99:
87:
172:
31:
151:), as well as foaming problems encountered in sewage treatment and contamination of drinking water. As such, BAS was phased out of most detergent products during the 1960s, being replaced with linear alkylbenzene sulfonates (LAS), which biodegrade much more rapidly. BAS is still important in certain agrochemical and industrial applications, where rapid
867:
Mackay, Donald; Di Guardo, Antonio; Paterson, Sally; Kicsi, Gabriel; Cowan, Christina E.; Kane, David M. (September 1996). "Assessment of chemical fate in the environment using evaluative, regional and local-scale models: Illustrative application to chlorobenzene and linear alkylbenzene sulfonates".
68:
and may be found in numerous personal-care products (soaps, shampoos, toothpaste etc.) and household-care products (laundry detergent, dishwashing liquid, spray cleaner etc.). They were introduced in the 1930s in the form of branched alkylbenzene sulfonates (BAS). However following environmental
69:
concerns these were replaced with linear alkylbenzene sulfonates (LAS) during the 1960s. Since then production has increased significantly from about one million tons in 1980, to around 3.5 million tons in 2016, making them most produced anionic surfactant after
270:
of 2.3 mg/liter for fish, about four times more toxic than the branched compound; however the linear compound biodegrades far more quickly, making it the safer choice over time. It is biodegraded rapidly under aerobic conditions with a
115:
Branched alkylbenzene sulfonates (BAS) were introduced in the early 1930s and saw significant growth from the late 1940s onwards, in early literature these synthetic detergents are often abbreviated as syndets. They were prepared by the
655:
Matheson, K. Lee; Matsoim, Ted P. (September 1983). "Effect of carbon chain and phenyl isomer distribution on use properties of linear alkylbenzene sulfonate: A comparison of 'high' and 'low' 2-phenyl LAS homologs".
2104:
247:, foaming etc.) are noticeably different. In particular the Krafft point of the high 2-phenyl product (i.e. the least branched isomer) remains below 0 °C up to 25% LAS whereas the low 2-phenyl
275:
of approximately 1–3 weeks; oxidative degradation initiates at the alkyl chain. Under anaerobic conditions it degrades very slowly or not at all, causing it to exist in high concentrations in
912:
2097:
239:
Under ideal conditions the cleaning power of BAS and LAS is very similar, however LAS performs slightly better in normal use conditions, due to it being less affected by
2070:
1836:
2090:
98:
2059:
718:
Drozd, Joseph C.; Gorman, Wilma (March 1988). "Formulating characteristics of high and low 2-phenyl linear alkylbenzene sulfonates in liquid detergents".
905:
373:
Scheibel, Jeffrey J. (17 December 2015). "The evolution of anionic surfactant technology to meet the requirements of the laundry detergent industry".
147:. BAS was widely blamed for the formation of large expanses of stable foam in areas of wastewater discharge such as lakes, rivers and coastal areas (
620:
Matheson, K. Lee (August 1985). "Detergency performance comparison between LAS and ABS using calcium sulfonate precipitation boundary diagrams".
1535:
3118:
898:
805:
3138:
1523:
3133:
753:
Sweeney, W. A.; Olson, A. C. (December 1964). "Performance of straight-chain alkylbenzene sulfonates (LAS) in heavy-duty detergents".
2052:
544:
2899:
2124:
2581:
604:
1775:
117:
279:, but this is not thought to be a cause for concern as it will rapidly degrade once returned to an oxygenated environment.
3113:
1822:
1531:
1519:
1382:
1377:
824:
Jensen, John (February 1999). "Fate and effects of linear alkylbenzene sulphonates (LAS) in the terrestrial environment".
3123:
3091:
2045:
1851:
171:
86:
2320:
2626:
2113:
438:
Hashim, M. A.; Kulandai, J.; Hassan, R. S. (24 April 2007). "Biodegradability of branched alkylbenzene sulphonates".
3049:
2401:
2396:
1693:
2884:
2431:
2270:
1527:
691:
Baumgartner, F. N. (June 1954). "Relation of
Molecular Structure to Detergency of Some Alkylbenzene Sulfonates".
243:. Within LAS itself the detergency of the various isomers are fairly similar, however their physical properties (
3009:
2924:
1697:
346:
Dee, Foster; Snell, Cornelia T. (August 1958). "50th ANNIVERSARY FEATURE—Fifty Years of
Detergent Progress".
1001:
975:
932:
2140:
2571:
2200:
1701:
1607:
1491:
1417:
1294:
970:
587:
Bipin V. Vora; Joseph A. Kocal; Paul T. Barger; Robert J. Schmidt; James A. Johnson (2003). "Alkylation".
61:
1481:
299:
Kurt
Kosswig,"Surfactants" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2005, Weinheim.
251:
is ~15 °C. This behavior is often exploited by producers to create either clear or cloudy products.
2330:
2325:
2315:
1981:
1911:
1868:
1515:
1486:
1436:
1342:
938:
2416:
2406:
1372:
1367:
492:
Sawyer, Clair N.; Ryckman, Devere W. (1957). "Anionic
Synthetic Detergents and Water Supply Problems".
220:
1506:
2979:
2754:
2726:
2716:
2411:
2335:
2310:
2009:
1709:
1254:
1220:
833:
501:
319:
Kocal, Joseph A; Vora, Bipin V; Imai, Tamotsu (November 2001). "Production of linear alkylbenzenes".
