1179:
333:
202:
771:
934:
1507:
1864:
2262:
1034:
937:
26:
939:
938:
1564:. These substances condense to form tetraaminotriphenylmethane, which, on heating with acids, loses ammonia and yields 3,6-diamino-9,10-dihydrophenylacridine, from which benzoflavin is obtained by oxidation. It is a yellow powder, soluble in hot water.
1097:, acridine is mildly basic. It is an almost colorless solid, which crystallizes in needles. There are few commercial applications of acridines; at one time acridine dyes were popular, but they are now relegated to niche applications, such as with
779:
1899:
Maier W, Baumert A, Schumann B, Furukawa H, Gröger D (1993). "Synthesis of 1,3-dihydroxy-N-methylacridone and its conversion to rutacridone by cell-free extracts of Ruta-graveolens cell cultures".
751:
1534:
in a fine yellow; and the solutions of the salts are characterized by their fine yellowish-green fluorescence. Chrysaniline was synthesized by O. Fischer and G. Koerner by condensing
1304:
869:
1289:
940:
2563:
948:
1812:
1000:
3577:
2396:
1047:
3154:
2703:
2022:
1961:
3411:
3094:
3179:
3119:
3049:
2693:
962:
3531:
3367:
3299:
3164:
3546:
3476:
3461:
3451:
3284:
3044:
3039:
3501:
3456:
3446:
3279:
3174:
3009:
2763:
2593:
382:
3541:
3421:
3244:
3139:
3114:
3054:
1884:
1879:
955:
865:
2320:
2287:
1178:
720:
2153:
2069:
1744:
1676:
1659:
693:
2351:
1948:
610:
2039:
1085:
N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to
2244:
347:
1042:
1940:
1593:
1518:
or 3,6-diamino-9-phenylacridine, which is the chief constituent of the dyestuff phosphine (not to be confused with
1054:
25:
3572:
1766:
853:
107:
100:
1468:
1229:
1144:
861:
827:
280:
197:
311:
1491:
At one time acridine dyes were commercially significant, but they are now uncommon because they are not
849:
159:
1728:
1391:
Acridines can be reduced to the 9,10-dihydroacridines, sometimes called leucoacridines. Reaction with
1011:
770:
592:
2266:
209:
1596:. All feature very similar planar molecules with nearly identical bond lengths and bond distances.
2856:
2451:
2344:
1901:
1725:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1281:
1244:
905:
328:
3342:
1424:
626:
1572:
Acridine is known to induce small insertions or deletions in nucleotide sequences, resulting in
2431:
1396:
1358:
Acridine and its homologues are weakly basic. Acridine is a photobase which has a ground state
1339:
1133:
1101:. The name is a reference to the acrid odour and acrid skin-irritating effect of the compound.
669:
2558:
2426:
1589:
1074:
793:
763:
565:
1869:
One or more of the preceding sentences incorporates text from a publication now in the
893:
2798:
2290:
2098:
1910:
1794:
1125:
889:
524:
289:
38:
1776:, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-06-22)
1338:
to form alkyl acridinium iodides, which are readily transformed by the action of alkaline
873:
179:
8:
2391:
2337:
1699:
1664:
1573:
1556:, an isomer of chrysaniline, is also a dyestuff, and has been prepared by K. Oehler from
1296:
531:
76:
66:
2102:
1914:
332:
201:
139:
3567:
2176:
2134:
2121:
2086:
1605:
1500:
1496:
1480:
1197:
119:
1922:
2483:
2401:
2305:
2297:
2240:
2180:
2138:
2126:
2065:
2035:
2002:
1944:
1740:
1672:
1432:
1420:
1392:
1259:
1240:
1189:
1164:
499:
484:
2198:
3259:
3224:
2232:
2213:
2168:
2116:
2106:
2027:
1994:
1969:
1918:
1839:
1732:
1089:
with one of the central CH groups replaced by nitrogen. Like the related molecules
1070:
507:
410:
1163:
is the carboxylic acid, the reaction yields the parent acridine. With the higher
1143:
Acridine and its derivatives can be prepared by many synthetic processes. In the
3441:
3377:
3337:
3294:
3289:
3099:
2999:
2861:
2411:
2236:
2152:
Schur E, Bernstein J, Price LS, Guo R, Price SL, Lapidus SH, Stephens PW (2019).
2059:
1936:
1472:
1205:
1152:
1098:
841:
253:
228:
1736:
3466:
3319:
3309:
3209:
2994:
2954:
2821:
2618:
2538:
2446:
2406:
2368:
1312:
1025:
833:
578:
2111:
1808:
988:
3561:
3362:
3357:
3352:
3327:
3264:
3249:
2946:
2836:
2753:
2718:
2698:
2543:
2478:
2421:
2386:
2154:"The (Current) Acridine Solid Form Landscape: Eight Polymorphs and a Hydrate"
2031:
1998:
1973:
1875:
1870:
1843:
1790:
1492:
1213:
1169:
1156:
1148:
1121:
1113:
845:
650:
535:
491:
476:
190:
2172:
1109:
3426:
3269:
3234:
3194:
3169:
3124:
3089:
3079:
3014:
2989:
2979:
2936:
2926:
2921:
2911:
2896:
2876:
2866:
2788:
2783:
2758:
2728:
2623:
2608:
2533:
2528:
2513:
2508:
2436:
2416:
2130:
2006:
1577:
1561:
1476:
1335:
961:
3536:
3506:
3491:
3390:
3385:
3332:
3274:
3214:
3199:
3184:
3144:
3084:
3074:
3064:
3024:
2984:
2959:
2916:
2906:
2901:
2891:
2886:
2851:
2846:
2816:
2748:
2743:
2723:
2688:
2678:
2663:
2658:
2643:
2633:
2588:
2573:
2553:
2518:
1428:
1285:
1247:
1160:
1129:
877:
1506:
947:
881:
857:
3526:
3516:
3431:
3254:
3239:
3219:
3159:
3134:
3109:
3069:
3059:
3029:
3004:
2974:
2931:
2881:
2841:
2831:
2826:
2778:
2773:
2738:
2713:
2708:
2673:
2613:
2598:
2568:
2503:
2498:
2493:
2473:
2381:
1888:. Vol. 1 (11th ed.). Cambridge University Press. p. 155.
