1069:
1080:
reaction so strong that the mixture boils, and sometimes even produces a sort of explosion. If the ammonia is in excess, all the ether disappears. It forms ammonium hydrochlorate and a new substance endowed with interesting properties." Dumas appears to be naming this compound urethane. However, later Dumas states "While waiting for opinion to settle on the nature of this body, I propose to designate by the names of urethane and oxamethane the two materials which I have just studied, and
630:
523:
20:
1088:
Dumas, the discoverer, called urethane, and which we are now in the habit of considering as the ether of carbamic acid." This suggests that instead of continuing with the urethane family naming convention Dumas coined, they altered the naming convention to ethyl ether of carbamic acid. Carbamate is derived from the words "carbamide", otherwise known as urea, and "-ate" a suffix which indicates the salt or ester of an acid.
1084:. These names which, in my eyes, do not prejudge anything in the question of alcohol and ethers, will at least have the advantage of satisfying chemists who still refuse to accept our theory." The word urethane is derived from the words "urea" and "ether" with the suffix "-ane" as a generic chemical suffix, making it specific for the R2NC(=O)OR' (R' not = H) bonding structure.
2177:
955:
carbamate exposure can vary from slightly toxic to highly toxic depending on a variety of factors including such as dose and route of exposure with ingestion and inhalation resulting in the most rapid clinical effects. These clinical manifestations of carbamate intoxication are muscarinic signs, nicotinic signs, and in rare cases central nervous system signs.
2209:
1864:
Sparks, Thomas; Crossthwaite, Andrew; Nauen, Ralf; Banba, Shinichi; Cordova, Daniel; Earley, Fergus; Ebbinghaus-Kintscher, Ulrich; Fujioka, Shinsuke; Hirao, Ayako; Karmon, Danny; Kennedy, Robert; Nakao, Toshifumi; Popham, Holly; Salgado, Vincent; Watson, Gerald; Wedel, Barbara; Wessels, Frank (2020).
765:
are still capable of inhibiting mammalian acetylcholinesterase enzymes at low enough concentrations that they pose a significant risk of poisoning to humans, especially when used in large amounts for agricultural applications. Other carbamate based acetylcholinesterase inhibitors are known with even
1079:
The etymology of the words "urethane" and "carbamate" are highly similar but not the same. The word "urethane" was first coined in 1833 by French chemist Jean-Baptiste Dumas. Dumas states "Urethane. The new ether, brought into contact with liquid and concentrated ammonia, exerts on this substance a
1105:
IUPAC states "The esters are often called urethanes or urethans, a usage that is strictly correct only for the ethyl esters." But also states, "An alternative term for the compounds R2NC(=O)OR' (R' not = H), esters of carbamic acids, R,NC(=O)OH, in strict use limited to the ethyl esters, but
1087:
The use of the word "carbamate" appears to come later only being traced back to at least 1849, in a description of Dumas's work by Henry
Medlock. Medlock states "It is well known that the action of ammonia on chloro-carbonate (phosgene) of ethyl gives rise to the formation of the substance which
954:
Besides inhibiting human acetylcholinesterase (although to a lesser degree than the insect enzyme), carbamate insecticides also target human melatonin receptors. The human health effects of carbamates are well documented in the list of known endocrine disruptor compounds. Clinical effects of
1091:
Both words have roots deriving from urea. Carbamate is less-specific because the -ate suffix is ambiguous for either the salt or ester of a carbamic acid. However, the -ate suffix is also more specific because it suggests carbamates must be derived from the acid of carbamate, or carbamic
1101:
is not a carbamate ester but instead a urethane. Furthermore, carbamate esters are urethanes but not all urethanes are carbamate esters. This further suggests that polyurethanes are not simply polycarbamate-esters because polyurethanes are not typically synthesized using carbamic acids.
1664:
Adam, Norbert; Avar, Geza; Blankenheim, Herbert; Friederichs, Wolfgang; Giersig, Manfred; Weigand, Eckehard; Halfmann, Michael; Wittbecker, Friedrich-Wilhelm; Larimer, Donald-Richard; Maier, Udo; Meyer-Ahrens, Sven; Noble, Karl-Ludwig; Wussow, Hans-Georg (2005). "Polyurethanes".
1928:
Oakeshott, John; Devonshire, Alan; Claudianos, Charles; Sutherland, Tara; Horne, Irene; Campbell, Peter; Ollis, David; Russell, Robyn (2005). "Comparing the organophosphorus and carbamate insecticide resistance mutations in cholin- and carboxyl-esterases".
756:
While the carbamate acetylcholinesterase inhibitors are commonly referred to as "carbamate insecticides" due to their generally high selectivity for insect acetylcholinesterase enzymes over the mammalian versions, the most potent compounds such as
419:
Within nature carbon dioxide can bind with neutral amine groups to form a carbamate, this post-translational modification is known as carbamylation. This modification is known to occur on several important proteins; see examples below.
1096:
Although, a urethane has the same chemical structure as a carbamate ester moiety, a urethane not derived from a carbamic acid is not a carbamate ester. In other words, any synthesis of the R2NC(=O)OR' (R' not = H) moiety that
1871:
2257:
Holland, J. R.; Hosley, H.; Scharlau, C.; Carbone, P. P.; Frei, E. III; Brindley, C. O.; Hall, T. C.; Shnider, B. I.; Gold, G. L.; Lasagna, L.; Owens, A. H. Jr; Miller, S. P. (1 March 1966).
1453:
Linthwaite, Victoria L.; Janus, Joanna M.; Brown, Adrian P.; Wong-Pascua, David; O'Donoghue, AnnMarie C.; Porter, Andrew; Treumann, Achim; Hodgson, David R. W.; Cann, Martin J. (2018-08-06).
573:
contain multiple carbamate groups as part of their structure. The "urethane" in the name "polyurethane" refers to these carbamate groups; the term "urethane links" describe how carbamates
729:
842:
agent and for other medicinal purposes. It was found to be toxic and largely ineffective. It is occasionally used in veterinary medicine in combination with other drugs to produce
1627:
T, Lundqvist; G, Schneider (1991-01-29). "Crystal
Structure of the Ternary Complex of ribulose-1,5-bisphosphate Carboxylase, Mg(II), and Activator CO2 at 2.3-A Resolution".
283:
salt to an ammonium carbamate/carbonate solution will precipitate some calcium carbonate immediately, and then slowly precipitate more as the carbamate hydrolyzes.
2052:
2230:
Marullo, N. P.; Wagener, E. H. (1969-01-01). "Structural organic chemistry by nmr. III. Isomerization of compounds containing the carbon-nitrogen double bond".
786:
penetration, and also are only stable as crystalline salts or aqueous solutions, and so were not considered to have suitable properties for weaponisation.
2674:
1774:
1667:
1156:
436:
exist as carbamates. They help to stabilise the protein when it becomes deoxyhemoglobin, and increases the likelihood of the release of remaining
689:
pesticides also inhibit this enzyme, although irreversibly, and cause a more severe form of cholinergic poisoning (the similar IRAC MoA 1b).