1187:
3128:
2750:
2556:
2456:
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1471:
1208:
1093:
184:
105:
65:
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1966:
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1951:
1857:
1109:
924:
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637:
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390:
264:
46:
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1916:
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2019:
1901:
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797:
30:
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540:
192:
2759:
2365:
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2024:
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1159:
219:
rather than the final product, perfectly linear addition products are not seen, in-line with
3019:
2739:
2621:
2551:
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2426:
2421:
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2190:
1727:
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417:
382:
355:
328:
300:
212:
152:
1881:
560:
Roberts, David W. (May 1998). "Sulfonation
Technology for Anionic Surfactant Manufacture".
537:
5th World
Conference on Detergents: Reinventing the industry - opportunities and challenges
17:
2696:
2591:
2471:
1617:
1461:
1432:
1302:
1164:
1154:
1116:
259:
The biodegradability of alkylbenzene sulfonates has been well studied, and is affected by
204:
129:
2082:
837:
505:
3044:
2964:
2834:
2691:
2546:
2511:
2170:
2004:
1906:
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2215:
2195:
2185:
1769:
1713:
1705:
1661:
1629:
1239:
1216:
244:
187:(LABs), which can themselves be prepared in several ways. In the most common route
965:
128:. Propylene tetramer being a broad term for a mixture of compounds formed by the
3054:
3024:
3004:
2954:
2829:
2824:
2809:
2779:
2606:
2561:
2521:
2516:
2466:
2461:
2446:
2285:
2245:
2150:
2014:
1931:
1797:
1739:
1731:
1621:
1476:
1397:
1387:
1334:
1284:
1183:
1168:
1140:
1011:
248:
200:
180:
125:
57:
50:
3034:
2994:
2939:
2929:
2869:
2854:
2839:
2819:
2794:
2789:
2769:
2764:
2721:
2711:
2676:
2651:
2631:
2596:
2575:
2531:
2506:
2290:
2255:
2240:
2235:
2204:
2165:
2145:
1971:
1946:
1926:
1921:
1896:
1801:
1789:
1761:
1679:
1653:
1649:
1635:
1625:
1596:
1584:
1580:
1551:
1546:
1501:
1440:
1422:
1407:
1326:
1310:
1306:
1288:
1272:
1224:
1212:
1198:
1135:
1058:
1016:
890:
408:
Hill, J. A. (22 October 2008). "The
Chemistry and Application of Detergents".
386:
240:
228:
156:
144:
140:
304:
2959:
2949:
2944:
2934:
2919:
2904:
2849:
2804:
2774:
2636:
2616:
2541:
2481:
2476:
2345:
2275:
2265:
2210:
1999:
1956:
1941:
1936:
1807:
1751:
1747:
1640:
1571:
1511:
1451:
1446:
1412:
1322:
1318:
1259:
1249:
1228:
1174:
1078:
1045:
272:
160:
53:
881:
853:
451:
143:
and better foaming. However, the highly branched tail made it difficult to
2864:
2844:
2814:
2686:
2646:
2496:
2486:
2360:
1994:
1780:
1765:
1755:
1743:
1612:
1602:
1588:
1402:
1268:
1244:
1203:
1068:
224:
148:
704:
521:
478:
359:
3074:
3059:
2989:
2451:
2175:
1891:
1723:
1392:
1338:
1276:
1179:
1083:
1029:
1021:
1006:
985:
980:
766:
731:
669:
633:
188:
133:
121:
573:
179:
Linear alkylbenzene sulfonates (LAS) are prepared industrially by the
1719:
1037:
993:
216:
124:
with 'propylene tetramer' (also called tetrapropylene) followed by
1352:
263:, in this case, branching. The salt of the linear material has an
29:
139:
Compared to traditional soaps, BAS offered superior tolerance to
1812:
1684:
1357:
70:
2086:
894:
1298:
191:
is alkylated by long chain monoalkenes (e.g. dodecene) using
2125:
465:
McKinney, Ross E. (1957). "Syndets and Waste
Disposal".
136:, its use gave a mixture of highly branched structures.
1823:
211:. The sulfonic acid is subsequently neutralized with
92:
An example of a branched alkylbenzene sulfonate (BAS)
2379:
2123:
1980:
1867:
1850:
1821:
948:
931:
175:
An example of a linear alkylbenzene sulfonate (LAS)
155:is of reduced importance. For instance, inhibiting
440:Journal of Chemical Technology & Biotechnology
64:, they are one of the oldest and most widely used
38:, prominent examples of alkylbenzene sulphonates
589:Kirk-Othmer Encyclopedia of Chemical Technology
223:. Thus, the alkylation of linear alkenes, even
410:Journal of the Society of Dyers and Colourists
2098:
1982:
1869:
906:
755:Journal of the American Oil Chemists' Society
720:Journal of the American Oil Chemists' Society
658:Journal of the American Oil Chemists' Society
622:Journal of the American Oil Chemists' Society
8:
597:10.1002/0471238961.0112112508011313.a01.pub2
2381:
231:, gives several isomers of phenyldodecane.
215:. The term "linear" refers to the starting
2432:Allopregnanedione (5α-dihydroprogesterone)
2105:
2091:
2083:
1864:
945:
913:
899:
891:
562:Organic Process Research & Development
539:( ed.). Champaign, Ill.: AOCS Press.
