1058:
418:
277:
1042:
53:
1026:
1217:
73:
83:
43:
723:
1195:
Recent studies suggest that guanidinium is produced by bacteria as a toxic byproduct. To alleviate the toxicity of guanidinium, bacteria have developed a class of transporters known as guanidinium exporters or Gdx proteins to expel the extra amounts of this ion to the outside of the cell. Gdx
822:
can be seen as the carbon analogue in much the same way. A detailed crystallographic analysis of guanidine was elucidated 148 years after its first synthesis, despite the simplicity of the molecule. In 2013, the positions of the hydrogen atoms and their displacement parameters were accurately
2114:
2107:
2100:
1018:
of 0.4) meaning that guanidine is a very strong base in water; in neutral water, it exists almost exclusively as guanidinium. Due to this, most guanidine derivatives are salts containing the conjugate acid.
1196:
proteins, are highly selective for guanidinium and mono-substituted guanidinyl compounds and share an overlapping set of non-canonical substrates with drug exporter EmrE.
933:
The resulting guanidinium ions can often be deprotonated to give the guanidine. This approach is sometimes called the Rathke synthesis, in honor of its discoverer. after
52:
2715:
3203:
1443:
Sawynok J, Dawborn JK (1975). "Plasma concentration and urinary excretion of guanidine derivatives in normal subjects and patients with renal failure".
736:
1602:
1352:
1168:
properties and is used to denature proteins. Guanidinium chloride is known to denature proteins with a linear relationship between concentration and
3284:
2708:
2847:
457:
1131:, further research for blood sugar control was suspended at first after the discovery of insulin. Later development of nontoxic, safe
2701:
1139:, introduced to Europe in the 1950s & United States in 1995 and now prescribed to over 17 million patients per year in the US.
1521:
Yamada T, Liu X, Englert U, Yamane H, Dronskowski R (June 2009). "Solid-state structure of free base guanidine achieved at last".
2092:
1150:. Recent studies have shown some significant subsets of patients who see no improvement after the administration of this drug.
602:
3230:
2659:
1885:
1376:
575:
325:
1422:
1619:
1057:
895:
step affords salts of the guanidinium cation (see below). In the second step, the salt is treated with base, such as
731:
432:
2767:
3247:
2676:
743:
1642:[Studies on the chemical relationships between guanine, xanthine, theobromine, caffeine and creatinine].
3151:
3012:
1915:
1701:
1659:
72:
2693:
3128:
1640:"Untersuchungen über die chemischen Beziehungen zwischen Guanin, Xanthin, Theobromin, Caffeïn und Kreatinin"
2814:
1418:
375:
272:
2746:
2956:
396:
1025:
342:
82:
3279:
2524:
1360:
1041:
1002:
541:
1486:
Göbel M, Klapötke TM (August 2007). "First structural characterization of guanidine, HN=C(NH(2))(2)".
214:
1169:
284:
846:
A laboratory method of producing guanidine is gentle (180-190 °C) thermal decomposition of dry
806:. That is, the C=O group in carbonic acid is replaced by a C=NH group, and each OH is replaced by a
2153:
413:
336:
1990:
Kermani AA, Macdonald CB, Burata OE, Ben Koff B, Koide A, Denbaum E, et al. (November 2020).
3235:
2664:
2598:
2435:
1189:
994:
42:
2122:
162:
3155:
2469:
2444:
2241:
56:
Skeletal formula of guanidine with the implicit carbon shown, and all explicit hydrogens added.
2928:
2620:
2356:
2252:
2247:
1048:
528:
3185:
2905:
2872:
2372:
2003:
1944:
1161:
1032:
847:
642:
384:
102:
1287:, and the group is related structurally to amidines and ureas. Examples of guanidines are
234:
8:
3274:
3119:
2211:
1292:
1181:
1119:
Since the Middle Ages in Europe, guanidine has been used to treat diabetes as the active
1093:
902:
138:
128:
2007:
1948:
417:
276:
194:
2901:
2320:
2024:
1991:
1967:
1932:
1854:
1827:
1805:
1468:
1456:
1124:
1076:
1075:
Guanidine can be selectively detected using sodium 1,2-naphthoquinone-4-sulfonic acid (
787:
174:
2073:
2048:
2130:
2078:
2029:
1972:
1911:
1859:
1797:
1697:
1615:
1538:
1503:
1460:
1372:
1120:
990:
1809:
1472:
2750:
2728:
2591:
2541:
2068:
2060:
2019:
2011:
1962:
1952:
1849:
1839:
1789:
1762:
1729:
1689:
1651:
1607:
1577:
1530:
1495:
1452:
1364:
1232:
1228:
896:
633:
480:
1877:
1611:
3041:
2615:
2551:
1635:
1410:
1357:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013
1351:
934:
832:
364:
303:
1992:"The structural basis of promiscuity in small multidrug resistance transporters"
831:
Guanidine can be obtained from natural sources, being first isolated in 1861 by
3241:
2992:
2974:
2723:
2670:
2487:
2392:
2326:
2257:
2176:
2134:
2123:
2015:
1937:
Proceedings of the
National Academy of Sciences of the United States of America
1322:
1128:
950:
879:
The commercial route involves a two step process starting with the reaction of
767:
714:
559:
1793:
1693:
1216:
1158:
Guanidine exists protonated, as guanidinium, in solution at physiological pH.
