47:
413:
278:
735:
38:
586:
680:
A 2010 pilot study investigated the effect of crocetin on sleep. The clinical trial comprised a double-blind, placebo-controlled, crossover trial of 21 healthy adult men with a mild sleep complaint. It concluded that crocetin may (p=0.025) contribute to improving the quality of sleep.
1236:
1212:
1629:
Lautenschläger M, Sendker J, Hüwel S, Galla HJ, Brandt S, Düfer M, Riehemann K, Hensel A (2015). "Intestinal formation of trans-crocetin from saffron extract (Crocus sativus L.) and in vitro permeation through intestinal and blood brain barrier".
762:
and colleagues have investigated the effects of transcrocetinate sodium in animal models. They discovered that the drug could reverse the potentially fatal decrease in blood pressure produced by the loss of large volumes of blood in severe
1415:
853:
between the water molecules. This in turn causes the overall organization of water molecules in plasma to become more structured, which facilitates the diffusion of oxygen through plasma and promotes the movement of oxygen into tissues.
1043:
Mizuma H, Tanaka M, Nozaki S, Mizuno K, Tahara T, Ataka S, Sugino T, Shirai T, Kajimoto Y, Kuratsune H, Kajimoto O, Watanabe Y (March 2009). "Daily oral administration of crocetin attenuates physical fatigue in human subjects".
1290:
Lapchak P (2010). "Efficacy and safety profile of the carotenoid trans sodium crocetinate administered to rabbits following multiple infarct ischemic strokes: A combination therapy study with tissue plasminogen activator".
1118:
Yamauchi, M; Tsuruma, K; Imai, S; Nakanishi, T; Umigai, N; Shimazawa, M; Hara, H (2011). "Crocetin prevents retinal degeneration induced by oxidative and endoplasmic reticulum stresses via inhibition of caspase activity".
2054:
778:. Additional studies, carried out in animal models, and in clinical trials in humans, indicated that transcrocetinate sodium might prove beneficial in the treatment of a variety of conditions associated with
2074:
805:(PAD) in which reduced delivery of oxygen-rich blood to tissues can cause severe leg pain and impair mobility. The drug has also been under investigation in a clinical trial sponsored by drug developer
1594:
Lautenschläger M, Lechtenberg M, Sendker J, Hensel A (2014). "Effective isolation protocol for secondary metabolites from saffron: semi-preparative scale preparation of crocin-1 and trans-crocetin".
1006:
Nam KN, Park YM, Jung HJ, Lee JY, Min BD, Park SU, Jung WS, Cho KH, Park JH, Kang I, Hong JW, Lee EH (2010). "Anti-inflammatory effects of crocin and crocetin in rat brain microglial cells".
4071:
2047:
599:
4064:
165:
2040:
930:
Umigai N, Murakami K, Ulit MV, et al. (May 2011). "The pharmacokinetic profile of crocetin in healthy adult human volunteers after a single oral administration".
801:
Transcrocetinate sodium has shown promise of effectiveness in restoring tissue oxygen levels and improving the ability to walk in a clinical trial of patients with
436:
InChI=1S/C20H24O4/c1-15(11-7-13-17(3)19(21)22)9-5-6-10-16(2)12-8-14-18(4)20(23)24/h5-14H,1-4H3,(H,21,22)(H,23,24)/b6-5+,11-7+,12-8+,15-9+,16-10+,17-13+,18-14+
462:
446:
InChI=1/C20H24O4/c1-15(11-7-13-17(3)19(21)22)9-5-6-10-16(2)12-8-14-18(4)20(23)24/h5-14H,1-4H3,(H,21,22)(H,23,24)/b6-5+,11-7+,12-8+,15-9+,16-10+,17-13+,18-14+
727:(oxygen-starved) tissues. Transcrocetinate sodium belongs to a group of substances known as bipolar trans carotenoid salts, which constitute a subclass of
1390:"Safety and Efficacy Study of Trans Sodium Crocetinate (TSC) With Concomitant Radiation Therapy and Temozolomide in Newly Diagnosed Glioblastoma (GBM)"
1475:
Laidig, K.E.; J.L. Gainer; V. Daggett (1998). "Altering
Diffusivity in Biological Solutions through Modification of Solution Structure and Dynamics".
3123:
1551:
Berger F, Hensel A, Nieber K (2011). "Saffron extract and trans-crocetin inhibit glutamatergic synaptic transmission in rat cortical brain slices".
1339:"Evaluation of trans sodium crocetinate on safety and exercise performance in patients with peripheral artery disease and intermittent claudication"
677:
A 2009 study involving 14 individuals indicated that oral administration of crocetin may decrease the effects of physical fatigue in healthy men.
3155:
1682:
2744:
1255:
Giassi L; et al. (2001). "Trans-Sodium
Crocetinate Restores Blood Pressure, Heart Rate, and Plasma Lactate after Hemorrhagic Shock".
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838:
728:
46:
4103:
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2819:
712:
427:
1416:"Diffusion Pharmaceuticals Announces FDA Accelerated Review of TSC Clinical Development Plan to Treat COVID-19 Patients with ARDS"
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1234:, Gainer J, "Trans-sodium crocetinate, methods of making and methods of use thereof", issued 2000-05-09
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1210:, Gainer J, "New Class of Therapeutics that Enhance Small Molecule Diffusion", issued 2009-04-30
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fruits. It is also known as crocetic acid. It forms brick red crystals with a melting point of 285 °C.
273:
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786:(a lack of oxygen reaching the tissues, usually due to a disruption in the circulatory system), including
235:
37:
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2502:
1231:
1207:
825:. The drug is currently under investigation for its possible use in enhancing the oxygenation status of
791:
715:, also known as trans sodium crocetinate or TSC) is an experimental drug that increases the movement of
544:
69:
59:
2021:
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in rats by reducing the production of various neurotoxic molecules, based on an in-vitro cell study.
642:
408:
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775:
657:. Crocetin is usually extracted commercially from gardenia fruit, due to the high cost of saffron.
123:
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Kuratsune H, Umigai N, Takeno R, Kajimoto Y, Nakano T (September 2010). "Effect of crocetin from
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195:
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2011:
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Early investigations of transcrocetinate sodium suggested that it had potential applications in
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patients at risk for developing multiple organ failure due to severe respiratory distress.