819:
817:
433:
431:
295:
293:
291:
2130:Tooltip Constitutive androstane receptor
2071:Ionotropic glutamate receptor modulators
950:
170:
792:Chemistry and technology of surfactants
287:
2885:Pregnanedione (5β-dihydroprogesterone)
2271:Pregnanedione (5β-dihydroprogesterone)
870:Environmental Toxicology and Chemistry
693:Industrial & Engineering Chemistry
348:Industrial & Engineering Chemistry
1828:Tooltip N-Methyl-D-aspartate receptor
375:Journal of Surfactants and Detergents
314:
312:
7:
1520:4-hydroxyquinoline-3-carboxylic acid
1378:4-Phenyl-4-formyl-N-methylpiperidine
60:alkylbenzene tail-group. Along with
1343:trichloroethane (methyl chloroform)
199:(and related derivatives) are then
1947:Pesampator (BIIB-104, PF-04958242)
514:10.1002/j.1551-8833.1957.tb16814.x
422:10.1111/j.1478-4408.1947.tb02430.x
25:
796:. Oxford: Blackwell Pub. p.
826:Science of the Total Environment
494:American Water Works Association
235:Structure property relationships
97:
85:
77:Branched alkylbenzene sulfonates
535:Cahn, AOCS]. Ed.: Arno (2003).
36:Sodium dodecylbenzenesulfonates
2437:Allopregnanolone (brexanolone)
167:Linear alkylbenzene sulfonates
1:
3092:Receptor/signaling modulators
3050:Tropanyl 3,5-dimethulbenzoate
2900:Pregnenolone 16α-carbonitrile
2046:Receptor/signaling modulators
1987:Tooltip Glycine transporter 2
1897:Bitopertin (RG1678/RO4917838)
1874:Tooltip Glycine transporter 1
846:10.1016/S0048-9697(98)00395-7
333:10.1016/S0926-860X(01)00808-0
2064:receptor positive modulators
467:Sewage and Industrial Wastes
321:Applied Catalysis A: General
195:as a catalyst. The purified
3119:Cleaning product components
2627:Dodecylbenzenesulfonic acid
2386:Tooltip Pregnane X receptor
2114:Xenobiotic-sensing receptor
27:Class of chemical compounds
18:Dodecylbenzenesulfonic acid
3155:
3139:Alkyl-substituted benzenes
1102:chlorobutanol (chloretone)
3134:Glycine receptor agonists
3083:
2037:
1217:pregnenolone (eltanolone)
1194:Glutamic acid (glutamate)
788:Farn, Richard J. (2006).
387:10.1007/s11743-004-0317-7
118:Friedel–Crafts alkylation
34:The general structure of
3010:Testosterone isocaproate
2925:Reverse triiodothyronine
2053:GABA receptor modulators
955:Tooltip Glycine receptor
305:10.1002/14356007.a25_747
2402:17α-Hydroxyprogesterone
2397:17α-Hydroxypregnenolone
1698:3β-androsterone sulfate
1694:3α-androsterone sulfate
43:Alkylbenzene sulfonates
1942:ORG-25935 (SCH-900435)
1131:Alkylbenzene sulfonate
882:10.1002/etc.5620150930
452:10.1002/jctb.280540302
176:
62:sodium laureth sulfate
39:
2141:6,7-Dimethylesculetin
2015:Opiranserin (VVZ-149)
1315:diethyl ether (ether)
174:
33:
3114:Organic sodium salts
2728:Hypericum perforatum
2717:Hetacillin potassium
1710:pregnenolone sulfate
1690:Neuroactive steroids
1648:constituents (e.g.,
1608:Cyanotriphenylborate
1569:Negative modulators:
1492:N,N-Dimethylmuscimol
1418:Cyanotriphenylborate
1255:Tetrahydrocannabinol
1221:pregnenolone acetate
1209:Neuroactive steroids
1182:constituents (e.g.,
1091:Positive modulators:
185:linear alkylbenzenes
66:synthetic detergents
3124:Anionic surfactants
2557:Cyproterone acetate
2457:Amlodipine besylate
1702:deoxycorticosterone
1482:N-Methylbicuculline
838:1999ScTEn.226...93J
705:10.1021/ie50534a061
506:1957JAWWA..49d.480S
360:10.1021/ie50584a005
106:Fremont, California
47:anionic surfactants
3030:Thonzonium bromide
2785:Methylprednisolone
2586:prasterone sulfate
1912:Glycyldodecylamide
1516:4-hydroxyquinoline
1487:N-Methylstrychnine
767:10.1007/BF02663964
732:10.1007/BF02663085
670:10.1007/BF02662436
634:10.1007/BF02541841
255:Environmental fate
221:Markovnikov's rule
177:
104:Extensive foaming
49:, consisting of a
40:
3101:
3100:
2735:Indinavir sulfate
2442:Alpha-Lipoic acid
2417:Δ-Androstenedione
2407:Δ-Androstenedione
2080:
2079:
2033:
2032:
2005:Ethanol (alcohol)
1907:Ethanol (alcohol)
1861:
1846:
1845:
1467:Isonipecotic acid
1373:2-Nitrostrychnine
1368:2-Aminostrychnine
1347:trichloroethylene
1149:sodium thiopental
1106:ethanol (alcohol)
1048:
1040:
1032:
1024:
996:
988:
942:
574:10.1021/op9700439
193:hydrogen fluoride
56:head-group and a
16:(Redirected from
3146:
3020:Thiamylal sodium
2755:γ-linolenic acid
2751:α-Linolenic acid
2749:Linolenic acid:
2740:Lasalocid sodium
2730:(St John's wort)
2622:Docusate calcium
2552:Cyclophosphamide
2427:Allopregnanediol
2412:Δ-Androstenediol
2387:
2383:
2341:Ethinylestradiol
2191:Cyclophosphamide
2131:
2127:
2107:
2100:
2093:
2084:
1988:
1984:
1875:
1871:
1865:
1855:
1829:
1825:
1728:dextromethorphan
1618:Dihydropyridines
1557:Thiocolchicoside
1507:Pseudostrychnine
1447:Gaboxadol (THIP)
1441:anandamide (AEA)
1433:Endocannabinoids
1165:Dihydropyridines
1125:trifluoroethanol
1121:trichloroethanol
1046:
1038:
1030:
1022:
994:
986:
956:
952:
946:
936:
922:Glycine receptor
915:
908:
901:
892:
886:
885:
876:(9): 1638–1648.
