1129:
641:
611:
450:
427:
3284:
47:
3298:
38:
896:
2139:
Mean theobromine and caffeine levels respectively, were 0.695 mg/g and 0.071 mg/g in cocoa cereals; 1.47 mg/g and 0.152 mg/g in chocolate bakery products; 1.95 mg/g and 0.138 mg/g in chocolate toppings; 2.66 mg/g and 0.208 mg/g in cocoa beverages; 0.621 mg/g and 0.032 mg/g in chocolate ice creams;
1286:
for a smaller dog and 400 g (14 oz), or around nine 44-gram (1.55 oz) small milk chocolate bars, for an average-sized dog. The concentration of theobromine in dark chocolates (about 10 g/kg (0.16 oz/lb)) is up to 10 times that of milk chocolate (1 to 5 g/kg (0.016 to
1294:
of theobromine for dogs is 100–200 mg/kg (0.0016–0.0032 oz/lb); therefore, a 10 kg (22 lb) dog would need to consume a minimum of 200 g (7.1 oz) of the most theobromine-rich (5 g/kg (0.080 oz/lb)) dark chocolate, or a maximum of 1 kg (2.2 lb) (of
922:
There are approximately 60 milligrams (1 grain) of theobromine in 28 grams (1 oz) of milk chocolate, while the same amount of dark chocolate contains about 200 milligrams (3 grains). Cocoa beans naturally contain approximately 1% theobromine.
1182:
Unlike caffeine, which is highly water-soluble, theobromine is only slightly water-soluble and is more fat soluble, and thus peaks more slowly in the blood. While caffeine peaks after only 30 minutes, theobromine requires 2–3 hours to peak.
2140:
0.226 mg/g and 0.011 mg/g in chocolate milks; 74.8 mg/serving and 6.5 mg/serving in chocolate puddings.... Theobromine and caffeine levels in carob products ranged from 0–0.504 mg/g and 0-0.067 mg/g, respectively.
3989:
2577:
1352:
Drouillard DD, Vesell ES, Dvorchik BH (March 1978). "Studies on theobromine disposition in normal subjects. Alterations induced by dietary abstention from or exposure to methylxanthines".
6697:
2320:
Mumford GK, Benowitz NL, Evans SM, Kaminski BJ, Preston KL, Sannerud CA, et al. (1 December 1996). "Absorption rate of methylxanthines following capsules, cola and chocolate".
1874:
103:
4761:
1919:
Kuribara H, Tadokoro S (April 1992). "Behavioral effects of cocoa and its main active compound theobromine: evaluation by ambulatory activity and discrete avoidance in mice".
4626:
3982:
1295:
theobromine-rich milk chocolate), to have a 50% chance of receiving a lethal dose. However, even 40 g (1.4 oz) of milk chocolate may induce vomiting and diarrhea.
3197:
1116:. Cleavage of the ribose and N-methylation yields 7-methylxanthosine. 7-Methylxanthosine in turn is the precursor to theobromine, which in turn is the precursor to
4611:
3128:
2459:
3975:
4651:
4621:
533:
6722:
3165:
2205:
6690:
1255:
At doses of 0.8–1.5 g/day (50–100 g cocoa), sweating, trembling and severe headaches were noted, with limited mood effects found at 250 mg/day.
6770:
4754:
3140:
2516:
7551:
5934:
1950:
4865:
3145:
1946:
2619:
7571:
6683:
6295:
6217:
6154:
4705:
4490:
4155:
4109:
4007:
3933:
3407:
3170:
3160:
2413:
2085:
1832:
1790:
1612:
1546:
1310:
and death. If caught early on, theobromine poisoning is treatable. Although not common, the effects of theobromine poisoning can be fatal.
1302:. Complications include digestive issues, dehydration, excitability, and a slow heart rate. Later stages of theobromine poisoning include
1660:
1247:
effect of theobromine is seen only at amounts much higher than what people normally would consume in a typical diet including chocolate.
4747:
3339:
2674:
1618:
2566:
1878:
7380:
5117:
5097:
4646:
3266:
1585:
1400:"Comparative pharmacokinetics of caffeine and its primary demethylated metabolites paraxanthine, theobromine and theophylline in man"
7566:
4641:
4636:
3659:
2169:
553:
7561:
3757:
3261:
3155:
3106:
1719:
7581:
6270:
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4508:
3919:
3836:
3805:
3786:
3187:
3024:
1282:
theobromine (found in chocolate) more slowly can succumb to theobromine poisoning from as little as 50 g (1.8 oz) of
220:
143:
2455:
4661:
4631:
3233:
1225:. The amount of theobromine found in chocolate is small enough that chocolate can, in general, be safely consumed by humans.
519:
5819:
5389:
5799:
5959:
5949:
5924:
4601:
1796:
705:
7531:
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4870:
3376:
2917:
2539:
326:
6074:
7461:
7357:
6706:
5929:
5829:
4722:
3950:
3192:
1319:
1244:
1191:
619:
406:
5919:
4846:
5556:
1287:
0.080 oz/lb)), meaning dark chocolate is far more toxic to dogs per unit weight or volume than milk chocolate.
919:
only contains trace amounts of theobromine. There are usually higher concentrations in dark than in milk chocolate.
6137:
5974:
5774:
5374:
5027:
4273:
3999:
3645:
3134:
2429:
1263:
3150:
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4221:
4033:
3791:
3572:
3484:
3019:
2209:
1782:
6029:
5804:
5561:
2029:"More than just caffeine: psychopharmacology of methylxanthine interactions with plant-derived phytochemicals"
1298:
The same risk is reported for cats as well, although cats are less likely to ingest sweet food, as cats lack
1144:
Even without dietary intake, theobromine may occur in the body as it is a product of the human metabolism of
6570:
6520:
5939:
5369:
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4889:
4781:
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3332:
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89:
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1218:
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1203:
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395:
5349:
7214:
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5673:
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4356:
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3253:
3243:
2999:
2861:
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1459:
1324:
1168:
828:
186:
77:
4814:
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6119:
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5914:
5721:
5514:
5399:
4924:
4860:
4341:
3533:
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3218:
3065:
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1240:
1236:
1071:
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636:
422:
241:
7511:
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6143:
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5002:
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4773:
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4331:
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3538:
3325:
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2826:
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2345:
2179:
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1377:
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1232:
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7313:
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5287:
4939:
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4145:
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1571:
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5651:
5551:
5439:
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7209:
7111:
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6838:
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6059:
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6034:
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5434:
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5187:
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5102:
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4949:
4944:
3873:
3847:
3180:
3096:
3050:
2994:
2979:
2969:
2929:
2924:
2841:
2609:
2494:
2409:
2386:
2337:
2302:
2253:
2165:
2081:
2050:
2009:
1928:
1828:
1786:
1640:
1608:
1581:
1552:
1542:
1429:
1369:
1229:
1222:
1001:
974:
942:
756:
375:
7349:
6951:
6197:
6009:
5237:
5232:
1602:
1213:
Theobromine has no significant stimulant effect on the human central nervous system. It is a
6339:
6328:
6069:
6064:
5964:
5894:
5616:
5611:
5606:
5601:
5596:
5541:
5534:
5504:
5459:
5419:
5227:
5222:
5067:
5017:
4374:
3749:
3548:
3518:
3101:
2984:
2836:
2703:
2614:
2581:
2376:
2329:
2292:
2284:
2243:
2157:
2130:
2040:
1999:
1989:
1921:
Arukoru Kenkyu to
Yakubutsu Izon = Japanese Journal of Alcohol Studies & Drug Dependence
1756:
1711:
1652:
1534:
1467:
1419:
1411:
1361:
1037:
861:
857:
808:
686:
462:
159:
6004:
5969:
5683:
5646:
5576:
5394:
4909:
2152:
Ashihara H, Yokota T, Crozier A (2013). "Biosynthesis and catabolism of purine alkaloids".
2119:
Craig WJ, Nguyen TT (1984). "Caffeine and theobromine levels in cocoa and carob products".
335:
7420:
7229:
6285:
5693:
5688:
5661:
5636:
5207:
5147:
4770:
4318:
4241:
4020:
3795:
3753:
3380:
3248:
3223:
2989:
2959:
2891:
2886:
2719:
2191:
931:
730:
315:
167:
1463:
640:
610:
449:
426:
250:
7415:
7189:
7169:
7141:
6913:
6780:
6372:
6275:
6235:
5197:
5152:
4716:
4532:
4265:
4089:
3944:
3842:
3702:
3513:
3431:
3366:
3029:
2974:
2949:
2944:
2934:
2907:
2881:
2866:
2856:
2766:
2297:
2272:
2161:
2134:
2004:
1977:
1424:
1415:
1399:
1283:
1214:
1081:
966:
765:
699:
2248:
2231:
1278:
Theobromine is the reason chocolate is poisonous to dogs. Dogs and other animals that
7545:
7496:
7456:
7365:
7149:
6362:
5519:
5277:
5212:
5042:
4437:
4432:
4407:
4308:
4278:
4246:
4231:
3884:
3581:
3523:
3461:
3399:
3389:
3113:
3055:
3014:
2912:
2876:
2771:
2288:
1818:
1450:
Ford KA, Ebisuzaki Y, Boyle PD (1998). "Methylxanthines. II. Anhydrous
Theobromine".
1329:
739:
675:
599:
438:
175:
2062:
1381:
1128:
7491:
7430:
7395:
7385:
7295:
7051:
6991:
6833:
6645:
6585:
6482:
6467:
6462:
6441:
6389:
6367:
6280:
6250:
6207:
5748:
5282:
5192:
5137:
5127:
4570:
4442:
4427:
4402:
4251:
4236:
4135:
4011:
3727:
3696:
3626:
3553:
3352:
3118:
3034:
2816:
2791:
2713:
2708:
2349:
1839:(note: the book incorrectly states that the name "theobroma" is derived from Latin)
1157:
1153:
1137:
1133:
1027:
958:
916:
804:
796:
769:
126:
121:
116:
111:
46:
776:. It is a white or colourless solid, but commercial samples can appear yellowish.
1494:
1186:
The primary mechanism of action for theobromine inside the body is inhibition of
275:
7471:
7466:
7390:
7318:
7285:
7199:
7131:
7091:
7071:
7026:
6986:
6971:
6903:
6898:
6818:
6808:
6750:
6732:
6457:
6414:
6357:
6352:
6308:
6265:
6230:
6114:
6019:
5621:
5312:
5292:
5257:
5252:
5202:
5072:
5052:
4982:
4967:
4798:
4545:
4521:
4480:
4470:
4422:
4412:
4293:
4288:
4177:
4126:
4099:
4094:
3903:
3892:
3869:
3677:
3596:
3586:
3441:
3123:
3075:
2756:
2045:
2028:
1538:
6675:
1820:
The World of
Caffeine: The Science and Culture of the World's Most Popular Drug
7481:
7323:
7249:
7224:
7154:
7056:
7001:
6961:
6926:
6921:
6893:
6888:
6868:
6823:
6798:
6477:
6436:
6409:
6394:
6384:
6240:
6202:
6109:
5839:
5631:
5546:
5424:
5317:
5302:
5162:
5122:
5107:
5037:
5007:
4934:
4585:
4580:
4516:
4475:
4452:
4397:
4379:
4283:
4226:
4187:
4182:
4172:
4167:
4140:
4131:
4121:
4085:
4075:
4070:
4065:
4060:
4050:
4045:
3821:
3816:
3811:
3733:
3712:
3621:
3606:
3601:
3543:
3466:
3456:
3446:
3426:
3416:
2801:
2796:
2776:
2751:
2746:
2736:
2693:
1774:
1471:
1279:
1149:
1113:
1109:
995:
991:
908:
900:
735:
495:
306:
4739:
2482:
2273:"Cytochrome P450 isoform selectivity in human hepatic theobromine metabolism"
2232:"A study of the metabolism of theobromine, theophylline, and caffeine in man"
1760:
1715:
1682:
1656:
7501:
7435:
7400:
7333:
7267:
7239:
7219:
7194:
7016:
6996:
6878:
6858:
6853:
6828:
6788:
6727:
6565:
6515:
6431:
6399:
6255:
6182:
6172:
6084:
6024:
6014:
5834:
5789:
5586:
5359:
5267:
5262:
5247:
5132:
5082:
5057:
4929:
4879:
4834:
4575:
4565:
4540:
4203:
4080:
4055:
3826:
3707:
3667:
3616:
3611:
3591:
3528:
3451:
3421:
2683:
2381:
2364:
1994:
1824:
1299:
1267:
1259:
1187:
912:
844:
747:
743:
738:(330 mg/L) with a bitter taste. In industry, theobromine is used as an
199:
29:
2498:
2390:
2306:
2257:
2054:
2013:
1556:
561:
InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
2341:
2333:
2208:. The Pharmacogenetics and Pharmacogenomics Knowledge Base. Archived from
1932:
1533:. Handbook of Experimental Pharmacology. Vol. 200. pp. 201–234.