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841:, transcrocetinate sodium appears to improve oxygenation in hypoxic tissues by exerting
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215:
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Stennett a; et al. (2006). "Trans sodium crocetinate and diffusion enhancement".
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1504:"Protection against focal ischemic injury to the brain by trans-sodium crocetinate"
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Gainer, J (2008). "Trans-sodium crocetinate for treating hypoxia/ischemia".
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Ichi, T; Higashimura, Y; Katayama, T; Koda, T; Shimizu, T; Tada, M (1995).
951:
731:. Transcrocetinate sodium was one of the first such compounds discovered.
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In high concentrations, it has protective effects against retinal damage
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Tooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
1923:
1845:
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755:
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637:
629:
226:
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Except where otherwise noted, data are given for materials in their
312:
102:)-2,6,11,15-Tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid
3897:
3322:
3113:
2839:
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2175:
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733:
206:
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2315:
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2103:
303:
2036:
1664:
774:, specifically in treatment of the many combat casualties with
3028:
1660:
649:
The chemical structure of crocetin forms the central core of
396:
594:
3320:
Uncompetitive pore blockers (mostly dizocilpine site):
1257:
Journal of Trauma-Injury
Infection & Critical Care
2726:
742:
Transcrocetinate sodium can be prepared by reacting
2724:
2482:
2073:
1967:
1937:
1884:
1776:
1698:
821:, in patients with a form of brain cancer known as
182:
967:"Analysis of Crocetin Derivatives from Gardenia"
350:
139:
132:
111:8,8'-Diapocarotenedioic acid; Transcrocetinate
2978:
2963:
2048:
1676:
470:CC(C=CC=C(C)C(O)=O)=CC=CC=C(C)C=CC=C(C)C(O)=O
8:
1156:
1154:
1152:
1150:
653:, the compound responsible for the color of
1435:
1433:
1226:
1224:
1222:
857:Trans-crocetin has been found to act as an
4065:Metabotropic glutamate receptor modulators
2055:
2041:
2033:
1683:
1669:
1661:
1202:
1200:
411:
276:
254:
29:
4072:Glutamate metabolism/transport modulators
1527:
1384:
1382:
1362:
1332:
1330:
1250:
1248:
1246:
982:
377:
370:
2484:
1477:Journal of the American Chemical Society
1418:. Diffusion Pharmaceuticals. May 5, 2020
1163:Expert Opinion on Investigational Drugs
895:
893:
889:
467:
432:
407:
328:
3795:Alcohols/volatile anesthetics/related:
711:of crocetin, transcrocetinate sodium (
539:285 °C (545 °F; 558 K)
267:
2951:Other positive allosteric modulators:
2731:Tooltip N-Methyl-D-aspartate receptor
439:Key: PANKHBYNKQNAHN-MQQNZMFNSA-N
234:
214:
7:
971:Nippon Shokuhin Kagaku Kogaku Kaishi
839:oxygen diffusion-enhancing compounds
729:oxygen diffusion-enhancing compounds
3692:Ifenprodil (NR2B) site antagonists:
1442:The Journal of Physical Chemistry B
813:, increasing the susceptibility of
449:Key: PANKHBYNKQNAHN-MQQNZMFNBY
341:
311:
2256:Pesampator (BIIB-104, PF-04958242)
1565:10.1016/j.neuroscience.2011.02.037
63:8,8′-Diapocarotene-8,8′-dioic acid
25:
865:, and has been implicated in the
1269:10.1097/00005373-200111000-00018
1121:European Journal of Pharmacology
1083:Ellis on sleep: a pilot study".
1009:European Journal of Pharmacology
767:, and thereby improve survival.
665:Crocin and crocetin may provide
584:
497:
45:
36:
3732:Rislenemdaz (CERC-301, MK-0657)
2679:Negative allosteric modulators:
2567:Positive allosteric modulators:
2390:Negative allosteric modulators:
2143:Positive allosteric modulators:
580:(at 25 °C , 100 kPa).
2968:Tooltip Dehydroepiandrosterone
2276:Tulrampator (S-47445, CX-1632)
2171:Farampator (CX-691, ORG-24448)
1502:Manabe H; et al. (2010).
1337:Mohler E; et al. (2010).
1305:10.1016/j.brainres.2009.10.067
845:effects on water molecules in
503:
491:
1:
4058:Receptor/signaling modulators
3907:Unknown/unsorted antagonists:
2471:Unknown/unsorted antagonists:
2064:Ionotropic glutamate receptor
1644:10.1016/j.phymed.2014.10.009
1608:10.1016/j.fitote.2013.11.014
1133:10.1016/j.ejphar.2010.09.081
1097:10.1016/j.phymed.2010.03.025
1058:10.1016/j.nutres.2009.02.003
1022:10.1016/j.ejphar.2010.09.003
944:10.1016/j.phymed.2010.10.019
27:Carotenoid chemical compound
3756:NR2A-selective antagonists:
3288:Polyamine site antagonists:
2513:Acromelic acid (acromelate)
2099:Acromelic acid (acromelate)
849:and thereby increasing the
4125:
2196:Hydrochlorothiazide (HCTZ)
4104:NMDA receptor antagonists
4049:
3138:Glycine site antagonists:
1175:10.1517/13543784.17.6.917
807:Diffusion Pharmaceuticals
803:peripheral artery disease
632:flower together with its
574:
478:
458:
423:
116:
108:
68:
58:
53:
44:
35:
3026:Competitive antagonists:
2934:Polyamine site agonists:
2920:Neboglamine (nebostinel)
2489:Tooltip Kainate receptor
1520:10.3171/2009.10.JNS09562
1355:10.1177/1358863X11422742
859:NMDA receptor antagonist
18:Trans sodium crocetinate
4008:Pentamidine isethionate
3752:Traxoprodil (CP-101606)
2991:Epipregnanolone sulfate
1508:Journal of Neurosurgery
1232:US patent 6,060,511
1208:US patent 8,206,751
809:for potential use as a
738:Transcrocetinate sodium
700:Transcrocetinate sodium
4038:Allosteric modulators:
3973:Ipenoxazone (MLV-6976)
3628:Pethidine (meperidine)
3249:Licostinel (ACEA-1021)
3171:Apimostinel (NRX-1074)
2835:Apimostinel (NRX-1074)
2803:Glycine site agonists:
2635:Licostinel (ACEA-1021)
2346:Licostinel (ACEA-1021)
2231:Mibampator (LY-451395)
1938:Vitamin A retinoids (C
754:of the trans crocetin
739:
3707:CO-101244 (PD-174494)
3423:Delucemine (NPS-1506)
3373:Alazocine (SKF-10047)
792:myocardial infarction
737:
673:Physiological effects
628:that is found in the
70:Systematic IUPAC name
3727:Radiprodil (RGH-896)
3702:Buphenine (nylidrin)
3279:Rapastinel (GLYX-13)
3094:Midafotel (d-CPPene)
3001:Pregnenolone sulfate
2925:Rapastinel (GLYX-13)
2716:Pregnenolone sulfate
2457:Pregnenolone sulfate
1081:Gardenia jasminoides
984:10.3136/nskkk.42.776
815:hypoxic cancer cells
794:(heart attack), and
772:battlefield medicine
643:Gardenia jasminoides
2958:-Hydroxycholesterol
2769:Homoquinolinic acid
2742:Main site agonists:
2500:Main site agonists:
2094:5-Fluorowillardiine
2091:Main site agonists:
1448:(37): 18078–18080.