2929:
810:
3848:
2309:
1257:
3853:
1758:
818:
806:
581:, is neither a component of polyurethanes, nor is it used in their manufacture. Urethanes are usually formed by reaction of an
2791:"XXVII.—On the precipitation of solutions of ammonium carbonate, sodium carbonate, and ammonium carbamate by calcium chloride"
2630:
2195:
2026:
2001:
1867:"Insecticides, biologics and nematicides: Updates to IRAC's mode of action classification - a tool for resistance management"
1684:
1393:
2863:"Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)"
2307:
1807:
1791:
2545:
2152:
2119:
1706:
1173:
920:
2679:
2922:
2795:
1931:
1423:
519:
the substrate carbon dioxide molecule), which then renders it charged, and, therefore, able to bind the Mg ion.
1195:
1063:
859:
3752:
464:
also feature carbamate. The carbamate derived from aminoimidazole is an intermediate in the biosynthesis of
1284:
Clark, K. G.; Gaddy, V. L.; Rist, C. E. (1933). "Equilibria in the
Ammonium Carbamate-Urea-Water System".
912:
drugs widely used in the 1960s before the rise of benzodiazepines, and still used nowadays in some cases.
794:
1068:
3876:
3325:
2915:
2867:
2654:
1346:
929:
779:
741:
2790:
1414:
1337:
3362:
1130:
526:
Carbamate formation is a critical step in the formation of biomass from atmospheric carbon dioxide.
3835:
783:
696:
2308:
The
Chemical/Biological Safety Section (CBSS) of the Office of Environmental Health and Safety.
3735:
1629:
1154:
Jäger, Peter; Rentzea, Costin N.; Kieczka, Heinz (2000). "Carbamates and
Carbamoyl Chlorides".
58:
1991:
1253:"The equilibrium between ammonium carbonate and ammonium carbamate in aqueous solution at 25°"
3842:
3730:
2095:
1459:
1376:
Brooks, L. A.; Audrieta, L. F.; Bluestone, H.; Jofinsox, W. C. (1946). "Ammonium
Carbamate".
385:
544:
is produced on a large scale as an intermediate in the production of the commodity chemical
3811:
3256:
1940:
1884:
1577:
Bartoschek, S.; Vorholt, J. A.; Thauer, R. K.; Geierstanger, B. H.; Griesinger, C. (2001).
1468:
814:
737:
678:
605:
8:
3881:
3117:
2404:
1312:
Mani, Fabrizio; Peruzzini, Maurizio; Stoppioni, Piero (2006). "CO2 absorption by aqueous
949:
604:, and solids. Typically, polyurethane polymers are made by combining diisocyanates, e.g.
582:
511:
residues as well as a lysine carbamate. The carbamate is formed when an uncharged lysine
2316:
1944:
1888:
1472:
1455:"The identification of carbon dioxide mediated protein post-translational modifications"
1375:
440:
molecules bound to the protein. This stabilizing effect should not be confused with the
2894:
2765:
2648:
2592:
2477:
2450:
2426:
2399:
2201:
1972:
1811:
1754:
1728:
1701:
1554:
1521:
1497:
1454:
1225:
1190:
870:
541:
461:
333:
297:
104:
51:
2243:
2144:
1412:
Chaturvedi, Devdutt (1 May 2011). "Recent
Developments on the Carbamation of Amines".
3801:
3771:
3529:
3151:
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2812:
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2636:
2626:
2541:
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2191:
2158:
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2115:
2076:
2068:
2032:
2022:
1997:
1964:
1956:
1910:
1902:
1833:
1787:
1733:
1680:
1646:
1609:
1604:
1578:
1559:
1541:
1502:
1484:
1435:
1389:
1358:
1230:
1212:
1169:
1106:
widely used in the general sense". IUPAC provides these statements without citation.
1007:
976:
276:
28:
2898:
2205:
1976:
3506:
3000:
2938:
2876:
2837:
2804:
2739:
2731:
2604:
2573:
2533:
2472:
2468:
2464:
2455:
2421:
2413:
2372:
2363:
Hikino H, Ogata K, Kasahara Y, Konno C (May 1985). "Pharmacology of ephedroxanes".
2272:
2239:
2183:
2140:
2135:
Wellings, Donald A.; Atherton, Eric (1997). "[4] Standard Fmoc protocols".
2107:
2060:
1948:
1892:
1779:
1723:
1715:
1672:
1638:
1599:
1591:
1549:
1537:
1533:
1492:
1476:
1427:
1381:
1350:
1294:
1266:
1220:
1204:
1161:
1115:
745:
135:
89:
85:
40:
36:
1676:
3725:
3484:
3479:
3462:
3445:
3246:
2995:
2263:
1983:
1897:
1866:
1587:
in methanogenic archaea: Thermodynamics and kinetics of the spontaneous reaction"
1286:
1120:
992:
909:
855:
835:
686:
578:
77:
2417:
2277:
2258:
3796:
3791:
3667:
3662:
3657:
3450:
3417:
3201:
3183:
3173:
2831:
1480:
1431:
1385:
682:
553:
485:
305:
2187:
2111:
1952:
1522:"The direct chemical estimation of carbamino compounds of CO2 with hæmoglobin"
3870:
3816:
3764:
3695:
3581:
3571:
3566:
3556:
3551:
3501:
3496:
3412:
3407:
3397:
3251:
3206:
3168:
3156:
3127:
3005:
2890:
2816:
2751:
2640:
2608:
2537:
2398:
Colović, MB; Krstić, DZ; Lazarević-Pašti, TD; Bondžić, AM; Vasić, VM (2013).
2286:
2093:
2072:
1996:. Cambridge, Massachusetts, United States: Academic Press. pp. 338–339.
1960:
1906:
1783:
1545:
1488:
1439:
1362:
1216:
1165:
1055:
980:
897:
877:
612:, where the carbamate groups are formed by reaction of the alcohols with the
508:
504:
357:
62:
2881:
2862:
2841:
2064:
2036:
1324:
solutions: speciation of ammonium carbamate, bicarbonate and carbonate by a
3747:
3634:
3629:
3606:
3357:
3196:
3122:
3059:
3054:
3032:
2988:
2973:
2963:
2698:
2591:
Newman, Melvin S.; Hetzel, Frederick W. (1971). "Thiophenols from
Phenols:
2577:
2486:
2435:
2334:
2080:
1968:
1914:
1613:
1563:
1506:
1234:
1125:
1030:
885:
866:
839:
570:
565:
496:
484:
Perhaps the most prevalent carbamate is the one involved in the capture of
119:
2384:
2294:
2162:
1737:
1650:
3806:
3759:
3720:
3601:
3489:
3474:
3469:
3457:
3022:
3017:
2983:
2978:
2968:
2946:
2808:
2743:
2625:. John Daintith (6th ed.). New York: Oxford University Press. 2008.
1936:
1831:
979:
of carbamates with only one of the oxygens replaced by sulfur are called
881:
862:
775:
710:
662:
645:
feature the carbamate ester functional group. Included in this group are
642:
600:
have a wide range of properties and are commercially available as foams,
441:
177:
2350:
2102:. Amino Acids, Peptides and Proteins in Organic Chemistry. Vol. 4.
