280:
36:
27:
1046:
symptoms, including incoordination, flaccid prostration, respiratory and cardiac depression, ptosis, mydriasis, erythema, and death from respiratory paralysis and circulatory collapse. After non-lethal doses, symptoms abated within 15–60 minutes. There was little evidence of toxicity from chronic administration of non-lethal doses. These investigators recorded the following acute toxicities, as LD
395:
885:. Typically, the four ethyl groups surrounding the nitrogen are too small to facilitate efficient ion transfer between aqueous and organic phases, but tetraethylammonium salts have been found to be effective in a number of such applications, and these are exemplified under the headings of the individual salts.
1100:) paralysis of the skeletal muscles, as well as marked drowsiness. These effects were largely dissipated within 2 hours. Citing the work of other investigators, Graham noted that Birchall had also produced "alarming curariform effects" in humans with i.v. doses of 32 mg/kg of tetraethylammonium chloride.
1028:
TEA is not orally active. Typical symptoms produced in humans include the following: dry mouth, suppression of gastric secretion, drastic reduction of gastric motility, paralysis of urinary bladder, and relief of some forms of pain. Most studies with TEA seem to have been performed using either its
1004:
A partial effect of these voltage-dependent and permeability properties within each system mentioned above is not only due to the aforementioned inhibitory properties of TEA, but also its ability to inhibit Na,K-ATPase. Acting on the extracellular vestibule of the Na,K-ATPase, inhibiting K+ access
1045:
in mice, rats and dogs was published by
Gruhzit and co-workers in 1948. These workers reported the following symptoms in mice and rats receiving toxic parenteral doses: tremors, incoordination, flaccid prostration, and death from respiratory failure within 10–30 minutes; dogs exhibited similar
984:
At the mechanistic level, TEA has long been known to block voltage-dependent K channels in nerve, and it is thought that this action is involved in the effects of TEA at sympathetic nerve terminals. With respect to activity at the neuromuscular junction, TEA has been found to be a competitive
1095:
Writing in 1950, Graham made some observations on the toxic effects of tetraethylammonium bromide in humans. In one subject, described as a "healthy woman", 300 mg of tetraethylammonium bromide, i.v., produced incapacitating "curariform" (i.e., resembling the effects of
1316:
H. Tsubaki, E. Nakajima, T. Komai and H. Shindo (1986). "The relation between structure and distribution of quaternary ammonium ions in mice and rats. Simple tetraalkylammonium and a series of m-substituted trimethylphenylammonium ions."
837:
1603:
R. Birchall et al. (1947). "Clinical studies of the pharmacological effects of tetraethyl ammonium chloride in hypertensive persons made in an attempt to select patients suitable for lumbodorsal sympathectomy and ganglioectomy."
1252:
1522:
1988. Inhibition of the electrogenic Na,K pump and Na,K-ATPase activity by tetraethylammonium, tetrabutylammonium, and apamin. Zemková H, Teisinger J, Vyskocil F. J Neurosci Res. Apr;19(4):497-503
1173:
R. L. Dieck, E. J. Peterson, A. Galliart, T. M. Brown, T. Moeller "Tetraethylammonium, Tetraphenylarsonium, and
Ammonium Cyanates and Cyanides" Inorganic Syntheses, 1976, Vol. 16, pp. 131–137
578:
1458:
R. Latorre, C. Vergara, and C. Hidalgo (1982). "Reconstitution in planar lipid bilayers of a Ca-dependent K channel from transverse tubule membranes isolated from rabbit skeletal muscle."
1029:
chloride or bromide salt without comment as to any distinctions in effect, but
Birchall and his co-workers preferred the use of TEA chloride in order to avoid the sedative effects of the
1410:
V. Ceña, A. G. García, C. Gonzalez-Garcia, and S. M. Kirpekar (1985). "Ion dependence of the release of noradrenaline by tetraethylammonium and 4-aminopyridine from cat splenic slices."
1284:
D. H. Aue, H. M. Webb and M. T. Bowers (1976). "A thermodynamic analysis of solvation effects on the basicities of alkylamines. An electrostatic analysis of substituent effects."
1230:
J. Huang, B. G. Sumpter and V. Meunier (2008). "A universal model for nanoporous carbon supercapacitors applicable to diverse pore regimes, carbon materials, and electrolytes."
1506:
R. Søgaard and T. Zeuthen (2008). "Test of blockers of AQP1 water permeability by a high-resolution method: no effects of tetraethylammonium ions or acetazolamide."
1157:
I. M. Kolthoff and J. F. Coetzee (1957). "Polarography in acetonitrile. I. Metal ions which have comparable polarographic properties in acetonitrile and in water."
4723:
4674:
962:
The literature dealing with the pharmacologically-related properties of tetraethylammonium is vast, and research continues. It is clear that TEA blocks autonomic
3439:
3284:
1547:
S. W. Hoobler, G. K. Moe and R. H. Lyons (1949). "The cardiovascular effects of tetraethylammonium in animals and man with special reference to hypertension."
2235:
620:
2106:
4556:
4551:
4541:
4491:
3780:
2164:
2159:
1474:
D. G. Lang and A. K. Ritchie (1990. "Tetraethylammonium blockade of apamin-sensitive and insensitive Ca-activated K channels in a pituitary cell line."
1205:
Naida S. Gill, F. B. Taylor "Tetrahalo
Complexes of Dipositive Metals in the First Transition Series" Inorganic Syntheses, 1967, Vol. 9, pp. 136–142.
1025:. Because of dangerous, even fatal reactions in some patients, as well as inconsistent cardiovascular responses, TEA was soon replaced by other drugs.
903:, especially for the zeolite beta. TEA can act as a template for micropore of zeolites under hydrothermal conditions during crystallization processes.
408:
2230:
1346:, TEA chloride, TEA bromide, or TEA iodide have actually been used, but not always specified as such. Here, the term "TEA" is written for convenience.
1300:
J. Palomo and P. N. Pintauro (2003). "Competitive absorption of quaternary ammonium and alkali metal cations into a Nafion cation-exchange membrane."
2116:
1826:
1766:
1671:
1221:
C. M. Starks, C. L. Liotta and M. Halpern (1994). "Phase-Transfer
Catalysis: Fundamentals, Applications, and Industrial Perspectives." Springer.
4625:
3246:
1991:
1936:
1931:
1896:
989:, although the details of its effect on these receptor proteins are complex. TEA also blocks Ca - activated K channels, such as those found in
4107:
3870:
3800:
2729:
2586:
2461:
2205:
2053:
2016:
1916:
1911:
1811:
1796:
1791:
1756:
881:
The principal chemical characteristic of tetraethylammonium salts is their ability to engage in processes involving phase-transfer, such as
3426:
2849:
2824:
2739:
2386:
2376:
1966:
1956:
1926:
1921:
1886:
1841:
1786:
1776:
1771:
329:
4309:
3431:
3411:
3396:
3366:
2784:
2694:
2126:
2031:
2021:
2001:
1981:
1961:
1620:
O. M. Gruhzit, R. A. Fisken and B. J. Cooper (1948). "Tetraethylammonium chloride . Acute and chronic toxicity in experimental animals."
1013:
Although TEA (sometimes under the name "Etamon") was explored in a number of different clinical applications, including the treatment of
4345:
4102:
4097:
4082:
3386:
2300:
2083:
1189:
G. W. Parshall "Tetraethylammonium
Trichlorogermanate(1−) and Trichlorostannate(1−)" Inorganic Syntheses, 1974, Vol. 15, pp. 222–225.
2834:
2814:
2210:
2190:
911:
The effective radius of the tetraethylammonium ion is reported as ~0.45 nm, which is comparable in size to that of the hydrated
594:
reactions. For example, the synthesis of tetraethylammonium perchlorate, a salt that has been useful as a supporting electrolyte for
4127:
3449:
3098:
2195:
4365:
2318:
4748:
2215:
2141:
403:
4660:
3150:
1138:
A. A. Vernon and J. L. Sheard (1948). "The solubility of tetraethylammonium iodide in benzene-ethylene dichloride mixtures."
201:
3590:
3568:
1664:
1442:
G. Akk and J. H. Steinbach (2003). "Activation and block of mouse muscle-type nicotinic receptors by tetraethylammonium."