1523:
1452:
1448:
1300:
1236:
1193:
1086:
954:
518:
435:
210:
170:
2231:. Advances in Heterocyclic Chemistry. Vol. 15. pp. 287–353.
901:
3521:
3486:
3481:
3471:
3436:
3416:
3406:
3347:
3229:
3204:
3129:
3034:
3019:
2969:
2964:
2871:
2811:
2806:
2768:
2733:
2648:
2628:
2603:
2578:
2548:
2523:
2488:
2468:
2463:
2360:
2218:
1965:
1668:
1620:
1519:
1456:
1416:
1380:
1255:
1094:
300:
1827:
1228:
dust. Another classic method for the synthesis of acridones is the
1024:
Except where otherwise noted, data are given for materials in their
3511:
3304:
3189:
3104:
2683:
2668:
2653:
2638:
1369:
1347:
1221:
1217:
1201:
1117:
1090:
920:
1806:
1611:(rats, oral) is 2,000 mg/kg and 500 mg/kg (mice, oral).
1447:
and drugs feature the acridine skeleton. Many acridines, such as
1200:, by passing the vapours of orthoaminodiphenylmethane over heated
913:
106:
99:
3149:
2583:
1985:
Denny (2002). "Acridine
Derivatives as Chemotherapeutic Agents".
1576:. This compound was useful to identify the triplet nature of the
1209:
1137:
837:
551:
466:
240:
1120:. Acridine is separated from coal tar by extracting with dilute
2261:
1395:
gives the 9-cyano-9,10-dehydro derivative. On oxidation with
1251:
356:
InChI=1S/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9H
150:
819:
366:
InChI=1/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9H
2329:
2084:
2020:
1769:
in
Linstrom, Peter J.; Mallard, William G. (eds.);
897:
264:
130:
89:
1898:
1546:-diaminotriphenylmethane being reduced to the corresponding
316:
3496:
1531:
1527:
1326:
Acridine displays the reactions expected of an unsaturated
1225:
811:
456:
2199:"Synthesis of Acridine-based DNA Bis-intercalating Agents"
1771:
803:
1550:-amino compound, which on oxidation yields chrysaniline.
1464:
1460:
1444:
1359:
2057:
2151:
2085:
Stephens PW, Schur E, Lapidus SH, Bernstein J (2019).
1455:
properties. Acridine and related derivatives (such as
2064:. Jones & Bartlett Learning. pp. 157, 2927.
1813:
National
Institute for Occupational Safety and Health
1431:. The carbon 9-position of acridine is activated for
2058:
Krebs JE, Goldstein ES, Kilpatrick ST (2017-03-02).
807:
1623:, a chemiluminescent compound derived from acridine
1526:. Chrysaniline forms red-coloured salts, which dye
1192:of acridines include condensing diphenylamine with
1510:Synthesis of C.I. Basic Yellow 9, an acridine dye.
799:
481:106–110 °C (223–230 °F; 379–383 K)
3559:
2196:
1495:. Acridine dyes are prepared by condensation of
1269:-methylanthraniloyl-CoA ⇌ 4 CoA + 1,3-dihydroxy-
815:
252:
1538:-nitrobenzaldehyde with aniline, the resulting
936:
496:344.86 °C (652.75 °F; 618.01 K)
75:
2023:Ullmann's Encyclopedia of Industrial Chemistry
1962:Ullmann's Encyclopedia of Industrial Chemistry
1832:Berichte der Deutschen Chemischen Gesellschaft
1499:derivatives. Illustrative is the reaction of
909:
2345:
2229:Recent Advances in the Chemistry of Acridines
1018:TWA 0.2 mg/m (benzene-soluble fraction)
1774:, NIST Standard Reference Database Number 69
1419:-1,2-dicarboxylic acid. Acridine is easily
2352:
2338:
2226:
1857:
1855:
1853:
1386:
1104:
885:
331:
200:
178:
3578:Substances discovered in the 19th century
2217:
2120:
2110:
1825:
288:
2019:
1874:
1807:NIOSH Pocket Guide to Chemical Hazards.
1717:
1522:gas), a byproduct in the manufacture of
1505:
1379:of 10.6. It also shares properties with
1132:acridine bichromate. The bichromate is
1937:Principles of Fluorescence Spectroscopy
1850:
1786:
1784:
1782:
1514:9-Phenylacridine is the parent base of
327:
3560:
1762:
1760:
1758:
1756:
1592:, acridine has been obtained in eight
191:
2333:
2197:Moloney GP, Kelly DP, Mack P (2001).
2053:
2051:
1984:
1694:
1692:
1690:
1688:
1660:CRC Handbook of Chemistry and Physics
1652:
1650:
1648:
1646:
1644:
1642:
1640:
1638:
1636:
1483:useful for cell cycle determination.