672:
3268:
3088:
3002:
2913:
2741:
2724:
2557:
2509:
2440:
2170:
1801:
1766:
1734:
1717:
1655:
1327:
880:
803:
518:
265:
1957:
3173:
3096:
2982:
2918:
2852:
2832:
2732:
2640:
2534:
2494:
2377:
2273:
2226:
2138:
2082:
2033:
1976:
1863:
1844:
1542:
1534:
1507:
1205:
1464:
1368:
3211:
3199:
2987:
2923:
2886:
2842:
2822:
2804:
2794:
2572:
2460:
2382:
2216:
2186:
1185:
914:
892:
888:
819:
790:
also appears in larger organic molecules, including on the side chain of
771:
254:
3207:
3181:
3141:
3136:
3073:
3058:
3020:
2891:
2881:
2799:
2789:
2645:
2635:
2630:
2567:
2562:
2519:
2514:
2504:
2465:
2294:
2267:
2231:
2127:
1310:
1165:
1132:
986:
779:
505:
315:
285:
225:
25:
1933:"Guanidinium export is the primal function of SMR family transporters"
1821:
1819:
1582:
1557:
1192:
is also used for its denaturing effect on various biological samples.
985:
groups each bonded to the central carbon atom with a covalent bond of
3189:
3063:
3053:
2997:
2964:
2857:
2837:
2827:
2784:
2779:
2450:
2425:
2367:
2339:
2310:
2304:
2288:
2278:
2221:
2196:
2191:
2064:
1499:
1296:
1136:
998:
702:
21:
1931:
Kermani AA, Macdonald CB, Gundepudi R, Stockbridge RB (March 2018).
1930:
1750:
1639:
713:
Except where otherwise noted, data are given for materials in their
3177:
3078:
3068:
2862:
2499:
2420:
2409:
2405:
2347:
2206:
2201:
2181:
1816:
1306:
1300:
1288:
1177:
1173:
1147:
1143:
906:
884:
791:
775:
245:
786:
predominantly in patients experiencing renal failure. A guanidine
161:
2415:
2352:
1828:"Treatment approach to type 2 diabetes: Past, present and future"
1332:
1108:
836:
351:
17:
1782:
Proceedings of the
Society for Experimental Biology and Medicine
1600:
Güthner T, Mertschenk B, Schulz B. "Guanidine and
Derivatives".
2396:
2362:
1780:
Sullivan MX (1935-10-01). "A Colorimetric Test for
Guanidine".
1722:
Berichte der
Deutschen Chemischen Gesellschaft (A and B Series)
1555:
1204:
Guanidinium hydroxide is the active ingredient in some non-lye
205:
1989:
835:
via the oxidative degradation of an aromatic natural product,
2625:
1284:
982:
910:
840:
783:
185:
151:
1826:
Blaslov K, Naranđa FS, Kruljac I, Renar IP (December 2018).
401:
1397:
Dissociation
Constants of Organic Bases in Aqueous Solution
697:
1825:
1558:"Single-Crystal Neutron Diffraction Study on Guanidine, CN
1135:
led to the long-used first-line diabetes control medicine
957:
802:
Guanidine can be thought of as a nitrogenous analogue of
1908:
Pediatric
Anaerobic Infections: Diagnosis and Management
1751:"Ueber Derivate und Constitution des Schwefelharnstoffs"
1556:
Sawinski PK, Meven M, Englert U, Dronskowski R (2013).
1445:
1520:
1686:
E-EROS Encyclopedia of
Reagents for Organic Synthesis
1172:
of unfolding. In aqueous solutions containing 6
823:
determined using single-crystal neutron diffraction.
1910:(3rd ed.). Taylor & Francis. p. 529.
1599:
1283:. The central bond within this group is that of an
324:
1353:International Union of Pure and Applied Chemistry
3266:
993:cation in aqueous solution due to the efficient
981:). This planar, symmetric ion consists of three
363:
137:
3156:
1755:Berichte der Deutschen Chemischen Gesellschaft
1603:Ullmann's Encyclopedia of Industrial Chemistry
1442:
2709:
2108:
1485:
1107:. It is used as a propellant, for example in
766:. It is a colourless solid that dissolves in
3089:Non-selective α-adrenergic receptor blockers
1399:(Supplement ed.). London: Butterworths.
1164:(also known as guanidine hydrochloride) has
1142:Guanidinium chloride is a now-controversial
2040:
2716:
2702:
2115:
2101:
416:
275:
233:
2072:
2023:
1966:
1956:
1853:
1843:
1733:
1595:
1593:
1581:
383:
1779:
1634:
1390:
1388:
1215:
1211:
1092:The main salt of commercial interest is
1070:
2046:
1718:"Heinrich Bernhard Rathke. (1840-1923)"
758:is the compound with the formula HNC(NH
412:
341:
253:
3267:
1748:
1679:
1590:
1394:
266:
2697:
2096:
2053:The Journal of Clinical Investigation
1905:
1385:
1001:by water molecules. As a result, its
944:
523:50 °C (122 °F; 323 K)
444:Key: ZRALSGWEFCBTJO-UHFFFAOYSA-N
213:
193:
3285:Organic compounds with 1 carbon atom
1220:The general structure of a guanidine
2480:Intestinal anti-inflammatory agents
441:InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)
354:
13:
2049:"The blooming of the French lilac"
1457:10.1111/j.1440-1681.1975.tb02368.x
774:that is used in the production of
81:
71:
51:
41:
14:
3296:
2537:agents, excluding corticosteroids
1176:guanidinium chloride, almost all
76:Ball and stick model of guanidine
1056:
1040:
1024:
721:
495:
489:
3152:Endothelin receptor antagonists
3013:Tyrosine hydroxylase inhibitors
1983:
1924:
1899:
1888:from the original on 2021-02-12
1870:
1773:
1742:
1710:
1673:
1662:from the original on 2021-07-16
1425:from the original on 2014-08-12
1153:
887:salts. Via the intermediacy of
717:(at 25 °C , 100 kPa).