1433:
1365:
926:
Plant species and components with substantial amounts of theobromine are:
7516:
7451:
7410:
7370:
7244:
7159:
7096:
7046:
7006:
6931:
6793:
6765:
6540:
6535:
6426:
6099:
5656:
5177:
5157:
5062:
4899:
4498:
4389:
4024:
3888:
3771:
3766:
3672:
3631:
3508:
3498:
3489:
3476:
3436:
3348:
3060:
2811:
2806:
2761:
2741:
2406:
Goodman & Gilman's the pharmacological basis of therapeutics, 10th ed
1976:
Crown PL, Emerson TE, Gu J, Hurst WJ, Pauketat TR, Ward T (August 2012).
1373:
1303:
1164:
1145:
1117:
983:
824:
800:
792:
773:
725:
286:
2433:
1779:
The
American Heritage Dictionary of the English Language, Fourth Edition
1228:
Compared with caffeine, theobromine is weaker in both its inhibition of
895:
811:, each of which differ in the number or placement of the methyl groups.
295:
37:
7204:
7179:
7106:
7011:
6946:
6883:
6649:
6620:
6590:
6560:
6510:
6260:
6245:
6104:
5854:
5733:
5711:
5509:
5047:
4819:
4802:
3865:
3070:
3009:
1307:
987:
880:
819:
Theobromine was first discovered in 1841 in cacao beans by the chemist
665:
261:
22:
7234:
7126:
6843:
6615:
6610:
6322:
5529:
5524:
5489:
5217:
4686:
4211:
4003:
1179:. The elimination half life of theobromine is between 6 and 8 hours.
1176:
1172:
1132:
Caffeine is metabolized in the liver into three primary metabolites:
789:
785:
386:
204:
1744:
1699:
1604:
Plant
Intoxicants: A Classic Text on the Use of Mind-Altering Plants
698:
Except where otherwise noted, data are given for materials in their
1853:
860:
nitrogen-containing compounds. That name in turn is made up of the
355:
7343:
7305:
6079:
5641:
5581:
4681:
4215:
3317:
3004:
1091:
1008:
894:
849:
761:
518:
509:
366:
179:
172:
96:
1452:
899:
A chocolate bar and molten chocolate. Chocolate is made from the
7405:
7277:
7259:
6760:
6742:
6714:
5738:
5449:
5142:
5112:
3776:
2033:
Progress in Neuro-Psychopharmacology & Biological
Psychiatry
936:
346:
6679:
4743:
3971:
3321:
2656:
2641:"HEALTH WATCH: How to Avoid a Canine Chocolate Catastrophe!".
869:
751:
6296:
6218:
6155:
1529:
Smit HJ (2011). "Theobromine and the
Pharmacology of Cocoa".
2652:
2458:. Toxnet, US National Library of Medicine. 1 December 2017.
624:
411:
1899:
1497:. PubChem, US National Library of Medicine. 27 August 2022
1949:. Dr. Duke's Phytochemical and Ethnobotanical Databases,
1398:
Lelo A, Birkett DJ, Robson RA, Miners JO (August 1986).
1266:
muscle in a way that permits stomach acids to enter the
2154:
New Light on
Alkaloid Biosynthesis and Future Prospects
578:
982:
Theobromine can also be found in trace amounts in the
1900:"USDA Nutrient database, entries for dark chocolate"
1875:"USDA Nutrient database, entries for milk chocolate"
7444:
7356:
7342:
7304:
7276:
7258:
7140:
6912:
6779:
6741:
6713:
6500:
6450:
6338:
6321:
6294:
6216:
6153:
6136:
5747:
5326:
5311:
4828:
4797:
4780:
4627:
Fluticasone furoate/umeclidinium bromide/vilanterol
4594:
4558:
4530:
4507:
4489:
4461:
4451:
4388:
4365:
4317:
4264:
4196:
4154:
4108:
4032:
4019:
3912:
3858:
3785:
3748:
3686:
3658:
3644:
3567:
3475:
3398:
3375:
3360:
3211:
3089:
3043:
2900:
2825:
2729:
2692:
2080:. New York: Routledge. pp. 137, 175, 178–180.
750:, as well as in a number of other foods, including
507:
494:
461:
456:
437:
405:
385:
365:
345:
325:
305:
285:
260:
240:
211:
198:
185:
166:
158:
142:
137:
102:
88:
76:
58:
53:
4866:4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil
2513:"Chocolate – Toxicology – Merck Veterinary Manual"
1700:"Umwandlung des Xanthin in Theobromin und Caffein"
1607:. Inner Traditions / Bear & Co. pp. 67–.
1262:in some people because theobromine may affect the
1007:The mean theobromine concentrations in cocoa and
784:Theobromine is a flat molecule, a derivative of
274:
4612:Beclometasone/formoterol/glycopyrronium bromide
249:
5333:
2369:The Journal of Allergy and Clinical Immunology
1745:"Über Caffein, Theobromin, Xanthin und Guanin"
1704:Berichte der Deutschen Chemischen Gesellschaft
1163:In the liver, theobromine is metabolized into
1108:Theobromine is a purine alkaloid derived from
6691:
6301:Tooltip Plasma membrane monoamine transporter
6223:Tooltip Equilibrative nucleoside transporters
6160:Tooltip Concentrative nucleoside transporters
4755:
4652:Indacaterol/glycopyrronium bromide/mometasone
3983:
3333:
2668:
907:Theobromine is the primary alkaloid found in
734:(cacao plant). Theobromine is slightly water-
8:
4622:Budesonide/glycopyrronium bromide/formoterol
2483:"Chocolate/cocoa and human health: a review"
1850:"AmerMed cocoa extract with 10% theobromine"
28:
2230:Cornish HH, Christman AA (September 1957).
1978:"Ritual Black Drink consumption at Cahokia"
1393:
1391:
1347:
1345:
903:, which is a natural source of theobromine.
879:Despite its name, the compound contains no
6698:
6684:
6676:
6335:
6150:
5323:
4794:
4762:
4748:
4740:
4458:
4029:
3990:
3976:
3968:
3655:
3372:
3340:
3326:
3318:
2675:
2661:
2653:
639:
609:
587:
448:
425:
314:
2380:
2322:European Journal of Clinical Pharmacology
2296:
2247:
2044:
2003:
1993:
1489:
1487:
1485:
1483:
1481:
1423:
334:
6340:
2645:. Belfast, Northern Ireland. 2005-03-01.
2604:
2602:
2277:British Journal of Clinical Pharmacology
1645:Liebigs Annalen der Chemie und Pharmacie
1404:British Journal of Clinical Pharmacology
1127:
1013:
1951:United States Department of Agriculture
1341:
635:
558:
538:
421:
294:
225:
4491:Arachidonate 5-lipoxygenase inhibitors
3146:European Cocoa and Chocolate Directive
2610:"The Poisonous Chemistry of Chocolate"
2408:. New York: McGraw-Hill. p. 745.
2365:"Cyclic nucleotide phosphodiesterases"
2187:
2177:
2027:Schuster J, Mitchell ES (March 2019).
1947:"Theobromine content in plant sources"
1445:
1443:
1354:Clinical Pharmacology and Therapeutics
1152:in the liver into 12% theobromine, 4%
876:("food"), meaning "food of the gods".
680:351 °C (664 °F; 624 K)
600:
439:
27:
3161:International Cocoa Quarantine Centre
1524:
1522:
1520:
1518:
1516:
1514:
1512:
394:
374:
7:
4687:Theophylline/ephedrine/phenobarbital
3129:Côte d'Ivoire–Ghana Cocoa Initiative
2622:from the original on 8 February 2017
2456:"3,7-Dimethylxanthine (Theobromine)"
1258:Also, chocolate may be a factor for
207:(10% unchanged, rest as metabolites)
125:
115:
3198:Production in São Tomé and Príncipe
2487:The Netherlands Journal of Medicine
2462:from the original on 7 October 2018
2404:Hardman J, Limbird L, eds. (2001).
2236:The Journal of Biological Chemistry
852:of the cacao tree, with the suffix
354:
265:
5722:Tetramethylpyrazine (ligustrazine)
4682:Theophylline/ephedrine/hydroxyzine
4647:Indacaterol/glycopyrronium bromide
2162:10.1016/B978-0-12-408061-4.00004-3
2156:. Vol. 68. pp. 111–138.
2135:10.1111/j.1365-2621.1984.tb13737.x
1416:10.1111/j.1365-2125.1986.tb05246.x
16:Bitter alkaloid of the cacao plant
14:
4672:Salbutamol (albuterol)/budesonide
4642:Glycopyrronium bromide/formoterol
4637:Fluticasone propionate/salmeterol
2519:from the original on 12 July 2014
2271:Gates S, Miners JO (March 1999).
1953:. 6 February 2019. Archived from
1749:Justus Liebigs Annalen der Chemie
4509:Thromboxane receptor antagonists
3296:
3283:
3282:
3156:International Cocoa Organization
3107:Child labour in cocoa production
2540:"Chocolate Toxicosis in Animals"
2289:10.1046/j.1365-2125.1999.00890.x
1221:. It is not currently used as a
823:. Synthesis of theobromine from
479:
473:
45:
36:
4692:Umeclidinium bromide/vilanterol
3920:Hydrochlorothiazide/triamterene
3787:Vasopressin receptor inhibitors
3297:
1799:from the original on 2016-03-03
1725:from the original on 2019-05-05
1663:from the original on 2016-06-10
1621:from the original on 2019-09-18
702:(at 25 °C , 100 kPa).
566:Key:YAPQBXQYLJRXSA-UHFFFAOYSA-N
7552:Adenosine receptor antagonists
5338:Tooltip Adenosine triphosphate
4662:Ipratropium bromide/salbutamol
4632:Fluticasone furoate/vilanterol
4247:Orciprenaline (metaproterenol)
2078:The Cultural History of Plants
1817:Bennett AW, Bealer BK (2002).
1684:Essays in Historical Chemistry
1136:(84%), theobromine (12%), and
827:was first reported in 1882 by
485:
467:
1:
7532:Receptor/signaling modulators
6666:Receptor/signaling modulators
5028:8-Phenyl-1,3-dipropylxanthine
4602:Aclidinium bromide/formoterol
4090:Levosalbutamol (levalbuterol)
3171:Philippine chocolate industry
2432:. DrugBank.ca. Archived from
2249:10.1016/S0021-9258(18)70714-X
1570:Baer DM, Pinkston EM (1997).
856:given to alkaloids and other
788:. It is also classified as a
7572:Phosphodiesterase inhibitors
6707:Phosphodiesterase inhibitors
4237:Isoprenaline (isoproterenol)
2363:Essayan DM (November 2001).
2076:Prance G, Nesbitt M (2004).
1982:Proc. Natl. Acad. Sci. U.S.A
1245:phosphodiesterase inhibitory
1190:receptors. Its effect as a
1171:. Important enzymes include
795:. Related compounds include
4212:+theophylline/phenobarbital
4000:obstructive airway diseases
2046:10.1016/j.pnpbp.2018.09.005
1601:von Bibra E, Ott J (1995).
1539:10.1007/978-3-642-13443-2_7
1320:Health effects of chocolate
1192:phosphodiesterase inhibitor
1022:Mean theobromine per 100 g
7600:
6168:6-Hydroxy-7-methoxyflavone
4875:-ethylcarboxamidoadenosine
3135:The Dark Side of Chocolate
1576:. Westview Press. p.