3463:
923:
1268:
C. M. Armstrong (1971). "Interaction of tetraethylammonium ion derivatives with the potassium channels of giant axons."
1068:
Another research group, working at about the same time, but using tetraethylammonium bromide, published the following LD
4392:
1697:
4758:
986:
506:
294:
2662:
1636:
L. O. Randall, W. G. Peterson and G. Lehmann (1949). "The ganglionic blocking actions of thiophanium derivatives."
415:
3353:
3173:
1657:
119:
1490:
E. M. Müller, J. S. Hub, H. Grubmüller, and B. L. de Groot (2008). "Is TEA an inhibitor for human
Aquaporin-1?"
1426:
B. Hille (1967). "The selective inhibition of delayed potassium currents in nerve by tetraethylammonium ions."
3920:
3650:
1005:
similar to ouabain, TEA further accentuates the disrupted K, and Na, gradients within each of these systems.
4719:
237:
888:
TEA salts such as tetraethylammonium tetrafluoroborate and tetraethylammonium methylsulfonate are used in
865:). In some cases, salts are produced of anions that cannot be generated in water, such as the tetrahedral
4699:
1114:
1042:
1022:
258:
1247:
1109:
975:
919:
for TEA is given as 0.385 nm; several thermodynamic parameters for the TEA ion are also recorded.
843:
603:
435:
159:
4685:
4259:
3582:
3480:
3164:
2676:
1119:
584:
4587:
4505:
4406:
4323:
4192:
3615:
3512:
3344:
3113:
882:
275:
4533:
4469:
3805:
1711:
4337:
4273:
3664:
2630:
2621:
2185:
2172:
2154:
2096:
1720:
971:
4301:
4202:
1568:
A. J. P. Graham (1950). "Toxic effects in animals and man after tetraethylammonium bromide."
4743:
3895:
2426:
2361:
2341:
246:
48:
970:" drug to be introduced into clinical practice. However, TEA also produces effects at the
179:
8:
4546:
2684:
2088:
85:
1391:
R. C. Elliott (1982). "The action of tetraethylammonium at the neuromuscular junction."
832:{\displaystyle {\ce {Et4N+Br_{(aq)}- + Na+_{(aq)}- -> Na+Br_{(aq)}- + Et4N+_{(s)}-}}}
279:
139:
95:
2956:
2951:
2561:
2331:
967:
607:
477:
4605:
4216:
3890:
3534:
3406:
2653:
2546:
1680:
35:
4753:
4383:
3880:
3795:
3595:
3314:
3103:
2441:
1206:
1190:
1174:
439:
352:
4635:
4630:
4600:
4429:
4424:
4027:
3992:
3982:
3947:
3554:
3529:
2996:
2689:
2571:
1726:
1688:
990:
591:
226:
4610:
4566:
4157:
4057:
3967:
3641:
3497:
3440:
3285:
3241:
3196:
2941:
2931:
2551:
2471:
2068:
1971:
1210:
1194:
1178:
889:
386:
2101:
1696:
4737:
4620:
4513:
4459:
4444:
4230:
4167:
3900:
3845:
3840:
3830:
3785:
3605:
3539:
3391:
3201:
3186:
3031:
2724:
2606:
2446:
2326:
2305:
2280:
2200:
1821:
1816:
978:
497:
4492:
4240:
4152:
4142:
4052:
3987:
3885:
3815:
3750:
3740:
3695:
3319:
3304:
3251:
3206:
3061:
3016:
3001:
2991:
2976:
2916:
2556:
2536:
2476:
2026:
1881:
1741:
1097:
1018:
1014:
916:
595:
481:
4291:
4245:
4122:
4117:
4112:
4037:
4022:
4017:
3972:
3951:
3943:
3855:
3850:
3835:
3820:
3755:
3700:
3276:
3266:
3261:
3256:
3236:
3221:
3211:
3191:
3093:
3076:
3066:
3056:
3046:
3041:
3011:
2986:
2981:
2961:
2946:
2911:
2896:
2859:
2794:
2754:
2744:
2601:
2596:
2581:
2566:
2506:
2371:
2275:
2270:
2265:
2255:
2250:
2131:
2078:
2073:
2058:
1901:
1876:
1866:
1856:
1846:
1836:
1751:
1746:
1736:
1649:
1017:, its major use seems to have been as a probe to assess the capacity for
893:
611:
450:
610:
in water, from which the water-insoluble tetraethylammonium perchlorate
4595:
4523:
4518:
4454:
4449:
4439:
4434:
4414:
4235:
4224:
4220:
4187:
4072:
4067:
4042:
4032:
4007:
4002:
3997:
3938:
3928:
3910:
3905:
3875:
3865:
3825:
3790:
3745:
3735:
3730:
3725:
3710:
3675:
3600:
3544:
3521:
3489:
3416:
3376:
3334:
3324:
3299:
3271:
3231:
3216:
3136:
3131:
3071:
3051:
3036:
3026:
2891:
2881:
2809:
2804:
2799:
2789:
2749:
2704:
2699:
2611:
2591:
2531:
2521:
2451:
2431:
2416:
2406:
2396:
2381:
2366:
2356:
2346:
2336:
2295:
2290:
2285:
2260:
2240:
2220:
2146:
2136:
2121:
2111:
2063:
2011:
1946:
1871:
1861:
1851:
1831:
1806:
1801:
1781:
1761:
1731:
899:
TEA halide and its hydroxide are used for the synthesis of high-silica
480:, the difference being that its salts are less lipophilic, more easily
473:
469:
374:
191:
170:
1146:
4615:
4561:
4477:
4360:
4350:
4281:
4210:
4172:
4147:
4137:
4062:
4012:
3957:
3933:
3860:
3770:
3765:
3760:
3720:
3715:
3705:
3690:
3549:
3421:
3401:
3381:
3371:
3329:
3309:
3226:
3021:
2936:
2926:
2906:
2844:
2829:
2819:
2779:
2764:
2734:
2719:
2714:
2709:
2635:
2576:
2526:
2516:
2511:
2496:
2486:
2466:
2456:
2436:
2411:
2041:
2006:
1986:
1951:
1941:
1906:
1891:
1375:
G. K. Moe and W. A. Freyburger (1950). "Ganglionic blocking agents."
998:
994:
26:
385:
Except where otherwise noted, data are given for materials in their
4286:
4092:
4087:
4047:
3962:
3810:
3685:
3623:
3006:
2971:
2876:
2491:
2421:
2391:
2351:
2245:
2036:
1996:
1976:
485:
465:
1584:
A. M. Boyd et al. (1948). "Action of tetraethylammonium bromide."
118:
4355:
4177:
3977:
3502:
2901:
2839:
2501:
2481:
2177:
2048:
1342:
Since tetraethylammonium is always paired with an anion, the TEA
1030:
963:
900:
599:
213:
1361:(1971). J. R. DiPalma (Ed.), pp. 723-724, New York: McGraw-Hill.
4181:
3445:
Tooltip G protein-coupled inwardly rectifying potassium channel
3294:
3290:
Tooltip G protein-coupled inwardly rectifying potassium channel
2966:
2886:
2769:
2759:
2541:
2310:
150:
4661:
3151:
2921:
2774:
1001:(APQ) channels, but this still seems to be a disputed issue.
130:
108:
3569:
1333:
There are over 8500 citations in PubMed, as of
October 2012.
263:
4497:
Tooltip Cystic fibrosis transmembrane conductance regulator
4419:
3464:
3122:
3084:
2867:
1531:
J. P. Hendrix (1949. "Neostigmine as antidote to Etamon®."
1076:
Mouse: 38 mg/kg, i.v.; 60 mg/kg, i.p.; >2000 mg/kg, p.o.
602:
solvents, is carried out by mixing the water-soluble salts
4393:
1698:
802:
774:
699:
635:
546:
521:
2663:
1250:, "Synthesis of zeolite beta", issued 1992-08-18
3354:
3174:
1059:
Rat: ~56 mg/kg, i.v.; 110 mg/kg, i.m.; 2630 mg/kg, p.o.