3161:Tooltip Pulmonary hypertension
3129:Serotonin receptor antagonists
1728:(9): A83–A92. 8 October 1924.
1628:
1549:
1514:
1479:
1436:
1403:
1361:The Royal Society of Chemistry
1345:
623:−1.0511 – −1.0531 MJ mol
486:
1:
3046:-Adrenergic receptor blockers
2815:Adrenergic release inhibitors
2772:-Adrenergic receptor agonists
2584:Antidiarrheal micro-organisms
1612:10.1002/14356007.a12_545.pub2
1523:Chemistry: A European Journal
1338:
826:
46:Skeletal formula of guanidine
2957:Monoamine oxidase inhibitors
1419:National Library of Medicine
997:of the charge and efficient
939:
797:
86:Spacefill model of guanidine
7:
2047:Witters LA (October 2001).
1570:Crystal Growth & Design
1316:
1235:with the general structure
1114:
1087:
989:4/3. It is a highly stable
661:or concentration (LD, LC):
67:
37:
10:
3301:
2426:Camphorated opium tincture
2163:Intestinal anti-infectives
2016:10.1038/s41467-020-19820-8
1680:Palmer, David C. (2001). "
15:
3225:
3150:
3127:
3117:
3087:
3040:
3033:
3011:
2973:
2955:
2948:
2941:
2900:
2871:
2813:
2766:
2759:
2740:
2654:
2608:
2583:
2479:
2391:
2337:
2162:
2146:
1832:World Journal of Diabetes
1794:10.3181/00379727-33-8270C
1694:10.1002/047084289X.rm199s
1411:"Guanidine hydrochloride"
850:in anhydrous conditions:
839:, isolated from Peruvian
711:
683:
657:
652:
632:
627:
568:
473:
453:
428:
121:
113:
101:
96:
66:
36:
2359:, known as Pepto-Bismol)
2154:Oral rehydration therapy
1767:10.1002/cber.18810140247
1749:Rathke, B. (July 1881).
1735:10.1002/cber.19240570929
1656:10.1002/jlac.18611180203
1199:
16:Not to be confused with
2599:Saccharomyces boulardii
1958:10.1073/pnas.1719187115
1606:. Weinheim: Wiley-VCH.
1488:Chemical Communications
1190:Guanidinium thiocyanate
1127:. Due to its long-term
1082:
995:resonance stabilization
2727:(and closely related)
1845:10.4239/wjd.v9.i12.209
1535:10.1002/chem.200900508
1221:
1079:) and acidified urea.
679:475 mg/kg (oral, rat)
596:−57 – −55 kJ mol
87:
77:
57:
47:
2906:nicotinic antagonists
2621:Bismuth subsalicylate
2357:bismuth subsalicylate
2253:Succinylsulfathiazole
2248:Phthalylsulfathiazole
1996:Nature Communications
1878:"The Top 300 of 2019"
1684:-Methylisothiourea".
1369:10.1039/9781849733069
1219:
1212:Guanidine derivatives
1071:Testing for guanidine
85:
75:
55:
45:
2873:Imidazoline receptor
2609:Other antidiarrheals
1162:Guanidinium chloride
1033:ball-and-stick model
903:Isothiouronium salts
848:ammonium thiocyanate
643:Biological half-life
103:Preferred IUPAC name
2458:does not cross BBB:
2008:2020NatCo..11.6064K
1949:2018PNAS..115.3060K
1293:triazabicyclodecene
1182:secondary structure
513: g·mol
175:Beilstein Reference
116:Iminomethanediamine
33:
3252:Never to phase III
2681:Never to phase III
1395:Perrin DD (1972).
1222:
1180:lose their entire
945:Guanidinium cation
770:solvents. It is a
744:Infobox references
684:Related compounds
88:
78:
58:
48:
31:
3280:Bases (chemistry)
3262:
3261:
3221:
3220:
3113:
3112:
3109:
3108:
3105:
3104:
3029:
3028:
2937:
2936:
2902:Ganglion-blocking
2729:antihypertensives
2691:
2690:
2131:anti-inflammatory
1943:(12): 3060–3065.
1644:Liebigs Ann. Chem
1583:10.1021/cg400054k
1529:(23): 5651–5655.
1494:(30): 3180–3182.
1378:978-0-85404-182-4
1231:sharing a common
1229:organic compounds
1121:antihyperglycemic
782:. It is found in
752:Chemical compound
750:
749:
690:Related compounds
397:CompTox Dashboard
163:Interactive image
92:
91:
62:
61:
3292:
3162:
3158:
3125:
3124:
3038:
3037:
2953:
2952:
2946:
2945:
2764:
2763:
2757:
2756:
2751:vasoconstriction
2718:
2711:
2704:
2695:
2694:
2592:Escherichia coli
2552:Aminosalicylates
2542:Cromoglicic acid
2117:
2110:
2103:
2094:
2093:
2087:
2086:
2076:
2065:10.1172/JCI14178
2059:(8): 1105–1107.