1201:
1055:Chocolate bakery products
883:, which is based on Greek
457:Chemical and physical data
68:3,7-dihydro-3,7-dimethyl-1
20:
7525:
6659:
4700:
3928:
3277:
3188:Production in Ivory Coast
1852:. AmerMed. Archived from
1472:10.1107/S0108270198009469
1217:and causes relaxation of
696:
651:
593:
574:
549:
529:
216:
44:
35:
7567:IARC Group 3 carcinogens
6345:Tooltip Xanthine oxidase
4607:Beclometasone/formoterol
4216:theophylline/hydroxyzine
4156:Ultra-long-acting β
3166:Manufacturers (vertical)
2567:"Chocolate intoxication"
1783:Houghton Mifflin Company
1761:10.1002/jlac.18822150302
1716:10.1002/cber.18820150194
1687:. The MacMillan Company.
1657:10.1002/jlac.18420410117
1573:Environment and Behavior
1194:is thought to be small.
151:In general: Unscheduled.
21:Not to be confused with
7562:Components of chocolate
5935:UDP-N-acetylglucosamine
4463:Leukotriene antagonists
3688:Aldosterone antagonists
3025:Chocolate-covered foods
2544:Merck Veterinary Manual
2382:10.1067/mai.2001.119555
2122:Journal of Food Science
1995:10.1073/pnas.1208404109
1639:Woskresensky A (1842).
7582:Human drug metabolites
7376:Choline theophyllinate
6379:Cinnamomum osmophloeum
5088:Choline theophyllinate
4677:Theophylline/ephedrine
4657:Indacaterol/mometasone
4418:Choline theophyllinate
4337:Glycopyrronium bromide
4299:Fluticasone propionate
4086:Salbutamol (albuterol)
3203:World Cocoa Foundation
2546:. Merck & Co., Inc
2481:Latif R (March 2013).
1698:Fischer, Emil (1882).
1219:vascular smooth muscle
1167:and subsequently into
1141:
904:
742:and precursor to some
541:Cn1cnc2c1c(=O)c(=O)n2C
6794:Amrinone (inamrinone)
5622:Opiranserin (VVZ-149)
4963:-Cyclopentyladenosine
4667:Mometasone/formoterol
4617:Budesonide/formoterol
4367:Mast cell stabilizers
4324:muscarinic antagonist
3193:Production in Nigeria
3151:Harkin–Engel Protocol
2940:Chocolate chip cookie
2334:10.1007/s002280050205
1641:"Über das Theobromin"
1366:10.1002/cpt1978233296
1300:sweet taste receptors
1204:Theobromine poisoning
1131:
898:
6421:Pistacia integerrima
5727:Ligusticum wallichii
5705:Ligusticum wallichii
5033:8-Phenyltheophylline
5023:8-Chlorotheophylline
4973:Neladenoson dalanate
4595:Combination products
4357:Umeclidinium bromide
3913:Combination products
3718:Potassium canrenoate
3141:Environmental impact
3000:Cioccolato di Modica
2618:. 14 February 2013.
1325:History of chocolate
1264:esophageal sphincter
1072:Chocolate ice creams
829:Hermann Emil Fischer
66:3,7-dimethylxanthine
4342:Ipratropium bromide
4034:Short-acting β
3880:mercurial diuretics
3534:Hydrochlorothiazide
3504:Bendroflumethiazide
3258:Military chocolate
3219:Chocolate addiction
3176:Production in Ghana
2965:Chocolate ice cream
2782:Tetramethylpyrazine
2436:on 13 November 2018
1464:1998AcCrC..54.1980F
1241:adenosine receptors
1047:Chocolate toppings
1015:
997:Ilex paraguariensis
951:Ilex paraguariensis
724:, is the principal
687:Solubility in water
590:
32:
4727:Never to phase III
4352:Tiotropium bromide
4347:Oxitropium bromide
4332:Aclidinium bromide
4110:Long-acting β
3955:Never to phase III
3559:Trichlormethiazide
3539:Hydroflumethiazide
3229:Chocolate fountain
2955:Chocolate crackles
2587:on 8 February 2017
2565:Gwaltney-Brant S.
2538:Gwaltney-Brant S.
2102:"FoodData Central"
1743:Fischer E (1882).
1681:Thorpe TE (1902).
1292:median lethal dose
1233:phosphodiesterases
1142:
1097:0.00–50.4 mg
1014:
905:
848:, the name of the
706:Infobox references
588:
7539:
7538:
7210:Nitrosoprodenafil
6673:
6672:
6496:
6495:
6473:Mycophenolic acid
6332:
6317:
6316:
6147:
6132:
6131:
6128:
6127:
5699:Angelica sinensis
4791:
4737:
4736:
4554:
4553:
4260:
4259:
3965:
3964:
3848:Lithium carbonate
3750:Osmotic diuretics
3744:
3743:
3646:Potassium-sparing
3640:
3639:
3315:
3314:
3239:Chocolate museums
3234:Legal definitions
3181:Ghana Cocoa Board
3097:Organic chocolate
3051:Aerated chocolate
2995:Chocolate truffle
2980:Chocolate pudding
2970:Chocolate liqueur
2930:Chocolate brownie
2925:Chocolate biscuit
2415:978-0-07-135469-1
2087:978-0-415-92746-8
1834:978-0-415-92723-9
1792:978-0-395-71146-0
1614:978-0-89281-498-5
1548:978-3-642-13442-5
1458:(12): 1980–1983.
1230:cyclic nucleotide
1223:prescription drug
1101:
1100:
975:Camellia sinensis
946:– seed coat
943:Theobroma bicolor
935:– seed and
760:), some American
757:Camellia sinensis
746:. It is found in
714:Chemical compound
712:
711:
620:CompTox Dashboard
586:
585:
520:Interactive image
407:CompTox Dashboard
232:-purine-2,6-dione
72:-purine-2,6-dione
7589:
7557:Bitter compounds
6700:
6693:
6686:
6677:
6346:
6342:
6336:
6326:
6302:
6298:
6224:
6220:
6161:
6157:
6151:
6141:
5535:Rheum officinale
5339:
5335:
5324:
5068:Caffeine citrate
5018:7-Methylxanthine
4851:-methyladenosine
4795:
4785:
4764:
4757:
4750:
4741:
4459:
4319:Anticholinergics
4030:
3992:
3985:
3978:
3969:
3656:
3549:Methyclothiazide
3519:Cyclopenthiazide
3373:
3342:
3335:
3328:
3319:
3305:
3300:
3299:
3291:
3286:
3285:
3102:Fair trade cocoa
2985:Chocolate spread
2829:
2704:Chocolate liquor
2696:
2686:
2677:
2670:
2663:
2654:
2647:
2646:
2638:
2632:
2631:
2629:
2627:
2606:
2597:
2596:
2594:
2592:
2586:
2580:. Archived from
2571:
2562:
2556:
2555:
2553:
2551:
2535:
2529:
2528:
2526:
2524:
2509:
2503:
2502:
2478:
2472:
2471:
2469:
2467:
2452:
2446:
2445:
2443:
2441:
2426:
2420:
2419:
2401:
2395:
2394:
2384:
2360:
2354:
2353:
2328:(3–4): 319–325.
2317:
2311:
2310:
2300:
2268:
2262:
2261:
2251:
2227:
2221:
2220:
2218:
2217:
2202:
2196:
2195:
2189:
2185:
2183:
2175:
2149:
2143:
2142:
2116:
2110:
2109:
2106:fdc.nal.usda.gov
2098:
2092:
2091:
2073:
2067:
2066:
2048:
2024:
2018:
2017:
2007:
1997:
1973:
1967:
1966:
1964:
1962:
1943:
1937:
1936:
1916:
1910:
1909:
1907:
1906:
1896:
1890:
1889:
1887:
1886:
1877:. Archived from
1871:
1865:
1864:
1862:
1861:
1846:
1840:
1838:
1814:
1808:
1807:
1805:
1804:
1771:
1765:
1764:
1740:
1734:
1733:
1731:
1730:
1724:
1695:
1689:
1688:
1678:
1672:
1671:
1669:
1668:
1636:
1630:
1629:
1627:
1626:
1598:
1592:
1591:
1567:
1561:
1560:
1526:
1507:
1506:
1504:
1502:
1491:
1476:
1475:
1447:
1438:
1437:
1427:
1395:
1386:
1385:
1349:
1243:. The potential
1016:
842:is derived from
809:7-methylxanthine
720:, also known as
644:
643:
628:
626:
613:
602:
591:
582:
581:
522:
502:
487:
481:
475:
469:
452:
441:
430:
429:
415:
413:
398:
378:
358:
338:
318:
298:
278:
268:
267:
253:
190:
129:
119:
49:
40:
33:
31:
7599:
7598:
7592:
7591:
7590:
7588:
7587:
7586:
7542:
7541:
7540:
7535:
7521:
7440:
7421:Propentofylline
7352:
7338:
7300:
7272:
7254:
7230:Sulfoaildenafil
7215:Norcarbodenafil
7136:
6908:
6775:
6737:
6709:
6704:
6674:
6669:
6655:
6492:
6446:
6344:
6325:
6313:
6300:
6290:
6286:Propentofylline
6236:Benzodiazepines
6222:
6212:
6159:
6140:
6124:
5743:
5694:Sodium ferulate
5662:Radix puerariae
5637:Phenolphthalein
5337:
5330:
5315:
5307:
5208:Propentofylline
5148:Isovaleric acid
4832:
4824:
4784:
4776:
4771:Purine receptor
4768:
4738:
4733:
4732:
4717:Clinical trials
4696:
4590:
4550:
4533:PDE4 inhibitors
4526:
4503:
4485:
4447:
4384:
4361:
4322:
4313:
4266:Glucocorticoids
4256:
4242:Methylephedrine
4192:
4159:
4150:
4113:
4104:
4037:
4015:
3996:
3966:
3961:
3960:
3945:Clinical trials
3924:
3908:
3854:
3789:
3781:
3740:
3682:
3636:
3563:
3490:Calcium-sparing
3488:
3471:
3394:
3364:
3356:
3346:
3316:
3311:
3310:
3303:
3289:
3273:
3249:Cocoa smuggling
3224:Chocolate bloom
3207:
3085:
3039:
2990:Chocolate syrup
2960:Chocolate gravy
2950:Chocolate coins
2896:
2827:
2821:
2725:
2720:Theobroma cacao
2694:
2688:
2684:
2681:
2651:
2650:
2643:The News Letter
2640:
2639:
2635:
2625:
2623:
2608:
2607:
2600:
2590:
2588:
2584:
2569:
2564:
2563:
2559:
2549:
2547:
2537:
2536:
2532:
2522:
2520:
2511:
2510:
2506:
2480:
2479:
2475:
2465:
2463:
2454:
2453:
2449:
2439:
2437:
2428:
2427:
2423:
2416:
2403:
2402:
2398:
2362:
2361:
2357:
2319:
2318:
2314:
2270:
2269:
2265:
2229:
2228:
2224:
2215:
2213:
2204:
2203:
2199:
2186:
2176:
2172:
2151:
2150:
2146:
2118:
2117:
2113:
2100:
2099:
2095:
2088:
2075:
2074:
2070:
2026:
2025:
2021:
1988:(35): 13944–9.