3651:
623:
509:
997:cells. It has also been reported that TEA inhibits
476:salts of inorganic anions. It is used similarly to
303:
InChI=1S/C8H20N/c1-5-9(6-2,7-3)8-4/h5-8H2,1-4H3/q+1
200:
831:
572:
313:InChI=1/C8H20N/c1-5-9(6-2,7-3)8-4/h5-8H2,1-4H3/q+1
4686:
4260:
4735:
4324:
573:{\displaystyle {\ce {Et3N + EtX -> Et4N+X-}}}
225:
4724:Transient receptor potential channel modulators
496:The halide salt is prepared by the reaction of
94:
590:Most tetraethylammonium salts are prepared by
583:This method works well for the preparation of
4666:Tooltip Transient receptor potential channels
3156:Tooltip Inwardly rectifying potassium channel
1665:
1050:s for TEA chloride (error ranges not shown):
3574:Tooltip Tandem pore domain potassium channel
3472:Tooltip Calcium-activated potassium channel
1599:
1597:
472:used in the research laboratory to prepare
4398:Tooltip Calcium-activated chloride channel
2690:4-Aminopyridine (fampridine/dalfampridine)
1703:Tooltip Voltage-dependent calcium channels
1679:
1672:
1658:
1008:
278:
178:
1564:
1562:
1560:
1359:Drill's Pharmacology in Medicine, 4th Ed.
245:
2668:Tooltip Voltage-gated potassium channels
1594:
1354:
1352:
1041:An extensive study of the toxicology of
3362:Tooltip ATP-sensitive potassium channel
3182:Tooltip ATP-sensitive potassium channel
1406:
1404:
274:
4736:
1557:
1371:
1369:
1367:
1054:Mouse: 65 mg/kg, i.p.; 900 mg/kg, p.o.
3656:Tooltip Voltage-gated sodium channels
1653:
1349:
1264:
1262:
306:Key: CBXCPBUEXACCNR-UHFFFAOYSA-N
158:
138:
3591:12-O-Tetradecanoylphorbol-13-acetate
1401:
1081:Rat: 63 mg/kg, i.v.; 115 mg/kg, i.p.
1064:Dog: ~36 mg/kg, i.v.; 58 mg/kg, i.m.
933:was determined experimentally to be
464:, denoted Et) attached to a central
16:Polyatomic ion (N(C₂H₅)₄, charge +1)
2685:3,4-Diaminopyridine (amifampridine)
1364:
1147:https://doi.org/10.1021/ja01186a015
924:octanol-water partition coefficient
316:Key: CBXCPBUEXACCNR-UHFFFAOYAM
216:
13:
1259:
14:
4770:
4691:Tooltip Ligand gated ion channels
4265:Tooltip Epithelial sodium channel
987:nicotinic acetylcholine receptors
4329:Tooltip Acid-sensing ion channel
393:
34:
25:
1630:
1614:
1578:
1541:
1525:
1516:
1500:
1497:663–669, and references herein.
1484:
1468:
1452:
1436:
1420:
1385:
1336:
1327:
1310:
1294:
1278:
957:
389:(at 25 °C , 100 kPa).
2147:Ziconotide (ω-conotoxin MVIIA)
1240:
1224:
1215:
1199:
1183:
1167:
1151:
1132:
817:
811:
805:
789:
750:
744:
725:
714:
708:
702:
686:
660:
654:
533:
491:
1:
4749:Quaternary ammonium compounds
4720:Receptor/signaling modulators
2122:Leconotide (ω-conotoxin CVID)
1125:
1036:
906:
7:
1115:Tetraethylammonium chloride
1103:
1043:tetraethylammonium chloride
1023:peripheral vascular disease
10:
4775:
3683:Antiarrhythmics (class I):
1211:10.1002/9780470132401.ch37
1195:10.1002/9780470132463.ch48
1179:10.1002/9780470132470.ch36
1110:Tetraethylammonium bromide
952:
854:), and trichlorostannate (
844:tetraethylammonium cyanide
604:tetraethylammonium bromide
436:quaternary ammonium cation
379:130.25 g/mol
4713:
4684:
4659:
4652:
4586:
4579:
4532:
4504:
4490:
4468:
4405:
4391:
4382:
4336:
4322:
4300:
4272:
4258:
4201:
4193:Tricyclic antidepressants
3663:
3649:
3640:
3614:
3581:
3567:
3511:
3479:
3462:
3343:
3202:Glibenclamide (glyburide)
3163:
3149:
3112:
2675:
2661:
2652:
2620:
1710:
1687:
1120:Tetraethylammonium iodide
585:tetraethylammonium iodide
383:
345:
325:
290:
78:
70:
47:
42:
33:
24:
4759:Tetraethylammonium salts
1638:J. Pharmacol. Exp. Ther.
1622:J. Pharmacol. Exp. Ther.
883:phase-transfer catalysis
3806:Eslicarbazepine acetate
1009:Clinical considerations
876:
842:Other examples include
3550:Rottlerin (mallotoxin)
1681:Ion channel modulators
1460:Proc. Natl. Acad. Sci.
1248:US patent 5139759A
1091:Rabbit: 72 mg/kg, i.v.
972:neuromuscular junction
833:
574:
1907:Ryodipine (riodipine)
834:
575:
500:and an ethyl halide:
449:, consisting of four
64:-Triethylethanaminium
3896:Valproate semisodium
2427:Carboxyamidotriazole
2362:Gabapentin enacarbil
2342:Arbaclofen placarbil
966:- it was the first "
621:
507:
49:Preferred IUPAC name
4547:1,10-Phenanthroline
3104:Spooky toxin (SsTx)
2089:Tetrahydropalmatine
1549:Med. Clin. N. Amer.
1319:J. Pharmacobio-Dyn.
1086:Dog: 55 mg/kg, i.v.
827:
804:
776:
760:
724:
701:
670:
637:
548:
523:
21:
20:Tetraethylammonium
4557:7,8-Benzoquinoline
4552:4,7-Phenanthroline
4542:1,7-Phenanthroline
3918:Local anesthetics:
3450:ML-297 (VU0456810)
2957:Diallyl trisulfide
2952:Dextropropoxyphene
2855:Tetraethylammonium
2562:Pinaverium bromide
2332:4-Methylpregabalin
968:ganglionic blocker
829:
792:
787:
764:
738:
689:
684:
648:
625:
608:sodium perchlorate
570:
536:
511:
478:tetrabutylammonium
428:Tetraethylammonium
416:Infobox references
19:
4731:
4730:
4709:
4708:
4648:
4647:
4644:
4643:
4606:Meclofenamic acid
4575:
4574:
4486:
4485:
4378:
4377:
4374:
4373:
4318:
4317:
4254:
4253:
4128:RG7893 (GDC-0287)
3891:Valproate pivoxil
3781:Acetylpheneturide
3636:
3635:
3632:
3631:
3563:
3562:
3535:Meclofenamic acid
3498:Ethanol (alcohol)
3458:
3457:
3407:Minoxidil sulfate
3145:
3144:
2648:
2647:
2644:
2643:
2547:Otilonium bromide
2472:Ethanol (alcohol)
2236:ω-Conotoxin MVIIC
1972:Phenylalkylamines
1412:Br. J. Pharmacol.
1286:J. Am. Chem. Soc.
1159:J. Am. Chem. Soc.
1140:J. Am. Chem. Soc.
816:
795:
780:
767:
749:
741:
731:
713:
692:
677:
659:
651:
641:
628:
562:
552:
539:
532:
526:
514:
424:Chemical compound
422:
421:
259:CompTox Dashboard
120:Interactive image
73:Tetraethylazanium
4766:
4692:
4688:
4667:
4663:
4657:
4656:
4584:
4583:
4502:
4501:
4498:
4494:
4403:
4402:
4399:
4395:
4389:
4388:
4334:
4333:
4330:
4326:
4270:
4269:
4266:
4262:
3881:Sodium valproate
3796:Chlorphenacemide
3778:Anticonvulsants:
3661:
3660:
3657:
3653:
3647:
3646:
3596:Arachidonic acid
3579:
3578:
3575:
3571:
3477:
3476:
3473:
3469:
3446:
3442:
3363:
3359:
3315:Dextromethorphan
3291:
3287:
3183:
3179:
3161:
3160:
3157:
3153:
2673:
2672:
2669:
2665:
2659:
2658:
2631:L-type-selective
2442:Dimeditiapramine
2404:Others/unsorted:
2186:T-type-selective
2173:R-type-selective
2155:P-type-selective
2107:ω-Conotoxin GVIA
2097:N-type-selective
1727:Dihydropyridines
1721:L-type-selective
1708:
1707:
1704:
1700:
1694:
1693:
1674:
1667:
1660:
1651:
1650:
1644:
1634:
1628:
1618:
1612:
1606:Am. J. Med. Sci.
1601:
1592:
1582:
1576:
1566:
1555:
1545:
1539:
1529:
1523:
1520:
1514:
1504:
1498:
1488:
1482:
1472:
1466:
1456:
1450:
1440:
1434:
1428:J. Gen. Physiol.