2044:
2038:
2037:
2027:
1987:
1981:
1980:
1970:
1960:
1928:
1922:
1921:
1906:Brook I (2001).
1903:
1897:
1896:
1894:
1893:
1874:
1868:
1867:
1857:
1847:
1823:
1814:
1813:
1777:
1771:
1770:
1761:(2): 1774–1780.
1746:
1740:
1739:
1737:
1714:
1708:
1707:
1677:
1671:
1670:
1668:
1667:
1632:
1626:
1625:
1597:
1588:
1587:
1585:
1553:
1547:
1546:
1518:
1512:
1511:
1500:10.1039/B705100J
1483:
1477:
1476:
1440:
1434:
1433:
1431:
1430:
1407:
1401:
1400:
1392:
1383:
1382:
1349:
1282:
1281:
1280:
1272:
1271:
1263:
1262:
1254:
1253:
1245:
1244:
1233:functional group
1188:peptide chains.
1146:in treatment of
1106:
1105:
1104:
1060:
1049:resonance hybrid
1044:
1028:
980:
979:
978:
970:
969:
897:sodium methoxide
875:
817:
816:
815:
734:
728:
725:
724:
634:Pharmacokinetics
619:
592:
569:Thermochemistry
512:
497:
491:
488:
481:Chemical formula
421:
420:
405:
403:
387:
367:
356:
345:
328:
304:Gmelin Reference
287:
279:
268:
257:
237:
217:
197:
165:
141:
68:
38:
34:
30:
3300:
3299:
3295:
3294:
3293:
3291:
3290:
3289:
3265:
3264:
3263:
3258:
3257:
3242:Clinical trials
3217:
3160:
3146:
3101:
3083:
3045:
3025:
3007:
2975:VMAT inhibitors
2969:
2933:
2896:
2867:
2809:
2771:
2749:
2744:
2736:
2722:
2692:
2687:
2686:
2671:Clinical trials
2650:
2616:Albumin tannate
2604:
2579:
2488:corticosteroids
2475:
2393:Antipropulsives
2387:
2333:
2158:
2142:
2121:
2091:
2090:
2045:
2041:
1988:
1984:
1929:
1925:
1918:
1904:
1900:
1891:
1889:
1876:
1875:
1871:
1838:(12): 209–219.
1824:
1817:
1778:
1774:
1747:
1743:
1716:
1715:
1711:
1704:
1678:
1674:
1665:
1663:
1633:
1629:
1622:
1598:
1591:
1565:
1561:
1554:
1550:
1519:
1515:
1484:
1480:
1441:
1437:
1428:
1426:
1409:
1408:
1404:
1393:
1386:
1379:
1363:. p. 883.
1350:
1346:
1341:
1319:
1279:
1276:
1275:
1274:
1270:
1267:
1266:
1265:
1261:
1258:
1257:
1256:
1252:
1249:
1248:
1247:
1243:
1240:
1239:
1238:
1236:
1227:are a group of
1214:
1202:
1186:randomly coiled
1156:
1117:
1103:
1100:
1099:
1098:
1096:
1090:
1085:
1077:Folin's reagent
1073:
1066:
1065:
1064:canonical forms
1061:
1052:
1051:
1045:
1036:
1035:
1029:
1017:
1009:
977:
974:
973:
972:
968:
965:
964:
963:
961:
947:
942:
935:Bernhard Rathke
928:
924:
874:
870:
866:
862:
858:
854:
833:Adolph Strecker
829:
814:
811:
810:
809:
807:
800:
765:
761:
753:
746:
741:
740:
739: ?)