1975:
1974:
1970:
1960:
1958:
1945:
1944:
1940:
1918:
1917:
1913:
1904:
1902:
1898:
1897:
1893:
1884:
1882:
1873:
1872:
1868:
1859:
1857:
1848:
1847:
1843:
1835:
1816:
1815:
1811:
1802:
1800:
1793:
1773:
1772:
1768:
1742:
1741:
1737:
1728:
1726:
1722:
1697:
1696:
1692:
1680:
1679:
1675:
1666:
1664:
1638:
1637:
1633:
1624:
1622:
1615:
1600:
1599:
1595:
1588:
1569:
1568:
1564:
1549:
1531:Methylxanthines
1528:
1527:
1510:
1500:
1498:
1493:
1492:
1479:
1449:
1448:
1441:
1397:
1396:
1389:
1351:
1350:
1343:
1338:
1316:
1276:
1253:
1211:
1206:
1200:
1169:methyluric acid
1126:
1106:
1082:Chocolate milks
1038:Cocoa beverages
932:Theobroma cacao
893:
837:
821:A. Woskresensky
817:
782:
731:Theobroma cacao
715:
708:
703:
692:330 mg/L)
689:
647:
629:
622:
577:
575:
570:
567:
562:
557:
556:
545:
542:
537:
536:
525:
500:
490:
484:
478:
472:
433:
409:
401:
381:
361:
341:
321:
301:
281:
264:
256:
236:
233:
224:
223:
188:
160:Pharmacokinetic
154:
133:
91:
79:
67:
65:
63:
26:
17:
12:
11:
5:
7597:
7596:
7593:
7585:
7584:
7579:
7574:
7569:
7564:
7559:
7554:
7544:
7543:
7537:
7536:
7526:
7523:
7522:
7520:
7519:
7514:
7509:
7504:
7499:
7494:
7489:
7484:
7479:
7474:
7469:
7464:
7459:
7454:
7448:
7446:
7442:
7441:
7439:
7438:
7433:
7428:
7423:
7418:
7416:Pentoxifylline
7413:
7408:
7403:
7398:
7393:
7388:
7383:
7378:
7373:
7368:
7362:
7360:
7354:
7353:
7348:
7346:
7340:
7339:
7337:
7336:
7331:
7326:
7321:
7316:
7310:
7308:
7302:
7301:
7299:
7298:
7293:
7288:
7282:
7280:
7274:
7273:
7271:
7270:
7264:
7262:
7256:
7255:
7253:
7252:
7247:
7242:
7237:
7232:
7227:
7222:
7217:
7212:
7207:
7202:
7197:
7192:
7190:Homosildenafil
7187:
7182:
7177:
7172:
7170:Benzamidenafil
7167:
7162:
7157:
7152:
7146:
7144:
7138:
7137:
7135:
7134:
7129:
7124:
7119:
7114:
7109:
7104:
7099:
7094:
7089:
7084:
7079:
7074:
7069:
7064:
7059:
7054:
7049:
7044:
7039:
7034:
7029:
7024:
7019:
7014:
7009:
7004:
6999:
6994:
6989:
6984:
6979:
6974:
6969:
6964:
6959:
6954:
6949:
6944:
6939:
6934:
6929:
6924:
6918:
6916:
6910:
6909:
6907:
6906:
6901:
6896:
6891:
6886:
6881:
6876:
6871:
6866:
6861:
6856:
6851:
6846:
6841:
6836:
6831:
6826:
6821:
6816:
6811:
6806:
6801:
6796:
6791:
6785:
6783:
6777:
6776:
6774:
6773:
6768:
6763:
6758:
6753:
6747:
6745:
6739:
6738:
6736:
6735:
6730:
6725:
6719:
6717:
6711:
6710:
6705:
6703:
6702:
6695:
6688:
6680:
6671:
6670:
6660:
6657:
6656:
6654:
6653:
6639:
6638:
6633:
6628:
6623:
6618:
6613:
6608:
6603:
6598:
6593:
6588:
6583:
6578:
6573:
6568:
6563:
6558:
6553:
6548:
6543:
6538:
6533:
6528:
6523:
6518:
6513:
6504:
6502:
6498:
6497:
6494:
6493:
6491:
6490:
6485:
6480:
6475:
6470:
6465:
6460:
6454:
6452:
6448:
6447:
6445:
6444:
6439:
6434:
6429:
6424:
6417:
6412:
6407:
6402:
6397:
6392:
6387:
6382:
6375:
6373:Cinnamaldehyde
6370:
6365:
6360:
6355:
6349:
6347:
6333:
6319:
6318:
6315:
6314:
6312:
6311:
6305:
6303:
6292:
6291:
6289:
6288:
6283:
6278:
6276:Pentoxifylline
6273:
6268:
6263:
6258:
6253:
6248:
6243:
6238:
6233:
6227:
6225:
6214:
6213:
6211:
6210:
6205:
6200:
6195:
6190:
6185:
6180:
6175:
6170:
6164:
6162:
6148:
6134:
6133:
6130:
6129:
6126:
6125:
6123:
6122:
6117:
6112:
6107:
6102:
6097:
6092:
6087:
6082:
6077:
6072:
6067:
6062:
6057:
6052:
6047:
6042:
6037:
6032:
6027:
6022:
6017:
6012:
6007:
6002:
5997:
5992:
5987:
5982:
5977:
5972:
5967:
5962:
5953:
5952:
5947:
5942:
5937:
5932:
5927:
5922:
5917:
5912:
5907:
5902:
5897:
5892:
5887:
5882:
5877:
5872:
5867:
5862:
5857:
5852:
5847:
5842:
5837:
5832:
5827:
5822:
5817:
5812:
5807:
5802:
5797:
5792:
5787:
5782:
5777:
5772:
5767:
5762:
5753:
5751:
5745:
5744:
5742:
5741:
5736:
5731:
5719:
5714:
5709:
5691:
5686:
5681:
5676:
5671:
5666:
5654:
5649:
5644:
5639:
5634:
5629:
5624:
5619:
5614:
5609:
5604:
5599:
5594:
5589:
5584:
5579:
5574:
5569:
5564:
5559:
5554:
5549:
5544:
5539:
5527:
5522:
5517:
5512:
5507:
5502:
5497:
5492:
5487:
5482:
5477:
5472:
5467:
5462:
5453:
5452:
5447:
5442:
5437:
5432:
5427:
5422:
5417:
5412:
5407:
5402:
5397:
5392:
5387:
5382:
5377:
5372:
5367:
5362:
5357:
5352:
5343:
5341:
5321:
5309:
5308:
5306:
5305:
5300:
5295:
5290:
5285:
5280:
5275:
5270:
5265:
5260:
5255:
5250:
5245:
5240:
5235:
5230:
5225:
5220:
5215:
5210:
5205:
5200:
5198:Pentoxifylline
5195:
5190:
5185:
5180:
5175:
5170:
5165:
5160:
5155:
5153:Istradefylline
5150:
5145:
5140:
5135:
5130:
5125:
5120:
5115:
5110:
5105:
5100:
5095:
5090:
5085:
5080:
5075:
5070:
5065:
5060:
5055:
5050:
5045:
5040:
5035:
5030:
5025:
5020:
5011:
5010:
5005:
5000:
4995:
4990:
4985:
4980:
4975:
4970:
4965:
4957:
4952:
4947:
4942:
4937:
4932:
4927:
4922:
4917:
4912:
4907:
4902:
4897:
4892:
4887:
4882:
4877:
4868:
4863:
4858:
4853:
4847:2-(1-Hexynyl)-
4840:
4838:
4826:
4825:
4823:
4822:
4817:
4815:8-Aminoadenine
4808:
4806:
4792:
4778:
4777:
4769:
4767:
4766:
4759:
4752:
4744:
4735:
4734:
4731:
4730:
4729:
4728:
4725:
4714:
4708:
4702:
4701:
4698:
4697:
4695:
4694:
4689:
4684:
4679:
4674:
4669:
4664:
4659:
4654:
4649:
4644:
4639:
4634:
4629:
4624:
4619:
4614:
4609:
4604:
4598:
4596:
4592:
4591:
4589:
4588:
4583:
4578:
4573:
4568:
4562:
4560:
4559:Others/unknown
4556:
4555:
4552:
4551:
4549:
4548:
4543:
4537:
4535:
4528:
4527:
4525:
4524:
4519:
4513:
4511:
4505:
4504:
4502:
4501:
4495:
4493:
4487:
4486:
4484:
4483:
4478:
4473:
4467:
4465:
4456:
4449:
4448:
4446:
4445:
4440:
4435:
4430:
4425:
4420:
4415:
4410:
4405:
4400:
4394:
4392:
4386:
4385:
4383:
4382:
4377:
4371:
4369:
4363:
4362:
4360:
4359:
4354:
4349:
4344:
4339:
4334:
4328:
4326:
4315:
4314:
4312:
4311:
4306:
4301:
4296:
4291:
4286:
4281:
4276:
4270:
4268:
4262:
4261:
4258:
4257:
4255:
4254:
4249:
4244:
4239:
4234:
4229:
4224:
4219:
4200:
4198:
4194:
4193:
4191:
4190:
4185:
4180:
4175:
4170:
4164:
4162:
4157:
4152:
4151:
4149:
4148:
4143:
4138:
4129:
4124:
4118:
4116:
4111:
4106:
4105:
4103:
4102:
4097:
4092:
4083:
4078:
4073:
4068:
4063:
4058:
4053:
4048:
4042:
4040:
4035:
4027:
4017:
4016:
3997:
3995:
3994:
3987:
3980:
3972:
3963:
3962:
3959:
3958:
3957:
3956:
3953:
3942:
3936:
3930:
3929:
3926:
3925:
3923:
3922:
3916:
3914:
3910:
3909:
3907:
3906:
3901:
3896:
3876:
3862:
3860:
3856:
3855:
3853:
3852:
3851:
3850:
3845:
3843:Demeclocycline
3832:
3831:
3830:
3829:
3824:
3819:
3814:
3801:
3799:
3783:
3782:
3780:
3779:
3774:
3769:
3763:
3761:
3746:
3745:
3742:
3741:
3739:
3738:
3737:
3736:
3723:
3722:
3721:
3720:
3715:
3710:
3705:
3703:Spironolactone
3692:
3690:
3684:
3683:
3681:
3680:
3675:
3670:
3664:
3662:
3653:
3642:
3641:
3638:
3637:
3635:
3634:
3629:
3624:
3619:
3614:
3609:
3604:
3599:
3594:
3589:
3584:
3578:
3576:
3569:Thiazide-likes
3565:
3564:
3562:
3561:
3556:
3551:
3546:
3541:
3536:
3531:
3526:
3521:
3516:
3514:Chlorothiazide
3511:
3506:
3501:
3495:
3493:
3473:
3472:
3470:
3469:
3464:
3459:
3454:
3449:
3444:
3439:
3434:
3432:Etacrynic acid
3429:
3424:
3419:
3413:
3411:
3396:
3395:
3393:
3392:
3386:
3384:
3370:
3367:etacrynic acid
3358:
3357:
3347:
3345:
3344:
3337:
3330:
3322:
3313:
3312:
3309:
3308:
3294:
3279:
3278:
3275:
3274:
3272:
3271:
3270:
3269:
3264:
3256:
3251:
3246:
3241:
3236:
3231:
3226:
3221:
3215:
3213:
3209:
3208:
3206:
3205:
3200:
3195:
3190:
3185:
3184:
3183:
3173:
3168:
3163:
3158:
3153:
3148:
3143:
3138:
3131:
3126:
3121:
3116:
3111:
3110:
3109:
3099:
3093:
3091:
3087:
3086:
3084:
3083:
3078:
3073:
3068:
3063:
3058:
3053:
3047:
3045:
3041:
3040:
3038:
3037:
3032:
3030:Mint chocolate
3027:
3022:
3017:
3012:
3007:
3002:
2997:
2992:
2987:
2982:
2977:
2975:Chocolate milk
2972:
2967:
2962:
2957:
2952:
2947:
2945:Chocolate chip
2942:
2937:
2935:Chocolate cake
2932:
2927:
2922:
2921:
2920:
2910:
2904:
2902:
2898:
2897:
2895:
2894:
2889:
2884:
2879:
2874:
2869:
2864:
2859:
2854:
2849:
2844:
2839:
2833:
2831:
2823:
2822:
2820:
2819:
2814:
2809:
2804:
2799:
2794:
2789:
2784:
2779:
2774:
2769:
2767:Phenethylamine
2764:
2759:
2754:
2749:
2744:
2739:
2733:
2731:
2727:
2726:
2724:
2723:
2716:
2711:
2706:
2700:
2698:
2690:
2689:
2682:
2680:
2679:
2672:
2665:
2657:
2649:
2648:
2633:
2598:
2557:
2530:
2504:
2473:
2447:
2421:
2414:
2396:
2375:(5): 671–680.
2355:
2312:
2283:(3): 299–305.
2263:
2242:(1): 315–323.