833:Mechanism of action
758:from the solution.
750:and extracting the
521: g·mol
382: (sodium salt)
196:Beilstein Reference
144: (sodium salt)
32:
4099:Dicarboxylic acids
3306:Diethylenetriamine
2985:prasterone sulfate
2760:Homocysteic acid (
2503:5-Bromowillardiine
1394:ClinicalTrials.gov
1046:Nutrition Research
740:
607:Infobox references
30:
4081:
4080:
3932:
3888:Trichloroethylene
3833:Ethanol (alcohol)
3198:
3141:4-Cl-KYN (AV-101)
2909:
2901:
2868:
2860:
2852:
2809:
2794:Tetrazolylglycine
2763:
2701:Ethanol (alcohol)
2690:sodium thiopental
2508:5-Iodowillardiine
2417:Ethanol (alcohol)
2401:sodium thiopental
2030:
2029:
2022:Zuretinol acetate
1489:10.1021/ja981656j
1483:(36): 9394–9395.
1454:10.1021/jp064308+
1343:Vascular Medicine
837:Similar to other
819:radiation therapy
776:hemorrhagic shock
626:dicarboxylic acid
615:Chemical compound
613:
612:
392:CompTox Dashboard
166:Interactive image
16:(Redirected from
4116:
3930:
3883:Trichloroethanol
3443:Dextromethorphan
3196:
2980:
2969:
2965:
2907:
2899:
2866:
2858:
2850:
2807:
2761:
2732:
2728:
2490:
2486:
2321:Fanapanel (MPQX)
2081:
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996:
986:
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927:
921:
912:
906:
902:, 11th Edition,
897:
851:hydrogen bonding
748:sodium hydroxide
597:
591:
588:
587:
520:
505:
499:
493:
486:Chemical formula
416:
415:
400:
398:
381:
374:
354:
343:
332:
315:
288:
280:
269:
258:
238:
218:
186:
168:
143:
136:
49:
40:
33:
21:
4124:
4123:
4119:
4118:
4117:
4115:
4114:
4113:
4084:
4083:
4082:
4077:
4045:
3943:Flufenamic acid
3878:Trichloroethane
3653:Rhynchophylline
3573:Methoxphenidine
3538:Levomilnacipran
3438:Dextromethadone
3363:α-Endopsychosin
2967:
2879:Dimethylglycine
2789:Quinolinic acid
2730:
2720:
2558:Quisqualic acid
2488:
2478:
2134:Quisqualic acid
2079:
2069:
2061:
2031:
2026:
1963:
1941:
1933:
1891:
1880:
1783:
1772:
1705:
1694:
1689:
1659:
1628:
1627:
1623:
1593:
1592:
1588:
1550:
1549:
1545:
1501:
1500:
1496:
1474:
1473:
1469:
1439:
1438:
1431:
1421:
1419:
1414:
1413:
1409:
1399:
1397:
1396:. November 2011
1388:
1387:
1380:
1336:
1335:
1328:
1289:
1288:
1284:
1254:
1253:
1244:
1237:
1230:
1229:
1220:
1213:
1206:
1205:
1198:
1160:
1159:
1148:
1117:
1116:
1112:
1078:
1077:
1073:
1042:
1041:
1037:
1005:
1004:
1000:
977:(10): 776–783.
964:
963:
959:
929:
928:
924:
913:
909:
898:
891:
887:
875:
835:
811:radiosensitizer
721:red blood cells
702:
675:
667:neuroprotection
663:
616:
609:
604:
603:
602: ?)