730:
726:
722:
718:
707:
691:
676:
670:
645:
620:
617:
611:
607:
604:
603:Std enthalpy of
593:
590:
584:
580:
577:
576:Std enthalpy of
550:
510:
500:
494:
483:
469:
466:
461:
460:
449:
446:
445:
442:
436:
435:
424:
406:
399:
390:
370:
357:
331:
318:
306:
297:
260:
240:
220:
200:
177:
168:
155:
144:
131:
117:
109:
108:
29:
12:
11:
5:
3298:
3288:
3287:
3282:
3277:
3260:
3259:
3256:
3255:
3254:
3253:
3250:
3239:
3233:
3227:
3226:
3223:
3222:
3219:
3218:
3216:
3215:
3193:
3166:
3164:
3148:
3147:
3145:
3144:
3139:
3133:
3131:
3122:
3115:
3114:
3111:
3110:
3107:
3106:
3103:
3102:
3100:
3099:
3093:
3091:
3085:
3084:
3082:
3081:
3076:
3071:
3066:
3061:
3056:
3050:
3048:
3043:
3035:
3031:
3030:
3027:
3026:
3024:
3023:
3017:
3015:
3009:
3008:
3006:
3005:
3000:
2995:
2993:Methoserpidine
2990:
2985:
2979:
2977:
2971:
2970:
2968:
2967:
2961:
2959:
2950:
2943:
2939:
2938:
2935:
2934:
2932:
2931:
2926:
2921:
2916:
2910:
2908:
2898:
2897:
2895:
2894:
2889:
2884:
2878:
2876:
2869:
2868:
2866:
2865:
2860:
2855:
2850:
2845:
2840:
2835:
2830:
2825:
2819:
2817:
2811:
2810:
2808:
2807:
2802:
2797:
2792:
2787:
2782:
2776:
2774:
2769:
2761:
2754:
2742:Sympatholytics
2738:
2737:
2721:
2720:
2713:
2706:
2698:
2689:
2688:
2685:
2684:
2683:
2682:
2679:
2668:
2662:
2656:
2655:
2652:
2651:
2649:
2648:
2643:
2638:
2633:
2628:
2623:
2618:
2612:
2610:
2606:
2605:
2603:
2602:
2595:
2587:
2585:
2581:
2580:
2578:
2577:
2576:
2575:
2570:
2565:
2560:
2547:
2546:
2545:
2544:
2530:
2529:
2528:
2527:
2522:
2517:
2512:
2507:
2502:
2500:Hydrocortisone
2497:
2490:acting locally
2483:
2481:
2477:
2476:
2474:
2473:
2463:
2454:
2453:
2448:
2430:
2429:
2423:
2418:
2413:
2406:Opium tincture
2402:
2400:
2389:
2388:
2386:
2385:
2380:
2375:
2370:
2365:
2360:
2350:
2344:
2342:
2335:
2334:
2332:
2331:
2330:
2329:
2327:Broxyquinoline
2316:
2315:
2314:
2313:
2300:
2299:
2298:
2297:
2284:
2283:
2282:
2281:
2276:
2263:
2262:
2261:
2260:
2258:Sulfaguanidine
2255:
2250:
2237:
2236:
2235:
2234:
2229:
2224:
2219:
2214:
2209:
2204:
2199:
2194:
2189:
2184:
2179:
2177:Amphotericin B
2166:
2164:
2160:
2159:
2157:
2156:
2150:
2148:
2144:
2143:
2135:anti-infective
2124:Antidiarrheals
2120:
2119:
2112:
2105:
2097:
2089:
2088:
2039:
1982:
1923:
1916:
1898:
1869:
1815:
1788:(1): 106–108.
1772:
1741:
1709:
1702:
1672:
1650:(2): 151–177.
1627:
1621:978-3527306732
1620:
1589:
1563:
1559:
1548:
1513:
1478:
1435:
1402:
1384:
1377:
1343:
1342:
1340:
1337:
1336:
1335:
1330:
1325:
1323:Sakaguchi test
1318:
1315:
1277:
1268:
1259:
1250:
1241:
1213:
1210:
1201:
1198:
1155:
1152:
1129:hepatotoxicity
1123:ingredient in
1116:
1113:
1101:
1089:
1086:
1084:
1081:
1072:
1069:
1068:
1067:
1063:
1062:
1055:
1053:
1047:
1046:
1039:
1037:
1031:
1030:
1023:
1015:
1007:
975:
966:
953:is called the
951:conjugate acid
946:
943:
941:
938:
931:
930:
926:
922:
877:
876:
872:
868:
864:
860:
856:
828:
825:
812:
799:
796:
763:
759:
751:
748:
747:
742:
720:
719:
715:standard state
712:
709:
708:
706:
705:
700:
694:
692:
689:
686:
685:
681:
680:
677:
668:
666:
663:
662:
655:
654:
650:
649:
646:
641:
638:
637:
630:
629:
625:
624:
621:
615:
609:
601:
598:
597:
594:
588:
582:
574:
571:
570:
566:
565:
562:
560:Conjugate acid
556:
555:
552:
548:
538:
537:
534:
525:
524:
521:
515:
514:
508:
502:
501:
498:
492:
484:
479:
476:
475:
471:
470:
468:
467:
464:
456:
455:
454:
451:
450:
448:
447:
443:
440:
439:
431:
430:
429:
426:
425:
423:
422:
409:
407:
395:
392:
391:
389:
388:
380:
378:
372:
371:
369:
368:
360:
358:
350:
347:
346:
339:
333:
332:
330:
329:
321:
319:
314:
311:
310:
307:
302:
299:
298:
296:
295:
291:
289:
281:
280:
270:
262:
261:
259:
258:
250:
248:
242:
241:
239:
238:
230:
228:
222:
221:
219:
218:
210:
208:
202:
201:
199:
198:
190:
188:
182:
181:
178:
173:
170:
169:
167:
166:
158:
156:
149:
146:
145:
143:
142:
134:
132:
127:
124:
123:
119:
118:
115:
111:
110:
106:
105:
99:
98:
94:
93:
90:
89:
79:
64:
63:
60:
59:
49:
9:
6:
4:
3:
2:
3297:
3286:
3283:
3281:
3278:
3276:
3273:
3272:
3270:
3251:
3249:
3246:
3245:
3243:
3240:
3237:
3234:
3232:
3229:
3228:
3224:
3213:
3209:
3205:
3201:
3197:
3194:
3191:
3187:
3183:
3179:
3175:
3171:
3168:
3167:
3165:
3159:
3153:
3149:
3143:
3140:
3138:
3135:
3134:
3132:
3130:
3126:
3123:
3121:
3116:
3098:
3095:
3094:
3092:
3090:
3086:
3080:
3077:
3075:
3072:
3070:
3067:
3065:
3062:
3060:
3057:
3055:
3052:
3051:
3049:
3047:
3039:
3036:
3032:
3022:
3019:
3018:
3016:
3014:
3010:
3004:
3003:Syrosingopine
3001:
2999:
2996:
2994:
2991:
2989:
2986:
2984:
2981:
2980:
2978:
2976:
2972:
2966:
2963:
2962:
2960:
2958:
2954:
2951:
2947:
2944:
2940:
2930:
2927:
2925:
2922:
2920:
2917:
2915:
2914:Hexamethonium
2912:
2911:
2909:
2907:
2903:
2899:
2893:
2890:
2888:
2885:
2883:
2880:
2879:
2877:
2874:
2870:
2864:
2861:
2859:
2856:
2854:
2851:
2849:
2846:
2844:
2841:
2839:
2836:
2834:
2831:
2829:
2826:
2824:
2821:
2820:
2818:
2816:
2812:
2806:
2803:
2801:
2798:
2796:
2793:
2791:
2788:
2786:
2783:
2781:
2778:
2777:
2775:
2773:
2765:
2762:
2758:
2755:
2752:
2748:
2743:
2739:
2734:
2730:
2726:
2725:Sympatholytic
2719:
2714:
2712:
2707:
2705:
2700:
2699:
2696:
2680:
2678:
2675:
2674:
2672:
2669:
2666:
2663:
2661:
2658:
2657:
2653:
2647:
2644:
2642:
2639:
2637:
2634:
2632:
2629:
2627:
2624:
2622:
2619:
2617:
2614:
2613:
2611:
2607:
2601:
2600:
2596:
2594:
2593:
2589:
2588:
2586:
2582:
2574:
2571:
2569:
2566:
2564:
2561:
2559:
2558:Sulfasalazine
2556:
2555:
2554:
2553:
2549:
2548:
2543:
2540:
2539:
2538:
2536:
2532:
2531:
2526:
2525:Beclometasone
2523:
2521:
2518:
2516:
2513:
2511:
2510:Betamethasone
2508:
2506:
2503:
2501:
2498:
2496:
2493:
2492:
2491:
2489:
2485:
2484:
2482:
2478:
2471:
2467:
2464:
2462:
2459:
2456:
2455:
2452:
2449:
2446:
2442:
2441:Diphenoxylate
2439:
2437:
2432:
2431:
2427:
2424:
2422:
2419:
2417:
2414:
2411:
2407:
2404:
2403:
2401:
2398:
2394:
2390:
2384:
2381:
2379:
2376:
2374:
2371:
2369:
2366:
2364:
2361:
2358:
2354:
2351:
2349:
2346:
2345:
2343:
2341:
2336:
2328:
2325:
2324:
2323:
2322:
2318:
2317:
2312:
2309:
2308:
2307:
2306:
2302:
2301:
2296:
2293:
2292:
2291:
2290:
2286:
2285:
2280:
2277:
2275:
2272:
2271:
2270:
2269:
2265:
2264:
2259:
2256:
2254:
2251:
2249:
2246:
2245:
2244:
2243:
2239:
2238:
2233:
2230:
2228:
2225:
2223:
2220:
2218:
2215:
2213:
2210:
2208:
2205:
2203:
2200:
2198:
2195:
2193:
2190:
2188:
2185:
2183:
2180:
2178:
2175:
2174:
2173:
2172:
2168:
2167:
2165:
2161:
2155:
2152:
2151:
2149:
2145:
2140:
2136:
2132:
2129:
2125:
2118:
2113:
2111:
2106:
2104:
2099:
2098:
2095:
2084:
2080:
2075:
2070:
2066:
2062:
2058:
2054:
2050:
2043:
2035:
2031:
2026:
2021:
2017:
2013:
2009:
2005:
2001:
1997:
1993:
1986:
1978:
1974:
1969:
1964:
1959:
1954:
1950:
1946:
1942:
1938:
1934:
1927:
1919:
1913:
1909:
1902:
1887:
1883:
1879:
1873:
1865:
1861:
1856:
1851:
1846:
1841:
1837:
1833:
1829:
1822:
1820:
1811:
1807:
1803:
1799:
1795:
1791:
1787:
1783:
1776:
1768:
1764:
1760:
1756:
1752:
1745:
1736:
1731:
1727:
1723:
1719:
1713:
1705:
1699:
1695:
1691:
1687:
1683:
1676:
1661:
1657:
1653:
1649:
1645:
1641:
1637:
1631:
1623:
1617:
1613:
1609:
1605:
1604:
1596:
1594:
1584:
1579:
1576:(4): 1730–5.