864:
858:
857:
821:
812:
811:
807:978-14051-2696-0
795:
785:
779:
778:
750:
744:
743:
715:
709:
708:
699:(6): 1349–1352.
688:
682:
681:
664:(9): 1693–1698.
652:
646:
645:
628:(8): 1269–1274.
617:
611:
610:
584:
578:
577:
557:
551:
550:
532:
526:
525:
489:
483:
482:
462:
456:
455:
435:
426:
425:
405:
399:
398:
370:
364:
363:
343:
337:
336:
327:(1–2): 295–301.
316:
307:
297:
213:sodium hydroxide
159:deposition from
153:biodegradability
101:
89:
21:
3154:
3153:
3149:
3148:
3147:
3145:
3144:
3143:
3104:
3103:
3102:
3097:
3079:
2980:Suberoylanilide
2697:Fluorometholone
2592:Dibunate sodium
2472:Aurothioglucose
2385:
2375:
2311:3,17β-Estradiol
2129:
2119:
2111:
2081:
2076:
2063:
2029:
1986:
1976:
1887:ALX-5407 (NFPS)
1873:
1854:
1842:
1827:
1817:
1577:Benzodiazepines
1462:Isobutyric acid
1303:chloral hydrate
1155:Chlormethiazole
1117:tribromoethanol
1113:-butanol (2M2P)
954:
935:
927:
919:
889:
866:
865:
861:
832:(2–3): 93–111.
823:
822:
815:
808:
787:
786:
782:
761:(12): 815–822.
752:
751:
747:
717:
716:
712:
690:
689:
685:
654:
653:
649:
619:
618:
614:
607:
586:
585:
581:
559:
558:
554:
547:
534:
533:
529:
491:
490:
486:
464:
463:
459:
437:
436:
429:
416:(10): 319–322.
407:
406:
402:
372:
371:
367:
345:
344:
340:
318:
317:
310:
298:
289:
285:
268:
257:
237:
205:sulfur trioxide
197:dodecylbenzenes
169:
130:oligomerization
113:
112:
111:
110:
109:
102:
94:
93:
90:
79:
45:are a class of
28:
23:
22:
15:
12:
11:
5:
3152:
3150:
3142:
3141:
3136:
3131:
3126:
3121:
3116:
3106:
3105:
3099:
3098:
3096:
3095:
3088:
3084:
3081:
3080:
3078:
3077:
3072:
3063:
3062:
3057:
3052:
3047:
3045:Troleandomycin
3042:
3037:
3032:
3027:
3022:
3017:
3012:
3007:
3002:
2997:
2992:
2987:
2982:
2977:
2972:
2967:
2965:Spironolactone
2962:
2957:
2952:
2947:
2942:
2937:
2932:
2927:
2922:
2917:
2912:
2907:
2902:
2897:
2892:
2887:
2882:
2877:
2872:
2867:
2862:
2857:
2852:
2847:
2842:
2837:
2835:Norelgestromin
2832:
2827:
2822:
2817:
2812:
2807:
2802:
2797:
2792:
2787:
2782:
2777:
2772:
2767:
2762:
2757:
2747:
2742:
2737:
2732:
2724:
2719:
2714:
2709:
2704:
2699:
2694:
2692:Flucloxacillin
2689:
2684:
2679:
2674:
2669:
2664:
2659:
2654:
2649:
2644:
2639:
2634:
2629:
2624:
2619:
2614:
2609:
2604:
2599:
2594:
2589:
2579:
2569:
2564:
2559:
2554:
2549:
2547:Corticosterone
2544:
2539:
2534:
2529:
2524:
2519:
2514:
2512:Chlorpromazine
2509:
2504:
2499:
2494:
2489:
2484:
2479:
2474:
2469:
2464:
2459:
2454:
2449:
2444:
2439:
2434:
2429:
2424:
2419:
2414:
2409:
2404:
2399:
2390:
2388:
2377:
2376:
2374:
2373:
2368:
2363:
2358:
2353:
2348:
2343:
2338:
2333:
2331:17-Androstanol
2328:
2326:3β-Androstanol
2323:
2321:3α-Androstenol
2318:
2316:3α-Androstanol
2313:
2304:
2303:
2298:
2293:
2288:
2283:
2278:
2273:
2268:
2263:
2258:
2253:
2248:
2243:
2238:
2233:
2228:
2223:
2218:
2213:
2208:
2198:
2193:
2188:
2183:
2178:
2173:
2171:Chlorpromazine
2168:
2163:
2158:
2153:
2148:
2143:
2134:
2132:
2121:
2120:
2112:
2110:
2109:
2102:
2095:
2087:
2078:
2077:
2075:
2074:
2067:
2061:
2056:
2049:
2042:
2038:
2035:
2034:
2031:
2030:
2028:
2027:
2022:
2017:
2012:
2007:
2002:
1997:
1991:
1989:
1978:
1977:
1975:
1974:
1969:
1964:
1959:
1954:
1949:
1944:
1939:
1934:
1929:
1924:
1919:
1914:
1909:
1904:
1899:
1894:
1889:
1884:
1878:
1876:
1862:
1848:
1847:
1844:
1843:
1841:
1840:
1832:
1830:
1819:
1818:
1816:
1815:
1810:
1805:
1783:
1778:
1773:
1759:
1717:
1687:
1682:
1677:
1643:
1638:
1633:
1615:
1610:
1605:
1600:
1574:
1565:
1564:
1559:
1554:
1549:
1544:
1539:
1509:
1504:
1499:
1497:Nipecotic acid
1494:
1489:
1484:
1479:
1474:
1469:
1464:
1459:
1454:
1449:
1444:
1430:
1425:
1420:
1415:
1410:
1405:
1400:
1395:
1390:
1385:
1380:
1375:
1370:
1361:
1360:
1355:
1350:
1331:methoxyflurane
1292:
1262:
1257:
1252:
1247:
1242:
1237:
1232:
1206:
1201:
1196:
1191:
1188:ginsenoside-Rf
1177:
1172:
1162:
1157:
1152:
1138:
1133:
1128:
1087:
1086:
1081:
1076:
1071:
1066:
1064:Picolinic acid
1061:
1056:
1051:
1043:
1035:
1027:
1019:
1014:
1009:
1004:
999:
991:
983:
978:
973:
968:
959:
957:
943:
929:
928:
920:
918:
917:
910:
903:
895:
888:
887:
859:
813:
806:
780:
745:
726:(3): 398–404.