1167:, the derivatives substituted at the
1116:first isolated acridine in 1870 from
359:Key: DZBUGLKDJFMEHC-UHFFFAOYSA-N
158:
138:
1800:
1779:
1656:
1567:
1753:
369:Key: DZBUGLKDJFMEHC-UHFFFAOYAF
243:
13:
2048:
1685:
1633:
1604:Acridine is a skin irritant. Its
1177:
932:
14:
3589:
3100:Levomepromazine/Methotrimeprazine
2254:
1960:G. Collin, H. Höke,"Acridine" in
1475:(3,6-dimethylaminoacridine) is a
2719:Nortriptyline (noramitriptyline)
2303:Synthesis of 9-aminoacridine in
2260:
2091:Acta Crystallographica Section E
1862:
1182:The Bernthsen acridine synthesis
1032:
769:
428:
422:
24:
2145:
2078:
2013:
1978:
1954:
1929:
1438:
1028:(at 25 °C , 100 kPa).
2359:
1892:
1819:
1729:The Royal Society of Chemistry
416:
1:
2190:
1923:10.1016/S0031-9422(00)95155-0
1826:Gräbe C, Caro H (July 1870).
1627:
1399:, it yields acridinic acid (C
1005:(US health exposure limits):
587:11.13 kPa (250 °C)
471:1.005 g/cm (20 °C)
2237:10.1016/bs.aihch.2015.04.004
1583:
1330:-heterocycle. It undergoes
1321:
1230:Lehmstedt-Tanasescu reaction
1188:Other older methods for the
1145:Bernthsen acridine synthesis
995:500 mg/kg (mice, oral)
7:
2161:Crystal Growth & Design
1987:Current Medicinal Chemistry
1737:10.1039/9781849733069-FP001
1731:. 2014. pp. 211, 214.
1614:
1368:of 5.1, similar to that of
1353:
1173:carbon atom are generated.
977:or concentration (LD, LC):
585:2.39 kPa (200 °C)
583:0.34 kPa (150 °C)
10:
3594:
2985:Carfenazine (carphenazine)
1797:. Retrieved on 2014-06-22.
1467:due to their abilities to
3399:
3376:
3318:
2945:
2797:
2714:Northiaden (nordosulepin)
2452:Tricyclic antidepressants
2445:
2367:
2272:Synthesis of acridone in
2227:Schmidt A, Liu M (2015).
2112:10.1107/S2056989019003645
1599:
1479:-selective metachromatic
1022:
999:
973:
750:
745:
643:
403:
378:
343:
59:
49:
37:
32:
23:
2857:Hydroxyethylpromethazine
2326:-phenylanthranilic acid.
2032:10.1002/14356007.a27_179
1999:10.2174/0929867023369277
1974:10.1002/14356007.a01_147
1844:10.1002/cber.18700030223
1372:, and an excited state p
828:Precautionary statements
3343:Eslicarbazepine acetate
2549:Depramine (balipramine)
2173:10.1021/acs.cgd.9b00557
2026:. Weinheim: Wiley-VCH.
1885:Encyclopædia Britannica
1486:
1425:peroxymonosulfuric acid
1387:Reduction and oxidation
1293:-methylanthraniloyl-CoA
1165:larger carboxylic acids
1105:Isolation and syntheses
627:Magnetic susceptibility
3245:Savoxepin/Cipazoxapine
2432:Pyridinobenzodiazepine
1951:. Chapter 7. page 260.
1772:NIST Chemistry WebBook
1560:-phenylenediamine and
1511:
1397:potassium permanganate
1340:potassium ferricyanide
1273:-methylacridone + 3 CO
1183:
943:
395:c1ccc2c(c1)cc3ccccc3n2
390:n1c3c(cc2c1cccc2)cccc3
3573:Simple aromatic rings
2579:Dosulepin (dothiepin)
2564:Desmethyltrimipramine
2559:Desmethylclomipramine
2554:(desmethylimipramine)
2427:Pyridazinobenzoxazine
1657:Lide DR, ed. (2009).
1590:X-ray crystallography
1509:
1415:) otherwise known as
1181:
942:
2269:at Wikimedia Commons
1935:Joseph R. Lakowicz.
1574:frameshift mutations
1295:, whereas its three
1126:potassium dichromate
1075:nitrogen heterocycle
925:(fire diamond)
687:208.03 J/mol·K
663:205.07 J/mol·K
39:Preferred IUPAC name
2392:Dibenzocycloheptene
2294:-chlorobenzoic acid
2103:2019AcCrE..75..489S
1915:1993PChem..32..691M
1706:. Fisher Scientific
1665:Boca Raton, Florida
1503:with acetaldehyde:
1284:of this enzyme are
1196:in the presence of
1155:in the presence of
741:6581.3 kJ/mol
508:Solubility in water
443: g·mol
120:Beilstein Reference
20:
2087:"Acridine form IX"
1700:"MSDS of Acridine"
1588:As established by
1512:
1501:2,4-diaminotoluene
1497:1,3-diaminobenzene
1433:addition reactions
1334:-alkylation with
1198:aluminium chloride
1184:
1151:is condensed with
1077:with the formula C
1055:Infobox references
944:
714:179.4 kJ/mol
605:5.58 (20 °C)
54:2,3-Benzoquinoline
18:
3555:
3554:
2484:Amitriptylinoxide
2402:Dibenzothiazepine
2306:Organic Syntheses
2298:Goldberg reaction
2296:and aniline in a
2274:Organic Syntheses
2265:Media related to
2071:978-1-284-10449-3
2061:Lewin's GENES XII
1791:Sigma-Aldrich Co.
1746:978-0-85404-182-4
1678:978-1-4200-9084-0
1663:(90th ed.).