1575:
1571:
1567:
1552:
1544:
1540:
1536:
1532:
1528:
1524:
1517:
1509:
1505:
1501:
1497:
1493:
1489:
1482:
1474:
1470:
1466:
1462:
1458:
1454:
1450:
1446:
1439:
1424:
1420:
1416:
1412:
1406:
1398:
1391:
1389:
1380:
1374:
1370:
1366:
1362:
1358:
1354:
1348:
1344:
1334:
1331:
1329:
1328:Y-aromaticity
1326:
1324:
1321:
1320:
1314:
1312:
1308:
1304:
1302:
1298:
1294:
1290:
1286:
1234:
1230:
1226:
1218:
1209:
1207:
1206:hair relaxers
1197:
1193:
1191:
1187:
1183:
1179:
1175:
1171:
1167:
1163:
1159:
1151:
1149:
1145:
1140:
1138:
1134:
1130:
1126:
1122:
1112:
1110:
1095:
1080:
1078:
1059:
1054:
1050:
1043:
1038:
1034:
1027:
1022:
1021:
1020:
1014:
1010:
1006:
1000:
996:
992:
988:
984:
959:
956:
952:
937:
936:
920:
919:
918:
916:
912:
909:) react with
908:
905:(S-alkylated
904:
900:
898:
894:
890:
886:
882:
881:dicyandiamide
853:
852:
851:
849:
844:
842:
838:
834:
824:
821:
805:
804:carbonic acid
795:
793:
789:
785:
781:
777:
773:
769:
757:
745:
738:
733:
716:
710:
704:
701:
699:
696:
695:
693:
688:
687:
682:
678:
674:
665:
664:
660:
656:
651:
647:
644:
640:
639:
635:
631:
628:Pharmacology
626:
622:
614:
606:
600:
599:
595:
587:
579:
573:
572:
567:
563:
561:
558:
557:
553:
547:
543:
540:
539:
535:
533:
532:
527:
526:
522:
520:
519:Melting point
517:
516:
509:
507:
504:
503:
485:
482:
478:
477:
472:
463:
462:
459:
452:
438:
437:
434:
427:
419:
415:
414:DTXSID0023117
411:
410:
408:
398:
394:
393:
386:
382:
381:
379:
377:
374:
373:
366:
362:
361:
359:
353:
349:
348:
344:
340:
338:
335:
334:
327:
323:
322:
320:
317:
313:
312:
308:
305:
301:
300:
293:
292:
290:
288:
283:
282:
278:
274:
271:
269:
267:ECHA InfoCard
264:
263:
256:
252:
251:
249:
247:
244:
243:
236:
232:
231:
229:
227:
224:
223:
216:
212:
211:
209:
207:
204:
203:
196:
192:
191:
189:
187:
184:
183:
179:
176:
172:
171:
164:
160:
159:
157:
153:
148:
147:
140:
136:
135:
133:
130:
126:
125:
120:
112:
104:
100:
95:
84:
80:
74:
70:
69:
65:
54:
50:
44:
40:
39:
35:
27:
23:
19:
3195:
3174:Aprocitentan
3169:
3097:Phentolamine
2983:Bietaserpine
2929:Trimethaphan
2919:Mecamylamine
2853:Guanethidine
2833:Debrisoquine
2747:α-adrenergic
2745:(antagonize
2641:Racecadotril
2597:
2590:
2550:
2535:antiallergic
2533:
2495:Prednisolone
2486:
2470:+simethicone
2457:
2433:
2373:Crospovidone
2321:Oxyquinoline
2319:
2303:
2287:
2274:Nifuroxazide
2266:
2242:Sulfonamides
2240:
2227:Streptomycin
2169:
2056:
2052:
2042:
1999:
1995:
1985:
1940:
1936:
1926:
1907:
1901:
1890:. Retrieved
1882:clincalc.com
1881:
1872:
1835:
1831:
1785:
1781:
1775:
1758:
1754:
1744:
1725:
1721:
1712:
1685:
1681:
1675:
1664:. Retrieved
1647:
1643:
1630:
1601:
1573:
1569:
1551:
1526:
1522:
1516:
1491:
1487:
1481:
1448:
1444:
1438:
1427:. Retrieved
1414:
1405:
1396:
1356:
1347:
1305:
1224:
1223:
1203:
1194:
1160:
1157:
1154:Biochemistry
1141:
1125:French lilac
1118:
1091:
1074:
1012:
1004:
954:
948:
932:
925:+ X → X + CH
901:
878:
859:SCN → 2 CH
845:
830:
801:
755:
754:
658:
612:
585:
564:Guanidinium
545:
530:
122:Identifiers
114:Other names
3238:from market
3212:Sotatercept
3200:Ambrisentan
3120:antagonists
2988:Deserpidine
2924:Pentolinium
2887:Rilmenidine
2843:Guanazodine
2823:Bethanidine
2805:Tiamenidine
2795:Guanoxabenz
2667:from market
2573:Balsalazide
2461:Eluxadoline
2428:(paregoric)
2383:Diosmectite
2378:Attapulgite
2355:(including
2338:Intestinal
2217:Polymyxin B
2212:Paromomycin
2187:Fidaxomicin
2171:Antibiotics
2147:Rehydration
2002:(1): 6064.
1451:(1): 1–15.
1313:guanidine.