2222:
2197:
2188:|journal=
2170:
2144:
2129:(1): 302–303.
2111:
2093:
2086:
2068:
2019:
1968:
1938:
1927:(2): 168–179.
1911:
1891:
1866:
1841:
1833:
1809:
1791:
1766:
1755:(3): 253–320.
1735:
1710:(1): 453–456.
1690:
1673:
1631:
1613:
1593:
1587:978-0813331591
1586:
1562:
1547:
1508:
1477:
1439:
1410:(2): 177–182.
1387:
1360:(3): 296–302.
1340:
1339:
1337:
1334:
1333:
1332:
1327:
1322:
1315:
1312:
1284:milk chocolate
1275:
1272:
1252:
1249:
1215:bronchodilator
1210:
1207:
1199:
1196:
1125:
1122:
1105:
1102:
1099:
1098:
1095:
1088:
1087:
1084:
1078:
1077:
1074:
1068:
1067:
1064:
1063:Cocoa cereals
1060:
1059:
1056:
1052:
1051:
1048:
1044:
1043:
1040:
1034:
1033:
1030:
1024:
1023:
1020:
1011:products are:
980:
979:
971:
967:Ilex vomitoria
963:
955:
947:
939:
892:
889:
836:
833:
816:
813:
781:
778:
713:
710:
709:
704:
700:standard state
697:
694:
693:
690:
685:
682:
681:
678:
672:
671:
668:
662:
661:
658:
654:
653:
649:
648:
646:
645:
632:
630:
618:
615:
614:
604:
596:
595:
584:
583:
572:
571:
569:
568:
565:
563:
560:
552:
551:
550:
547:
546:
544:
543:
540:
532:
531:
530:
527:
526:
524:
523:
515:
513:
505:
504:
498:
492:
491:
488:
482:
476:
470:
465:
459:
458:
454:
453:
443:
435:
434:
432:
431:
418:
416:
403:
402:
400:
399:
391:
389:
383:
382:
380:
379:
371:
369:
363:
362:
360:
359:
351:
349:
343:
342:
340:
339:
331:
329:
323:
322:
320:
319:
311:
309:
303:
302:
300:
299:
291:
289:
283:
282:
280:
279:
271:
269:
258:
257:
255:
254:
246:
244:
238:
237:
235:
234:
228:3,7-dimethyl-1
227:
219:
218:
217:
214:
213:
209:
208:
202:
196:
195:
192:
183:
182:
170:
164:
163:
156:
155:
153:
152:
148:
146:
140:
139:
135:
134:
132:
131:
108:
106:
100:
99:
94:
92:administration
86:
85:
82:
74:
73:
60:
56:
55:
51:
50:
42:
41:
15:
13:
10:
9:
6:
4:
3:
2:
7595:
7594:
7583:
7580:
7578:
7575:
7573:
7570:
7568:
7565:
7563:
7560:
7558:
7555:
7553:
7550:
7549:
7547:
7534:
7533:
7530:
7524:
7518:
7515:
7513:
7510:
7508:
7505:
7503:
7500:
7498:
7497:Proxyphylline
7495:
7493:
7490:
7488:
7485:
7483:
7480:
7478:
7475:
7473:
7470:
7468:
7465:
7463:
7460:
7458:
7457:Diprophylline
7455:
7453:
7450:
7449:
7447:
7443:
7437:
7434:
7432:
7429:
7427:
7424:
7422:
7419:
7417:
7414:
7412:
7409:
7407:
7404:
7402:
7399:
7397:
7394:
7392:
7389:
7387:
7384:
7382:
7379:
7377:
7374:
7372:
7369:
7367:
7366:Aminophylline
7364:
7363:
7361:
7359:
7358:Non-selective
7355:
7351:
7347:
7345:
7341:
7335:
7332:
7330:
7327:
7325:
7322:
7320:
7317:
7315:
7312:
7311:
7309:
7307:
7303:
7297:
7294:
7292:
7289:
7287:
7284:
7283:
7281:
7279:
7275:
7269:
7266:
7265:
7263:
7261:
7257:
7251:
7248:
7246:
7243:
7241:
7238:
7236:
7233:
7231:
7228:
7226:
7223:
7221:
7218:
7216:
7213:
7211:
7208:
7206:
7203:
7201:
7198:
7196:
7193:
7191:
7188:
7186:
7183:
7181:
7178:
7176:
7173:
7171:
7168:
7166:
7163:
7161:
7158:
7156:
7153:
7151:
7150:Acetildenafil
7148:
7147:
7145:
7143:
7139:
7133:
7130:
7128:
7125:
7123:
7120:
7118:
7115:
7113:
7110:
7108:
7105:
7103:
7100:
7098:
7095:
7093:
7090:
7088:
7085:
7083:
7080:
7078:
7075:
7073:
7070:
7068:
7065:
7063:
7060:
7058:
7055:
7053:
7050:
7048:
7045:
7043:
7040:
7038:
7035:
7033:
7030:
7028:
7025:
7023:
7020:
7018:
7015:
7013:
7010:
7008:
7005:
7003:
7000:
6998:
6995:
6993:
6990:
6988:
6985:
6983:
6980:
6978:
6975:
6973:
6970:
6968:
6965:
6963:
6960:
6958:
6955:
6953:
6950:
6948:
6945:
6943:
6940:
6938:
6935:
6933:
6930:
6928:
6925:
6923:
6920:
6919:
6917:
6915:
6911:
6905:
6902:
6900:
6897:
6895:
6892:
6890:
6887:
6885:
6882:
6880:
6877:
6875:
6872:
6870:
6867:
6865:
6862:
6860:
6857:
6855:
6852:
6850:
6847:
6845:
6842:
6840:
6837:
6835:
6832:
6830:
6827:
6825:
6822:
6820:
6817:
6815:
6812:
6810:
6807:
6805:
6802:
6800:
6797:
6795:
6792:
6790:
6787:
6786:
6784:
6782:
6778:
6772:
6769:
6767:
6764:
6762:
6759:
6757:
6754:
6752:
6749:
6748:
6746:
6744:
6740:
6734:
6731:
6729:
6726:
6724:
6721:
6720:
6718:
6716:
6712:
6708:
6701:
6696:
6694:
6689:
6687:
6682:
6681:
6678:
6668:
6667:
6664:
6658:
6651:
6647:
6644:
6641:
6640:
6637:
6634:
6632:
6629:
6627:
6624:
6622:
6619:
6617:
6614:
6612:
6609:
6607:
6604:
6602:
6599:
6597:
6594:
6592:
6589:
6587:
6584:
6582:
6579:
6577:
6574:
6572:
6569:
6567:
6564:
6562:
6559:
6557:
6554:
6552:
6549:
6547:
6544:
6542:
6539:
6537:
6534:
6532:
6529:
6527:
6524:
6522:
6519:
6517:
6514:
6512:
6509:
6506:
6505:
6503:
6499:
6489:
6486:
6484:
6481:
6479:
6476:
6474:
6471:
6469:
6466:
6464:
6461:
6459:
6456:
6455:
6453:
6449:
6443:
6440:
6438:
6435:
6433:
6430:
6428:
6425:
6423:
6422:
6418:
6416:
6413:
6411:
6408:
6406:
6403:
6401:
6398:
6396:
6393:
6391:
6388:
6386:
6383:
6381:
6380:
6376:
6374:
6371:
6369:
6366:
6364:
6363:Benzbromarone
6361:
6359:
6356:
6354:
6351:
6350:
6348:
6343:
6337:
6334:
6330:
6324:
6320:
6310:
6307:
6306:
6304:
6299:
6293:
6287:
6284:
6282:
6279:
6277:
6274:
6272:
6269:
6267:
6264:
6262:
6259:
6257:
6254:
6252:
6249:
6247:
6244:
6242:
6239:
6237:
6234:
6232:
6229:
6228:
6226:
6221:
6215:
6209:
6206:
6204:
6201:
6199:
6196:
6194:
6191:
6189:
6186:
6184:
6181:
6179:
6176:
6174:
6171:
6169:
6166:
6165:
6163:
6158:
6152:
6149:
6145:
6139:
6135:
6121:
6118:
6116:
6113:
6111:
6108:
6106:
6103:
6101:
6098:
6096:
6093:
6091:
6088:
6086:
6083:
6081:
6078:
6076:
6073:
6071:
6068:
6066:
6063:
6061:
6058:
6056:
6053:
6051:
6048:
6046:
6043:
6041:
6038:
6036:
6033:
6031:
6028:
6026:
6023:
6021:
6018:
6016:
6013:
6011:
6008:
6006:
6003:
6001:
5998:
5996:
5995:AR-C 118925XX
5993:
5991:
5988:
5986:
5983:
5981:
5978:
5976:
5973:
5971:
5968:
5966:
5963:
5961:
5958:
5955:
5954:
5951:
5948:
5946:
5943:
5941:
5938:
5936:
5933:
5931:
5928:
5926:
5925:UDP-galactose
5923:
5921:
5918:
5916:
5913:
5911:
5908:
5906:
5903:
5901:
5898:
5896:
5893:
5891:
5888:
5886:
5883:
5881:
5878:
5876:
5873:
5871:
5868:
5866:
5863:
5861:
5858:
5856:
5853:
5851:
5848:
5846:
5843:
5841:
5838:
5836:
5833:
5831:
5828:
5826:
5823:
5821:
5818:
5816:
5813:
5811:
5808:
5806:
5803:
5801:
5798:
5796:
5793:
5791:
5788:
5786:
5783:
5781:
5778:
5776:
5773:
5771:
5768:
5766:
5763:
5761:
5758:
5755:
5754:
5752:
5750:
5746:
5740:
5737:
5735:
5732:
5729:
5728:
5723:
5720:
5718:
5715:
5713:
5710:
5707:
5706:
5701:
5700:
5695:
5692:
5690:
5687:
5685:
5682:
5680:
5677:
5675:
5672:
5670:
5667:
5664:
5663:
5658:
5655:
5653:
5650:
5648:
5645:
5643:
5640:
5638:
5635:
5633:
5630:
5628:
5625:
5623:
5620:
5618:
5615:
5613:
5610:
5608:
5605:
5603:
5600:
5598:
5595:
5593:
5590:
5588:
5585:
5583:
5580:
5578:
5575:
5573:
5570:
5568:
5565:
5563:
5560:
5558:
5555:
5553:
5550:
5548:
5545:
5543:
5540:
5537:
5536:
5531:
5528:
5526:
5523:
5521:
5520:Chelerythrine
5518:
5516:
5515:Calmidazolium
5513:
5511:
5508:
5506:
5503:
5501:
5498:
5496:
5493:
5491:
5488:
5486:
5483:
5481:
5478:
5476:
5473:
5471:
5468:
5466:
5463:
5461:
5458:
5455:
5454:
5451:
5448:
5446:
5443:
5441:
5438:
5436:
5433:
5431:
5428:
5426:
5423:
5421:
5418:
5416:
5413:
5411:
5408:
5406:
5403:
5401:
5400:Cibacron blue
5398:
5396:
5393:
5391:
5388:
5386:
5383:
5381:
5378:
5376:
5373:
5371:
5368:
5366:
5363:
5361:
5358:
5356:
5353:
5351:
5348:
5345:
5344:
5342:
5336:
5329:
5325:
5322:
5319:
5314:
5310:
5304:
5301:
5299:
5296:
5294:
5291:
