1299:
1280:
1279:
1272:
1262:
1260:
1253:
1234:
1233:
1226:
1216:
1203:
1202:
1198:
1187:"1,3-Dioxolane"
1185:
1184:
1180:
1173:
1148:
1147:
1143:
1136:
1132:
1121:
1117:
1112:
1100:
1060:
1057:
1056:
1055:
1051:
1048:
1047:
1046:
1044:
1036:
1033:
1032:
1031:
1029:
1021:
1018:
1017:
1016:
1014:
1007:
1004:
1003:
1002:
998:
995:
994:
993:
989:
986:
985:
984:
980:
977:
976:
975:
973:
966:
963:
962:
961:
957:
954:
953:
952:
950:
927:total synthesis
915:natural product
908:
897:
893:
840:
839:
835:
829:
825:
810:
794:ethylene glycol
771:sometimes need
769:carbonyl groups
765:
723:ethylene glycol
701:are a group of
696:
665:
661:
657:
652:methylene group
648:tetrahydrofuran
645:
641:
637:
633:
614:
607:
602:
601:
600: ?)
591:
587:
583:
579:
523:
509:
495:
479:
413:
409:
405:
399:
385:
382:
377:
376:
365:
362:
361:
358:
352:
351:
348:
342:
341:
330:
312:
305:
286:
266:
253:
241:
204:
184:
164:
144:
131:
120:
107:
93:
91:
89:
81:
80:
69:
68:
21:
12:
11:
5:
3106:
3104:
3096:
3095:
3090:
3085:
3080:
3075:
3065:
3064:
3058:
3057:
3055:
3054:
3049:
3044:
3039:
3035:
3032:
3031:
3029:
3028:
3023:
3018:
3013:
3008:
3003:
2998:
2993:
2988:
2983:
2973:
2968:
2962:
2960:
2946:
2945:
2942:
2941:
2939:
2938:
2933:
2928:
2923:
2913:
2890:chlorpromazine
2883:
2878:
2873:
2868:
2863:
2858:
2853:
2848:
2843:
2761:
2756:
2751:
2746:
2741:
2736:
2731:
2709:
2704:
2699:
2680:
2675:
2670:
2665:
2660:
2655:
2650:
2645:
2640:
2635:
2630:
2625:
2620:
2615:
2610:
2605:
2600:
2595:
2590:
2585:
2580:
2575:
2570:
2565:
2560:
2555:
2550:
2545:
2540:
2535:
2530:
2525:
2520:
2515:
2510:
2505:
2500:
2495:
2493:Oxapium iodide
2490:
2485:
2480:
2475:
2470:
2465:
2460:
2455:
2450:
2445:
2440:
2435:
2433:Methylatropine
2430:
2425:
2420:
2415:
2410:
2405:
2400:
2395:
2390:
2385:
2380:
2375:
2365:
2360:
2355:
2350:
2345:
2340:
2335:
2330:
2325:
2307:
2302:
2297:
2292:
2287:
2282:
2277:
2272:
2267:
2262:
2257:
2252:
2247:
2242:
2237:
2232:
2227:
2222:
2217:
2212:
2207:
2202:
2197:
2195:Cyclopentolate
2192:
2187:
2182:
2177:
2172:
2167:
2162:
2157:
2152:
2147:
2142:
2137:
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1127:Sigma-Aldrich
1124:
1123:1,3-Dioxolane
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1074:allyl alcohol
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179:ChEMBL3187281
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92:Formal glycol
84:
76:
72:
67:1,3-Dioxolane
64:
60:
55:
45:
41:
36:
32:
31:
27:
19:
18:1,2-dioxolane
2910:thioridazine
2906:mesoridazine
2840:trimipramine
2836:quinupramine
2788:clomipramine
2780:butriptyline
2598:Procyclidine
2563:Piperidolate
2478:Orphenadrine
2378:Isopropamide
2363:Imidafenacin
2322:+neostigmine
2318:+indacaterol
2300:Fesoterodine
2230:Dihexyverine
2180:Cloperastine
2050:fluperlapine
2021:triprolidine
2017:propiomazine
2013:promethazine
2001:phenindamine
1818:Talsaclidine
1778:Oxotremorine
1753:Methacholine
1743:LY-2,033,298
1502:
1499:Corey, E. J.