1568:Molecular biology
1393:potassium cyanide
1260:chemical reaction
1241:acridone synthase
1216:or by distilling
1190:organic synthesis
1128:to this solution
1063:Chemical compound
1061:
1060:
794:Hazard statements
500:standard pressure
485:standard pressure
312:CompTox Dashboard
108:Interactive image
101:Interactive image
3585:
3378:Anticholinergics
3260:Thiethylperazine
3225:Prochlorperazine
2456:
2397:Dibenzodiazepine
2354:
2347:
2340:
2331:
2330:
2264:
2250:
2223:
2221:
2219:10.3390/60300230
2203:
2185:
2184:
2167:(8): 4884–4893.
2158:
2149:
2143:
2142:
2124:
2114:
2082:
2076:
2075:
2055:
2046:
2045:
2017:
2011:
2010:
1982:
1976:
1958:
1952:
1949:978-0387-31278-1
1933:
1927:
1926:
1896:
1890:
1889:
1868:
1866:
1865:
1859:
1848:
1847:
1823:
1817:
1816:
1804:
1798:
1788:
1777:
1764:
1751:
1750:
1721:
1715:
1714:
1712:
1711:
1704:www.fishersci.ca
1696:
1683:
1682:
1654:
1427:to the acridine
1265:3 malonyl-CoA +
1153:carboxylic acids
1071:organic compound
1045:
1039:
1036:
1035:
964:
957:
950:
935:
915:
911:
907:
903:
899:
895:
891:
887:
883:
879:
875:
871:
867:
863:
859:
855:
851:
847:
843:
839:
835:
821:
817:
813:
809:
805:
801:
773:
737:
710:
683:
659:
644:Thermochemistry
639:
637:
442:
430:
424:
418:
411:Chemical formula
336:
335:
320:
318:
292:
256:
245:
229:Gmelin Reference
212:
204:
193:
182:
162:
142:
110:
103:
79:
28:
21:
17:
3593:
3592:
3588:
3587:
3586:
3584:
3583:
3582:
3558:
3557:
3556:
3551:
3442:Cyclobenzaprine
3395:
3372:
3338:Eslicarbazepine
3320:Anticonvulsants
3314:
3295:Triflupromazine
3290:Trifluoperazine
3155:Octomethothepin
3000:Chlorprothixene
2941:
2862:Isopromethazine
2793:
2704:Norbutriptyline
2454:
2449:
2447:Antidepressants
2441:
2412:Dibenzoxazepine
2363:
2358:
2257:
2247:
2201:
2193:
2188:
2156:
2150:
2146:
2083:
2079:
2072:
2056:
2049:
2042:
2018:
2014:
1993:(18): 1655–65.
1983:
1979:
1959:
1955:
1934:
1930:
1897:
1893:
1878:, ed. (1911). "
1863:
1861:
1860:
1851:
1828:"Ueber Acridin"
1824:
1820:
1805:
1801:
1789:
1780:
1765:
1754:
1747:
1723:
1722:
1718:
1709:
1707:
1698:
1697:
1686:
1679:
1655:
1634:
1630:
1617:
1609:
1602:
1586:
1570:
1489:
1473:Acridine orange
1441:
1414:
1410:
1406:
1402:
1389:
1378:
1366:
1356:
1324:
1316:
1309:-methylacridone
1276:
1206:salicylaldehyde
1107:
1099:acridine orange
1084:
1080:
1064:
1057:
1052:
1051:
1050: ?)
1041:
1037:
1033:
1029:
1015:
992:
986:
969:
968:
967:
966:
959:
952:
945:
941:
933:
830:
796:
782:
766:
738:
735:
729:
725:
722:
721:Std enthalpy of
711:
708:
702:
698:
695:
694:Std enthalpy of
684:
681:
674:
671:
660:
653:
635:
633:
630:
616:
601:
586:
584:
559:
555:
547:
543:
539:
528:
513:46.5 mg/L
510:
497:
482:
440:
427:
421:
413:
399:
396:
391:
386:
385:
374:
371:
370:
367:
361:
360:
357:
351:
350:
339:
321:
314:
295:
275:
259:
246:
231:
222:
185:
165:
145:
122:
113:
93:
82:
69:
55:
53:
52:Dibenzopyridine
45:
44:
12:
11:
5:
3591:
3581:
3580:
3575:
3570:
3553:
3552:
3550:
3549:
3544:
3539:
3534:
3529:
3524:
3519:
3514:
3509:
3504:
3499:
3494:
3489:
3484:
3479:
3474:
3469:
3467:Methylene blue
3464:
3459:
3454:
3449:
3444:
3439:
3434:
3429:
3424:
3419:
3414:
3412:Aminopromazine
3409:
3403:
3401:
3397:
3396:
3394:
3393:
3388:
3382:
3380:
3374:
3373:
3371:
3370:
3365:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3324:
3322:
3316:
3315:
3313:
3312:
3310:Zuclopenthixol
3307:
3302:
3297:
3292:
3287:
3282:
3277:
3272:
3267:
3262:
3257:
3252:
3247:
3242:
3237:
3232:
3227:
3222:
3217:
3212:
3210:Piperacetazine
3207:
3202:
3197:
3192:
3187:
3182:
3177:
3172:
3167:
3162:
3157:
3152:
3147:
3142:
3137:
3132:
3127:
3122:
3117:
3112:
3107:
3102:
3097:
3095:Isofloxythepin
3092:
3087:
3082:
3077:
3072:
3067:
3062:
3057:
3052:
3047:
3042:
3037:
3032:
3027:
3022:
3017:
3012:
3007:
3002:
2997:
2995:Chlorpromazine
2992:
2987:
2982:
2977:
2972:
2967:
2962:
2957:
2955:Acetophenazine
2951:
2949:
2947:Antipsychotics
2943:
2942:
2940:
2939:
2934:
2929:
2924:
2919:
2914:
2909:
2904:
2899:
2894:
2889:
2884:
2879:
2874:
2869:
2864:
2859:
2854:
2849:
2844:
2839:
2834:
2829:
2824:
2822:Cyproheptadine
2819:
2814:
2809:
2803:
2801:
2799:Antihistamines
2795:
2794:
2792:
2791:
2786:
2781:
2776:
2771:
2766:
2761:
2756:
2751:
2746:
2741:
2736:
2731:
2726:
2721:
2716:
2711:
2706:
2701:
2696:
2691:
2686:
2681:
2676:
2671:
2666:
2661:
2656:
2651:
2646:
2641:
2636:
2631:
2626:
2621:
2619:Imipraminoxide
2616:
2611:
2606:
2601:
2596:
2591:
2586:
2581:
2576:
2571:
2566:
2561:
2556:
2551:
2546:
2541:
2539:Cyanodothiepin
2536:
2531:
2526:
2521:
2516:
2511:
2506:
2501:
2496:
2491:
2486:
2481:
2476:
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2460:
2458:
2443:
2442:
2440:
2439:
2434:
2429:
2424:
2419:
2414:
2409:
2407:Dibenzothiepin
2404:
2399:
2394:
2389:
2384:
2379:
2373:
2371:
2365:
2364:
2357:
2356:
2349:
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2328:
2327:
2301:
2270:
2256:
2255:External links
2253:
2252:
2251:
2245:
2224:
2212:(3): 230–243.