1719:
1642:
1298:
1270:
709:
Besides their common use as arthropodocides/insecticides, they are also
677:. These insecticides kill insects by reversibly inactivating the enzyme
495:(RuBisCO) fixes a molecule of carbon dioxide as phosphoglycerate in the
3715:
3706:
3586:
3541:
3437:
3402:
3392:
3332:
3268:
3191:
3139:
2448:
1927:
905:
893:
843:
762:
692:
666:
654:
629:
613:
601:
590:
586:
574:
512:
475:
468:. Carbamoyl phosphate is generated from carboxyphosphate rather than CO
433:
389:
1208:
3682:
3596:
3561:
3546:
3534:
3352:
3161:
2564:
2103:
1354:
1082:
which I regard as types of a new family, among nitrogenous substances
937:
923:
913:
889:
522:
500:
162:
146:
In water solutions, the carbamate anion slowly equilibrates with the
19:
2907:
2726:
2699:"urethane | Etymology, origin and meaning of urethane by etymonline"
1702:"Mechanism of action of organophosphorus and carbamate insecticides"
1252:
3690:
3644:
3611:
3307:
3213:
3087:
3042:
3027:
2397:
2347:
1880:
1583:-Carboxymethanofuran (carbamate) formation from methanofuran and CO
1576:
1283:
1026:
933:
901:
874:
758:
733:
703:
674:
658:
646:
634:
491:
by plants. This process is necessary for their growth. The enzyme
147:
81:
2100:
Protection
Reactions, Medicinal Chemistry, Combinatorial Synthesis
3652:
3576:
3427:
3422:
3387:
3372:
3367:
3337:
3320:
3144:
3071:
3037:
1838:
771:
597:
549:
515:
near the ion reacts with a carbon dioxide molecule from the air (
492:
465:
301:
280:
115:
2528:
Rüdiger Schubart (2000). "Dithiocarbamic Acid and Derivatives".
589:. Commonly, urethanes made by a non-isocyanate route are called
110:
Polymers whose repeat units are joined by carbamate like groups
3740:
3672:
3516:
3225:
3218:
3112:
3093:
3082:
3066:
3012:
2505:
Marais, Simone; Diase, Elsa; Pereira, Maria de Lourdes (2012).
2449:
Popovska-Gorevski, M; Dubocovich, ML; Rajnarayanan, RV (2017).
1452:
972:
767:
714:
670:
457:
453:
437:
429:
2400:"Acetylcholinesterase inhibitors: pharmacology and toxicology"
2259:"A controlled trial of urethane treatment in multiple myeloma"
1663:
991:). Carbamates with both oxygens replaced by sulfur are called
926:
for HIV treatment also contains a carbamate functional group.
3621:
3591:
3524:
3382:
3347:
3342:
3315:
3263:
3230:
3134:
2958:
971:, and either or both of them can be conceptually replaced by
650:
361:
141:
134:
While carbamic acids are unstable, many carbamate esters and
93:
74:
2256:
1863:
3049:
1191:"Organic Carbamates in Drug Design and Medicinal Chemistry"
838:) was once produced commercially in the United States as a
609:
545:
2861:
Moss, G. P.; Smith, P. a. S.; Tavernier, D. (1995-01-01).
2451:"Carbamate Insecticides Target Human Melatonin Receptors"
805:
Some of the most common amine protecting groups, such as
577:. In contrast, the substance commonly called "urethane",
2362:
2139:. Methods in Enzymology. Vol. 289. pp. 44–67.
2094:
Vommina V. Sureshbabu; Narasimhamurthy Narendra (2011).
797:
is a wood and paint preservative and used in cosmetics.
1755:"IRAC Mode of Action Classification Scheme Version 9.4"
1311:
720:
Sales have declined dramatically over recent decades.
2050:
Badreshia, S. (2002). "Iodopropynyl butylcarbamate".
1520:
Ferguson, J. K. W.; Roughton, F. J. W. (1934-12-14).
1047:, where the R–O– group is replaced with an R–S– group
80:), formally obtained by replacing one or more of the
1834:"PubChem Compound Summary for CID 125098, Icaridin"
1189:Ghosh, Arun K.; Brindisi, Margherita (2015-04-09).
1153:
916:is primarily used for various ophthalmic purposes.
778:. However, since all compounds of this type have a
73:). The term includes organic compounds (e.g., the
2860:
2566:Angewandte Chemie International Edition in English
2504:
2315:. Virginia Commonwealth University. Archived from
2019:Handbook of chemical and biological warfare agents
1993:Handbook of Toxicology of Chemical Warfare Agents
782:with a permanent positive charge, they have poor
699:, rather than inactivating acetylcholinesterase.
3868:
2527:
2134:
1749:
1747:
1519:
1407:
1405:
774:were investigated for potential military use as
540:Although not usually isolated as such, the salt
480:capture by ribulose 1,5-bisphosphate carboxylase
447:
2507:"Carbamates: Human Exposure and Health Effects"
1989:
1832:National Center for Biotechnology Information.
854:In addition, some carbamates are used in human
493:ribulose 1,5-bisphosphate carboxylase/oxygenase
444:(an indirect effect caused by carbon dioxide).
332:Carbamate esters also arise via alcoholysis of
275:Calcium carbamate is soluble in water, whereas
2559:
2557:
2530:Ullmann's Encyclopedia of Industrial Chemistry
2229:
1775:Ullmann's Encyclopedia of Industrial Chemistry
1668:Ullmann's Encyclopedia of Industrial Chemistry
1251:Burrows, George H.; Lewis, Gilbert N. (1912).
1157:Ullmann's Encyclopedia of Industrial Chemistry
789:
736:, carbamate resistance most commonly involves
2923:
2043:
1744:
1402:
1188:
356:Alternatively, carbamates can be formed from
2590:
1250:
766:higher toxicity to humans, and some such as
2554:
2175:
1808:"Pesticide Information Project: Fenoxycarb"
963:There are two oxygen atoms in a carbamate (
2930:
2916:
2563:
1859:
1857:
1855:
1411:
1246:
1244:
940:, also falls into the carbamate category.
142:Equilibrium with carbonate and bicarbonate
2880:
2476:
2425:
2276:
2049:
1921:
1896:
1727:
1603:
1553:
1496:
1369:
1224:
751:
624:
1258:Journal of the American Chemical Society
628:
559:
521:
18:
2724:
2016:
1852:
1765:
1759:Insecticide Resistance Action Committee
1305:
1241:
1149:
1147:
1145:
3869:
2788:
1699:
499:. At the active site of the enzyme, a
2937:
2911:
2727:"XXIX.—Researches on the amyl series"
2720:
2718:
2672:
2668:
2666:
2664:
2500:
2498:
2496:
2333:
1872:Pesticide Biochemistry and Physiology
1772:Metcalf, Robert L. "Insect Control".
414:
1277:
1142:
1062:-thiocarbamates, for example in the
800:
695:has a carbamate group but acts as a
535:
392:formed are reacted with an alcohol.