593:
589:
585:
581:
566:
518:
508:
502:
496:
488:
474:
471:
466:
465:
454:
451:
450:
447:
441:
440:
437:
431:
430:
419:
409:DTXSID201015585
401:
394:
385:
357:
344:
318:
298:
261:
241:
221:
198:
189:
171:
158:
147:
126:
112:
104:
103:
64:
28:
23:
22:
15:
12:
11:
5:
4122:
4120:
4112:
4111:
4106:
4101:
4096:
4094:Apocarotenoids
4086:
4085:
4079:
4078:
4076:
4075:
4068:
4061:
4050:
4047:
4046:
4044:
4043:
4031:
4030:
4020:
4015:
4010:
4005:
4000:
3995:
3990:
3985:
3980:
3975:
3970:
3965:
3960:
3955:
3950:
3945:
3940:
3935:
3927:
3922:
3917:
3912:
3900:
3895:
3890:
3885:
3880:
3875:
3870:
3865:
3860:
3855:
3853:Methoxyflurane
3850:
3845:
3840:
3835:
3830:
3825:
3820:
3815:
3810:
3805:
3800:
3788:
3783:
3771:
3766:
3761:
3749:
3744:
3739:
3734:
3729:
3724:
3719:
3714:
3709:
3704:
3699:
3694:
3685:
3680:
3675:
3670:
3665:
3660:
3655:
3650:
3645:
3640:
3635:
3630:
3625:
3620:
3615:
3610:
3605:
3600:
3598:Nitromemantine
3595:
3590:
3585:
3580:
3575:
3570:
3565:
3560:
3555:
3550:
3545:
3540:
3535:
3533:Levomethorphan
3530:
3525:
3520:
3515:
3510:
3505:
3500:
3495:
3490:
3485:
3480:
3475:
3470:
3465:
3460:
3455:
3453:Dieticyclidine
3450:
3445:
3440:
3435:
3433:Dextrallorphan
3430:
3425:
3420:
3415:
3410:
3405:
3400:
3395:
3390:
3388:Argiotoxin-636
3385:
3380:
3375:
3370:
3365:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3325:
3313:
3308:
3303:
3301:Diaminopropane
3298:
3293:
3281:
3276:
3271:
3266:
3261:
3256:
3251:
3246:
3241:
3236:
3231:
3229:Kynurenic acid
3226:
3221:
3216:
3211:
3206:
3201:
3193:
3188:
3183:
3178:
3173:
3168:
3163:
3158:
3153:
3148:
3143:
3131:
3126:
3121:
3116:
3111:
3106:
3101:
3096:
3091:
3086:
3081:
3076:
3071:
3066:
3061:
3056:
3051:
3046:
3041:
3036:
3031:
3019:
3018:
3013:
3008:
3003:
2998:
2993:
2988:
2975:
2960:
2944:
2939:
2927:
2922:
2917:
2912:
2904:
2896:
2891:
2886:
2881:
2876:
2871:
2863:
2855:
2847:
2842:
2837:
2832:
2827:
2822:
2817:
2812:
2796:
2791:
2786:
2781:
2776:
2771:
2766:
2757:
2752:
2747:
2735:
2733:
2722:
2721:
2719:
2718:
2713:
2708:
2703:
2698:
2693:
2672:
2667:
2662:
2657:
2652:
2647:
2642:
2637:
2632:
2630:Kynurenic acid
2627:
2622:
2617:
2612:
2607:
2602:
2593:
2592:
2587:
2582:
2577:
2572:
2560:
2555:
2550:
2545:
2540:
2535:
2530:
2525:
2520:
2515:
2510:
2505:
2493:
2491:
2480:
2479:
2477:
2476:
2464:
2459:
2454:
2449:
2444:
2439:
2434:
2429:
2424:
2419:
2414:
2409:
2404:
2383:
2378:
2373:
2368:
2363:
2358:
2353:
2348:
2343:
2338:
2336:Kynurenic acid
2333:
2328:
2323:
2318:
2313:
2308:
2303:
2298:
2293:
2288:
2279:
2278:
2273:
2268:
2263:
2258:
2253:
2248:
2243:
2238:
2233:
2228:
2223:
2218:
2213:
2208:
2203:
2198:
2193:
2188:
2183:
2178:
2173:
2168:
2163:
2158:
2153:
2148:
2136:
2131:
2126:
2121:
2116:
2111:
2106:
2101:
2096:
2084:
2082:
2071:
2070:
2062:
2060:
2059:
2052:
2045:
2037:
2028:
2027:
2025:
2024:
2019:
2014:
2009:
2004:
1999:
1994:
1989:
1984:
1979:
1973:
1971:
1969:Retinoid drugs
1965:
1964:
1962:
1961:
1956:
1951:
1945:
1943:
1939:
1935:
1934:
1932:
1931:
1926:
1921:
1916:
1911:
1906:
1901:
1895:
1893:
1889:
1886:Apocarotenoids
1882:
1881:
1879:
1878:
1873:
1868:
1863:
1858:
1853:
1848:
1843:
1838:
1833:
1828:
1823:
1818:
1816:Diadinoxanthin
1813:
1808:
1806:Citranaxanthin
1803:
1798:
1793:
1791:Antheraxanthin
1787:
1785:
1781:
1774:
1773:
1771:
1770:
1765:
1760:
1755:
1750:
1745:
1740:
1735:
1730:
1725:
1720:
1715:
1709:
1707:
1703:
1696:
1695:
1690:
1688:
1687:
1680:
1673:
1665:
1658:
1657:
1621:
1586:
1543:
1514:(4): 802–809.
1494:
1467:
1429:
1407:
1378:
1349:(5): 346–352.
1326:
1293:Brain Research
1282:
1263:(5): 932–938.
1242:
1218:
1196:
1169:(6): 917–924.
1146:
1110:
1071:
1035:
1016:(1–3): 110–6.
998:
957:
922:
907:
888:
886:
883:
882:
881:
874:
871:
867:psychoactivity
834:
831:
760:John L. Gainer
701:
698:
674:
671:
662:
659:
614:
611:
610:
605:
583:
582:
578:standard state
575:
572:
571:
568:
564:
554:
553:
550:
541:
540:
537:
531:
530:
527:
523:
522:
516:
510:
509:
506:
500:
494:
489:
484:
481:
480:
476:
475:
473:
472:
469:
461:
460:
459:
456:
455:
453:
452:
448:
445:
444:
442:
438:
435:
434:
426:
425:
424:
421:
420:
418:
417:
404:
402:
390:
387:
386:
384:
383:
375:
367:
365:
359:
358:
356:
355:
347:
345:
337:
334:
333:
326:
320:
319:
317:
316:
308:
306:
300:
299:
297:
296:
292:
290:
282:
281:
271:
263:
262:
260:
259:
251:
249:
243:
242:
240:
239:
231:
229:
223:
222:
220:
219:
211:
209:
203:
202:
199:
194:
191:
190:
188:
187:
179:
177:
173:
172:
170:
169:
161:
159:
152:
149:
148:
146:
145:
137:
129:
127:
122:
119:
118:
114:
113:
110:
106:
105:
73:
72:
66:
65:
62:
56:
55:
51:
50:
42:
41:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
4121:
4110:
4107:
4105:
4102:
4100:
4097:
4095:
4092:
4091:
4089:
4074:
4073:
4069:
4067:
4066:
4062:
4060:
4059:
4056:
4052:
4051:
4048:
4042:
4039:
4036:
4033:
4032:
4028:
4024:
4023:Transcrocetin
4021:
4019:
4018:Psychotridine
4016:
4014:
4011:
4009:
4006:
4004:
4001:
3999:
3998:Niflumic acid
3996:
3994:
3991:
3989:
3986:
3984:
3981:
3979:
3976:
3974:
3971:
3969:
3966:
3964:
3961:
3959:
3956:
3954:
3951:
3949:
3946:
3944:
3941:
3939:
3936:
3934:
3928:
3926:
3923:
3921:
3918:
3916:
3913:
3911:
3908:
3904:
3901:
3899:
3896:
3894:
3891:
3889:
3886:
3884:
3881:
3879:
3876:
3874:
3871:
3869:
3866:
3864:
3861:
3859:
3858:Nitrous oxide
3856:
3854:
3851:
3849:
3846:
3844:
3841:
3839:
3836:
3834:
3831:
3829:
3826:
3824:
3823:Diethyl ether
3821:
3819:
3816:
3814:
3811:
3809:
3806:
3804:
3801:
3799:
3796:
3792:
3789:
3787:
3784:
3782:
3779:
3775:
3772:
3770:
3767:
3765:
3762:
3760:
3757:
3753:
3750:
3748:
3745:
3743:
3740:
3738:
3735:
3733:
3730:
3728:
3725:
3723:
3720:
3718:
3715:
3713:
3710:
3708:
3705:
3703:
3700:
3698:
3695:
3693:
3689:
3686:
3684:
3681:
3679:
3678:Tenocyclidine
3676:
3674:
3673:Tabernanthine
3671:
3669:
3666:
3664:
3663:Rolicyclidine
3661:
3659:
3656:
3654:
3651:
3649:
3646:
3644:
3641:
3639:
3638:Phencyclidine
3636:
3634:
3633:Phencyclamine
3631:
3629:
3626:
3624:
3621:
3619:
3616:
3614:
3611:
3609:
3606:
3604:
3601:
3599:
3596:
3594:
3591:
3589:
3586:
3584:
3581:
3579:
3576:
3574:
3571:
3569:
3568:Methoxetamine
3566:
3564:
3561:
3559:
3556:
3554:
3551:
3549:
3546:
3544:
3541:
3539:
3536:
3534:
3531:
3529:
3528:Levomethadone
3526:
3524:
3521:
3519:
3516:
3514:
3511:
3509:
3506:
3504:
3501:
3499:
3496:
3494:
3491:
3489:
3488:Fluorolintane
3486:
3484:
3481:
3479:
3476:
3474:
3471:
3469:
3466:
3464:
3461:
3459:
3456:
3454:
3451:
3449:
3446:
3444:
3441:
3439:
3436:
3434:
3431:
3429:
3426:
3424:
3421:
3419:
3416:
3414:
3411:
3409:
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3384:
3381:
3379:
3376:
3374:
3371:
3369:
3366:
3364:
3361:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3317:
3314:
3312:
3309:
3307:
3304:
3302:
3299:
3297:
3294:
3292:
3289:
3285:
3282:
3280:
3277:
3275:
3272:
3270:
3267:
3265:
3262:
3260:
3257:
3255:
3252:
3250:
3247:
3245:
3242:
3240:
3237:
3235:
3232:
3230:
3227:
3225:
3222:
3220:
3217:
3215:
3212:
3210:
3207:
3205:
3202:
3200:
3194:
3192:
3189:
3187:
3184:
3182:
3179:
3177:
3174:
3172:
3169:
3167:
3164:
3162:
3159:
3157:
3154:
3152:
3149:
3147:
3144:
3142:
3139:
3135:
3132:
3130:
3127:
3125:
3122:
3120:
3117:
3115:
3112:
3110:
3107:
3105:
3102:
3100:
3097:
3095:
3092:
3090:
3087:
3085:
3082:
3080:
3077:
3075:
3072:
3070:
3069:Kaitocephalin
3067:
3065:
3062:
3060:
3057:
3055:
3052:
3050:
3047:
3045:
3042:
3040:
3037:
3035:
3032:
3030:
3027:
3024:
3021:
3020:
3017:
3014:
3012:
3009:
3007:
3004:
3002:
2999:
2997:
2994:
2992:
2989:
2986:
2982:
2976:
2973:
2966:
2961:
2959:
2957:
2952:
2948:
2945:
2943:
2940:
2938:
2935:
2931:
2928:
2926:
2923:
2921:
2918:
2916:
2913:
2911:
2905:
2903:
2897:
2895:
2892:
2890:
2887:
2885:
2882:
2880:
2877:
2875:
2872:
2870:
2864:
2862:
2856:
2854:
2848:
2846:
2843:
2841:
2838:
2836:
2833:
2831:
2828:
2826:
2823:
2821:
2818:
2816:
2813:
2811:
2804:
2800:
2797:
2795:
2792:
2790:
2787:
2785:
2782:
2780:
2777:
2775:
2774:Ibotenic acid
2772:
2770:
2767:
2765:
2758:
2756:
2753:
2751:
2748:
2746:
2743:
2740:
2737:
2736:
2734:
2729:
2723:
2717:
2714:
2712:
2709:
2707:
2704:
2702:
2699:
2697:
2694:
2691:
2687:
2686:pentobarbital
2683:
2680:
2676:
2673:
2671:
2668:
2666:
2663:
2661:
2658:
2656:
2653:
2651:
2648:
2646:
2643:
2641:
2638:
2636:
2633:
2631:
2628:
2626:
2625:Kaitocephalin
2623:
2621:
2618:
2616:
2613:
2611:
2608:
2606:
2603:
2601:
2598:
2595:
2594:
2591:
2588:
2586:
2583:
2581:
2578:
2576:
2573:
2571:
2570:Cyclothiazide
2568:
2564:
2561:
2559:
2556:
2554:
2551:
2549:
2546:
2544:
2541:
2539:
2538:Ibotenic acid
2536:
2534:
2531:
2529:
2526:
2524:
2521:
2519:
2516:
2514:
2511:
2509:
2506:
2504:
2501:
2498:
2495:
2494:
2492:
2487:
2481:
2475:
2472:
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:
2402:
2398:
2397:pentobarbital
2394:
2391:
2387:
2384:
2382:
2379:
2377:
2374:
2372:
2369:
2367:
2364:
2362:
2359:
2357:
2354:
2352:
2349:
2347:
2344:
2342:
2339:
2337:
2334:
2332:
2331:Kaitocephalin
2329:
2327:
2324:
2322:
2319:
2317:
2314:
2312:
2309:
2307:
2304:
2302:
2299:
2297:
2294:
2292:
2289:
2287:
2284:
2281:
2280:
2277:
2274:
2272:
2269:
2267:
2264:
2262:
2259:
2257:
2254:
2252:
2249:
2247:
2244:
2242:
2239:
2237:
2234:
2232:
2229:
2227:
2224:
2222:
2219:
2217:
2214:
2212:
2209:
2207:
2204:
2202:
2199:
2197:
2194:
2192:
2189:
2187:
2184:
2182:
2179:
2177:
2174:
2172:
2169:
2167:
2164:
2162:
2159:
2157:
2154:
2152:
2151:Cyclothiazide
2149:
2147:
2144:
2140:
2137:
2135:
2132:
2130:
2127:
2125:
2124:Ibotenic acid
2122:
2120:
2117:
2115:
2112:
2110:
2107:
2105:
2102:
2100:
2097:
2095:
2092:
2089:
2086:
2085:
2083:
2078:
2072:
2068:
2065:
2058:
2053:
2051:
2046:
2044:
2039:
2038:
2035:
2023:
2020:
2018:
2015:
2013:
2010:
2008:
2005:
2003:
2000:
1998:
1995:
1993:
1990:
1988:
1985:
1983:
1980:
1978:
1975:
1974:
1972:
1970:
1966:
1960:
1957:
1955:
1954:Retinoic acid
1952:
1950:
1947:
1946:
1944:
1936:
1930:
1927:
1925:
1922:
1920:
1919:Food orange 7
1917:
1915:
1912:
1910:
1907:
1905:
1902:
1900:
1899:Abscisic acid
1897:
1896:
1894:
1887:
1883:
1877:
1874:
1872:
1869:
1867:
1864:
1862:
1859:
1857:
1854:
1852:
1849:
1847:
1844:
1842:
1839:
1837:
1834:
1832:
1829:
1827:
1824:
1822:
1819:
1817:
1814:
1812:
1811:Cryptoxanthin
1809:
1807:
1804:
1802:
1801:Canthaxanthin
1799:
1797:
1794:
1792:
1789:
1788:
1786:
1779:
1775:
1769:
1766:
1764:
1761:
1759:
1756:
1754:
1751:
1749:
1746:
1744:
1741:
1739:
1736:
1734:
1731:
1729:
1726:
1724:
1721:
1719:
1716:
1714:
1711:
1710:
1708:
1701:
1697:
1693:
1686:
1681:
1679:
1674:
1672:
1667:
1666:
1663:
1653:
1649:
1645:
1641:
1637:
1633:
1632:Phytomedicine
1625:
1622:
1617:
1613:
1609:
1605:
1601:
1597:
1590:
1587:
1582:
1578:
1574:
1570:
1566:
1562:
1558:
1554:
1547:
1544:
1539:
1535:
1530:
1525:
1521:
1517:
1513:
1509:
1505:
1498:
1495:
1490:
1486:
1482:
1478:
1471:
1468:
1463:
1459:
1455:
1451:
1447:
1443:
1436:
1434:
1430:
1417:
1411:
1408:
1395:
1391:
1385:
1383:
1379:
1374:
1370:
1365:
1360:
1356:
1352:
1348:
1344:
1340:
1333:
1331:
1327:
1322:
1318:
1314:
1310:
1306:
1302:
1298:
1294:
1286:
1283:
1278:
1274:
1270:
1266:
1262:
1258:
1251:
1249:
1247:
1243:
1233:
1227:
1225:
1223:
1219:
1209:
1203:
1201:
1197:
1192:
1188:
1184:
1180:
1176:
1172:
1168:
1164:
1157:
1155:
1153:
1151:
1147:
1142:
1138:
1134:
1130:
1126:
1122:
1114:
1111:
1106:
1102:
1098:
1094:
1091:(11): 840–3.
1090:
1086:
1085:Phytomedicine
1082:
1075:
1072:
1067:
1063:
1059:
1055:
1052:(3): 145–50.
1051:
1047:
1039:
1036:
1031:
1027:
1023:
1019:
1015:
1011:
1010:
1002:
999:
994:
990:
985:
980:
976:
972:
968:
961:
958:
953:
949:
945:
941:
937:
933:
932:Phytomedicine
926:
923:
920:
916:
911:
908:
905:
901:
896:
894:
890:
884:
880:
877:
876:
872:
870:
868:
864:
860:
855:
852:
848:
844:
840:
832:
830:
828:
824:
820:
816:
812:
808:
804:
799:
797:
793:
789:
785:
781:
777:
773:
768:
766:
761:
757:
753:
749:
745:
736:
732:
730:
726:
722:
718:
714:
710:
707:
699:
697:
695:
694:
689:
688:
682:
678:
672:
670:
668:
660:
658:
656:
652:
647:
645:
644:
639:
635:
631:
627:
624:
623:apocarotenoid
621:is a natural
620:
608:
601:
596:
579:
573:
569:
563:
559:
556:
555:
551:
549:
548:
543:
542:
538:
536:
535:Melting point
533:
532:
529:Red crystals
528:
525:
524:
517:
515:
512:
511:
490:
487:
483:
482:
477:
468:
464:
457:
443:
433:
429:
422:
414:
410:
406:
405:
403:
393:
389:
388:
380:
376:
373:
369:
368:
366:
364:
361:
360:
353:
349:
348:
346:
340:
336:
335:
331:
327:
325:
322:
321:
314:
310:
309:
307:
305:
302:
301:
294:
293:
291:
289:
284:
283:
279:
275:
272:
270:
268:ECHA InfoCard
265:
264:
257:
253:
252:
250:
248:
245:
244:
237:
233:
232:
230:
228:
225:
224:
217:
213:
212:
210:
208:
205:
204:
200:
197:
193:
192:
185:
181:
180:
178:
175:
174:
167:
163:
162:
160:
156:
151:
150:
142:
138:
135:
131:
130:
128:
125:
121:
120:
115:
107:
101:
97:
93:
89:
85:
81:
77:
71:
67:
61:
57:
52:
48:
43:
39:
34:
19:
4070:
4063:
4054:
4053:
4037:
4034:
3906:
3813:Cyclopropane
3794:
3777:
3755:
3691:
3643:Propoxyphene
3613:Orphenadrine
3518:Ketobemidone
3483:Eticyclidine
3418:Coronaridine
3403:ARL-15896-AR
3319:
3287:
3199:-Cycloserine
3181:Carisoprodol
3137:
3025:
3023:Antagonists:
3022:
2955:
2950:
2933:
2861:-Cycloserine
2802:
2741:
2738:
2682:Barbiturates
2678:
2655:Selurampanel
2610:Dasolampanel
2597:Antagonists:
2596:
2566:
2499:
2496:
2470:
2407:Cyclopropane
2393:Barbiturates
2389:
2361:Selurampanel
2311:Dasolampanel
2283:Antagonists:
2282:
2266:Pramiracetam
2142:
2090:
2087:
2002:Isotretinoin
1982:Alitretinoin
1913:
1904:Apocarotenal
1876:Zeinoxanthin
1866:Violaxanthin
1856:Rhodoxanthin
1836:Flavoxanthin
1821:Diatoxanthin
1778:Xanthophylls
1748:Neurosporene
1638:(1): 36–44.