710:
683:
647:
612:
605:
579:
568:(3): 194–202.
552:
545:
527:
500:(4): 480–490.
484:
473:(6): 654–666.
457:
446:(3): 207–214.
427:
400:
381:(4): 319–328.
365:
354:(8): 48A–51A.
338:
308:
286:
284:
281:
266:
256:
253:
236:
233:
168:
165:
103:
96:
95:
91:
84:
83:
82:
81:
80:
78:
75:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3151:
3140:
3137:
3135:
3132:
3130:
3127:
3125:
3122:
3120:
3117:
3115:
3112:
3111:
3109:
3094:
3093:
3089:
3086:
3085:
3082:
3076:
3073:
3071:
3068:
3065:
3064:
3061:
3058:
3056:
3053:
3051:
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:
2985:Sulfisoxazole
2983:
2981:
2978:
2976:
2973:
2971:
2968:
2966:
2963:
2961:
2958:
2956:
2953:
2951:
2948:
2946:
2943:
2941:
2938:
2936:
2933:
2931:
2928:
2926:
2923:
2921:
2918:
2916:
2913:
2911:
2908:
2906:
2903:
2901:
2898:
2896:
2893:
2891:
2888:
2886:
2883:
2881:
2878:
2876:
2873:
2871:
2868:
2866:
2863:
2861:
2860:Phenobarbital
2858:
2856:
2853:
2851:
2848:
2846:
2843:
2841:
2838:
2836:
2833:
2831:
2828:
2826:
2823:
2821:
2818:
2816:
2813:
2811:
2808:
2806:
2803:
2801:
2798:
2796:
2793:
2791:
2788:
2786:
2783:
2781:
2778:
2776:
2773:
2771:
2768:
2766:
2763:
2761:
2758:
2756:
2752:
2748:
2746:
2745:Levothyroxine
2743:
2741:
2738:
2736:
2733:
2731:
2729:
2725:
2723:
2720:
2718:
2715:
2713:
2710:
2708:
2707:Guggulsterone
2705:
2703:
2700:
2698:
2695:
2693:
2690:
2688:
2685:
2683:
2680:
2678:
2675:
2673:
2670:
2668:
2665:
2663:
2660:
2658:
2655:
2653:
2650:
2648:
2645:
2643:
2640:
2638:
2635:
2633:
2630:
2628:
2625:
2623:
2620:
2618:
2615:
2613:
2610:
2608:
2605:
2603:
2602:Dicloxacillin
2600:
2598:
2595:
2593:
2590:
2587:
2583:
2580:
2577:
2573:
2570:
2568:
2567:Dexamethasone
2565:
2563:
2560:
2558:
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2518:
2515:
2513:
2510:
2508:
2505:
2503:
2502:Cephaloridine
2500:
2498:
2495:
2493:
2490:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2468:
2465:
2463:
2460:
2458:
2455:
2453:
2450:
2448:
2445:
2443:
2440:
2438:
2435:
2433:
2430:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2398:
2395:
2392:
2391:
2389:
2384:
2378:
2372:
2369:
2367:
2364:
2362:
2359:
2357:
2354:
2352:
2349:
2347:
2344:
2342:
2339:
2337:
2334:
2332:
2329:
2327:
2324:
2322:
2319:
2317:
2314:
2312:
2309:
2306:
2305:
2302:
2301:Valproic acid
2299:
2297:
2294:
2292:
2289:
2287:
2284:
2282:
2279:
2277:
2274:
2272:
2269:
2267:
2264:
2262:
2261:Phenobarbital
2259:
2257:
2254:
2252:
2249:
2247:
2244:
2242:
2239:
2237:
2234:
2232:
2229:
2227:
2224:
2222:
2219:
2217:
2214:
2212:
2209:
2206:
2202:
2199:
2197:
2194:
2192:
2189:
2187:
2184:
2182:
2179:
2177:
2174:
2172:
2169:
2167:
2164:
2162:
2161:Carbamazepine
2159:
2157:
2154:
2152:
2149:
2147:
2144:
2142:
2139:
2136:
2135:
2133:
2128:
2122:
2118:
2115:
2108:
2103:
2101:
2096:
2094:
2089:
2088:
2085:
2073:
2072:
2068:
2066:
2065:
2057:
2055:
2054:
2050:
2048:
2047:
2043:
2040:
2039:
2036:
2026:
2023:
2021:
2018:
2016:
2013:
2011:
2008:
2006:
2003:
2001:
1998:
1996:
1993:
1992:
1990:
1985:
1979:
1973:
1970:
1968:
1965:
1963:
1960:
1958:
1955:
1953:
1950:
1948:
1945:
1943:
1940:
1938:
1935:
1933:
1930:
1928:
1925:
1923:
1920:
1918:
1915:
1913:
1910:
1908:
1905:
1903:
1900:
1898:
1895:
1893:
1890:
1888:
1885:
1883:
1880:
1879:
1877:
1872:
1866:
1863:
1859:
1853:
1849:
1838:
1834:
1833:
1831:
1826:
1820:
1814:
1811:
1809:
1806:
1803:
1799:
1795:
1791:
1787:
1784:
1782:
1779:
1777:
1774:
1771:
1767:
1763:
1760:
1757:
1753:
1749:
1745:
1741:
1737:
1736:levomethadone
1733:
1729:
1725:
1721:
1718:
1715:
1711:
1707:
1703:
1699:
1695:
1691:
1688:
1686:
1683:
1681:
1678:
1675:
1671:
1667:
1663:
1659:
1655:
1651:
1647:
1644:
1642:
1639:
1637:
1634:
1631:
1627:
1623:
1619:
1616:
1614:
1611:
1609:
1606:
1604:
1601:
1598:
1594:
1593:flunitrazepam
1590:
1586:
1582:
1578:
1575:
1573:
1570:
1567:
1566:
1563:
1560:
1558:
1555:
1553:
1550:
1548:
1545:
1543:
1540:
1537:
1533:
1529:
1525:
1521:
1517:
1513:
1510:
1508:
1505:
1503:
1500:
1498:
1495:
1493:
1490:
1488:
1485:
1483:
1480:
1478:
1475:
1473:
1472:Isostrychnine
1470:
1468:
1465:
1463:
1460:
1458:
1455:
1453:
1450:
1448:
1445:
1442:
1438:
1434:
1431:
1429:
1426:
1424:
1421:
1419:
1416:
1414:
1411:
1409:
1406:
1404:
1401:
1399:
1396:
1394:
1391:
1389:
1386:
1384:
1381:
1379:
1376:
1374:
1371:
1369:
1366:
1363:
1362:
1359:
1356:
1354:
1351:
1348:
1344:
1340:
1336:
1332:
1328:
1324:
1320:
1316:
1312:
1308:
1304:
1300:
1296:
1293:
1290:
1286:
1282:
1278:
1274:
1270:
1266:
1263:
1261:
1258:
1256:
1253:
1251:
1248:
1246:
1243:
1241:
1238:
1236:
1235:Nitrous oxide
1233:
1230:
1226:
1222:
1218:
1214:
1210:
1207:
1205:
1202:
1200:
1197:
1195:
1192:
1189:
1185:
1181:
1178:
1176:
1173:
1170:
1166:
1163:
1161:
1158:
1156:
1153:
1150:
1146:
1145:pentobarbital
1142:
1139:
1137:
1134:
1132:
1129:
1126:
1122:
1118:
1114:
1112:
1107:
1103:
1099:
1095:
1092:
1089:
1088:
1085:
1082:
1080:
1077:
1075:
1074:Quisqualamine
1072:
1070:
1067:
1065:
1062:
1060:
1057:
1055:
1052:
1050:
1044:
1042:
1036:
1034:
1028:
1026:
1020:
1018:
1015:
1013:
1010:
1008:
1005:
1003:
1000:
998:
992:
990:
984:
982:
979:
977:
974:
972:
969:
967:
964:
961:
960:
958:
953:
947:
944:
940:
934:
930:
926:
923:
916:
911:
909:
904:
902:
897:
896:
893:
883:
879:
875:
871:
863:
860:
855:
851:
847:
843:
839:
835:
831:
827:
820:
818:
814:
809:
803:
799:
794:
793:
784:
781:
776:
772:
768:
764:
760:
756:
749:
746:
741:
737:
733:
729:
725:
721:
714:
711:
706:
702:
698:
694:
687:
684:
679:
675:
671:
667:
663:
659:
651:
648:
643:
639:
635:
631:
627:
623:
616:
613:
608:
602:
598:
594:
590:
583:
580:
575:
571:
567:
563:
556:
553:
548:
546:1-893997-40-5
542:
538:
531:
528:
523:
519:
515:
511:
507:
503:
499:
495:
488:
485:
480:
476:
472:
468:
461:
458:
453:
449:
445:
441:
434:
432:
428:
423:
419:
415:
411:
404:
401:
396:
392:
388:
384:
380:
376:
369:
366:
361:
357:
353:
349:
342:
339:
334:
330:
326:
322:
315:
313:
309:
306:
302:
296:
294:
292:
288:
282:
280:
278:
277:sewage sludge
274:
269:
262:
261:isomerization
254:
252:
250:
246:
242:
234:
232:
230:
226:
222:
218:
214:
210:
209:sulfonic acid
206:
202:
198:
194:
190:
186:
182:
173:
166:
164:
162:
158:
154:
150:
146:
142:
137:
135:
131:
127:
123:
119:
107:
100:
88:
76:
74:
72:
67:
63:
59:
55:
52:
48:
44:
37:
32:
19:
3090:
3070:Ketoconazole
3067:Antagonists:
3066:
3040:Troglitazone
3015:Tetracycline
2970:Spiroxatrine
2915:Quingestrone
2910:Progesterone
2895:Pregnenolone
2890:Pregnanolone
2880:Pregnanediol
2875:Prednisolone
2800:Mifepristone
2727:
2702:Griseofulvin
2682:Fenbendazole
2667:Famprofazone
2662:Erythromycin
2657:Epothilone B
2642:Eburnamonine
2537:Clotrimazole
2527:Clofenvinfos
2462:Antimycotics
2393:
2356:Okadaic acid
2308:Antagonists:
2307:
2296:Troglitazone
2231:Mifepristone
2226:Methoxychlor
2221:Griseofulvin
2216:Ellagic acid
2196:Cypermethrin
2186:Clotrimazole
2137:
2069:
2058:
2051:
2044:
1770:picrotoxinin
1714:progesterone
1706:DHEA sulfate
1674:ginkgolide M