1184:and become
1170:free energy
1094:the nitrate
955:guanidinium
915:guanidinium
893:ammonolysis
889:biguanidine
772:strong base
673:median dose
659:Lethal dose
474:Properties
273:100.003.656
195:CHEBI:42820
3275:Guanidines
3269:Categories
3208:Sitaxentan
3204:+tadalafil
3186:+tadalafil
3182:Macitentan
3142:Lidanserin
3137:Ketanserin
3074:Trimazosin
3059:Ketanserin
3021:Metirosine
2942:Peripheral
2892:Tolonidine
2882:Moxonidine
2848:Guancydine
2800:Methyldopa
2790:Guanfacine
2646:Kaopectate
2636:Octreotide
2631:Crofelemer
2568:Olsalazine
2563:Mesalazine
2520:Budesonide
2515:Tixocortol
2505:Prednisone
2466:Loperamide
2340:adsorbents
2295:Miconazole
2268:Nitrofuran
2232:Vancomycin
2128:intestinal
1917:0824741862
1892:2022-02-17
1703:0471936235
1666:2019-07-02
1636:Strecker A
1429:2014-08-10
1415:ChemIDplus
1339:References
1311:isoamylene
1225:Guanidines
1166:chaotropic
1133:biguanides
1011:is 13.6 (p
827:Production
780:explosives
648:7–8 hours
605:combustion
506:Molar mass
385:JU58VJ6Y3B
316:IUPHAR/BPS
226:ChemSpider
150:3D model (
129:CAS Number
32:Guanidine
26:Guanfacine
3248:Phase III
3236:Withdrawn
3196:selective
3190:Riociguat
3064:Indoramin
3054:Doxazosin
2998:Reserpine
2965:Pargyline
2858:Guanoclor
2838:Guanadrel
2828:Bretylium
2785:Guanabenz
2780:Clonidine
2677:Phase III
2665:Withdrawn
2626:Ceratonia
2451:Difenoxin
2445:+atropine
2311:Acetarsol
2305:Arsenical
2289:Imidazole
2279:Nifurzide
2222:Rifaximin
2197:Natamycin
2192:Kanamycin
1802:0037-9727
1297:saxitoxin
1137:metformin
999:solvation
940:Chemistry
907:thioureas
820:Isobutene
798:Structure
756:Guanidine
703:Biguanide
578:formation
343:Guanidine
294:204-021-8
286:EC Number
215:ChEMBL821
107:Guanidine
22:Guanosine
3178:Bosentan
3079:Urapidil
3069:Prazosin
2949:Indirect
2875:agonists
2863:Guanoxan
2434:crosses
2421:Morphine
2410:laudanum
2348:Charcoal
2207:Nystatin
2202:Neomycin
2182:Colistin
2137:agents (
2083:11602616
2034:33247110
1977:29507227
1886:Archived
1864:30588282
1810:88290359
1660:Archived
1638:(1861).
1543:19388036
1508:17653381
1473:41794868
1423:Archived
1355:(2014).
1317:See also
1307:Galegine
1301:creatine
1289:arginine
1178:proteins
1148:botulism
1144:adjuvant
1115:Medicine
1109:air bags
1088:Industry
917:salts:
913:to give
885:ammonium
792:arginine
776:plastics
653:Hazards
542:Basicity
246:DrugBank
139:113-00-8
2760:Central
2416:Codeine
2397:opioids
2353:Bismuth
2025:7695847
2004:Bibcode
1968:5866581
1945:Bibcode
1855:6304295
1465:1126056
1333:Amidine
1273:N)C=N−R
891:, this
837:guanine
818:group.
737:what is
735: (
536:−1.251
465:NC(N)=N
352:PubChem
309:100679
255:DB00536
180:506044
18:Guanine
3231:WHO-EM
3118:Other
3034:Direct
2660:WHO-EM
2368:Kaolin
2363:Pectin
2081:
2074:209536
2071:
2032:
2022:
1975:
1965:
1914:
1862:
1852:
1808:
1800:
1700:
1618:
1541:
1506:
1471:
1463:
1375:
1309:is an
1299:, and
958:cation
911:amines
871:S + CS
788:moiety
732:verify
729:
511:59.072
458:SMILES
206:ChEMBL
97:Names
3154:(for
1806:S2CID
1469:S2CID
1285:imine
1200:Other
987:order
983:amino
883:with
841:guano
784:urine
768:polar
433:InChI
186:ChEBI
152:JSmol
24:, or
3170:dual
2133:and
2079:PMID
2030:PMID
1973:PMID
1912:ISBN
1860:PMID
1798:ISSN
1698:ISBN
1616:ISBN
1539:PMID
1504:PMID
1461:PMID
1373:ISBN
1255:N)(R
1083:Uses
962:C(NH
949:The
855:3 NH
778:and
698:Urea
554:0.4
529:log
376:UNII
365:3520
337:MeSH
326:4783
235:3400
3206:),
3188:),
2733:C02
2436:BBB
2139:A07
2069:PMC
2061:doi
2057:108
2020:PMC
2012:doi
1963:PMC
1953:doi
1941:115
1850:PMC
1840:doi
1790:doi
1763:doi
1730:doi
1690:doi
1652:doi
1648:118
1608:doi
1578:doi
1531:doi
1496:doi
1453:doi
1365:doi
960:, (
921:RNH
867:+ H
616:298
589:298
402:EPA
355:CID
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3210:,
3180:,
3176:,
3157:PH
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1097:NO
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794:.
669:50
667:LD
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608:(Δ
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1264:R
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1251:2
1246:R
1242:1
1174:M
1102:3
1016:b
1013:K
1005:K
1003:p
976:3
971:)
967:2
927:3
923:2
873:2
869:2
865:3
863:N
861:5
857:4
813:2
764:2
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760:2
727:Y
675:)
671:(
618:)
613:H
610:c
591:)
586:H
583:f
549:b
546:K
531:P
499:3
496:N
493:5
490:H
487:C
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400:(
154:)
28:.
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