1424:
1418:
1408:
1399:
1389:
1383:
1373:
1362:
1356:
1347:
1340:
1334:
1331:
1325:
1314:
1308:
1302:J. Membrane Sci.
1298:
1292:
1282:
1276:
1270:J. Gen. Physiol.
1266:
1257:
1256:
1255:
1251:
1244:
1238:
1228:
1222:
1219:
1213:
1203:
1197:
1187:
1181:
1171:
1165:
1155:
1149:
1136:
948:
940:
938:
914:
872:
864:
853:
838:
836:
835:
830:
828:
826:
821:
820:
814:
808:
803:
800:
793:
786:
785:
778:
775:
772:
765:
759:
754:
753:
747:
739:
737:
736:
729:
723:
718:
717:
711:
705:
700:
697:
690:
683:
682:
675:
669:
664:
663:
657:
649:
647:
646:
639:
636:
633:
626:
579:
577:
576:
571:
569:
568:
567:
560:
558:
557:
550:
547:
544:
537:
530:
524:
522:
519:
512:
463:
448:
440:chemical formula
406:
400:
397:
396:
368:
353:Chemical formula
283:
282:
267:
265:
249:
229:
218:
204:
182:
162:
142:
122:
98:
38:
29:
22:
18:
4774:
4773:
4769:
4768:
4767:
4765:
4764:
4763:
4734:
4733:
4732:
4727:
4705:
4690:
4680:
4665:
4640:
4636:Trifluoperazine
4631:Tolfenamic acid
4601:Flufenamic acid
4571:
4528:
4496:
4482:
4464:
4430:Flufenamic acid
4425:Ethacrynic acid
4397:
4370:
4328:
4314:
4296:
4264:
4250:
4197:
4028:Metabutoxycaine
3993:Diphenhydramine
3983:Cyclomethycaine
3948:Levobupivacaine
3655:
3628:
3610:
3573:
3559:
3555:Tolfenamic acid
3530:Flufenamic acid
3525:
3507:
3493:
3471:
3468:
3454:
3444:
3361:
3358:
3339:
3289:
3181:
3178:
3155:
3141:
3126:
3108:
3088:
2997:Norpropoxyphene
2874:11.1)-specific:
2873:
2667:
2640:
2616:
2572:Rhynchophylline
2322:
1702:
1683:
1678:
1648:
1647:
1635:
1631:
1619:
1615:
1602:
1595:
1583:
1579:
1567:
1558:
1546:
1542:
1530:
1526:
1521:
1517:
1505:
1501:
1489:
1485:
1473:
1469:
1457:
1453:
1441:
1437:
1425:
1421:
1409:
1402:
1393:Gen. Pharmacol.
1390:
1386:
1377:Pharmacol. Rev.
1374:
1365:
1357:
1350:
1341:
1337:
1332:
1328:
1315:
1311:
1299:
1295:
1283:
1279:
1267:
1260:
1253:
1246:
1245:
1241:
1229:
1225:
1220:
1216:
1204:
1200:
1188:
1184:
1172:
1168:
1156:
1152:
1137:
1133:
1128:
1106:
1071:
1049:
1039:
1011:
991:skeletal muscle
979:nerve terminals
960:
955:
942:
936:
934:
932:
926:of TEA iodide,
912:
909:
890:supercapacitors
879:
870:
866:
863:
859:
855:
851:
847:
822:
810:
809:
801:
796:
788:
781:
777:
773:
768:
755:
743:
742:
732:
728:
719:
707:
706:
698:
693:
685:
678:
674:
665:
653:
652:
642:
638:
634:
629:
624:
622:
619:
618:
598:studies in non-
592:salt metathesis
587:(where X = I).
563:
559:
553:
549:
545:
540:
520:
515:
510:
508:
505:
504:
494:
462:
458:
454:
446:
442:
425:
418:
413:
412:
411: ?)
402:
398:
394:
390:
366:
362:
358:
355:
341:
338:
333:
332:
321:
318:
317:
314:
308:
307:
304:
298:
297:
286:
268:
261:
252:
232:
219:
207:
194:
185:
165:
145:
125:
112:
101:
88:
74:
66:
65:
17:
12:
11:
5:
4772:
4762:
4761:
4756:
4751:
4746:
4729:
4728:
4714:
4711:
4710:
4707:
4706:
4704:
4703:
4695:
4693:
4682:
4681:
4679:
4678:
4670:
4668:
4654:
4650:
4649:
4646:
4645:
4642:
4641:
4639:
4638:
4633:
4628:
4623:
4618:
4613:
4611:Mefenamic acid
4608:
4603:
4598:
4592:
4590:
4581:
4577:
4576:
4573:
4572:
4570:
4569:
4567:Phenanthridine
4564:
4559:
4554:
4549:
4544:
4538:
4536:
4530:
4529:
4527:
4526:
4521:
4516:
4510:
4508:
4499:
4488:
4487:
4484:
4483:
4481:
4480:
4474:
4472:
4466:
4465:
4463:
4462:
4457:
4452:
4447:
4442:
4437:
4432:
4427:
4422:
4417:
4411:
4409:
4400:
4386:
4380:
4379:
4376:
4375:
4372:
4371:
4369:
4368:
4363:
4358:
4353:
4348:
4342:
4340:
4331:
4320:
4319:
4316:
4315:
4313:
4312:
4306:
4304:
4298:
4297:
4295:
4294:
4289:
4284:
4278:
4276:
4267:
4256:
4255:
4252:
4251:
4249:
4248:
4243:
4238:
4233:
4228:
4215:Atracotoxins (
4213:
4207:
4205:
4199:
4198:
4196:
4195:
4190:
4185:
4175:
4170:
4161:
4160:
4158:Zetekitoxin AB
4155:
4150:
4145:
4140:
4131:
4130:
4125:
4120:
4115:
4110:
4105:
4100:
4095:
4090:
4085:
4076:
4075:
4070:
4065:
4060:
4058:Proxymetacaine
4055:
4050:
4045:
4040:
4035:
4030:
4025:
4020:
4015:
4010:
4005:
4000:
3995:
3990:
3985:
3980:
3975:
3970:
3968:Chloroprocaine
3965:
3960:
3955:
3941:
3936:
3931:
3926:
3914:
3913:
3908:
3903:
3898:
3893:
3888:
3883:
3878:
3873:
3868:
3863:
3858:
3853:
3848:
3843:
3838:
3833:
3828:
3823:
3818:
3813:
3808:
3803:
3798:
3793:
3788:
3783:
3774:
3773:
3768:
3763:
3758:
3753:
3748:
3743:
3738:
3733:
3728:
3723:
3718:
3713:
3708:
3703:
3698:
3693:
3688:
3679:
3678:
3669:
3667:
3658:
3644:
3638:
3637:
3634:
3633:
3630:
3629:
3627:
3626:
3620:
3618:
3612:
3611:
3609:
3608:
3603:
3598:
3593:
3587:
3585:
3576:
3565:
3564:
3561:
3560:
3558:
3557:
3552:
3547:
3542:
3537:
3532:
3523:
3517:
3515:
3509:
3508:
3506:
3505:
3500:
3491:
3485:
3483:
3474:
3466:
3460:
3459:
3456:
3455:
3453:
3452:
3435:
3434:
3429:
3424:
3419:
3414:
3409:
3404:
3399:
3394:
3389:
3384:
3379:
3374:
3369:
3356:
3349:
3347:
3341:
3340:
3338:
3337:
3332:
3327:
3322:
3317:
3312:
3307:
3302:
3297:
3280:
3279:
3274:
3269:
3264:
3259:
3254:
3249:
3244:
3242:Glyclopyramide
3239:
3234:
3229:
3224:
3219:
3214:
3209:
3204:
3199:
3197:Chlorpropamide
3194:
3189:
3176:
3169:
3167:
3158:
3147:
3146:
3143:
3142:
3140:
3139:
3134:
3124:
3118:
3116:
3110:
3109:
3107:
3106:
3101:
3096:
3086:
3080:
3079:
3074:
3069:
3064:
3059:
3054:
3049:
3044:
3039:
3034:
3029:
3024:
3019:
3014:
3009:
3004:
2999:
2994:
2989:
2984:
2979:
2974:
2969:
2964:
2959:
2954:
2949:
2944:
2942:Clarithromycin
2939:
2934:
2932:Chlorpromazine
2929:
2924:
2919:
2914:
2909:
2904:
2899:
2894:
2889:
2884:
2879:
2871:
2863:
2862:
2857:
2852:
2847:
2842:
2837:
2832:
2827:
2822:
2817:
2812:
2807:
2802:
2797:
2792:
2787:
2782:
2777:
2772:
2767:
2762:
2757:
2752:
2747:
2742:
2737:
2732:
2727:
2722:
2717:
2712:
2707:
2702:
2697:
2692:
2687:
2681:
2679:
2670:
2656:
2650:
2649:
2646:
2645:
2642:
2641:
2639:
2638:
2626:
2624:
2618:
2617:
2615:
2614:
2609:
2604:
2599:
2594:
2589:
2584:
2579:
2574:
2569:
2564:
2559:
2554:
2552:Paramethadione
2549:
2544:
2539:
2534:
2529:
2524:
2519:
2514:
2509:
2504:
2499:
2494:
2489:
2484:
2479:
2474:
2469:
2464:
2459:
2454:
2449:
2444:
2439:
2434:
2429:
2424:
2419:
2414:
2409:
2400:
2399:
2394:
2389:
2384:
2379:
2374:
2369:
2364:
2359:
2354:
2349:
2344:
2339:
2334:
2327:gabapentinoids
2320:
2314:
2313:
2308:
2303:
2298:
2293:
2288:
2283:
2278:
2273:
2268:
2263:
2258:
2253:
2248:
2243:
2238:
2233:
2228:Non-selective:
2224:
2223:
2218:
2213:
2208:
2203:
2198:
2193:
2181:
2180:
2168:
2167:
2165:ω-Agatoxin IVB
2162:
2160:ω-Agatoxin IVA
2150:
2149:
2144:
2139:
2134:
2129:
2124:
2119:
2117:Huwentoxin XVI
2114:
2109:
2104:
2092:
2091:
2086:
2081:
2076:
2071:
2069:Cyproheptadine
2066:
2061:
2056:
2051:
2039:
2034:
2029:
2024:
2019:
2014:
2009:
2004:
1999:
1994:
1989:
1984:
1979:
1964:
1959:
1954:
1949:
1934:
1929:
1924:
1919:
1914:
1909:
1904:
1899:
1894:
1889:
1884:
1879:
1874:
1869:
1864:
1859:
1854:
1849:
1844:
1839:
1834:
1829:
1827:Levniguldipine
1824:
1819:
1814:
1809:
1804:
1799:
1794:
1789:
1784:
1779:
1774:
1769:
1767:Dexniguldipine
1764:
1759:
1754:
1749:
1744:
1739:
1734:
1716:
1714:
1705:
1691:
1685:
1684:
1677:
1676:
1669:
1662:
1654:
1646:
1645:
1629:
1613:
1593:
1577:
1556:
1540:
1524:
1515:
1508:Pflügers Arch.
1499:
1492:Pflügers Arch.
1483:
1467:
1451:
1435:
1419:
1400:
1384:
1363:
1348:
1335:
1326:
1309:
1293:
1277:
1258:
1239:
1223:
1214:
1198:
1182:
1166:
1150:
1130:
1129:
1127:
1124:
1123:
1122:
1117:
1112:
1105:
1102:
1093:
1092:
1088:
1087:
1083:
1082:
1078:
1077:
1069:
1066:
1065:
1061:
1060:
1056:
1055:
1047:
1038:
1035:
1010:
1007:
959:
956:
954:
951:
930:
908:
905:
878:
875:
868:
861:
857:
849:
840:
839:
825:
819:
813:
807:
799:
791:
784:
771:
763:
758:
752:
746:
735:
727:
722:
716:
710:
704:
696:
688:
681:
673:
668:
662:
656:
645:
632:
581:
580:
566:
556:
543:
535:
529:
518:
493:
490:
468:atom. It is a
460:
456:
444:
423:
420:
419:
414:
392:
391:
387:standard state
384:
381:
380:
377:
371:
370:
364:
360:
356:
351:
348:
347:
343:
342:
340:
339:
336:
328:
327:
326:
323:
322:
320:
319:
315:
312:
311:
309:
305:
302:
301:
293:
292:
291:
288:
287:
285:
284:
271:
269:
257:
254:
253:
251:
250:
242:
240:
234:
233:
231:
230:
222:
220:
212:
209:
208:
206:
205:
197:
195:
190:
187:
186:
184:
183:
175:
173:
167:
166:
164:
163:
155:
153:
147:
146:
144:
143:
135:
133:
127:
126:
124:
123:
115:
113:
106:
103:
102:
100:
99:
91:
89:
84:
81:
80:
76:
75:
72:
68:
67:
52:
51:
45:
44:
40:
39:
31:
30:
15:
9:
6:
4:
3:
2:
4771:
4760:
4757:
4755:
4752:
4750:
4747:
4745:
4742:
4741:
4739:
4726:
4725:
4721:
4718:
4712:
4701:
4697:
4696:
4694:
4689:
4683:
4676:
4672:
4671:
4669:
4664:
4658:
4655:
4651:
4637:
4634:
4632:
4629:
4627:
4624:
4622:
4621:Niflumic acid
4619:
4617:
4614:
4612:
4609:
4607:
4604:
4602:
4599:
4597:
4594:
4593:
4591:
4589:
4585:
4582:
4578:
4568:
4565:
4563:
4560:
4558:
4555:
4553:
4550:
4548:
4545:
4543:
4540:
4539:
4537:
4535:
4531:
4525:
4522:
4520:
4517:
4515:
4514:Glibenclamide
4512:
4511:
4509:
4507:
4503:
4500:
4495:
4489:
4479:
4476:
4475:
4473:
4471:
4467:
4461:
4460:Niflumic acid
4458:
4456:
4453:
4451:
4448:
4446:
4445:Glibenclamide
4443:
4441:
4438:
4436:
4433:
4431:
4428:
4426:
4423:
4421:
4418:
4416:
4413:
4412:
4410:
4408:
4404:
4401:
4396:
4390:
4387:
4385:
4381:
4367:
4364:
4362:
4359:
4357:
4354:
4352:
4349:
4347:
4344:
4343:
4341:
4339:
4335:
4332:
4327:
4321:
4311:
4308:
4307:
4305:
4303:
4299:
4293:
4290:
4288:
4285:
4283:
4280:
4279:
4277:
4275:
4271:
4268:
4263:
4257:
4247:
4244:
4242:
4241:Grayanotoxins
4239:
4237:
4234:
4232:
4231:Batrachotoxin
4229:
4226:
4222:
4218:
4217:ω-Atracotoxin
4214:
4212:
4209:
4208:
4206:
4204:
4200:
4194:
4191:
4189:
4186:
4183:
4179:
4176:
4174:
4171:
4169:
4168:Buprenorphine
4166:
4163:
4162:
4159:
4156:
4154:
4151:
4149:
4146:
4144:
4141:
4139:
4136:
4133:
4132:
4129:
4126:
4124:
4121:
4119:
4116:
4114:
4111:
4109:
4106:
4104:
4101:
4099:
4096:
4094:
4091:
4089:
4086:
4084:
4081:
4078:
4077:
4074:
4071:
4069:
4066:
4064:
4061:
4059:
4056:
4054:
4051:
4049:
4046:
4044:
4041:
4039:
4036:
4034:
4031:
4029:
4026:
4024:
4021:
4019:
4016:
4014:
4011:
4009:
4006:
4004:
4001:
3999:
3996:
3994:
3991:
3989:
3986:
3984:
3981:
3979:
3976:
3974:
3971:
3969:
3966:
3964:
3961:
3959:
3956:
3953:
3949:
3945:
3942:
3940:
3937:
3935:
3932:
3930:
3927:
3925:
3923:
3919:
3916:
3915:
3912:
3909:
3907:
3904:
3902:
3901:Valproic acid
3899:
3897:
3894:
3892:
3889:
3887:
3884:
3882:
3879:
3877:
3874:
3872:
3869:
3867:
3864:
3862:
3859:
3857:
3854:
3852:
3849:
3847:
3846:Oxitriptyline
3844:
3842:
3841:Oxcarbazepine
3839:
3837:
3834:
3832:
3831:Licarbazepine
3829:
3827:
3824:
3822:
3819:
3817:
3814:
3812:
3809:
3807:
3804:
3802:
3799:
3797:
3794:
3792:
3789:
3787:
3786:Carbamazepine
3784:
3782:
3779:
3776:
3775:
3772:
3769:
3767:
3764:
3762:
3759:
3757:
3754:
3752:
3749:
3747:
3744:
3742:
3739:
3737:
3734:
3732:
3729:
3727:
3724:
3722:
3719:
3717:
3714:
3712:
3709:
3707:
3704:
3702:
3699:
3697:
3694:
3692:
3689:
3687:
3684:
3681:
3680:
3677:
3674:
3673:Antianginals:
3671:
3670:
3668:
3666:
3662:
3659:
3654:
3648:
3645:
3643:
3639:
3625:
3622:
3621:
3619:
3617:
3613:
3607:
3606:Norfluoxetine
3604:
3602:
3599:
3597:
3594:
3592:
3589:
3588:
3586:
3584:
3580:
3577:
3572:
3566:
3556:
3553:
3551:
3548:
3546:
3543:
3541:
3540:Niflumic acid
3538:
3536:
3533:
3531:
3528:
3526:
3519:
3518:
3516:
3514:
3510:
3504:
3501:
3499:
3496:
3494:
3487:
3486:
3484:
3482:
3478:
3475:
3470:
3461:
3451:
3448:
3443:
3437:
3436:
3433:
3430:
3428:
3425:
3423:
3420:
3418:
3415:
3413:
3410:
3408:
3405:
3403:
3400:
3398:
3395:
3393:
3392:Levcromakalim
3390:
3388:
3385:
3383:
3380:
3378:
3375:
3373:
3370:
3368:
3365:
3360:
3351:
3350:
3348:
3346:
3342:
3336:
3333:
3331:
3328:
3326:
3323:
3321:
3318:
3316:
3313:
3311:
3308:
3306:
3303:
3301:
3298:
3296:
3293:
3288:
3282:
3281:
3278:
3275:
3273:
3270:
3268:
3265:
3263:
3260:
3258:
3255:
3253:
3250:
3248:
3245:
3243:
3240:
3238:
3235:
3233:
3230:
3228:
3225:
3223:
3220:
3218:
3215:
3213:
3210:
3208:
3205:
3203:
3200:
3198:
3195:
3193:
3190:
3188:
3187:Acetohexamide
3185:
3180:
3171:
3170:
3168:
3166:
3162:
3159:
3154:
3148:
3138:
3135:
3133:
3130:
3128:
3120:
3119:
3117:
3115:
3111:
3105:
3102:
3100:
3097:
3095:
3092:
3090:
3082:
3081:
3078:
3075:
3073:
3070:
3068:
3065:
3063:
3060:
3058:
3055:
3053:
3050:
3048:
3045:
3043:
3040:
3038:
3035:
3033:
3032:Roxithromycin
3030:
3028:
3025:
3023:
3020:
3018:
3015:
3013:
3010:
3008:
3005:
3003:
3000:
2998:
2995:
2993:
2990:
2988:
2985:
2983:
2980:
2978:
2975:
2973:
2970:
2968:
2965:
2963:
2960:
2958:
2955:
2953:
2950:
2948:
2945:
2943:
2940:
2938:
2935:
2933:
2930:
2928:
2925:
2923:
2920:
2918:
2915:
2913:
2910:
2908:
2905:
2903:
2900:
2898:
2895:
2893:
2890:
2888:
2885:
2883:
2880:
2878:
2875:
2869:
2865:
2864:
2861:
2858:
2856:
2853:
2851:
2848:
2846:
2843:
2841:
2838:
2836:
2833:
2831:
2828:
2826:
2823:
2821:
2818:
2816:
2813:
2811:
2808:
2806:
2803:
2801:
2798:
2796:
2793:
2791:
2788:
2786:
2783:
2781:
2778:
2776:
2773:
2771:
2768:
2766:
2763:
2761:
2758:
2756:
2753:
2751:
2748:
2746:
2743:
2741:
2738:
2736:
2733:
2731:
2728:
2726:
2725:Charybdotoxin
2723:
2721:
2718:
2716:
2713:
2711:
2708:
2706:
2703:
2701:
2698:
2696:
2693:
2691:
2688:
2686:
2683:
2682:
2680:
2678:
2674:
2671:
2666:
2660:
2657:
2655:
2651:
2637:
2634:
2632:
2628:
2627:
2625:
2623:
2619:
2613:
2610:
2608:
2607:Trimethadione
2605:
2603:
2600:
2598:
2595:
2593:
2590:
2588:
2585:
2583:
2580:
2578:
2575:
2573:
2570:
2568:
2565:
2563:
2560:
2558:
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2518:
2515:
2513:
2510:
2508:
2505:
2503:
2500:
2498:
2495:
2493:
2490:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2468:
2465:
2463:
2460:
2458:
2455:
2453:
2450:
2448:
2447:Diproteverine
2445:
2443:
2440:
2438:
2435:
2433:
2430:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2402:
2401:
2398:
2395:
2393:
2390:
2388:
2385:
2383:
2380:
2378:
2375:
2373:
2370:
2368:
2365:
2363:
2360:
2358:
2355:
2353:
2350:
2348:
2345:
2343:
2340:
2338:
2335:
2333:
2330:
2328:
2324:
2316:
2315:
2312:
2309:
2307:
2306:Ruthenium red
2304:
2302:
2299:
2297:
2294:
2292:
2289:
2287:
2284:
2282:
2281:Levetiracetam
2279:
2277:
2274:
2272:
2269:
2267:
2264:
2262:
2259:
2257:
2254:
2252:
2249:
2247:
2244:
2242:
2239:
2237:
2234:
2232:
2231:ω-Agatoxin TK
2229:
2226:
2225:
2222:
2219:
2217:
2214:
2212:
2209:
2207:
2204:
2202:
2201:Niflumic acid
2199:
2197:
2194:
2192:
2189:
2187:
2183:
2182:
2179:
2176:
2174:
2170:
2169:
2166:
2163:
2161:
2158:
2156:
2152:
2151:
2148:
2145:
2143:
2140:
2138:
2135:
2133:
2130:
2128:
2125:
2123:
2120:
2118:
2115:
2113:
2110:
2108:
2105:
2103:
2100:
2098:
2094:
2093:
2090:
2087:
2085:
2082:
2080:
2077:
2075:
2072:
2070:
2067:
2065:
2062:
2060:
2057:
2055:
2052:
2050:
2047:
2043:
2040:
2038:
2035:
2033:
2030:
2028:
2025:
2023:
2020:
2018:
2015:
2013:
2010:
2008:
2005:
2003:
2000:
1998:
1995:
1993:
1990:
1988:
1985:
1983:
1980:
1978:
1975:
1973:
1968:
1965:
1963:
1960:
1958:
1955:
1953:
1950:
1948:
1945:
1943:
1938:
1935:
1933:
1930:
1928:
1925:
1923:
1920:
1918:
1915:
1913:
1910:
1908:
1905:
1903:
1900:
1898:
1895:
1893:
1890:
1888:
1885:
1883:
1880:
1878:
1875:
1873:
1870:
1868:
1865:
1863:
1860:
1858:
1855:
1853:
1850:
1848:
1845:
1843:
1840:
1838:
1835:
1833:
1830:
1828:
1825:
1823:
1822:Levamlodipine
1820:
1818:
1817:Lercanidipine
1815:
1813:
1810:
1808:
1805:
1803:
1800:
1798:
1795:
1793:
1790:
1788:
1785:
1783:
1780:
1778:
1775:
1773:
1770:
1768:
1765:
1763:
1760:
1758:
1755:
1753:
1750:
1748:
1745:
1743:
1740:
1738:
1735:
1733:
1730:
1728:
1724:
1722:
1718:
1717:
1715:
1713:
1709:
1706:
1701:
1695:
1692:
1690:
1686:
1682:
1675:
1670:
1668:
1663:
1661:
1656:
1655:
1652:
1642:
1639:
1633:
1626:
1623:
1617:
1610:
1607:
1600:
1598:
1590:
1587:
1581:
1574:
1571:
1565:
1563:
1561:
1553:
1550:
1544:
1537:
1534:
1528:
1519:
1512:
1509:
1503:
1496:
1493:
1487:
1480:
1477:
1471:
1464:
1461:
1455:
1448:
1445:
1439:
1432:
1429:
1423:
1416:
1413:
1407:
1405:
1397:
1394:
1388:
1381:
1378:
1372:
1370:
1368:
1360:
1355:
1353:
1345:
1339:
1330:
1323:
1320:
1313:
1306:
1303:
1297:
1290:
1287:
1281:
1274:
1271:
1265:
1263:
1249:
1243:
1236:
1233:
1232:Chem. Eur. J.