2192:
2189:
2187:
2186:
2144:
2097:(4): 489–491.
2077:
2070:
2047:
2041:978-3527306732
2040:
2012:
1977:
1953:
1928:
1909:(3): 691–698.
1902:Phytochemistry
1891:
1849:
1838:(2): 746–747.
1818:
1799:
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1388:
1385:
1376:
1364:
1355:
1352:
1323:
1320:
1314:
1305:1,3-dihydroxy-
1280:Thus, the two
1278:
1277:
1274:
1220:(9-position a
1186:
1185:
1124:. Addition of
1106:
1103:
1082:
1078:
1062:
1059:
1058:
1053:
1031:
1030:
1026:standard state
1023:
1020:
1019:
1016:
1010:
1007:
1006:
997:
996:
993:
984:
982:
979:
978:
971:
970:
960:
953:
946:
931:
930:
929:
928:
926:
917:
916:
870:P305+P351+P338
831:
826:
823:
822:
797:
792:
789:
788:
783:
778:
775:
774:
767:
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692:
689:
688:
685:
679:
668:
665:
664:
661:
649:
646:
645:
641:
640:
638:10 cm/mol
631:
625:
622:
621:
618:
614:
607:
606:
603:
599:
589:
588:
581:
579:Vapor pressure
575:
574:
571:
562:
561:
557:
553:
545:
541:
537:
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521:
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511:
506:
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494:
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487:
479:
473:
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452:
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445:
444:
438:
432:
431:
425:
419:
414:
409:
406:
405:
401:
400:
398:
397:
394:
392:
389:
381:
380:
379:
376:
375:
373:
372:
368:
365:
364:
362:
358:
355:
354:
346:
345:
344:
341:
340:
338:
337:
324:
322:
310:
307:
306:
303:
297:
296:
294:
293:
285:
283:
277:
276:
274:
273:
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261:
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258:
257:
249:
247:
239:
236:
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232:
227:
224:
223:
221:
220:
216:
214:
206:
205:
195:
187:
186:
184:
183:
175:
173:
167:
166:
164:
163:
155:
153:
147:
146:
144:
143:
135:
133:
127:
126:
123:
118:
115:
114:
112:
111:
104:
96:
94:
87:
84:
83:
81:
80:
72:
70:
65:
62:
61:
57:
56:
51:
47:
46:
42:
41:
35:
34:
30:
29:
9:
6:
4:
3:
2:
3590:
3579:
3576:
3574:
3571:
3569:
3566:
3565:
3563:
3548:
3545:
3543:
3540:
3538:
3535:
3533:
3530:
3528:
3525:
3523:
3520:
3518:
3515:
3513:
3510:
3508:
3505:
3503:
3500:
3498:
3495:
3493:
3490:
3488:
3485:
3483:
3480:
3478:
3475:
3473:
3470:
3468:
3465:
3463:
3460:
3458:
3455:
3453:
3450:
3448:
3445:
3443:
3440:
3438:
3435:
3433:
3430:
3428:
3425:
3423:
3420:
3418:
3415:
3413:
3410:
3408:
3405:
3404:
3402:
3398:
3392:
3389:
3387:
3384:
3383:
3381:
3379:
3375:
3369:
3366:
3364:
3363:Oxitriptyline
3361:
3359:
3358:Oxcarbazepine
3356:
3354:
3353:Licarbazepine
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3328:Carbamazepine
3326:
3325:
3323:
3321:
3317:
3311:
3308:
3306:
3303:
3301:
3298:
3296:
3293:
3291:
3288:
3286:
3283:
3281:
3278:
3276:
3273:
3271:
3268:
3266:
3265:Thiopropazate
3263:
3261:
3258:
3256:
3253:
3251:
3250:Sulforidazine
3248:
3246:
3243:
3241:
3238:
3236:
3233:
3231:
3228:
3226:
3223:
3221:
3218:
3216:
3213:
3211:
3208:
3206:
3203:
3201:
3198:
3196:
3193:
3191:
3188:
3186:
3183:
3181:
3180:Peradithiepin
3178:
3176:
3173:
3171:
3168:
3166:
3163:
3161:
3158:
3156:
3153:
3151:
3148:
3146:
3143:
3141:
3138:
3136:
3133:
3131:
3128:
3126:
3123:
3121:
3120:Meperathiepin
3118:
3116:
3113:
3111:
3108:
3106:
3103:
3101:
3098:
3096:
3093:
3091:
3088:
3086:
3083:
3081:
3078:
3076:
3073:
3071:
3068:
3066:
3063:
3061:
3058:
3056:
3053:
3051:
3050:Docloxythepin
3048:
3046:
3043:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3023:
3021:
3018:
3016:
3013:
3011:
3008:
3006:
3003:
3001:
2998:
2996:
2993:
2991:
2988:
2986:
2983:
2981:
2978:
2976:
2973:
2971:
2968:
2966:
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2961:
2958:
2956:
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2952:
2950:
2948:
2944:
2938:
2935:
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2930:
2928:
2925:
2923:
2920:
2918:
2915:
2913:
2910:
2908:
2905:
2903:
2900:
2898:
2895:
2893:
2890:
2888:
2885:
2883:
2880:
2878:
2875:
2873:
2870:
2868:
2865:
2863:
2860:
2858:
2855:
2853:
2850:
2848:
2845:
2843:
2840:
2838:
2837:Desloratadine
2835:
2833:
2830:
2828:
2825:
2823:
2820:
2818:
2815:
2813:
2810:
2808:
2805:
2804:
2802:
2800:
2796:
2790:
2787:
2785:
2782:
2780:
2777:
2775:
2772:
2770:
2767:
2765:
2762:
2760:
2757:
2755:
2754:Protriptyline
2752:
2750:
2747:
2745:
2742:
2740:
2737:
2735:
2732:
2730:
2727:
2725:
2722:
2720:
2717:
2715:
2712:
2710:
2707:
2705:
2702:
2700:
2699:Nitroxazepine
2697:
2695:
2694:Monometacrine
2692:
2690:
2687:
2685:
2682:
2680:
2677:
2675:
2672:
2670:
2667:
2665:
2662:
2660:
2657:
2655:
2652:
2650:
2647:
2645:
2642:
2640:
2637:
2635:
2632:
2630:
2627:
2625:
2622:
2620:
2617:
2615:
2612:
2610:
2607:
2605:
2602:
2600:
2597:
2595:
2592:
2590:
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2585:
2582:
2580:
2577:
2575:
2572:
2570:
2567:
2565:
2562:
2560:
2557:
2555:
2552:
2550:
2547:
2545:
2544:Demexiptiline
2542:
2540:
2537:
2535:
2532:
2530:
2527:
2525:
2522:
2520:
2517:
2515:
2512:
2510:
2507:
2505:
2502:
2500:
2497:
2495:
2492:
2490:
2487:
2485:
2482:
2480:
2479:Amitriptyline
2477:
2475:
2472:
2470:
2467:
2465:
2462:
2461:
2459:
2453:
2448:
2444:
2438:
2435:
2433:
2430:
2428:
2425:
2423:
2422:Phenothiazine
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2398:
2395:
2393:
2390:
2388:
2387:Dibenzazepine
2385:
2383:
2380:
2378:
2375:
2374:
2372:
2370:
2366:
2362:
2355:
2350:
2348:
2343:
2341:
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2332:
2325:
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2315:
2311:
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2302:
2299:
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2288:
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2282:
2278:
2275:
2271:
2268:
2263:
2259:
2258:
2248:
2246:9780128021293
2242:
2238:
2234:
2230:
2225:
2220:
2215:
2211:
2207:
2200:
2195:
2194:
2182:
2178:
2174:
2170:
2166:
2162:
2155:
2148:
2140:
2136:
2132:
2128:
2123:
2118:
2113:
2108:
2104:
2100:
2096:
2092:
2088:
2081:
2073:
2067:
2063:
2062:
2054:
2052:
2043:
2037:
2033:
2029:
2025:
2024:
2016:
2008:
2004:
2000:
1996:
1992:
1988:
1981:
1975:
1971:
1967:
1963:
1957:
1950:
1946:
1942:
1939:3rd edition.
1938:
1932:
1924:
1920:
1916:
1912:
1908:
1904:
1903:
1895:
1887:
1886:
1881:
1877:
1872:
1871:public domain
1858:
1856:
1854:
1845:
1841:
1837:
1834:(in German).