1771:
1099:does not derive from carbamic acids
958:
432:residues in the α- and β-chains of
327:
13:
2715:
2661:
2493:
1626:
849:
829:
384:Carbamates may be formed from the
291:
14:
3893:
1707:Environmental Health Perspectives
2680:Annales de Chimie et de Physique
2675:"Recherches de chimie organique"
2176:Katsoyannis, P. G., ed. (1973).
1605:10.1046/j.1432-1327.2000.01331.x
1067:
23:Chemical structure of carbamates
2854:
2823:
2796:Journal of the Chemical Society
2782:
2758:
2691:
2615:
2584:
2521:
2517:: 38 – via Research Gate.
2442:
2391:
2356:
2341:
2326:
2301:
2250:
2223:
2169:
2128:
2087:
2010:
1932:Chemico-Biological Interactions
1825:
1800:
1693:
1657:
1620:
1570:
1424:Bentham Science Publishers Ltd.
1380:. Vol. 2. pp. 85–86.
1029:group (C=O) is replaced with a
860:acetylcholinesterase inhibitors
530:
428:The N-terminal amino groups of
16:Chemical group (>N–C(=O)–O–)
2469:10.1021/acs.chemrestox.6b00301
1538:10.1113/jphysiol.1934.sp003212
1513:
1446:
1196:Journal of Medicinal Chemistry
1182:
740:(AChE) desensitization, while
123:
1:
2789:Divers, Edward (1870-01-01).
2244:10.1016/S0040-4039(01)88566-X
2179:The Chemistry of Polypeptides
2145:10.1016/s0076-6879(97)89043-x
2137:Solid-Phase Peptide Synthesis
2098:. In Andrew B. Hughes (ed.).
1990:Gupta, Ramesh C, ed. (2015).
1677:10.1002/14356007.a21_665.pub3
1136:
723:
448:Urease and phosphotriesterase
423:
300:is generated by treatment of
129:
2377:10.1016/0378-8741(85)90005-4
2365:Journal of Ethnopharmacology
1898:10.1016/j.pestbp.2020.104587
1074:
819:trichloroethyl chloroformate
706:is a substituted carbamate.
286:
7:
2418:10.2174/1570159X11311030006
2335:Multum Consumer Information
2278:10.1182/blood.V27.3.328.328
1109:
943:
824:
795:Iodopropynyl butylcarbamate
790:Preservatives and cosmetics
138:are stable and well known.
114:are an important family of
10:
3898:
2868:Pure and Applied Chemistry
2182:. New York: Plenum Press.
1481:10.1038/s41467-018-05475-z
1432:10.2174/138527211795378173
1386:10.1002/9780470132333.ch23
1347:Royal Society of Chemistry
1064:Newman–Kwart rearrangement
947:
742:organophosphate resistance
633:The carbamate insecticide
620:RN=C=O + R′OH → RNHC(O)OR′
563:
452:The ε-amino groups of the
3825:
3784:
3704:
3681:
3643:
3620:
3515:
3436:
3306:
3283:
3239:
3182:
3105:
3080:
2945:
2766:"Definition of CARBAMATE"
2623:A dictionary of chemistry
2353:. Accessed 27 April 2021.
2338:. Accessed 27 April 2021.
2188:10.1007/978-1-4613-4571-8
2112:10.1002/9783527631827.ch1
2106:. pp. XVIII–LXXXIV.
2021:. Boca Raton: CRC Press.
1953:10.1016/j.cbi.2005.10.041
1526:The Journal of Physiology
1415:Current Organic Chemistry
884:and its derivatives like
780:quaternary ammonium group
2609:10.15227/orgsyn.051.0139
2538:10.1002/14356007.a09_001
2511:The Impact of Pesticides
1784:10.1002/14356007.a14_263
1166:10.1002/14356007.a05_051
1131:Cholinesterase inhibitor
1010:types of thiocarbamate:
1006:There are two different
873:is based on the natural
681:(AChE inhibition) (IRAC
641:The so-called carbamate
3836:chemical classification
2882:10.1351/pac199567081307
2842:10.1351/goldbook.C00803
2830:"Carbamates (C00803)".
2770:www.merriam-webster.com
2725:Medlock, Henry (1849).
2532:. Weinheim: Wiley-VCH.
2310:"Working with Urethane"
2065:10.1053/ajcd.2002.30728
1778:. Weinheim: Wiley-VCH.
1671:. Weinheim: Wiley-VCH.
1160:. Weinheim: Wiley-VCH.
84:atoms by other organic
2653:: CS1 maint: others (
2578:10.1002/anie.196702811
2096:"Protection Reactions"
2053:Am. J. Contact Dermat.
1700:Fukuto, T. R. (1990).
752:Carbamate nerve agents
697:juvenile hormone mimic
638:
625:Carbamate insecticides
527:
24:
3843:chemical nomenclature
1460:Nature Communications
1008:structurally isomeric
880:. Other examples are
702:The insect repellent
632:
560:Polyurethane plastics
525:
386:Curtius rearrangement
57:, which are formally
22:
2809:10.1039/JS8702300359
2744:10.1039/qj8490100368
2673:Dumas, Jean (1833).
1054:-thiocarbamates can
815:benzyl chloroformate
738:acetylcholinesterase
679:acetylcholinesterase
606:toluene diisocyanate
3299:not C, H or O)
2405:Curr Neuropharmacol
2232:Tetrahedron Letters
2017:Ellison, D (2008).
1945:2005CBI...157..269O
1889:2020PBioP.16704587S
1720:10.1289/ehp.9087245
1643:10.1021/bi00218a004
1473:2018NatCo...9.3092L
1378:Inorganic Syntheses
1299:10.1021/ie50286a008
1271:10.1021/ja02209a003
950:Carbamate poisoning
936:analogue used as a
858:, for example, the
784:blood–brain barrier
406:RNCO + R′OH → RNHCO
334:carbamoyl chlorides
126:for clarification.
92:with the carbamate
3741:Hypervalent iodine
2875:(8–9): 1307–1375.
2703:www.etymonline.com
2593:2-Naphthalenethiol
1812:Cornell University
921:protease inhibitor
871:chemical structure
639:
542:ammonium carbamate
528:
462:phosphotriesterase
415:Natural occurrence
344:NC(O)Cl + R'OH → R
298:ammonium carbamate
279:is not. Adding a
105:ammonium carbamate
25:
3877:Functional groups
3864:
3863:
3802:Sulfenyl chloride
3780:
3779:
3279:
3278:
3098:(only C, H and O)
2939:Functional groups
2632:978-1-61583-965-0
2238:(30): 2555–2558.
2197:978-1-4613-4571-8
2028:978-0-8493-1434-6
2003:978-0-12-800494-4
1686:978-3-527-30673-2
1598:(11): 3130–3138.
1395:978-0-470-13233-3
1293:(10): 1092–1096.