1488:
1471:
1465:
1455:
1426:
1400:
1395:
1361:
1331:
1325:
1319:
1307:. Retrieved
1283:
1261:. Retrieved
1237:
1217:
1209:
1199:
1190:
1181:
1150:
1144:
1133:
1118:
1093:
1067:
909:
814:benzaldehyde
805:
766:
749:
742:trivial name
737:
735:
715:ketalization
698:
697:
621:heterocyclic
616:
615:
498:
465:
98:Identifiers
86:Other names
3026:Pirisudanol
2991:Cyprodenate
2971:Adafenoxate
2936:Zamifenacin
2920:+vilanterol
2876:Tropicamide
2871:Tropatepine
2856:Trimebutine
2816:lofepramine
2792:desipramine
2759:Tolterodine
2728:mirtazapine
2720:maprotiline
2702:Telenzepine
2678:Solifenacin
2653:SCH-217,443
2628:Revefenacin
2613:Propiverine
2573:Piroheptine
2568:Pirenzepine
2533:Penthienate
2418:Mepenzolate
2413:Meladrazine
2388:Hyoscyamine
2372:+salbutamol
2358:Homatropine
2343:Hexocyclium
2200:Darifenacin
2160:CAR-302,668
2155:CAR-302,537
2150:CAR-302,368
2145:CAR-302,282
2140:CAR-302,196
2135:CAR-301,060
2130:CAR-226,086
2100:Benzydamine
2080:Benactyzine
2058:+fluoxetine
2005:pheniramine
1993:mequitazine
1977:dimetindene
1961:cinnarizine
1931:Anisodamine
1905:+formoterol
1883:Antagonists
1863:WAY-132,983
1833:Vedaclidine
1803:SDZ 210-086
1798:Sabcomeline
1788:Pilocarpine
1658:Bethanechol
688:polyacetals
682:and as a co
493:Signal word
390:Properties
217:100.010.422
159:CHEBI:87597
3073:Dioxolanes
3067:Categories
2986:Citicoline
2966:Acetyl-coA
2950:Precursors
2931:Xanomeline
2812:imipramine
2800:dibenzepin
2707:Terodiline
2696:paroxetine
2692:femoxetine
2648:SCH-72,788
2643:SCH-57,790
2633:Rociverine
2528:PD-0298029
2523:PD-102,807
2503:Oxybutynin
2408:Mebeverine
2353:HL-031,120
2338:Hexbutinol
2280:Etanautine
2235:Difemerine
2215:Dexetimide
2165:Caramiphen
2120:Bornaprine
2070:tenilapine
2066:quetiapine
2054:olanzapine
1985:doxylamine
1965:clemastine
1953:captodiame
1911:Abediterol
1868:Xanomeline
1858:VU-0238429
1853:VU-0152100
1848:VU-0152099
1843:VU-0090157
1838:VU-0029767
1823:Tazomeline
1783:PD-151,832
1773:Ocvimeline
1758:Milameline
1733:LY-593,039
1698:Cevimeline
1643:Alvameline
1618:Aceclidine
1613:AC-260,584
1603:77-LH-28-1
1573:modulators
1110:References
773:protection
699:Dioxolanes
477:Pictograms
434:1.06 g/cm
420:Molar mass
281:Y57RBG19JL
190:ChemSpider
126:3D model (
105:CAS Number
90:5-Crown-2
88:Dioxolane
24:Dioxolane
2866:Tropacine
2784:cidoxepin
2754:Tofenacin
2724:mianserin
2716:amoxapine
2638:RU-47,213
2618:Quinidine
2578:Pizotifen
2538:Pethidine
2403:Mazaticol
2383:J-104,129
2348:Himbacine
2305:Flavoxate
2250:Drofenine
2125:Camylofin
2115:Biperiden
2090:Benzilone
2046:clozapine
2027:AQ-RA 741
1997:perlapine
1989:meclizine
1949:buclizine
1936:Anisodine
1921:AF-DX 384
1916:AF-DX 250
1763:Muscarine
1738:L-689,660
1728:Itameline
1713:Clozapine
1668:Carbachol
1653:Arecoline
939:anhydrous
911:Neosporol
711:aldehydes
626:with the
617:Dioxolane
563:P403+P235
559:P370+P378
468:labelling
292:UN number
238:211-463-5
230:EC Number
3083:Solvents
3038:See also
2980:lecithin
2956:prodrugs
2926:WIN-2299
2902:loxapine
2588:Pridinol
2448:Metixene
2205:DAU-5884
2185:CS-27349
2105:Bevonium
2074:zotepine
2062:rilapine
2032:Atropine
1693:CDD-0102
1688:CDD-0098
1683:CDD-0097
1678:CDD-0078
1673:CDD-0034
1648:AQRA-741
1633:AF150(S)
1595:Agonists
1501:(eds.).