1833:
1829:
1822:
1814:
1810:
1803:
1796:
1792:
1787:
1785:
1783:
1775:
1773:
1768:
1763:
1761:
1759:
1757:
1748:
1742:
1738:
1734:
1730:
1727:. Cambridge:
1726:
1720:
1705:
1701:
1695:
1693:
1691:
1689:
1680:
1674:
1670:
1666:
1662:
1661:
1653:
1651:
1649:
1647:
1645:
1643:
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1637:
1632:
1622:
1619:
1618:
1612:
1610:
1597:
1595:
1591:
1581:
1579:
1578:genetic codes
1575:
1565:
1563:
1559:
1555:
1551:
1549:
1545:
1541:
1537:
1533:
1529:
1525:
1521:
1517:
1508:
1504:
1502:
1498:
1494:
1484:
1482:
1478:
1474:
1470:
1466:
1462:
1458:
1454:
1450:
1446:
1436:
1434:
1430:
1426:
1422:
1418:
1398:
1394:
1384:
1382:
1375:
1371:
1367:
1363:
1351:
1349:
1345:
1341:
1337:
1336:alkyl iodides
1333:
1329:
1319:
1317:
1310:
1308:
1302:
1298:
1294:
1292:
1287:
1283:
1272:
1268:
1264:
1263:
1262:
1261:
1257:
1253:
1249:
1246:
1242:
1238:
1233:
1231:
1227:
1223:
1219:
1215:
1214:zinc chloride
1211:
1207:
1204:, by heating
1203:
1199:
1195:
1191:
1180:
1176:
1175:
1174:
1172:
1171:
1166:
1162:
1158:
1157:zinc chloride
1154:
1150:
1149:diphenylamine
1146:
1141:
1139:
1135:
1131:
1127:
1123:
1122:sulfuric acid
1119:
1115:
1114:Heinrich Caro
1111:
1102:
1100:
1096:
1092:
1088:
1076:
1072:
1068:
1056:
1049:
1044:
1027:
1021:
1017:
1014:(Permissible)
1013:
1009:
1008:
1004:
1003:
998:
994:
990:
981:
980:
976:
972:
965:
958:
951:
927:
924:
923:
919:
918:
832:
829:
825:
824:
798:
795:
791:
790:
787:
784:
781:
777:
776:
772:
768:
765:
761:
760:
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749:
744:
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732:
724:
718:
717:
713:
705:
697:
691:
690:
686:
678:
673:
667:
666:
662:
657:
652:
651:Heat capacity
648:
647:
642:
632:
628:
624:
623:
619:
612:
609:
608:
604:
598:
594:
591:
590:
582:
580:
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572:
570:
569:
564:
563:
560:
549:
533:
529:
522:
520:
517:
516:
512:
509:
505:
504:
501:
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493:
492:Boiling point
490:
489:
486:
480:
478:
477:Melting point
475:
474:
470:
468:
465:
464:
460:
458:
455:
454:
451:White powder
450:
447:
446:
439:
437:
434:
433:
415:
412:
408:
407:
402:
393:
388:
387:
384:
377:
363:
353:
352:
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342:
334:
330:
329:DTXSID8059766
326:
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242:
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233:
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196:
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192:ECHA InfoCard
189:
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181:
177:
176:
174:
172:
169:
168:
161:
157:
156:
154:
152:
149:
148:
141:
137:
136:
134:
132:
129:
128:
124:
121:
117:
116:
109:
105:
102:
98:
97:
95:
91:
86:
85:
78:
74:
73:
71:
68:
64:
63:
58:
48:
40:
36:
31:
27:
22:
16:
3532:Siltenzepine
3427:Benzoctamine
3368:Rispenzepine
3300:Trifluthepin
3270:Thioridazine
3235:Prothipendyl
3195:Perphenazine
3170:Oxyprothepin
3165:Oxyclothepin
3125:Mesoridazine
3090:Homopipramol
3080:Fluphenazine
3015:Clocapramine
2990:Carpipramine
2980:Butaperazine
2937:Thiazinamium
2927:Propiomazine
2922:Promethazine
2912:Phenindamine
2897:Methdilazine
2877:Latrepirdine
2867:Isothipendyl
2789:Trimipramine
2784:Tienopramine
2759:Quinupramine
2729:Octriptyline
2624:Intriptyline
2609:Homopipramol
2534:Cotriptyline
2529:Clomipramine
2514:Cianopramine
2509:Butriptyline
2437:Thioxanthene
2417:Dibenzoxepin
2376:
2323:
2316:
2313:
2309:
2304:
2291:
2283:
2280:
2276:
2273:
2228:
2209:
2205:
2164:
2160:
2147:
2094:
2090:
2080:
2060:
2021:
2015:
1990:
1986:
1980:
1956:
1931:
1906:
1900:
1894:
1883:
1835:
1831:
1821:
1802:
1770:
1724:
1719:
1708:. Retrieved
1703:
1658:
1603:
1587:
1571:
1562:benzaldehyde
1557:
1553:
1552:
1547:
1543:
1539:
1535:
1516:chrysaniline
1515:
1513:
1490:
1477:nucleic acid
1451:, also have
1442:
1439:Applications
1390:
1373:
1361:
1357:
1343:
1331:
1327:
1325:
1306:
1290:
1279:
1270:
1266:
1234:
1224:group) over
1187:
1168:
1142:
1130:precipitates
1108:
1066:
1065:
1001:
974:
921:
785:
752:
730:
703:
676:
655:
596:
567:
265:RTECS number
60:Identifiers
50:Other names
15:
3547:Zolenzepine
3537:Telenzepine
3507:Pirenzepine
3492:Pipazethate
3477:Nuvenzepine
3462:Fluradoline
3452:Darenzepine
3391:Tropatepine
3386:Profenamine
3333:Dizocilpine
3285:Traboxopine
3275:Thiothixene
3215:Pipotiazine
3200:Periciazine
3185:Perathiepin
3145:Mosapramine
3085:Gevotroline
3075:Flupentixol
3065:Flumezapine
3045:Doclothepin
3040:Cyanothepin
3025:Clorotepine
2960:Alimemazine
2917:Pimethixene
2907:Oxomemazine
2902:Olopatadine
2892:Mequitazine
2887:Mebhydrolin
2852:Fenethazine
2847:Etymemazine
2817:Clobenzepam
2749:Propizepine
2744:Pirandamine
2724:Noxiptiline
2689:Mirtazapine
2679:Metapramine
2664:Mariptiline
2659:Maprotiline
2644:Lofepramine
2634:Ketipramine
2589:Enprazepine
2574:Dimetacrine
2519:Ciclazindol
1968:, Weinheim.