1209:10.1021/jm501371s
1039:-thiocarbamates (
1017:-thiocarbamates (
801:Chemical research
744:most commonly is
536:Synthesis of urea
277:calcium carbonate
86:functional groups
39:with the general
37:organic compounds
35:is a category of
29:organic chemistry
3889:
3831:
3736:Trifluoromethoxy
3304:
3303:
3300:
3103:
3102:
3099:
2952:
2932:
2925:
2918:
2909:
2908:
2903:
2902:
2884:
2858:
2852:
2851:
2849:
2848:
2827:
2821:
2820:
2786:
2780:
2779:
2777:
2776:
2762:
2756:
2755:
2732:Q. J. Chem. Soc.
2722:
2713:
2712:
2710:
2709:
2695:
2689:
2688:
2670:
2659:
2658:
2652:
2644:
2619:
2613:
2612:
2588:
2582:
2581:
2561:
2552:
2551:
2525:
2519:
2518:
2502:
2491:
2490:
2480:
2456:Chem Res Toxicol
2446:
2440:
2439:
2429:
2395:
2389:
2388:
2360:
2354:
2345:
2339:
2337:
2330:
2324:
2323:
2321:
2314:
2305:
2299:
2298:
2280:
2254:
2248:
2247:
2227:
2221:
2220:
2218:
2217:
2208:. Archived from
2173:
2167:
2166:
2132:
2126:
2125:
2091:
2085:
2084:
2047:
2041:
2040:
2014:
2008:
2007:
1987:
1981:
1980:
1925:
1919:
1918:
1900:
1861:
1850:
1849:
1847:
1846:
1829:
1823:
1822:
1820:
1818:
1804:
1798:
1797:
1769:
1763:
1762:
1751:
1742:
1741:
1731:
1697:
1691:
1690:
1661:
1655:
1654:
1624:
1618:
1617:
1607:
1592:Eur. J. Biochem.
1574:
1568:
1567:
1557:
1517:
1511:
1510:
1500:
1450:
1444:
1443:
1409:
1400:
1399:
1373:
1367:
1366:
1355:10.1039/b602051h
1334:
1332:
1331:
1323:
1322:
1321:
1309:
1303:
1302:
1281:
1275:
1274:
1248:
1239:
1238:
1228:
1203:(7): 2895–2940.
1186:
1180:
1179:
1151:
1116:Methyl carbamate
1071:
993:dithiocarbamates
959:Sulfur analogues
821:are carbamates.
748:metabolization.
746:carboxylesterase
503:ion is bound to
328:Carbamate esters
271:
270:
269:
266:
261:
260:
257:
248:
247:
244:
232:
230:
229:
226:
221:
220:
217:
208:
207:
204:
190:
189:
188:
175:
174:
173:
160:
159:
158:
124:§ Etymology
113:
102:
72:
56:
49:
3897:
3896:
3892:
3891:
3890:
3888:
3887:
3886:
3867:
3866:
3865:
3860:
3829:
3821:
3776:
3731:Trichloromethyl
3726:Trifluoromethyl
3700:
3677:
3639:
3616:
3511:
3480:Phosphine oxide
3432:
3298:
3296:
3295:
3293:
3291:
3289:
3287:
3285:
3275:
3235:
3178:
3097:
3096:
3091:
3086:
3076:
2950:
2949:
2941:
2936:
2906:
2859:
2855:
2846:
2844:
2829:
2828:
2824:
2787:
2783:
2774:
2772:
2764:
2763:
2759:
2723:
2716:
2707:
2705:
2697:
2696:
2692:
2671:
2662:
2646:
2645:
2633:
2621:
2620:
2616:
2589:
2585:
2562:
2555:
2548:
2526:
2522:
2503:
2494:
2447:
2443:
2396:
2392:
2361:
2357:
2346:
2342:
2331:
2327:
2319:
2312:
2306:
2302:
2255:
2251:
2228:
2224:
2215:
2213:
2198:
2174:
2170:
2155:
2133:
2129:
2122:
2092:
2088:
2048:
2044:
2029:
2015:
2011:
2004:
1988:
1984:
1926:
1922:
1862:
1853:
1844:
1842:
1830:
1826:
1816:
1814:
1806:
1805:
1801:
1794:
1770:
1766:
1753:
1752:
1745:
1698:
1694:
1687:
1662:
1658:
1625:
1621:
1586:
1575:
1571:
1518:
1514:
1451:
1447:
1410:
1403:
1396:
1374:
1370:
1338:Green Chemistry
1330:
1328:
1327:
1326:
1325:
1320:
1317:
1316:
1315:
1313:
1310:
1306:
1287:Ind. Eng. Chem.
1282:
1278:
1249:
1242:
1187:
1183:
1176:
1152:
1143:
1139:
1121:Ethyl carbamate
1112:
1077:
1046:
1024:
1002:
970:
961:
952:
946:
910:muscle relaxant
856:pharmacotherapy
852:
850:Carbamate drugs
836:ethyl carbamate
832:
830:Ethyl carbamate
827:
803:
792:
754:
726:
687:organophosphate
627:
579:ethyl carbamate
568:
562:
538:
533:
489:
482:
479:
471:
450:
434:deoxyhemoglobin
426:
417:
409:
403:
399:
379:
375:
371:
351:
347:
343:
330:
323:
319:
315:
294:
292:Carbamate salts
289:
267:
264:
263:
258:
255:
254:
252:
245:
242:
241:
239:
235:
227:
224:
223:
218:
215:
214:
212:
205:
202:
201:
199:
195:
187:
184:
183:
182:
180:
172:
169:
168:
167:
165:
161:cation and the
157:
154:
153:
152:
150:
144:
132:
111:
100:
96:
78:ethyl carbamate
70:
66:
54:
47:
43:
17:
12:
11:
5:
3895:
3885:
3884:
3879:
3862:
3861:
3859:
3858:
3857:
3856:
3851:
3839:
3832:
3826:
3823:
3822:
3820:
3819:
3817:Sulfinylamines
3814:
3809:
3804:
3799:
3797:Phosphoramides
3794:
3792:Isothiocyanate
3788:
3786:
3782:
3781:
3778:
3777:
3775:
3774:
3769:
3768:
3767:
3757:
3756:
3755:
3745:
3744:
3743:
3738:
3733:
3728:
3723:
3712:
3710:
3702:
3701:
3699:
3698:
3693:
3687:
3685:
3679:
3678:
3676:
3675:
3670:
3668:Selenenic acid
3665:
3663:Seleninic acid
3660:
3658:Selenonic acid
3655:
3649:
3647:
3641:
3640:
3638:
3637:
3632:
3626:
3624:
3618:
3617:
3615:
3614:
3609:
3604:
3599:
3594:
3589:
3584:
3579:
3574:
3569:
3564:
3559:
3554:
3549:
3544:
3539:
3538:
3537:
3527:
3521:
3519:
3513:
3512:
3510:
3509:
3504:
3499:
3494:
3493:
3492:
3482:
3477:
3472:
3467:
3466:
3465:
3455:
3454:
3453:
3451:Phosphodiester
3442:
3440:
3434:
3433:
3431:
3430:
3425:
3420:
3415:
3410:
3405:
3400:
3395:
3390:
3385:
3380:
3375:
3370:
3365:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3329:
3328:
3323:
3312:
3310:
3301:
3297:(one element,
3281:
3280:
3277:
3276:
3274:
3273:
3272:
3271:
3261:
3260:
3259:
3254:
3243:
3241:
3237:
3236:
3234:
3233:
3228:
3223:
3222:
3221:
3211:
3210:
3209:
3204:
3199:
3188:
3186:
3180:
3179:
3177:
3176:
3174:Methylenedioxy
3171:
3166:
3165:
3164:
3159:
3149:
3148:
3147:
3142:
3132:
3131:
3130:
3120:
3115:
3109:
3107:
3100:
3078:
3077:
3075:
3074:
3069:
3064:
3063:
3062:
3057:
3047:
3046:
3045:
3040:
3035:
3030:
3025:
3020:
3010:
3009:
3008:
3003:
2993:
2992:
2991:
2986:
2981:
2976:
2971:
2966:
2955:
2953:
2951:(only C and H)
2943:
2942:
2935:
2934:
2927:
2920:
2912:
2905:
2904:
2853:
2822:
2781:
2757:
2738:(4): 368–379.