1670:ginkgolide J
1666:ginkgolide C
1662:ginkgolide B
1658:ginkgolide A
1630:nitrendipine
1568:
1365:Antagonists:
1364:
1240:Penicillin G
1184:ginsenosides
1141:Barbiturates
1130:
1110:
1090:
971:β-ABA (BABA)
962:
873:
869:
862:
829:
825:
791:
783:
758:
754:
748:
723:
719:
713:
696:
692:
686:
661:
657:
650:
625:
621:
615:
588:
582:
565:
561:
555:
536:
530:
497:
493:
487:
470:
466:
460:
443:
439:
413:
409:
403:
378:
374:
368:
351:
347:
341:
324:
320:
258:
245:Krafft point
238:
207:to give the
178:
138:
114:
42:
41:
35:
3055:Zafirlukast
3025:Thiothixene
3005:Terconazole
2955:Simvastatin
2830:Nisoldipine
2825:Nilvadipine
2810:Nicardipine
2780:Metacycline
2607:Dimercaprol
2562:Demecolcine
2522:Clindamycin
2517:Ciglitazone
2467:Artemisinin
2447:Ambrisentan
2351:Nigramide J
2286:Telmisartan
2246:Nicardipine
2156:Benfuracarb
2151:Artemisinin
1967:SSR-504,734
1962:SSR-103,800
1952:PF-03463275
1932:Mardepodect
1852:Transporter
1798:tropisetron
1740:levorphanol
1732:dextrorphan
1654:ginkgolides
1622:nicardipine
1477:Laudanosine
1398:Cacotheline
1388:Bicuculline
1335:sevoflurane
1285:tropisetron
1169:nicardipine
1012:Hypotaurine
249:cloud point
181:sulfonation
126:sulfonation
58:hydrophobic
51:hydrophilic
3129:Sulfonates
3108:Categories
3035:Tianeptine
3000:Tenylidone
2995:Tacrolimus
2940:Rimexolone
2930:Rifampicin
2870:Plicamycin
2855:Paclitaxel
2840:Omeprazole
2820:Nifedipine
2795:Mevastatin
2790:Metyrapone
2770:Lovastatin
2765:Loratadine
2722:Hyperforin
2712:Haloprogin
2677:Felodipine
2652:Enzacamene
2632:Dronabinol
2597:Diclazuril
2576:prasterone
2532:Chloroxine
2507:Cephradine
2477:Bile acids
2291:Tolnaftate
2256:Permethrin
2241:Nevirapine
2236:Nefazodone
2205:prasterone
2166:Carvedilol
2146:Amiodarone
2117:modulators
1972:Tilapertin
1927:LY-2365109
1922:Iclepertin
1917:GSK1018921
1802:zatosetron
1790:bemesetron
1762:Picrotoxin
1680:Imipramine
1650:bilobalide
1636:Furosemide
1626:nifedipine
1597:flurazepam
1585:clonazepam
1581:bromazepam
1552:Strychnine
1547:Sinomenine
1512:Quinolines
1502:Pitrazepin
1423:Dendrobine
1408:Colchicine
1327:isoflurane
1311:desflurane
1307:chloroform
1289:zatosetron
1273:bemesetron
1225:minaxolone
1213:alfaxolone
1199:Ivermectin
1136:Anandamide
1059:Milacemide
1049:-Threonine
1017:Ivermectin
925:modulators
606:0471238961
283:References
241:hard water
229:1-dodecene
201:sulfonated
157:asphaltene
145:biodegrade
141:hard water
2960:Sirolimus
2950:Ritonavir
2945:Riodipine
2935:Rifaximin
2920:Reserpine
2905:Proadifen
2850:Oxatomide
2805:Nafcillin
2775:Meclizine
2637:Droxidopa
2617:Docetaxel
2542:Colforsin
2492:Bumecaine
2482:Bithionol
2394:Agonists:
2371:T-0901317
2346:Meclizine
2276:Reserpine
2266:Phenytoin
2251:Octicizer
2211:Efavirenz
2138:Agonists:
2020:ORG-25543
2000:Amoxapine
1957:Sarcosine
1937:ORG-24598
1902:CP-802079
1808:Verapamil
1794:LY-278584
1786:Tropeines
1752:pethidine
1748:oripavine
1641:Genistein
1572:Amiloride
1452:Gelsemine
1428:Diaboline
1413:Colubrine
1323:halothane
1319:enflurane
1295:Volatiles
1281:LY-278584
1265:Tropeines
1260:Triclofos
1250:Tamoxifen
1229:ORG-20599
1175:Etomidate
1098:brometone
1079:Sarcosine
1054:MDL-27531
966:β-Alanine
963:Agonists:
273:half-life
225:1-alkenes
161:crude oil
149:sea foams
54:sulfonate
3087:See also
2975:SR-12813
2865:Piperine
2845:Orlistat
2815:Nicotine
2687:Fentanyl
2672:Febantel
2647:Ecopipam
2612:Dinaline
2497:Cafestol
2487:Bosentan
2361:PK-11195
2041:See also
1995:ALX-1393
1858:blockers
1839:instead.