5289:
5286:
5284:
5281:
5279:
5278:Theodrenaline
5276:
5274:
5271:
5269:
5266:
5264:
5261:
5259:
5256:
5254:
5251:
5249:
5246:
5244:
5241:
5239:
5236:
5234:
5231:
5229:
5226:
5224:
5221:
5219:
5216:
5214:
5213:Proxyphylline
5211:
5209:
5206:
5204:
5201:
5199:
5196:
5194:
5191:
5189:
5186:
5184:
5181:
5179:
5176:
5174:
5171:
5169:
5166:
5164:
5161:
5159:
5156:
5154:
5151:
5149:
5146:
5144:
5141:
5139:
5136:
5134:
5131:
5129:
5126:
5124:
5121:
5119:
5116:
5114:
5111:
5109:
5106:
5104:
5101:
5099:
5096:
5094:
5091:
5089:
5086:
5084:
5081:
5079:
5076:
5074:
5071:
5069:
5066:
5064:
5061:
5059:
5056:
5054:
5051:
5049:
5046:
5044:
5043:Aminophylline
5041:
5039:
5036:
5034:
5031:
5029:
5026:
5024:
5021:
5019:
5016:
5013:
5012:
5009:
5006:
5004:
5001:
4999:
4996:
4994:
4991:
4989:
4986:
4984:
4981:
4979:
4976:
4974:
4971:
4969:
4966:
4964:
4962:
4958:
4956:
4953:
4951:
4948:
4946:
4943:
4941:
4938:
4936:
4933:
4931:
4928:
4926:
4923:
4921:
4918:
4916:
4913:
4911:
4908:
4906:
4903:
4901:
4898:
4896:
4893:
4891:
4888:
4886:
4883:
4881:
4878:
4876:
4874:
4869:
4867:
4864:
4862:
4859:
4857:
4854:
4852:
4850:
4845:
4842:
4841:
4839:
4836:
4831:
4827:
4821:
4818:
4816:
4813:
4810:
4809:
4807:
4804:
4800:
4796:
4793:
4789:
4783:
4779:
4775:
4772:
4765:
4760:
4758:
4753:
4751:
4746:
4745:
4742:
4726:
4724:
4721:
4720:
4718:
4715:
4712:
4709:
4707:
4704:
4703:
4699:
4693:
4690:
4688:
4685:
4683:
4680:
4678:
4675:
4673:
4670:
4668:
4665:
4663:
4660:
4658:
4655:
4653:
4650:
4648:
4645:
4643:
4640:
4638:
4635:
4633:
4630:
4628:
4625:
4623:
4620:
4618:
4615:
4613:
4610:
4608:
4605:
4603:
4600:
4599:
4597:
4593:
4587:
4584:
4582:
4579:
4577:
4574:
4572:
4569:
4567:
4564:
4563:
4561:
4557:
4547:
4544:
4542:
4539:
4538:
4536:
4534:
4531:Non-xanthine
4529:
4523:
4520:
4518:
4515:
4514:
4512:
4510:
4506:
4500:
4497:
4496:
4494:
4492:
4488:
4482:
4479:
4477:
4474:
4472:
4469:
4468:
4466:
4464:
4460:
4457:
4454:
4450:
4444:
4441:
4439:
4438:Proxyphylline
4436:
4434:
4433:Etamiphylline
4431:
4429:
4426:
4424:
4421:
4419:
4416:
4414:
4411:
4409:
4408:Aminophylline
4406:
4404:
4401:
4399:
4396:
4395:
4393:
4391:
4387:
4381:
4378:
4376:
4373:
4372:
4370:
4368:
4364:
4358:
4355:
4353:
4350:
4348:
4345:
4343:
4340:
4338:
4335:
4333:
4330:
4329:
4327:
4325:
4320:
4316:
4310:
4309:Triamcinolone
4307:
4305:
4302:
4300:
4297:
4295:
4292:
4290:
4287:
4285:
4282:
4280:
4279:Betamethasone
4277:
4275:
4274:Beclometasone
4272:
4271:
4269:
4267:
4263:
4253:
4250:
4248:
4245:
4243:
4240:
4238:
4235:
4233:
4232:Hexoprenaline
4230:
4228:
4225:
4223:
4220:
4217:
4213:
4209:
4208:+theophylline
4205:
4202:
4201:
4199:
4195:
4189:
4186:
4184:
4181:
4179:
4176:
4174:
4171:
4169:
4166:
4165:
4163:
4161:
4153:
4147:
4144:
4142:
4139:
4137:
4133:
4130:
4128:
4125:
4123:
4120:
4119:
4117:
4115:
4107:
4101:
4098:
4096:
4093:
4091:
4087:
4084:
4082:
4079:
4077:
4074:
4072:
4069:
4067:
4064:
4062:
4059:
4057:
4054:
4052:
4049:
4047:
4044:
4043:
4041:
4039:
4031:
4028:
4026:
4022:
4018:
4013:
4009:
4005:
4001:
3993:
3988:
3986:
3981:
3979:
3974:
3973:
3970:
3954:
3952:
3949:
3948:
3946:
3943:
3940:
3937:
3935:
3932:
3931:
3927:
3921:
3918:
3917:
3915:
3911:
3905:
3902:
3900:
3897:
3894:
3890:
3886:
3885:Chlormerodrin
3882:
3881:
3877:
3875:
3871:
3867:
3864:
3863:
3861:
3857:
3849:
3846:
3844:
3841:
3840:
3839:
3838:
3834:
3833:
3828:
3825:
3823:
3820:
3818:
3815:
3813:
3810:
3809:
3808:
3807:
3803:
3802:
3800:
3797:
3793:
3788:
3784:
3778:
3775:
3773:
3770:
3768:
3765:
3764:
3762:
3759:
3755:
3751:
3747:
3735:
3732:
3731:
3730:
3729:
3725:
3724:
3719:
3716:
3714:
3711:
3709:
3706:
3704:
3701:
3700:
3699:
3698:
3697:Spirolactones
3694:
3693:
3691:
3689:
3685:
3679:
3676:
3674:
3671:
3669:
3666:
3665:
3663:
3661:
3657:
3654:
3651:
3647:
3643:
3633:
3630:
3628:
3625:
3623:
3620:
3618:
3615:
3613:
3610:
3608:
3605:
3603:
3600:
3598:
3595:
3593:
3590:
3588:
3585:
3583:
3582:Chlortalidone
3580:
3579:
3577:
3574:
3570:
3566:
3560:
3557:
3555:
3552:
3550:
3547:
3545:
3542:
3540:
3537:
3535:
3532:
3530:
3527:
3525:
3524:Cyclothiazide
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3505:
3502:
3500:
3497:
3496:
3494:
3491:
3486:
3482:
3478:
3474:
3468:
3465:
3463:
3462:Tienilic acid
3460:
3458:
3455:
3453:
3450:
3448:
3445:
3443:
3440:
3438:
3435:
3433:
3430:
3428:
3425:
3423:
3420:
3418:
3415:
3414:
3412:
3409:
3405:
3401:
3397:
3391:
3390:Acetazolamide
3388:
3387:
3385:
3382:
3378:
3377:CA inhibitors
3374:
3371:
3368:
3363:
3359:
3354:
3350:
3343:
3338:
3336:
3331:
3329:
3324:
3323:
3320:
3307:
3306:
3295:
3293:
3292:
3281:
3280:
3276:
3268:
3267:United States
3265:
3263:
3260:
3259:
3257:
3255:
3252:
3250:
3247:
3245:
3242:
3240:
3237:
3235:
3232:
3230:
3227:
3225:
3222:
3220:
3217:
3216:
3214:
3210:
3204:
3201:
3199:
3196:
3194:
3191:
3189:
3186:
3182:
3179:
3178:
3177:
3174:
3172:
3169:
3167:
3164:
3162:
3159:
3157:
3154:
3152:
3149:
3147:
3144:
3142:
3139:
3137:
3136:
3132:
3130:
3127:
3125:
3122:
3120:
3117:
3115:
3114:Big Chocolate
3112:
3108:
3105:
3104:
3103:
3100:
3098:
3095:
3094:
3092:
3088:
3082:
3079:
3077:
3074:
3072:
3069:
3067:
3066:Dutch process
3064:
3062:
3059:
3057:
3056:Broma process
3054:
3052:
3049:
3048:
3046:
3042:
3036:
3033:
3031:
3028:
3026:
3023:
3021:
3018:
3016:
3015:Hot chocolate
3013:
3011:
3008:
3006:
3003:
3001:
2998:
2996:
2993:
2991:
2988:
2986:
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:
2919:
2916:
2915:
2914:
2913:Chocolate bar
2911:
2909:
2906:
2905:
2903:
2899:
2893:
2890:
2888:
2885:
2883:
2880:
2878:
2877:Raw chocolate
2875:
2873:
2870:
2868:
2865:
2863:
2860:
2858:
2855:
2853:
2850:
2848:
2845:
2843:
2840:
2838:
2835:
2834:
2832:
2830:
2824:
2818:
2815:
2813:
2810:
2808:
2805:
2803:
2800:
2798:
2795:
2793:
2790:
2788:
2785:
2783:
2780:
2778:
2775:
2773:
2772:Phenylalanine
2770:
2768:
2765:
2763:
2760:
2758:
2755:
2753:
2750:
2748:
2745:
2743:
2740:
2738:
2735:
2734:
2732:
2728:
2722:
2721:
2717:
2715:
2712:
2710:
2707:
2705:
2702:
2701:
2699:
2697:
2691:
2687:
2678:
2673:
2671:
2666:
2664:
2659:
2658:
2655:
2644:
2637:
2634:
2621:
2617:
2616:
2611:
2605:
2603:
2599:
2583:
2579:
2575:
2568:
2561:
2558:
2545:
2541:
2534:
2531:
2518:
2514:
2508:
2505:
2500:
2496:
2492:
2488:
2484:
2477:
2474:
2461:
2457:
2451:
2448:
2435:
2431:
2430:"Theobromine"
2425:
2422:
2417:
2411:
2407:
2400:
2397:
2392:
2388:
2383:
2378:
2374:
2370:
2366:
2359:
2356:
2351:
2347:
2343:
2339:
2335:
2331:
2327:
2323:
2316:
2313:
2308:
2304:
2299:
2294:
2290:
2286:
2282:
2278:
2274:
2267:
2264:
2259:
2255:
2250:
2245:
2241:
2237:
2233:
2226:
2223:
2212:on 2010-11-24
2211:
2207:
2201:
2198:
2193:
2181:
2173:
2171:9780124080614
2167:
2163:
2159:
2155:
2148:
2145:
2141:
2136:
2132:
2128:
2124:
2123:
2115:
2112:
2107:
2103:
2097:
2094:
2089:
2083:
2079:
2072:
2069:
2064:
2060:
2056:
2052:
2047:
2042:
2038:
2034:
2030:
2023:
2020:
2015:
2011:
2006:
2001:
1996:
1991:
1987:
1983:
1979:
1972:
1969:
1957:on 8 May 2019
1956:
1952:
1948:
1942:
1939:
1934:
1930:
1926:
1922:
1915:
1912:
1901:
1895:
1892:
1881:on 2017-07-08
1880:
1876:
1870:
1867:
1856:on 2015-08-11
1855:
1851:
1845:
1842:
1836:
1830:
1826:
1822:
1821:
1813:
1810:
1798:
1794:
1788:
1784:
1780:
1776:
1770:
1767:
1762:
1758:
1754:
1750:
1746:
1739:
1736:
1721:
1717:
1713:
1709:
1705:
1701:
1694:
1691:
1686:
1685:
1677:
1674:
1662:
1658:
1654:
1650:
1646:
1642:
1635:
1632:
1620:
1616:
1610:
1606:
1605:
1597:
1594:
1589:
1583:
1579:
1575:
1574:
1566:
1563:
1558:
1554:
1550:
1544:
1540:
1536:
1532:
1525:
1523:
1521:
1519:
1517:
1515:
1513:
1509:
1496:
1495:"Theobromine"
1490:
1488:
1486:
1484:
1482:
1478:
1473:
1469:
1465:
1461:
1457:
1453:
1446:
1444:
1440:
1435:
1431:
1426:
1421:
1417:
1413:
1409:
1405:
1401:
1394:
1392:
1388:
1383:
1379:
1375:
1371:
1367:
1363:
1359:
1355:
1348:
1346:
1342:
1335:
1331:
1330:Theodrenaline
1328:
1326:
1323:
1321:
1318:
1317:
1313:
1311:
1309:
1305:
1301:
1296:
1293:
1288:
1285:
1281:
1273:
1271:
1269:
1265:
1261:
1256:
1250:
1248:
1246:
1242:
1238:
1234:
1231:
1226:
1224:
1220:
1216:
1208:
1205:
1197:
1195:
1193:
1189:
1184:
1180:
1178:
1174:
1170:
1166:
1161:
1159:
1155:
1151:
1147:
1139:
1135:
1130:
1123:
1121:
1119:
1115:
1111:
1103:
1096:
1093:
1090:
1089:
1086:22.6 mg
1085:
1083:
1080:
1079:
1076:62.1 mg
1075:
1073:
1070:
1069:
1066:69.5 mg
1065:
1062:
1061:
1057:
1054:
1053:
1049:
1046:
1045:
1041:
1039:
1036:
1035:
1032:2060 mg
1031:
1029:
1026:
1025:
1021:
1018:
1017:
1012:
1010:
1005:
1003:
999:
998:
993:
989:
985:
977:
976:
972:
970:
968:
964:
962:
960:
956:
953:
952:
948:
945:
944:
940:
938:
934:
933:
929:
928:
927:
924:
920:
918:
914:
910:
902:
897:
890:
888:
886:
882:
877:
875:
871:
867:
863:
859:
855:
851:
847:
846:
841:
834:
832:
830:
826:
822:
814:
812:
810:
806:
802:
798:
794:
791:
787:
779:
777:
775:
771:
767:
763:
759:
758:
753:
749:
745:
741:
737:
733:
732:
727:
723:
719:
707:
701:
695:
691:
688:
684:
683:
679:
677:
676:Melting point
674:
673:
669:
667:
664:
663:
659:
656:
655:
650:
642:
638:
637:DTXSID9026132
634:
633:
631:
621:
617:
616:
612:
608:
605:
603:
601:ECHA InfoCard
598:
597:
592:
580:
573:
564:
559:
555:
548:
539:
535:
528:
521:
517:
516:
514:
511:
506:
499:
497:
493:
466:
464:
460:
455:
451:
447:
444:
442:
440:ECHA InfoCard
436:
428:
424:
423:DTXSID9026132
420:
419:
417:
408:
404:
397:
393:
392:
390:
388:
384:
377:
373:
372:
370:
368:
364:
357:
353:
352:
350:
348:
344:
337:
333:
332:
330:
328:
324:
317:
313:
312:
310:
308:
304:
297:
293:
292:
290:
288:
284:
277:
273:
272:
270:
263:
259:
252:
248:
247:
245:
243:
239:
231:
226:
222:
215:
210:
206:
203:
201:
197:
193:
191:
184:
181:
177:
176:demethylation
174:
171:
169:
165:
161:
157:
150:
149:
147:
145:
141:
136:
128:
123:
118:
113:
110:
109:
107:
105:
101:
98:
95:
93:
87:
83:
81:
75:
71:
61:
57:
54:Clinical data
52:
48:
43:
39:
34:
24:
19:
7528:
7527:
7512:Tolafentrine
7492:Pentifylline
7431:Theophylline
7425:
7396:Enprofylline
7386:Dipyridamole
7296:Paraxanthine
7077:Pumafentrine
7052:Mesembrenone
6992:Ensifentrine
6977:Denbutylline
6967:Cipamfylline
6937:Benafentrine
6874:Pumafentrine
6834:Ensifentrine
6804:Benafentrine
6662:
6661:
6646:Chrysophanol
6642:
6586:Hypoxanthine
6507:
6487:
6483:Pralatrexate
6468:Methotrexate
6463:Azathioprine
6442:Topiroxostat
6419:
6390:Myo-inositol
6377:
6368:Caffeic acid
6281:Progesterone
6251:Dipyridamole
6231:Barbiturates
6208:Progesterone
5990:AR-C 69931MX
5985:AR-C 67085MX
5957:Antagonists:
5956:
5810:AR-C 67085MX
5756:
5725:
5703:
5697:
5660:
5627:Oxidized-ATP
5572:JNJ-47965567
5533:
5457:Antagonists:
5456:
5430:L-β,γ-Me-ATP
5410:D-β,γ-Me-ATP
5346:
5283:Theophylline
5272:
5193:Paraxanthine
5138:Fenethylline
5128:Enprofylline
5093:Ciforadenant
5015:Antagonists:
5014:
4978:Piclidenoson
4960:
4872:
4856:2-Cl-IB-MECA
4848:
4843:
4811:
4571:Ensifentrine
4443:Theophylline
4428:Enprofylline
4403:Ambuphylline
4375:Cromoglicate
4252:Racephedrine
4136:Arformoterol
3898:
3878:
3835:
3804:
3728:Nonsteroidal
3726:
3695:
3660:ESC blockers
3627:Quinethazone
3554:Polythiazide
3362:Sulfonamides
3301:
3287:
3244:Chocolatiers
3212:Other topics
3133:
3119:Chocolaterie
2817:Valeric acid
2792:Theophylline
2786:
2718:
2714:Cocoa solids
2709:Cocoa butter
2642:
2636:
2624:. Retrieved
2613:
2589:. Retrieved
2582:the original
2574:aspcapro.org
2573:
2560:
2548:. Retrieved
2543:
2533:
2521:. Retrieved
2507:
2493:(2): 63–68.
2490:
2486:
2476:
2464:. Retrieved
2450:
2438:. Retrieved
2434:the original
2424:
2405:
2399:
2372:
2368:
2358:
2325:
2321:
2315:
2280:
2276:
2266:
2239:
2235:
2225:
2214:. Retrieved
2210:the original
2200:
2153:
2147:
2138:
2126:
2120:
2114:
2105:
2096:
2077:
2071:
2036:
2032:
2022:
1985:
1981:
1971:
1959:. Retrieved
1955:the original
1941:
1924:
1920:
1914:
1903:. Retrieved
1894:
1883:. Retrieved
1879:the original
1869:
1858:. Retrieved
1854:the original
1844:
1827:, New York.
1819:
1812:
1801:. Retrieved
1778:
1769:
1752:
1748:
1738:
1727:. Retrieved
1707:
1703:
1693:
1683:
1676:
1665:. Retrieved
1648:
1644:
1634:
1623:. Retrieved
1603:
1596:
1572:
1565:
1530:
1499:. Retrieved
1455:
1451:
1407:
1403:
1357:
1353:
1297:
1289:
1277:
1257:
1254:
1227:
1212:
1185:
1181:
1162:
1158:paraxanthine
1154:theophylline
1143:
1138:theophylline
1134:paraxanthine
1124:Pharmacology
1107:
1104:Biosynthesis
1058:147 mg
1050:195 mg
1042:266 mg
1028:Cocoa powder
1006:
996:
981:
978:– leaf
973:
969:– leaf
965:
961:– leaf
959:Ilex guayusa
957:
954:– leaf
949:
941:
930:
925:
921:
917:Cocoa butter
906:
887:("stench").
884:
878:
873:
865:
853:
843:
839:
838:
818:
805:paraxanthine
797:theophylline
783:
755:
729:
721:
717:
716:
660:white solid
594:Identifiers
589:Theobromine
576:
229:
187:Elimination
144:Legal status
138:Legal status
69:
64:diurobromine
18:
7472:Lisofylline
7467:Furafylline
7426:Theobromine
7391:Doxofylline
7319:Mardepodect
7291:PF-04447943
7286:BAY 73-6691
7200:Mirodenafil
7185:Gisadenafil
7132:Zardaverine
7092:Roflumilast
7072:Piclamilast
7027:Irsogladine
6987:Drotaverine
6972:Crisaborole
6942:Catramilast
6904:Zardaverine
6899:Vesnarinone
6819:Cilostamide
6809:Bucladesine
6751:BAY 60-7550
6733:Vinpocetine
6508:Precursors:
6488:Many others
6458:Aminopterin
6415:Phytic acid
6358:Amflutizole
6353:Allopurinol
6309:Decynium-22
6266:Hexobendine
6138:Transporter
6115:Ticlopidine
6020:Clopidogrel
5930:UDP-glucose
5669:Purotoxin 1
5500:AZ-11645373
5495:AZ-10606120
5293:Tracazolate
5273:Theobromine
5258:SCH-442,416
5253:Rolofylline
5203:Preladenant
5073:Cartazolate
5053:Bamifylline
5003:Tecadenoson
4998:Sonedenoson
4993:Selodenoson
4988:SDZ WAG 994
4983:Regadenoson
4968:Namodenoson
4920:Capadenoson
4915:Binodenoson
4910:BAY 60–6583
4713:from market
4546:Roflumilast
4522:Seratrodast
4481:Zafirlukast
4471:Montelukast
4423:Doxofylline
4413:Bamifylline
4294:Flunisolide
4289:Ciclesonide
4222:Epinephrine
4178:Indacaterol
4127:Clenbuterol
4100:Tulobuterol
4095:Terbutaline
4021:Adrenergics
3941:from market
3904:Cicletanine
3899:Theobromine
3893:Meralluride
3870:Isopropanol
3678:Triamterene
3597:Clorexolone
3587:Clofenamide
3571:(primarily
3442:Indacrinone
3262:Switzerland
3124:Chocolatier
3076:Sugar crust
2908:Caffè mocha
2787:Theobromine
2757:Flavan-3-ol
2591:23 December
2550:24 December
2523:23 December
2466:13 November
2039:: 263–274.
1651:: 125–127.