1309:June 20,
1303:Archived
1263:June 20,
1257:Archived
1098:See also
1082:carbonyl
849:→
822:PhCH(OCH
676:peroxide
672:isomeric
668:dioxanes
459:Hazards
115:646-06-0
3093:Formals
2976:Choline
2888:(e.g.,
2808:doxepin
2766:(e.g.,
2714:(e.g.,
2690:(e.g.,
2583:Poldine
2543:pFHHSiD
2468:Nefopam
2270:EA-3834
2265:EA-3580
2260:EA-3443
2255:EA-3167
2110:BIBN 99
2044:(e.g.,
1943:(e.g.,
1768:NGX-267
1748:McNA343
1703:Choline
1467:Synlett
1327:Synlett
1104:Dioxane
1078:epoxide
960:COOCOCF
838:
757:agonist
719:ketones
684:monomer
680:solvent
598:what is
596: (
430:Density
414:
381:O1CCOC1
248:PubChem
2245:Ditran
1896:4-DAMP
1873:YM-796
1638:AF267B
1582:mAChRs
1513:
1443:
1372:
1295:
1249:
1169:
992:•CO(NH
923:sporol
919:moiety
807:NaBArF
786:ketone
670:. The
624:acetal
593:verify
590:
499:Danger
374:SMILES
170:ChEMBL
57:Names
2954:(and
2684:SSRIs
1608:AC-42
1045:CO(NH
1024:COOOH
913:is a
862:NaBAr
790:ketal
748:-(+)-
721:with
619:is a
339:InChI
296:1166
261:12586
199:12066
150:ChEBI
128:JSmol
2518:PBID
2220:DIBD
1793:RS86
1628:AF30
1511:ISBN
1472:1990
1441:ISBN
1370:ISBN
1332:2007
1311:2017
1293:ISBN
1265:2017
1247:ISBN
1167:ISBN
1039:COOH
890:HOCH
744:for
736:(+)-
713:and
567:P501
551:P280
547:P243
543:P242
539:P241
535:P240
531:P233
527:P210
513:H225
272:UNII
2774:),
2060:),
1476:doi
1433:doi
1405:doi
1401:115
1336:doi
1159:doi
1125:at
750:cis
738:cis
717:of
709:of
686:in
654:(CH
630:(CH
466:GHS
308:EPA
251:CID
3069::
2908:,
2904:,
2900:,
2896:,
2892:,
2838:,
2834:,
2830:,
2826:,
2822:,
2818:,
2814:,
2810:,
2806:,
2802:,
2798:,
2794:,
2790:,
2786:,
2782:,
2778:,
2726:,
2722:,
2718:,
2694:,
2320:,
2316:,
2072:,
2068:,
2064:,
2052:,
2048:,
2019:,
2015:,
2011:,
2007:,
2003:,
1999:,
1995:,
1991:,
1987:,
1983:,
1979:,
1975:,
1971:,
1967:,
1963:,
1959:,
1955:,
1951:,
1947:,
1505:.
1470:.
1439:.
1431:.
1417:^
1384:^
1360:.
1348:^
1330:.
1301:.
1273:^
1255:.
1227:^
1215:;
1208:.
1189:.
1165:.
1030:CF
1015:CF
951:CF
945:.
898:OH
894:CH
759:.
725:.
690:.
642:CH
565:,
561:,
557:,
553:,
549:,
545:,
541:,
537:,
533:,
529:,
470::
2982:)
2978:(
2958:)
2922:)
2918:(
2912:)
2842:)
2770:(
2730:)
2698:)
2374:)
2370:(
2324:)
2312:(
2076:)
2056:(
2023:)
1907:)
1903:(
1562:e
1555:t
1548:v
1519:.
1482:.
1478::
1449:.
1435::
1411:.
1407::
1378:.
1342:.
1338::
1313:.
1267:.
1222:.
1193:.
1175:.
1161::
1059:2
1054:)
1050:2
1035:3
1020:3
1006:2
1001:)
997:2
988:2
983:O
979:2
974:H
965:3
956:3
896:2
892:2
866:4
836:O
834:2
832:H
828:2
826:)
824:2
809:4
746:L
664:2
662:O
660:4
656:2
644:2
640:2
638:O
636:2
634:)
632:2
588:N
412:2
410:O
408:6
406:H
404:3
402:C
310:)
306:(
130:)
20:.
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