2714:
2690:
2683:. 2nd series.
2660:
2631:
2614:
2583:
2572:(4): 281–293.
2553:
2546:
2520:
2492:
2463:(2): 574–582.
2441:
2390:
2371:(2): 175–191.
2355:
2340:
2325:
2322:on 2013-05-11.
2300:
2249:
2222:
2196:
2168:
2153:
2127:
2120:
2086:
2042:
2027:
2009:
2002:
1982:
1920:
1851:
1824:
1799:
1793:978-3527306732
1792:
1764:
1743:
1692:
1685:
1656:
1619:
1584:
1569:
1512:
1445:
1401:
1394:
1368:
1329:
1318:
1304:
1276:
1265:(8): 993–995.
1240:
1181:
1174:
1140:
1138:
1135:
1134:
1133:
1128:
1123:
1118:
1111:
1108:
1076:
1073:
1049:
1048:
1044:
1034:
1022:
1000:
981:thiocarbamates
968:
960:
957:
948:Main article:
945:
942:
851:
848:
831:
828:
826:
823:
802:
799:
791:
788:
753:
750:
725:
722:
713:. One such is
683:mode of action
626:
623:
622:
621:
564:Main article:
561:
558:
554:carbon dioxide
537:
534:
532:
529:
487:
481:
477:
474:
469:
449:
446:
425:
422:
416:
413:
412:
411:
407:
404:
401:
397:
382:
381:
377:
373:
369:
358:chloroformates
354:
353:
349:
345:
341:
329:
326:
325:
324:
321:
317:
313:
306:carbon dioxide
293:
290:
288:
285:
273:
272:
250:
237:
233:
210:
197:
185:
170:
155:
143:
140:
131:
128:
98:
68:
55:>N−C(=O)−O−
45:
15:
9:
6:
4:
3:
2:
3894:
3883:
3880:
3878:
3875:
3874:
3872:
3855:
3852:
3850:
3847:
3846:
3845:
3844:
3840:
3838:
3837:
3833:
3828:
3827:
3824:
3818:
3815:
3813:
3810:
3808:
3805:
3803:
3800:
3798:
3795:
3793:
3790:
3789:
3787:
3783:
3773:
3770:
3766:
3763:
3762:
3761:
3758:
3754:
3751:
3750:
3749:
3746:
3742:
3739:
3737:
3734:
3732:
3729:
3727:
3724:
3722:
3719:
3718:
3717:
3714:
3713:
3711:
3709:
3708:
3703:
3697:
3696:Telluroketone
3694:
3692:
3689:
3688:
3686:
3684:
3680:
3674:
3671:
3669:
3666:
3664:
3661:
3659:
3656:
3654:
3651:
3650:
3648:
3646:
3642:
3636:
3633:
3631:
3628:
3627:
3625:
3623:
3619:
3613:
3610:
3608:
3605:
3603:
3600:
3598:
3595:
3593:
3590:
3588:
3585:
3583:
3582:Sulfonic acid
3580:
3578:
3575:
3573:
3572:Sulfinic acid
3570:
3568:
3567:Thiosulfonate
3565:
3563:
3560:
3558:
3557:Thiosulfinate
3555:
3553:
3552:Sulfenic acid
3550:
3548:
3545:
3543:
3540:
3536:
3533:
3532:
3531:
3528:
3526:
3523:
3522:
3520:
3518:
3514:
3508:
3507:Phosphaallene
3505:
3503:
3502:Phosphaalkyne
3500:
3498:
3497:Phosphaalkene
3495:
3491:
3488:
3487:
3486:
3483:
3481:
3478:
3476:
3473:
3471:
3468:
3464:
3461:
3460:
3459:
3456:
3452:
3449:
3448:
3447:
3444:
3443:
3441:
3439:
3435:
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:
3327:
3324:
3322:
3319:
3318:
3317:
3314:
3313:
3311:
3309:
3305:
3302:
3282:
3270:
3267:
3266:
3265:
3262:
3258:
3255:
3253:
3250:
3249:
3248:
3245:
3244:
3242:
3238:
3232:
3229:
3227:
3224:
3220:
3217:
3216:
3215:
3212:
3208:
3205:
3203:
3200:
3198:
3195:
3194:
3193:
3190:
3189:
3187:
3185:
3181:
3175:
3172:
3170:
3169:Ethylenedioxy
3167:
3163:
3160:
3158:
3155:
3154:
3153:
3150:
3146:
3143:
3141:
3138:
3137:
3136:
3133:
3129:
3126:
3125:
3124:
3121:
3119:
3116:
3114:
3111:
3110:
3108:
3104:
3101:
3095:
3089:
3084:
3079:
3073:
3070:
3068:
3065:
3061:
3058:
3056:
3053:
3052:
3051:
3048:
3044:
3041:
3039:
3036:
3034:
3031:
3029:
3026:
3024:
3021:
3019:
3016:
3015:
3014:
3011:
3007:
3004:
3002:
2999:
2998:
2997:
2994:
2990:
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2878:
2874:
2871:(in German).
2870:
2869:
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2857:
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2826:
2818:
2814:
2810:
2806:
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2547:3-527-30673-0
2543:
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2462:
2458:
2457:
2452:
2445:
2437:
2433:
2428:
2423:
2419:
2415:
2412:(3): 315–35.
2411:
2407:
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2401:
2394:
2386:
2382:
2378:
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2366:
2359:
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2296:
2292:
2288:
2284:
2279:
2274:
2271:(3): 328–42.