1227:
1218:
1212:
1208:
1202:
1196:
1192:
1186:
1180:
1176:
1170:
1163:
1160:
1154:
1148:
1144:
1141:
1135:
1131:
1121:
1118:
1116:
1113:
1111:
1108:
1107:
1101:
1099:
1090:
1089:
1085:
1084:
1080:
1079:
1075:
1074:
1073:
1063:
1062:
1058:
1057:
1053:
1052:
1051:
1044:
1034:
1032:
1026:
1024:
1020:
1016:
1006:
1002:
1000:
996:
992:
988:
985:inhibitor at
982:
980:
977:
973:
969:
965:
950:
946:
929:
925:
920:
918:
904:
902:
897:
895:
891:
886:
884:
874:
845:
823:
797:
782:
769:
761:
756:
733:
720:
694:
679:
671:
666:
643:
630:
617:
616:
615:
613:
609:
605:
601:
597:
596:polarographic
593:
588:
586:
564:
554:
541:
527:
516:
503:
502:
501:
499:
498:triethylamine
489:
487:
483:
479:
475:
471:
467:
452:
441:
437:
433:
429:
417:
410:
405:
388:
382:
378:
376:
373:
372:
357:
354:
350:
349:
344:
335:
334:
331:
324:
310:
300:
299:
296:
289:
281:
277:
276:DTXSID2045024
273:
272:
270:
260:
256:
255:
248:
244:
243:
241:
239:
236:
235:
228:
224:
223:
221:
215:
211:
210:
203:
199:
198:
196:
193:
189:
188:
181:
177:
176:
174:
172:
169:
168:
161:
157:
156:
154:
152:
149:
148:
141:
137:
136:
134:
132:
129:
128:
121:
117:
116:
114:
110:
105:
104:
97:
93:
92:
90:
87:
83:
82:
77:
69:
63:
59:
55:
50:
46:
41:
37:
32:
28:
23:
4716:
4715:
4626:Talniflumate
4164:
4153:Tetrodotoxin
4143:Neosaxitoxin
4134:
4079:
4053:Propoxycaine
3988:Dimethocaine
3921:
3917:
3886:Valnoctamide
3816:Fosphenytoin
3777:
3751:Procainamide
3741:Pilsicainide
3696:Disopyramide
3682:
3672:
3520:
3488:
3438:
3352:
3320:Ethosuximide
3305:Cloperastine
3283:
3252:Metahexamide
3247:Glycyclamide
3207:Glibornuride
3172:
3121:
3083:
3062:Thioridazine
3017:Promethazine
3002:Orphenadrine
2992:Ketoconazole
2977:Erythromycin
2866:
2854:
2629:
2557:Phensuximide
2537:Ochratoxin A
2477:Ethosuximide
2403:
2325:-selective (
2317:
2227:
2184:
2171:
2153:
2102:ω-Conotoxins
2095:
2045:
2027:Norverapamil
1992:Dexverapamil
1970:
1944:derivatives:
1940:
1937:Vatanidipine
1932:Trombodipine
1897:Palonidipine
1882:Nitrendipine
1837:Mepirodipine
1742:Azelnidipine
1725:
1719:
1640:
1637:
1632:
1624:
1621:
1616:
1608:
1605:
1588:
1585:
1580:
1572:
1569:
1551:
1548:
1543:
1535:
1532:
1527:
1518:
1510:
1507:
1502:
1494:
1491:
1486:
1478:
1475:
1470:
1462:
1459:
1454:
1446:
1443:
1438:
1430:
1427:
1422:
1414:
1411:
1395:
1392:
1387:
1379:
1376:
1358:
1343:
1338:
1329:
1321:
1318:
1312:
1304:
1301:
1296:
1288:
1285:
1280:
1272:
1269:
1242:
1234:
1231:
1226:
1217:
1201:
1185:
1169:
1161:
1158:
1153:
1142:
1139:
1134:
1098:tubocurarine
1094:
1067:
1040:
1027:
1021:in cases of
1019:vasodilation
1015:hypertension
1012:
1003:
983:
961:
958:Pharmacology
944:
927:
921:
917:ionic radius
910:
898:
894:electrolytes
887:
880:
841:
612:precipitates
589:
582:
495:
482:crystallized
451:ethyl groups
431:
427:
426:
337:CC(CC)(CC)CC
79:Identifiers
71:Other names
61:
57:
53:
4744:Neurotoxins
4292:Triamterene
4246:Poneratoxin
4236:Ciguatoxins
4123:Raxatrigine
4118:Ralfinamide
4113:PF-05089771
4108:PF-04531083
4080:Analgesics:
4038:Piperocaine
4023:Meprylcaine
4018:Mepivacaine
3973:Cinchocaine
3952:Ropivacaine
3944:Bupivacaine
3871:Sipatrigine
3856:Pheneturide
3851:Phenacemide
3836:Mephenytoin
3821:Lamotrigine
3801:Elpetrigine
3756:Propafenone
3701:Dronedarone
3277:Tolbutamide
3267:Repaglinide
3262:Nateglinide
3257:Mitiglinide
3237:Glisoxepide
3222:Glimepiride
3212:Glicaramide
3192:Carbutamide
3094:Linopirdine
3077:Vernakalant
3067:Tolterodine
3057:Terfenadine
3047:Tamulotoxin
3042:Solifenacin
3012:PNU-282,987
2987:Haloperidol
2982:Gigactonine
2962:Domperidone
2947:Darifenacin
2912:Bedaquiline
2897:Azaspiracid
2860:Vernakalant
2795:Linopirdine
2755:Dronedarone
2745:Dendrotoxin
2730:Clamikalant
2602:Tolperisone
2597:Tetrandrine
2587:Sipatrigine
2582:Silperisone
2567:Prenylamine
2507:Lidoflazine
2462:Elpetrigine
2372:Mirogabalin
2276:Lamotrigine
2271:Flunarizine
2266:Efonidipine
2256:Cinnarizine
2251:Cilnidipine
2206:NNC 55-0396
2132:Ralfinamide
2079:Fantofarone
2074:Dronedarone
2059:Budiodarone
2054:Brinazarone
2017:Levemopamil
1917:Sornidipine
1912:Sagandipine
1902:Pranidipine
1877:Nisoldipine
1867:Nilvadipine
1857:Niguldipine
1847:Nicardipine
1812:Lemildipine
1797:Iganidipine
1792:Furnidipine
1757:Cronidipine
1752:Clevidipine
1747:Barnidipine
1737:Aranidipine
1570:Br. Med. J.
1476:J. Physiol.
1444:J. Physiol.
1145:2035-2036.
976:sympathetic
892:as organic
492:Preparation
346:Properties
140:CHEBI:44296
4738:Categories
4596:Bumetanide
4534:Activators
4524:Piretanide
4519:Lonidamine
4470:Activators
4455:Mibefradil
4450:Mefloquine
4440:Furosemide
4435:Fluoxetine
4415:Crofelemer
4302:Activators
4225:Versutoxin
4221:Robustoxin
4203:Activators
4188:Safinamide
4138:Conotoxins
4073:Trimecaine
4068:Tetracaine
4043:Prilocaine
4033:Orthocaine
4008:Iontocaine
4003:Hexylcaine
3998:Etidocaine
3939:Benzocaine
3929:Amylocaine
3911:Zonisamide
3906:Valpromide
3876:Topiramate
3866:Rufinamide
3826:Lacosamide
3791:Cenobamate
3746:Prajmaline
3736:Moricizine
3731:Mexiletine
3726:Lorcainide
3711:Flecainide
3676:Ranolazine
3616:Activators
3601:Fluoxetine
3545:Nimesulide
3527:-specific:
3513:Activators
3495:-specific:
3447:-specific:
3427:Rilmakalim
3417:Nicorandil
3377:Cromakalim
3364:-specific:
3345:Activators
3335:Tipepidine
3325:Ifenprodil
3300:Caramiphen
3292:-specific:
3272:Tolazamide
3232:Gliquidone
3217:Gliclazide
3184:-specific:
3137:Retigabine
3132:Flupirtine
3129:-specific:
3114:Activators
3091:-specific:
3072:Vanoxerine
3052:Terodiline
3037:Sertindole
3027:Ranolazine
2892:Astemizole
2882:Amiodarone
2850:Terikalant
2825:Pinokalant
2810:Nifekalant
2805:Maurotoxin
2800:Lolitrem B
2790:Kaliotoxin
2750:Dofetilide
2740:Dalazatide
2735:Conotoxins
2705:Amiodarone
2700:Almokalant
2622:Activators
2612:Valperinol
2592:Terodiline
2532:Naftopidil
2522:Mesuximide
2452:Enpiperate
2432:Cycleanine
2417:Bevantolol
2407:Bencyclane
2397:Pregabalin
2387:PD-299,685
2382:PD-217,014
2377:PD-200,347
2367:Imagabalin
2357:Gabapentin
2347:Atagabalin
2337:Arbaclofen
2296:Mibefradil
2291:Loperamide
2286:Lomerizine
2261:Dotarizine
2241:Benidipine
2221:Zonisamide
2137:Safinamide
2112:Caroverine
2064:Celivarone
2012:Gallopamil
1967:Siratiazem
1957:Iprotiazem
1947:Clentiazem
1927:Tiamdipine
1922:Teludipine
1887:Olradipine
1872:Nimodipine
1862:Niludipine
1852:Nifedipine
1842:Mesudipine
1832:Manidipine
1807:Lacidipine
1802:Isradipine
1787:Flordipine
1782:Felodipine
1777:Elnadipine
1772:Elgodipine
1762:Darodipine
1732:Amlodipine
1433:1287-1302.