1635:
1631:
1624:
1599:
1595:
1589:
1556:
1553:Neuroscience
1552:
1546:
1511:
1507:
1497:
1480:
1476:
1470:
1445:
1441:
1420:. Retrieved
1410:
1400:18 September
1398:. Retrieved
1346:
1342:
1296:
1292:
1285:
1260:
1256:
1166:
1162:
1127:(1): 110–9.
1124:
1120:
1113:
1088:
1084:
1080:
1074:
1049:
1045:
1038:
1013:
1007:
1001:
974:
970:
960:
938:(7): 575–8.
935:
931:
925:
910:
903:
899:
869:of saffron.
856:
847:blood plasma
836:
823:glioblastoma
800:
769:
741:
703:
691:
685:
683:
679:
676:
664:
661:Cell studies
648:
641:
618:
617:
561:
546:
236:ChEMBL464792
117:Identifiers
109:Other names
99:
95:
91:
87:
83:
79:
75:
4003:Pentamidine
3988:Minocycline
3968:Hodgkinsine
3938:Dexanabinol
3868:Sevoflurane
3722:Isoxsuprine
3717:Haloperidol
3697:Besonprodil
3658:Rimantadine
3608:Norketamine
3603:Noribogaine
3578:Milnacipran
3543:Levorphanol
3493:Gacyclidine
3463:Dizocilpine
3458:Diphenidine
3448:Dextrorphan
3368:Alaproclate
3311:Huperzine A
3264:Meprobamate
3224:Harkoseride
3119:Perzinfotel
2996:Plazinemdor
2543:Kainic acid
2528:Domoic acid
2474:Minocycline
2462:Sevoflurane
2139:Willardiine
2114:Domoic acid
1997:Fenretinide
1861:Rubixanthin
1841:Fucoxanthin
1826:Dinoxanthin
1796:Astaxanthin
1768:Lycopersene
1758:Phytofluene
1692:Carotenoids
1596:Fitoterapia
1299:: 136–145.
915:CID 5281232
900:Merck Index
843:hydrophobic
526:Appearance
479:Properties
274:100.044.265
141:591230-99-8
4088:Categories
4041:AGN-241751
4013:Piretanide
3963:Furosemide
3948:Flupirtine
3925:Conantokin
3920:Caroverine
3915:Bumetanide
3848:Isoflurane
3818:Desflurane
3808:Chloroform
3747:Safaprodil
3742:Ro 25-6981
3683:Tiletamine
3668:Sabeluzole
3648:Remacemide
3593:Neramexane
3563:Methorphan
3548:Loperamide
3523:Lanicemine
3508:Indantadol
3473:Esketamine
3468:Ephenidine
3428:Dexoxadrol
3393:Arketamine
3378:Amantadine
3338:3-MeO-PCMo
3316:Putrescine
3259:MDL-105519
3234:Kynurenine
3214:Gavestinel
3129:SDZ-220581
3089:MDL-100453
2972:prasterone
2942:Spermidine
2915:Milacemide
2820:ACC (ACPC)
2706:Evans blue
2670:Topiramate
2660:Tezampanel
2590:Isoflurane
2467:Talampanel
2452:Perampanel
2447:Isoflurane
2432:GYKI-53655
2427:GYKI-52466
2422:Evans blue
2386:Zonampanel
2376:Topiramate
2366:Tezampanel
2341:Kynurenine
2301:Caroverine
2296:Becampanel
2246:Oxiracetam
2146:Aniracetam
2067:modulators
2012:Temarotene
2007:Tazarotene
1992:Etretinate
1987:Bexarotene
1871:Zeaxanthin
1851:Neoxanthin
1831:Echinenone
1738:ζ-Carotene
1733:ε-Carotene
1728:δ-Carotene
1723:γ-Carotene
1718:β-Carotene
1713:α-Carotene
1559:: 238–47.
885:References
861:with high
765:hemorrhage
514:Molar mass
379:YP57637WMX
372:20TC155L9C
247:ChemSpider
216:CHEBI:3918
153:3D model (
134:27876-94-4
124:CAS Number
60:IUPAC name
4055:See also:
4035:Unsorted:
3978:MDL-27266
3958:FR-115427
3953:FPL-12495
3910:ARR-15896
3838:Halothane
3828:Enflurane
3786:Magnesium
3737:Ro 8-4304
3712:Eliprodil
3623:PD-137889
3583:Morphanol
3558:Methadone
3553:Memantine
3503:Ibogamine
3478:Etoxadrol
3408:ARL-16247
3398:ARL-12495
3383:Aptiganel
3348:4-MeO-PCP
3343:3-MeO-PCP
3333:3-MeO-PCE
3296:Co 101676
3269:MRZ 2/576
3219:GV-196771
3209:Felbamate
3186:CGP-39653
3166:ACEA-1328
3161:ACEA-1011
3104:NPC-17742
3099:NPC-12626
3084:LY-274614
3079:LY-235959
3074:LY-233053
3059:CGS-19755
3054:CGP-40116
3049:CGP-39653
3044:CGP-39551
3039:CGP-37849
3029:AP5 (APV)
2930:Sarcosine
2806:β-Fluoro-
2755:Glutamate
2750:Aspartate
2739:Agonists:
2696:Enflurane
2640:LY-382884
2600:ACEA-1011
2585:Halothane
2580:Enflurane
2575:Diazoxide
2548:LY-339434
2533:Glutamate
2497:Agonists:
2442:Irampanel
2437:Halothane
2412:Enflurane
2286:ACEA-1011
2261:Piracetam
2241:ORG-26576
2236:Nooglutyl
2226:LY-503430
2221:LY-451646
2216:LY-404187
2211:LY-395153
2206:LY-392098
2191:Diazoxide
2119:Glutamate
2088:Agonists:
2017:Tretinoin
1977:Acitretin
1929:Peridinin
1700:Carotenes
1602:: 290–5.