1501:3 September
1150:metabolised
1148:, which is
1000:), and the
840:Theobromine
718:Theobromine
670:1.524 g/cm
657:Appearance
652:Properties
607:100.001.359
503: g·mol
446:100.001.359
376:CHEBI:28946
212:Identifiers
59:Other names
30:Theobromine
7546:Categories
7487:Oxagrelate
7482:Moxaverine
7477:MDL-12330A
7324:Papaverine
7314:Balipodect
7250:Vardenafil
7225:Sildenafil
7175:Dasantafil
7155:Aildenafil
7122:Tofimilast
7117:Tetomilast
7102:Ronomilast
7087:Ro 20-1724
7082:Revamilast
7067:Oglemilast
7057:Mesembrine
7042:Lotamilast
7037:Lirimilast
7032:Lavamilast
7022:Indimilast
7002:Filaminast
6982:Difamilast
6962:Cilomilast
6927:Arofylline
6922:Apremilast
6894:Trequinsin
6889:Siguazodan
6869:Pimobendan
6864:Parogrelil
6849:Meribendan
6824:Cilostazol
6814:Carbazeran
6799:Anagrelide
6756:Carbazeran
6478:Pemetrexed
6437:Tisopurine
6410:Oxipurinol
6405:Niraxostat
6395:Kaempferol
6385:Febuxostat
6329:inhibitors
6241:Cilostazol
6203:Phloridzin
6110:Ticagrelor
5980:AR-C 66096
5840:Diquafosol
5785:α,β-Me-ATP
5770:2-Thio-UTP
5679:Ro 0437626
5632:Phenol Red
5547:Gefapixant
5542:Evans blue
5425:Ivermectin
5355:α,β-Me-ATP
5318:nucleotide
5303:ZM-241,385
5288:Tozadenant
5163:MRE3008F20
5123:Dyphylline
5108:Dimethazan
5038:Acefylline
5008:UK-432,097
4940:Evodenoson
4935:CP-532,903
4895:Apadenoson
4774:modulators
4586:Omalizumab
4581:Fenspiride
4517:Ramatroban
4476:Pranlukast
4455:inhibition
4453:Eicosanoid
4398:Acefylline
4380:Nedocromil
4304:Mometasone
4284:Budesonide
4227:Etafedrine
4188:Vilanterol
4183:Olodaterol
4173:Carmoterol
4168:Abediterol
4146:Salmefamol
4141:Salmeterol
4132:Formoterol
4122:Bambuterol
4076:Reproterol
4071:Procaterol
4066:Pirbuterol
4061:Isoetarine
4051:Carbuterol
4046:Bitolterol
3998:Drugs for
3822:Satavaptan
3817:Mozavaptan
3812:Conivaptan
3734:Finerenone
3713:Eplerenone
3622:Metolazone
3607:Indapamide
3602:Fenquizone
3544:Mebutizide
3467:Torasemide
3457:Piretanide
3447:Muzolimine
3427:Bumetanide
3417:Furosemide
2852:Couverture
2802:Tryptophan
2797:Tryptamine
2777:Salsolinol
2752:Enkephalin
2747:Endorphins
2737:Anandamide
2730:Components
2695:Cocoa bean
2440:3 November
2216:2011-01-08
2206:"Caffeine"
1905:2012-11-07
1885:2012-12-29
1860:2008-04-13
1803:2007-02-23
1729:2019-09-09
1667:2015-12-12
1625:2015-12-12
1336:References
1280:metabolize
1237:antagonism
1202:See also:
1156:, and 84%
1114:nucleoside
1110:xanthosine
992:yerba mate
901:cocoa bean
772:) and the
508:3D model (
496:Molar mass
396:ChEMBL1114
336:OBD445WZ5P
307:ChemSpider
242:CAS Number
221:IUPAC name
168:Metabolism
78:Dependence
7577:Xanthines
7529:See also:
7502:Quercetin
7436:Zaprinast
7401:Ibudilast
7334:Tofisopam
7329:TC-E 5005
7268:BRL-50481
7240:Tadalafil
7220:SCH-51866
7195:Lodenafil
7165:Beminafil
7017:ICI-63197
6997:Etazolate
6879:Quazinone
6859:Olprinone
6854:Milrinone
6829:Enoximone
6789:Adibendan
6728:SCH-51866
6663:See also:
6566:Guanosine
6516:Adenosine
6432:Quercetin
6400:Myricetin
6256:Estradiol
6183:Estradiol
6173:Adenosine
6085:Prasugrel
6025:Elinogrel
6015:Cangrelor
5960:2-Me-SAMP
5900:PAPET-ATP
5860:INS-37217
5835:Denufosol
5790:Adenosine
5780:5-OMe-UDP
5765:2-Me-SATP
5760:2-Me-SADP
5757:Agonists:
5652:PSB-12062
5587:Magnesium
5552:GW-791343
5440:PAPET-ATP
5360:Adenosine
5350:2-Me-SATP
5347:Agonists:
5268:Theacrine
5263:SCH-58261
5248:Reversine
5133:Etazolate
5083:CGS-15943
5058:Cafedrine
4930:CGS-21680
4880:Adenosine
4861:2'-MeCCPA
4844:Agonists:
4835:adenosine
4812:Agonists:
4723:Phase III
4711:Withdrawn
4576:Eprozinol
4566:Amlexanox
4541:Ibudilast
4390:Xanthines
4204:Ephedrine
4081:Rimiterol
4056:Fenoterol
4025:inhalants
3951:Phase III
3939:Withdrawn
3827:Tolvaptan
3708:Canrenone
3668:Amiloride
3617:Meticrane
3612:Mefruside
3592:Clopamide
3529:Epitizide
3477:Thiazides
3452:Ozolinone
3422:Azosemide
3349:Diuretics
3081:Tempering
3044:Processes
3020:beverages
2685:Chocolate
2190:ignored (
2180:cite book
1825:Routledge
1304:epileptic
1268:esophagus
1260:heartburn
1188:adenosine
1094:products
1002:tea plant
937:seed coat
913:chocolate
845:Theobroma
835:Etymology
780:Structure
748:chocolate
744:cosmetics
722:xantheose
200:Excretion
194:6–8 hours
189:half-life
180:oxidation
90:Routes of
80:liability
62:xantheose
7517:Trapidil
7507:Satigrel
7452:Diazepam
7445:Unsorted
7411:Luteolin
7371:Caffeine
7245:Udenafil
7160:Avanafil
7112:RS-25344
7097:Rolipram
7062:Mesopram
7047:Luteolin
7007:Glaucine
6957:CGH-2466
6932:Atizoram
6839:Imazodan
6766:Oxindole
6541:Cytidine
6536:Cytosine
6427:Propolis
6193:KGO-2173
6188:KGO-2142
6178:dMeThPmR
6144:blockers
6100:Regrelor
6090:PSB-0739
6060:MRS-2578
6055:MRS-2500
6050:MRS-2395
6045:MRS-2279
6040:MRS-2211
6035:MRS-2179
5910:PSB-1114
5905:PSB-0474
5890:MRS-4062
5885:MRS-2957
5880:MRS-2768
5875:MRS-2693
5870:MRS-2690
5865:MRS-2365
5775:5-Br-UDP
5717:TC-P 262
5657:Puerarin
5592:MRS-2159
5567:isoPPADS
5485:A-839977
5480:A-804598
5475:A-740003
5470:A-438079
5465:A-317491
5435:MRS-2219
5298:VUF-5574
5243:PSB-1115
5188:MRS-3777
5183:MRS-1754
5178:MRS-1706
5173:MRS-1334
5168:MRS-1220
5158:KF-26777
5103:CVT-6883
5078:CGH-2466
5063:Caffeine
4955:LUF-5845
4950:LUF-5835
4945:GR 79236
4900:ATL-146e
4782:Receptor
4499:Zileuton
4160:agonists
4114:agonists
4038:agonists
3889:Mersalyl
3772:Glycerol
3767:Mannitol
3673:Benzamil
3632:Xipamide
3509:Butizide
3499:Altizide
3437:Etozolin
3290:Category
3090:Industry
3061:Conching
2901:Products
2872:Modeling
2862:Gianduja
2847:Compound
2812:Tyrosine
2807:Tyramine
2762:Lecithin
2742:Caffeine
2626:12 March
2620:Archived
2517:Archived
2499:23462053
2460:Archived
2391:11692087
2307:10215755
2258:13475320
2063:52274913
2055:30213684
2014:22869743
1797:Archived
1785:. 2004.
1720:Archived
1661:Archived
1619:Archived
1557:20859797
1382:10519385
1314:See also
1308:seizures
1251:Toxicity
1235:and its
1165:xanthine
1146:caffeine
1118:caffeine
984:kola nut
825:xanthine
801:caffeine
793:xanthine
790:dimethyl
774:kola nut
740:additive
726:alkaloid
579:(verify)
287:DrugBank
104:ATC code
7350:BC11-38
7205:MY-5445
7180:Icariin
7107:RPL-554
7012:HT-0712
6952:CDP-840
6947:CC-1088
6884:RPL-554
6650:rhubarb
6643:Others:
6621:Uridine
6591:Inosine
6561:Guanine
6511:Adenine
6261:Ethanol
6246:Dilazep
6198:MeThPmR
6105:Suramin
6010:C1330-7
5855:INS-365
5734:TNP-ATP
5712:Suramin
5510:Calcium
5238:PSB-788
5233:PSB-603
5048:ATL-444
4820:Adenine
4803:adenine
4788:ligands
3866:Ethanol
3806:Vaptans
3404:Na-K-Cl
3304:Outline
3254:History
3071:Enrober
3010:Ganache
2842:Belgian
2350:8405909
2342:9010706
2298:2014222
2005:3435207
1961:9 March
1933:1586288
1460:Bibcode
1434:3756065
1425:1401099
1274:Animals
1198:Effects
990:berry,
988:guarana
891:Sources
881:bromine
872:") and
815:History
770:guayusa
762:hollies
736:soluble
666:Density
501:180.167
463:Formula
296:DB01412
262:PubChem
251:83-67-0
173:Hepatic
124: (
122:R03DA07
120:)
114: (
112:C03BD01
23:bromine
7235:T-0156
7127:YM-976
6844:KMUP-1
6616:Uracil
6611:Ribose
6501:Others
6451:Others
6323:Enzyme
6070:NF-340
6065:NF-157
5965:A3P5PS
5895:NF-546
5617:NF-449
5612:NF-279
5607:NF-157
5602:NF-110
5597:NF-023
5530:Emodin
5525:Copper
5490:AF-353
5460:5-BDBD
5420:HT-AMP
5228:PSB-36
5223:PSB-11
5218:PSB-10
4706:WHO-EM
4004:asthma
3934:WHO-EM
3837:Others
2918:brands
2837:Baking
2497:
2412:
2389:
2348:
2340:
2305:
2295:
2256:
2168:
2084:
2061:
2053:
2012:
2002:
1931:
1831:
1789:
1775:"-ine"
1611:
1584:
1555:
1545:
1432:
1422:
1380:
1374:627135
1372:
1306:-like
1209:Humans
1177:CYP2E1
1173:CYP1A2
986:, the
885:bromos
864:roots
807:, and
786:purine
766:yaupon
534:SMILES
387:ChEMBL
356:C07480
7462:DPCPX
7344:PDE11
7306:PDE10
6271:NBMPR
6080:PPADS
6005:BzATP
5970:AMPαS
5950:UTPγS
5920:UDPβS
5820:ATPγS
5800:ADPβS
5684:Ro 51
5647:PPNDS
5642:PPADS
5582:KN-62
5577:KN-04
5395:BzATP
5390:ATPγS
5118:DPCPX
4197:Other
3859:Other
3481:Na-Cl
3365:(and
3005:Fudge
2892:White
2887:Swiss
2828:Types
2615:Wired
2585:(PDF)
2578:ASPCA
2570:(PDF)
2346:S2CID
2059:S2CID
1723:(PDF)
1378:S2CID
1092:Carob
1019:Item
1009:carob
909:cocoa
874:broma
862:Greek
858:basic
850:genus
554:InChI
510:JSmol
367:ChEBI
205:Renal
7406:IBMX
7278:PDE9
7260:PDE7
7142:PDE5
6914:PDE4
6781:PDE3
6761:EHNA
6743:PDE2
6723:MMPX
6715:PDE1
6297:PMAT
6219:ENTs
6156:CNTs
6095:RB-2
6030:Ip5I
5975:Ap4A
5940:Up3U
5830:dATP
5805:Ap3A
5739:Zinc
5689:RO-3
5674:RB-2
5562:Ip5I
5450:Zinc
5380:Ap5A
5375:Ap4A
5143:IBMX
5113:DMPX
4925:CCPA
4008:COPD
3874:2M2B
3794:and
3777:Urea
3648:(at
3400:Loop
3379:(at
3035:Mole
2882:Ruby
2867:Milk
2857:Dark
2628:2017
2593:2017
2552:2023
2525:2017
2495:PMID
2468:2018
2442:2018
2410:ISBN
2387:PMID
2338:PMID
2303:PMID
2254:PMID
2192:help
2166:ISBN
2082:ISBN
2051:PMID
2010:PMID
1963:2019
1929:PMID
1829:ISBN
1787:ISBN
1609:ISBN
1582:ISBN
1553:PMID
1543:ISBN
1503:2022
1430:PMID
1370:PMID
1290:The
1175:and
1140:(4%)
1112:, a
911:and
866:theo
854:-ine
768:and
347:KEGG
327:UNII
316:5236
276:5429
178:and
162:data
97:Oral
84:None
7381:CPX
6771:PDP
6636:UTP
6631:UDP
6626:UMP
6606:ITP
6601:IDP
6596:IMP
6581:GTP
6576:GDP
6571:GMP
6556:CTP
6551:CDP
6546:CMP
6531:ATP
6526:ADP
6521:AMP
6120:UDP
6075:PIT
6000:ATP
5945:UTP
5915:UDP
5850:ITP
5845:IDP
5825:CTP
5815:ATP
5795:ADP
5749:P2Y
5557:HMA
5505:BBG
5445:UTP
5415:GTP
5405:CTP
5385:ATP
5370:AMP
5365:ADP
5334:ATP
5328:P2X
5098:CPX
4905:ATP
4890:AMP
4885:ADP
4871:5'-
4012:R03
3792:DCT
3573:DCT
3485:DCT
3483:at
3406:at
3353:C03
2377:doi
2373:108
2330:doi
2293:PMC
2285:doi
2244:doi
2240:228
2158:doi
2131:doi
2041:doi
2000:PMC
1990:doi
1986:109
1757:doi
1753:215
1712:doi
1653:doi
1578:200
1535:doi
1468:doi
1420:PMC
1412:doi
1362:doi
1239:of
870:god
752:tea
728:of
625:EPA
412:EPA
266:CID
127:WHO
117:WHO
7548::
6341:XO
5702:,
5313:P2
4830:P1
4799:P0
4719::
4214:,
4210:,
4023:,
4002::
3947::
3891:,
3887:,
3872:,
3868:,
3796:CD
3758:DL
3756:,
3754:PT
3650:CD
3408:AL
3381:PT
2612:.
2601:^
2576:.
2572:.
2542:.
2515:.
2491:71
2489:.
2485:.
2385:.
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2326:51
2324:.
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2275:.
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