1126:References
1037:Toxicology
907:Properties
474:lipophilic
470:counterion
375:Molar mass
247:5AV7G7EIEE
192:IUPHAR/BPS
171:ChemSpider
160:ChEMBL9324
107:3D model (
86:CAS Number
4717:See also:
4616:Mepacrine
4562:Ivacaftor
4478:Carbachol
4361:Ibuprofen
4351:Amiloride
4310:Solnatide
4282:Amiloride
4211:Aconitine
4173:Evenamide
4148:Saxitoxin
4063:Risocaine
4013:Lidocaine
3958:Butacaine
3934:Articaine
3861:Phenytoin
3771:Tocainide
3766:Sparteine
3761:Quinidine
3721:Lorajmine
3716:Lidocaine
3706:Encainide
3691:Aprindine
3432:Sarakalim
3422:Pinacidil
3412:Naminidil
3402:Minoxidil
3397:Mazokalim
3382:Diazoxide
3372:Bimakalim
3367:Aprikalim
3330:Tertiapin
3310:Clozapine
3227:Glipizide
3022:Quinidine
2972:Ergtoxins
2937:Cisapride
2927:BRL-32872
2907:Azimilide
2870:(KCNH2, K
2845:Tedisamil
2830:Quinidine
2820:Paxilline
2785:Inakalant
2780:Ibutilide
2765:Hanatoxin
2720:Bunaftine
2715:Bretylium
2710:Azimilide
2695:Adekalant
2654:Potassium
2636:Bay K8644
2577:Sesamodil
2527:Monatepil
2517:Manoalide
2512:Magnesium
2497:Imepitoin
2487:Fendiline
2467:Ethadione
2457:Eperisone
2437:Dauricine
2412:Berbamine
2323:δ subunit
2127:PD-173212
2042:Verapamil
2032:Ronipamil
2022:Nexopamil
2007:Falipamil
2002:Etripamil
1987:Devapamil
1982:Dagapamil
1962:Nictiazem
1952:Diltiazem
1942:Diltiazem
1892:Oxodipine
1237:6614-6626
999:aquaporin
995:pituitary
915:ion. The
867:[NiCl
824:−
757:−
726:⟶
721:−
667:−
565:−
534:⟶
484:and more
438:with the
4702:instead.
4677:instead.
4588:Blockers
4580:Unsorted
4506:Blockers
4407:Blockers
4384:Chloride
4346:A-317567
4338:Blockers
4287:Benzamil
4274:Blockers
4103:NKTR-171
4098:GDC-0276
4093:Funapide
4088:DSP-2230
4083:AZD-3161
4048:Procaine
3963:Butamben
3811:Ethotoin
3686:Ajmaline
3665:Blockers
3624:Riluzole
3583:Blockers
3481:Blockers
3387:Emakalim
3165:Blockers
3007:Pimozide
2877:Ajmaline
2677:Blockers
2492:Fostedil
2422:Canadine
2392:Phenibut
2352:Baclofen
2301:NP078585
2246:Bepridil
2084:SR-33805
2037:Tiapamil
1997:Emopamil
1977:Anipamil
1712:Blockers
1627:103-107.
1575:321-322.
1554:805-832.
1538:733-734.
1481:117-132.
1465:805-809.
1449:155-168.
1417:299–308.
1324:737-746.
1307:103-114.
1291:318–329.
1275:413-437.
1164:870-874.
1104:See also
466:nitrogen
4754:Cations
4356:Aspirin
4178:Menthol
4165:Others:
4135:Toxins:
3978:Cocaine
3503:GAL-021
3123:KCNQ (K
3085:KCNQ (K
2902:AZD1305
2840:Sotalol
2835:ShK-186
2815:Notoxin
2502:JTV-519
2482:Fasudil
2211:ProTx I
2191:ABT-639
2178:SNX-482
2049:AH-1058
2046:Others:
1689:Calcium
1611:572-578
1536:139(11)
1513:285-292
1031:bromide
974:and at
964:ganglia
953:Biology
947:≈ −3.16
901:zeolite
600:aqueous
443:[Et
434:) is a
409:what is
407: (
369:
214:PubChem
96:66-40-0
4653:Others
3642:Sodium
3295:Barium
3099:XE-991
2967:E-4031
2917:BeKm-1
2887:AmmTX3
2770:HgeTx1
2760:E-4031
2542:Osthol
2311:TROX-1
2196:ML-218
1643:48-57.
1591:15-18.
1586:Lancet
1398:11-14.
1382:61-95.
1254:
1072:data:
873:salt.
404:verify
401:
330:SMILES
151:ChEMBL
43:Names
4687:LGICs
4394:CaCCs
4366:PcTX1
4325:ASICs
3652:VGSCs
2922:BmTx3
2775:HsTx1
2664:VGKCs
1699:VDCCs
1344:salts
1033:ion.
860:NSnCl
486:toxic
295:InChI
131:ChEBI
109:JSmol
4700:here
4698:See
4675:here
4673:See
4662:TRPs
4493:CFTR
4420:DIDS
4261:ENaC
4182:mint
3570:K2Ps
3441:GIRK
3286:GIRK
3152:IRKs
2868:hERG
2216:Z944
2142:Z160
1533:JAMA
993:and
943:log
941:(or
922:The
877:Uses
606:and
238:UNII
227:5413
202:2343
180:5220
3924:FBT
3357:ATP
3177:ATP
1609:213
1589:251
1511:456
1495:456
1479:425
1447:551
1305:215
1207:doi
1191:doi
1175:doi
949:).
935:6.9
931:o-w
852:NCN
794:ClO
691:ClO
531:EtX
432:TEA
264:EPA
217:CID
4740::
4722:•
4223:,
4219:,
3950:,
3524:Ca
3522:BK
3492:Ca
3490:BK
3467:Ca
3127:7)
3089:7)
2329:):
2044:;
1969:;
1939:;
1641:97
1625:92
1596:^
1559:^
1552:33
1463:79
1431:50
1415:84
1403:^
1396:13
1366:^
1351:^
1289:98
1273:58
1261:^
1235:14
1162:79
1143:70
1070:50
1048:50
981:.
939:10
896:.
856:Et
848:Et
766:Et
748:aq
740:Br
730:Na
712:aq
676:Na
658:aq
650:Br
627:Et
614::
538:Et
513:Et
488:.
455:−C
447:N]
365:20
4227:)
4184:)
4180:(
3954:)
3946:(
3922:p
3465:K
3355:K
3175:K
3125:v
3087:v
2872:v
2633::
2321:2
2319:α
2188::
2175::
2157::
2099::
1974::
1729::
1723::
1673:e
1666:t
1659:v
1573:2
1380:2
1322:9
1209::
1193::
1177::
945:P
937:×
928:P
913:K
871:]
869:4
862:3
858:4
850:4
846:(
818:)
815:s
812:(
806:]
798:4
790:[
783:+
779:N
770:4
762:+
751:)
745:(
734:+
715:)
709:(
703:]
695:4
687:[
680:+
672:+
661:)
655:(
644:+
640:N
631:4
561:X
555:+
551:N
542:4
528:+
525:N
517:3
461:5
459:H
457:2
453:(
445:4
430:(
399:N
367:N
363:H
361:8
359:C
266:)
262:(
111:)
62:N
60:,
58:N
56:,
54:N
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