1554:Benzoflavin
1469:intercalate
1429:amine oxide
1286:malonyl-CoA
1161:formic acid
989:median dose
975:Lethal dose
780:Signal word
523:Soluble in
461:Irritating
448:Appearance
404:Properties
198:100.005.429
160:ChEMBL39677
140:CHEBI:36420
3562:Categories
3527:Serazapine
3517:Pitrazepin
3502:Pinadoline
3457:Elanzepine
3447:Damotepine
3432:Carvedilol
3280:Tilozepine
3255:Tenilapine
3240:Quetiapine
3220:Piquindone
3175:Pentiapine
3160:Olanzapine
3135:Metitepine
3110:Lurasidone
3070:Fluotracen
3060:Flucindole
3030:Clotiapine
3010:Citatepine
3005:Ciclindole
2975:Butaclamol
2932:Rupatadine
2882:Loratadine
2842:Epinastine
2832:Deptropine
2827:Dacemazine
2779:Tianeptine
2774:Tampramine
2764:Spiroxepin
2739:Pipofezine
2709:Nordoxepin
2674:Melitracen
2614:Imipramine
2599:Fluotracen
2594:Fantridone
2569:Dibenzepin
2504:Batelapine
2499:Azepindole
2494:Aptazapine
2474:Amineptine
2382:Anthracene
2361:Tricyclics
2314:Coll. Vol.
2281:Coll. Vol.
2191:Literature
1876:Chisholm H
1710:2014-06-22
1628:References
1594:polymorphs
1524:rosaniline
1459:) bind to
1453:antiseptic
1449:proflavine
1282:substrates
1237:enzymology
1194:chloroform
1134:decomposed
1110:Carl Gräbe
1087:anthracene
764:Pictograms
723:combustion
519:Solubility
436:Molar mass
290:42NI1P5Q1X
171:ChemSpider
88:3D model (
67:CAS Number
3568:Acridines
3542:Tipindole
3522:Pizotifen
3487:Perlapine
3482:Oxetorone
3472:Monatepil
3437:Cidoxepin
3422:Beloxepin
3417:Atiprosin
3407:Adosopine
3348:Etazepine
3230:Promazine
3205:Pinoxepin
3140:Metoxepin
3130:Metiapine
3115:Maroxepin
3055:Erizepine
3035:Clozapine
3020:Clomacran
2970:Asenapine
2965:Amoxapine
2872:Ketotifen
2812:Bisulepin
2807:Azatadine
2769:Tandamine
2734:Opipramol
2649:Losindole
2629:Iprindole
2604:Hepzidine
2524:Cidoxepin
2489:Amoxapine
2469:Amezepine
2464:Amoxapine
2206:Molecules
2181:198349955
2139:174807725
1966:Wiley-VCH
1669:CRC Press
1621:Lucigenin
1584:Structure
1520:phosphine
1493:lightfast
1457:amsacrine
1417:quinoline
1381:quinoline
1348:acridones
1322:Reactions
1256:catalyzes
1248:2.3.1.159
1095:quinoline
906:P403+P233
894:P337+P313
890:P332+P313
866:P304+P340
862:P304+P312
858:P302+P352
854:P301+P312
755:labelling
696:formation
670:Std molar
301:UN number
272:AR7175000
219:205-971-6
211:EC Number
19:Acridine
3512:Pirolate
3305:Zotepine
3190:Perazine
3105:Loxapine
2684:Mezepine
2669:Mazindol
2654:Loxapine
2639:Litracen
2377:Acridine
2267:Acridine
2131:31161062
2007:12171548
1943:(2006).
1941:Springer
1880:Acridine
1815:(NIOSH).
1795:Acridine
1767:Acridine
1615:See also
1443:Several
1421:oxidized
1370:pyridine
1354:Basicity
1297:products
1250:) is an
1222:carbonyl
1218:acridone
1202:litharge
1118:coal tar
1091:pyridine
1067:Acridine
922:NFPA 704
746:Hazards
629:(χ)
532:alcohols
77:260-94-6
43:Acridine
3150:Naranol
2584:Doxepin
2369:Classes
2122:6509685
2099:Bibcode
1911:Bibcode
1873::
1809:"#0145"
1542:-nitro-
1346:-alkyl
1210:aniline
1159:. When
1138:ammonia
1048:what is
1046: (
672:entropy
620:392 nm
593:Acidity
467:Density
441:179.222
241:PubChem
234:143403
125:120200
3400:Others
2455:(TCAs)
2243:
2179:
2137:
2129:
2119:
2068:
2038:
2005:
1964:2012,
1947:
1867:
1743:
1675:
1600:Safety
1311:, and
1252:enzyme
1136:using
1073:and a
1069:is an
1043:verify
1040:
786:Danger
634:−123.3
611:UV-vis
383:SMILES
151:ChEMBL
33:Names
2322:from
2319::53.
2289:from
2202:(PDF)
2177:S2CID
2157:(PDF)
2135:S2CID
1481:stain
1254:that
1239:, an
1208:with
1002:NIOSH
348:InChI
305:2713
131:ChEBI
90:JSmol
3497:P7C3
2312::5;
2286::15
2279::6;
2241:ISBN
2127:PMID
2066:ISBN
2036:ISBN
2003:PMID
1945:ISBN
1741:ISBN
1673:ISBN
1532:wool
1530:and
1528:silk
1487:Dyes
1463:and
1445:dyes
1407:N(CO
1299:are
1288:and
1258:the
1226:zinc
1212:and
1170:meso
1112:and
1093:and
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910:P405
902:P363
898:P362
886:P330
882:P322
878:P321
874:P312
850:P280
846:P271
842:P270
838:P264
834:P261
820:H335
816:H332
812:H319
808:H315
804:H312
800:H302
573:3.4
566:log
457:Odor
281:UNII
254:9215
180:8860
2233:doi
2214:doi
2169:doi
2117:PMC
2107:doi
2028:doi
1995:doi
1970:doi
1919:doi
1882:".
1840:doi
1733:doi
1471:.
1465:RNA
1461:DNA
1423:by
1342:to
1301:CoA
1235:In
1012:PEL
753:GHS
734:298
707:298
680:298
615:max
525:CCl
498:at
483:at
317:EPA
244:CID
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