879:Crocetane
634:glycoside
295:248-708-0
287:EC Number
31:Crocetin
3983:Metaphit
3893:Urethane
3781:Hydrogen
3778:Cations:
3688:Tramadol
3513:Ketamine
3498:Ibogaine
3413:Budipine
3328:3-HO-PCP
3254:LU-73068
3244:L-701324
3239:L-689560
3146:5,7-DCKA
3134:Selfotel
3016:SAGE-718
3011:SAGE-301
3006:SAGE-201
2947:Spermine
2937:Neomycin
2902:-Alanine
2894:L-687414
2853:-Alanine
2810:-alanine
2799:Theanine
2665:Theanine
2563:SYM-2081
2371:Theanine
1914:Crocetin
1763:Torulene
1753:Phytoene
1743:Lycopene
1652:25636868
1616:24321578
1581:23525322
1573:21352900
1538:19961314
1462:16970413
1373:22003000
1321:25369069
1313:19891959
1277:11706343
1191:71663644
1183:18491992
1141:20951131
1105:20537515
1066:19358927
1030:20854811
993:87600533
952:21112749
873:See also
863:affinity
827:COVID-19
784:ischemia
687:in vitro
619:Crocetin
330:crocetin
201:1715455
4109:Saffron
4027:saffron
3873:Toluene
3863:Octanol
3843:Hexanol
3798:Benzene
3774:TCN-213
3769:TCN-201
3764:MPX-007
3759:MPX-004
3353:8A-PDHQ
3291:Arcaine
3284:ZD-9379
2981:sulfate
2910:-Serine
2884:Glycine
2869:-Serine
2784:Proline
2711:NS-3763
2684:(e.g.,
2675:UBP-302
2553:Proline
2395:(e.g.,
2271:S-18986
2201:IDRA-21
2186:CX-1942
2181:CX-1739
2129:Proline
1959:Retinol
1949:Retinal
1924:Ionones
1529:3380430
1422:May 25,
1364:4182020
919:PubChem
780:hypoxia
744:saffron
725:hypoxic
693:in vivo
655:saffron
600:what is
598: (
558:Acidity
519:328.408
352:5281232
339:PubChem
256:4444644
3903:Xylene
3803:Butane
3176:AV-101
2889:HA-966
2176:CX-717
2166:CX-614
2161:CX-546
2156:CX-516
1890:<40
1846:Lutein
1650:
1614:
1579:
1571:
1536:
1526:
1460:
1371:
1361:
1319:
1311:
1275:
1238:
1214:
1189:
1181:
1139:
1103:
1064:
1028:
991:
950:
796:stroke
788:cancer
756:isomer
717:oxygen
706:sodium
651:crocin
640:, and
638:crocin
630:crocus
595:verify
592:
552:4.312
463:SMILES
313:C08588
227:ChEMBL
184:B02312
176:3DMet
54:Names
3898:Xenon
3358:18-MC
3323:2-MDP
3151:7-CKA
3114:PEAQX
2840:B6B21
2830:AK-51
2764:-HCA)
2727:NMDAR
2650:NS102
2381:YM90K
2076:AMPAR
1909:Bixin
1577:S2CID
1317:S2CID
1187:S2CID
989:S2CID
917:from
746:with
723:into
719:from
570:4.39
428:InChI
207:ChEBI
155:JSmol
3993:MPEP
3933:-αAA
3791:Zinc
3618:PCPr
3588:NEFA
3274:PNQX
3204:DNQX
3191:CNQX
3124:PPDA
3109:PBPD
2979:DHEA
2964:DHEA
2874:DHPG
2825:ACPD
2815:ACBD
2779:NMDA
2745:AMAA
2645:NBQX
2620:GAMS
2615:DNQX
2605:CNQX
2523:ATPA
2518:AMPA
2356:PNQX
2351:NBQX
2326:GAMS
2316:DNQX
2306:CNQX
2291:ATPO
2251:PEPA
2109:BOAA
2104:AMPA
1648:PMID
1612:PMID
1569:PMID
1534:PMID
1458:PMID
1424:2020
1402:2012
1369:PMID
1309:PMID
1297:1309
1273:PMID
1179:PMID
1137:PMID
1101:PMID
1062:PMID
1026:PMID
948:PMID
904:2592
782:and
752:salt
709:salt
704:The
690:and
545:log
363:UNII
324:MeSH
304:KEGG
3156:ACC
3064:CPP
3034:AP7
2845:CCG
2485:KAR
1640:doi
1604:doi
1561:doi
1557:180
1524:PMC
1516:doi
1512:113
1485:doi
1481:120
1450:doi
1446:110
1359:PMC
1351:doi
1301:doi
1265:doi
1171:doi
1129:doi
1125:650
1093:doi
1054:doi
1018:doi
1014:648
979:doi
940:doi
817:to
713:INN
397:EPA
342:CID
98:,14
94:,12
90:,10
4090::
3905:;
3793:;
3776:;
3754:;
3690:;
3318:;
3286:;
3136:;
2954:24
2949:;
2932:;
2801:;
2688:,
2677:;
2565:;
2469:;
2399:,
2388:;
2141:;
1940:20
1888:(C
1782:40
1780:(C
1704:40
1702:(C
1646:.
1636:22
1634:.
1610:.
1600:92
1598:.
1575:.
1567:.
1555:.
1532:.
1522:.
1510:.
1506:.
1479:.
1456:.
1444:.
1432:^
1392:.
1381:^
1367:.
1357:.
1347:16
1345:.
1341:.
1329:^
1315:.
1307:.
1295:.
1271:.
1261:51
1259:.
1245:^
1221:^
1199:^
1185:.
1177:.
1167:17
1165:.
1149:^
1135:.
1123:.
1099:.
1089:17
1087:.
1060:.
1050:29
1048:.
1024:.
1012:.
987:.
975:42
973:.
969:.
946:.
936:18
934:.
892:^
798:.
790:,
696:.
636:,
567:)
560:(p
501:24
495:20
86:,8
82:,6
78:,4
74:(2
4029:)
4025:(
3931:D
3197:D
2987:)
2983:(
2974:)
2970:(
2956:S
2908:L
2900:L
2867:D
2859:D
2851:D
2808:D
2762:L
2692:)
2403:)
2056:e
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