1781:Riluzole
1766:picrotin
1756:thebaine
1744:morphine
1613:Daidzein
1603:Corymine
1589:diazepam
1524:5,7-CIQA
1457:iso-THAZ
1403:Caffeine
1269:atropine
1245:Propofol
1204:Ketamine
1094:Alcohols
1069:Propofol
1033:-Proline
1025:-Alanine
989:-Alanine
933:Receptor
854:10085562
775:98586085
740:93127857
678:97659271
642:98677989
522:41254845
479:25033358
395:93889318
227:such as
3075:Sesamin
3060:Zeranol
2990:Suramin
2760:LOE-908
2452:AMI-193
2366:S-07662
2281:TCPOBOP
2176:Chrysin
2025:VVZ-368
1892:ASP2535
1788:(e.g.,
1764:(i.e.,
1724:codeine
1722:(e.g.,
1720:Opioids
1692:(e.g.,
1656:(e.g.,
1620:(e.g.,
1579:(e.g.,
1542:RU-5135
1514:(e.g.,
1435:(e.g.,
1393:Brucine
1339:toluene
1301:(e.g.,
1277:cocaine
1267:(e.g.,
1211:(e.g.,
1186:(e.g.,
1180:Ginseng
1167:(e.g.,
1160:D12-116
1143:(e.g.,
1096:(e.g.,
1084:Taurine
1041:-Serine
1007:Glycine
997:-Serine
981:Caesium
939:ligands
834:Bibcode
502:Bibcode
217:alkenes
189:benzene
134:propene
122:benzene
2582:DHEA-S
2422:AA-861
1646:Ginkgo
1536:7-TFQA
1383:αEMBTL
976:β-AIBA
852:
804:
773:
738:
676:
640:
603:
543:
520:
477:
393:
108:- 1972
2181:CITCO
2010:NAGly
1983:GlyT2
1882:ACPPB
1870:GlyT1
1824:NMDAR
1562:Tutin
1532:7-TFQ
1528:7-CIQ
1353:Xenon
1299:gases
771:S2CID
736:S2CID
674:S2CID
638:S2CID
518:JSTOR
475:JSTOR
391:S2CID
203:with
71:soaps
2753:and
2572:DHEA
2336:AITC
2201:DHEA
2060:GABA
1837:here
1835:See
1813:Zinc
1776:PMBA
1768:and
1685:NBQX
1437:2-AG
1358:Zinc
1111:tert
1002:GABA
951:GlyR
850:PMID
802:ISBN
601:ISBN
541:ISBN
2382:PXR
2126:CAR
878:doi
842:doi
830:226
763:doi
728:doi
701:doi
666:doi
630:doi
593:doi
570:doi
510:doi
448:doi
418:doi
383:doi
356:doi
329:doi
325:221
301:doi
183:of
132:of
120:of
3110::
1800:,
1796:,
1792:,
1754:,
1750:,
1746:,
1742:,
1738:,
1734:,
1730:,
1726:,
1712:,
1708:,
1704:,
1700:,
1696:,
1676:))
1672:,
1668:,
1664:,
1660:,
1652:,
1628:,
1624:,
1595:,
1591:,
1587:,
1583:,
1534:,
1530:,
1526:,
1522:,
1518:,
1439:,
1345:,
1341:,
1337:,
1333:,
1329:,
1325:,
1321:,
1317:,
1313:,
1309:,
1305:,
1287:,
1283:,
1279:,
1275:,
1271:,
1227:,
1223:,
1219:,
1215:,
1190:))
1147:,
1123:,
1119:,
1115:,
1108:,
1104:,
1100:,
874:15
872:.
848:.
840:.
828:.
816:^
800:.
798:96
769:.
759:41
757:.
734:.
724:65
722:.
697:46
695:.
672:.
662:60
660:.
636:.
626:62
624:.
599:.
591:.
564:.
516:.
508:.
498:49
496:.
471:29
469:.
444:54
442:.
430:^
414:63
412:.
389:.
377:.
352:50
350:.
323:.
311:^
290:^
267:50
265:LD
163:.
73:.
2588:)
2584:(
2578:)
2574:(
2207:)
2203:(
2106:e
2099:t
2092:v
2062:A
1860:)
1856:(
1804:)
1772:)
1758:)
1716:)
1632:)
1599:)
1538:)
1443:)
1349:)
1297:/
1291:)
1231:)
1171:)
1151:)
1127:)
1047:L
1039:L
1031:L
1023:L
995:D
987:D
941:)
937:(
914:e
907:t
900:v
884:.
880::
856:.
844::
836::
810:.
777:.
765::
742:.
730::
707:.
703::
680:.
668::
644:.
632::
609:.
595::
576:.
572::
566:2
549:.
524:.
512::
504::
481:.
454:.
450::
424:.
420::
397:.
385::
379:7
362:.
358::
335:.
331::
303::
20:)
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