2270:
2266:
2265:
2260:
2253:
2245:
2241:
2237:
2233:
2226:
2212:on 2022-10-13
2211:
2207:
2203:
2199:
2193:
2189:
2185:
2181:
2180:
2172:
2164:
2160:
2156:
2154:9780121821906
2150:
2146:
2142:
2138:
2131:
2123:
2121:9783527641574
2117:
2113:
2109:
2105:
2101:
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2090:
2082:
2078:
2074:
2070:
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2062:
2058:
2055:
2054:
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2038:
2034:
2030:
2024:
2020:
2013:
2005:
1999:
1995:
1994:
1986:
1978:
1974:
1970:
1966:
1962:
1958:
1954:
1950:
1946:
1942:
1938:
1934:
1933:
1924:
1916:
1912:
1908:
1904:
1899:
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1828:
1813:
1809:
1803:
1795:
1789:
1785:
1781:
1777:
1776:
1768:
1761:. March 2020.
1760:
1756:
1750:
1748:
1739:
1735:
1730:
1725:
1721:
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1474:
1470:
1466:
1462:
1461:
1456:
1449:
1441:
1437:
1433:
1429:
1426:: 1593–1624.
1425:
1421:
1417:
1416:
1408:
1406:
1397:
1391:
1387:
1383:
1379:
1372:
1364:
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1300:
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1289:
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1232:
1227:
1222:
1218:
1214:
1210:
1206:
1202:
1198:
1197:
1192:
1185:
1177:
1175:3-527-30673-0
1171:
1167:
1163:
1159:
1158:
1150:
1148:
1146:
1141:
1132:
1129:
1127:
1124:
1122:
1119:
1117:
1114:
1113:
1107:
1103:
1100:
1095:
1089:
1085:
1083:
1072:
1070:
1065:
1061:
1057:
1053:
1042:
1038:
1035:
1032:
1028:
1020:
1016:
1013:
1012:
1011:
1009:
1004:
998:
994:
990:
986:
982:
978:
974:
966:
956:
951:
941:
939:
935:
931:
927:
925:
922:
917:
915:
911:
907:
904:, a class of
903:
899:
898:phenprobamate
895:
891:
887:
883:
879:
878:physostigmine
876:
872:
868:
864:
861:
857:
847:
845:
841:
837:
822:
820:
816:
812:
808:
798:
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787:
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781:
777:
773:
769:
764:
760:
749:
747:
743:
739:
735:
731:
721:
718:
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712:
707:
705:
700:
698:
694:
690:
688:
684:
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676:
672:
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664:
660:
656:
652:
648:
644:
636:
631:
619:
618:
617:
615:
611:
607:
603:
599:
596:Polyurethane
594:
592:
588:
584:
580:
576:
572:
571:Polyurethanes
567:
557:
555:
551:
547:
543:
524:
520:
518:
514:
510:
506:
502:
498:
494:
490:
473:
467:
463:
459:
455:
445:
443:
439:
435:
431:
421:
405:
395:
394:
393:
391:
387:
368:R'OC(O)Cl + R
367:
366:
365:
363:
359:
339:
338:
337:
335:
311:
310:
309:
307:
303:
299:
284:
282:
278:
234:
194:
193:
192:
179:
164:
149:
139:
137:
127:
125:
121:
120:polyurethanes
117:
108:
106:
95:
91:
88:; as well as
87:
83:
79:
76:
64:
63:carbamic acid
60:
53:
42:
38:
34:
30:
21:
3841:
3834:
3748:Vinyl halide
3705:
3635:Borinic acid
3630:Boronic acid
3607:Thioxanthate
3377:
2947:Hydrocarbons
2872:
2866:
2856:
2845:. Retrieved
2832:
2825:
2800:
2794:
2784:
2773:. Retrieved
2769:
2760:
2735:
2730:
2706:. Retrieved
2702:
2693:
2684:
2678:
2622:
2617:
2600:
2596:
2586:
2569:
2565:
2529:
2523:
2514:
2510:
2460:
2454:
2444:
2409:
2403:
2393:
2368:
2364:
2358:
2343:
2328:
2317:the original
2303:
2268:
2262:
2252:
2235:
2231:
2225:
2214:. Retrieved
2210:the original
2178:
2171:
2136:
2130:
2099:
2089:
2059:(2): 77–79.
2056:
2051:
2045:
2018:
2012:
1992:
1985:
1930:
1923:
1876:
1870:
1843:. Retrieved
1837:
1827:
1815:. Retrieved
1802:
1773:
1767:
1711:
1705:
1695:
1666:
1659:
1637:(4): 904–8.
1634:
1630:Biochemistry
1628:
1622:
1595:
1590:
1580:
1572:
1532:(1): 68–86.
1529:
1525:
1515:
1464:
1458:
1448:
1419:
1413:
1377:
1371:
1342:
1336:
1335:NMR study".
1307:
1290:
1285:
1279:
1262:
1256:
1200:
1194:
1184:
1155:
1126:Polyurethane
1104:
1098:
1093:
1090:
1086:
1081:
1078:
1059:
1051:
1050:
1043:), RSC(=O)NR
1040:
1036:
1031:thiocarbonyl
1025:, where the
1021:), ROC(=S)NR
1018:
1014:
1005:
999:), RSC(=S)NR
996:
988:
984:
967:), ROC(=O)NR
964:
962:
953:
928:
918:
886:carisoprodol
867:rivastigmine
853:
840:chemotherapy
833:
804:
793:
776:nerve agents
755:
727:
719:
708:
701:
691:
643:insecticides
640:
595:
569:
566:Polyurethane
539:
531:Applications
516:
497:Calvin cycle
483:
456:residues in
451:
427:
418:
383:
355:
331:
295:
274:
145:
133:
112:−NH−C(=O)−O−
109:
32:
26:
3812:Thiocyanate
3807:Sulfonamide
3772:Perchlorate
3760:Acyl halide
3721:Fluoroethyl
3602:Thionoester
3490:Phosphonium
3475:Phosphinate
3470:Phosphonous
3458:Phosphonate
3157:Hydroperoxy
2979:Cyclopropyl
2803:: 359–364.
1939:: 269–275.
1937:Elsevier BV
1935:. 157–158.
1714:: 245–254.
1467:(1): 3092.
1033:group (C=S)
930:Ephedroxane
882:meprobamate
863:neostigmine
711:nematicidal
663:ethienocarb
657:(Furadan),
614:isocyanates
442:Bohr effect
390:isocyanates
178:bicarbonate
3882:Carbamates
3871:Categories
3716:Haloalkane
3587:Thioketone
3542:Persulfide
3438:Phosphorus
3403:Isocyanate
3393:Isonitrile
3294:or oxygen
3292:hydrogen,
3288:not being
3269:Orthoester
3162:Dioxiranes
3140:Enol ether
3028:1-Propenyl
2847:2023-03-29
2775:2023-03-29
2708:2023-03-29
2687:: 496–556.
2597:Org. Synth
2332:Carbachol
2216:2021-04-01
1883:: 104587.
1845:2024-01-08
1137:References
906:anxiolytic
894:mebutamate
844:anesthesia
834:Urethane (
763:carbofuran
724:Resistance
693:Fenoxycarb
667:fenobucarb
655:carbofuran
602:elastomers
591:carbamates
587:isocyanate
575:polymerize
513:side chain
424:Hemoglobin
400:→ RNCO + N
130:Properties
3849:inorganic
3683:Tellurium
3597:Thioester
3562:Sulfoxide
3547:Disulfide
3535:Sulfonium
3485:Phosphine
3463:Phosphite
3446:Phosphate
3378:Carbamate
3353:Hydrazone
3286:element,
3284:Only one
3257:Anhydride
2996:Methylene
2891:1365-3075
2836:. IUPAC.
2817:0368-1769
2752:1743-6893
2649:cite book
2641:713875281
2287:0006-4971
2104:Wiley-VCH
2073:1046-199X
1961:0009-2797
1907:0048-3575
1546:0022-3751
1489:2041-1723
1440:1385-2728
1363:1463-9262
1217:0022-2623
1075:Etymology
1056:isomerise
977:Analogues
938:stimulant
924:darunavir
914:Carbachol
890:felbamate
734:esterases
730:mutations
685:1a). The
661:(Sevin),
509:aspartate
505:glutamate
296:The salt
287:Synthesis
253:O ⇌ NH
163:carbonate
52:structure
33:carbamate
3830:See also
3765:Chloride
3691:Tellurol
3645:Selenium
3612:Xanthate
3326:Ammonium
3308:Nitrogen
3290:carbon,
3247:Carboxyl
3214:Aldehyde
3202:Acryloyl
3184:carbonyl
3088:hydrogen
3043:Cumulene
2899:95004254
2833:Goldbook
2487:28027439
2436:24179466
2348:DrugBank
2206:35144893
2081:12022126
2037:82473582
1977:32597626
1969:16289012
1915:32527435
1881:Elsevier
1614:10824097
1564:16994615
1507:30082797
1235:25565044
1110:See also
1027:carbonyl
944:Toxicity
934:aminorex
902:tybamate
875:alkaloid
869:, whose
825:Medicine
759:aldicarb
704:icaridin
675:methomyl
659:carbaryl
647:aldicarb
635:Carbaryl
598:polymers
585:with an
388:, where
380:R' + HCl
352:R' + HCl
213:O ⇌ NH
191:anions:
148:ammonium
116:plastics
82:hydrogen
3854:organic
3653:Selenol
3577:Sulfone
3530:Sulfide
3428:NONOate
3423:Nitroso
3413:Nitrite
3408:Nitrate
3398:Cyanate
3388:Nitrile
3373:Amidine
3368:Imidate
3338:Nitrene
3333:Hydrazo
3321:Enamine
3252:Acetoxy
3240:carboxy
3207:Benzoyl
3145:Epoxide
3128:Methoxy
3118:Alcohol
3072:Carbene
3006:Methine
2603:: 139.
2478:5318275
2427:3648782
2385:4021515
2351:DB01264
2295:5933438
2163:9353717
1941:Bibcode
1885:Bibcode
1839:Pubchem
1817:15 June
1757:(pdf).
1738:2176588
1729:1567830
1651:1899197
1555:1394306
1498:6078960
1469:Bibcode
1349:: 995.
1226:4393377
772:EA-3990
583:alcohol
550:ammonia
466:inosine
320:→ NH
302:ammonia
281:calcium
59:derived
48:NC(O)OR
41:formula
3753:Iodide
3673:Selone
3517:Sulfur
3226:Ketone
3219:Ketene
3197:Acetyl
3152:Peroxy
3123:Alkoxy
3113:Acetal
3094:oxygen
3083:carbon
3067:Alkyne
3060:Benzyl
3055:Phenyl
3038:Allene
3033:Crotyl
3013:Alkene
3001:Bridge
2989:Pentyl
2974:Propyl
2964:Methyl
2897:
2889:
2815:
2750:
2639:
2629:
2544:
2485:
2475:
2434:
2424:
2383:
2293:
2285:
2204:
2194:
2161:
2151:
2118:
2079:
2071:
2035:
2025:
2000:
1975:
1967:
1959:
1913:
1905:
1790:
1736:
1726:
1683:
1649:
1612:
1562:
1552:
1544:
1505:
1495:
1487:
1438:
1422:(10).
1392:
1361:
1345:(11).
1233:
1223:
1215:
1172:
973:sulfur
900:, and
768:T-1123
728:Among
715:Oxamyl
673:, and
671:oxamyl
608:, and
458:urease
454:lysine
438:oxygen
430:valine
372:NH → R
362:amines
222:+ HCO
209:+ 2 H
122:. See
118:, the
103:(e.g.
3785:Other
3622:Boron
3592:Thial
3525:Thiol
3418:Nitro
3383:Imide
3363:Amide
3348:Oxime
3343:Imine
3316:Amine
3264:Ester
3231:Ynone
3135:Ether
3106:R-O-R
3081:Only
3023:Allyl
3018:Vinyl
2984:Butyl
2969:Ethyl
2959:Alkyl
2895:S2CID
2320:(PDF)
2313:(PDF)
2264:Blood
2202:S2CID
1973:S2CID
1092:acids
932:, an
651:Temik
610:diols
548:from
316:+ CO
304:with
262:+ CO
249:+ H
231:+ OH
136:salts
94:anion
90:salts
75:ester
61:from
3707:Halo
3192:Acyl
3092:and
3050:Aryl
2887:ISSN
2813:ISSN
2748:ISSN
2655:link
2637:OCLC
2627:ISBN
2542:ISBN
2483:PMID
2432:PMID
2381:PMID
2291:PMID
2283:ISSN
2192:ISBN
2159:PMID
2149:ISBN
2116:ISBN
2077:PMID
2069:ISSN
2033:OCLC
2023:ISBN
1998:ISBN
1965:PMID
1957:ISSN
1911:PMID
1903:ISSN
1819:2019
1788:ISBN
1734:PMID
1681:ISBN
1647:PMID
1610:PMID
1560:PMID
1542:ISSN
1503:PMID
1485:ISSN
1436:ISSN
1390:ISBN
1359:ISSN
1231:PMID
1213:ISSN
1170:ISBN
987:and
919:The
908:and
865:and
817:and
811:FMOC
770:and
761:and
552:and
546:urea
507:and
460:and
396:RCON
360:and
312:2 NH
101:NCOO
71:COOH
50:and
31:, a
3358:Azo
2877:doi
2838:doi
2805:doi
2740:doi
2605:doi
2595:".
2574:doi
2534:doi
2473:PMC
2465:doi
2422:PMC
2414:doi
2373:doi
2273:doi
2240:doi
2184:doi
2141:doi
2108:doi
2061:doi
1949:doi
1893:doi
1877:167
1780:doi
1724:PMC
1716:doi
1673:doi
1639:doi
1600:doi
1596:267
1550:PMC
1534:doi
1493:PMC
1477:doi
1428:doi
1382:doi
1351:doi
1295:doi
1267:doi
1221:PMC
1205:doi
1162:doi
1058:to
807:BOC
732:in
653:),
517:not
376:NCO
348:NCO
240:NCO
200:NCO
181:HCO
176:or
107:).
27:In
3873::
3090:,
3085:,
2893:.
2885:.
2873:67
2865:.
2811:.
2801:23
2799:.
2793:.
2768:.
2746:.
2729:.
2717:^
2701:.
2685:56
2677:.
2663:^
2651:}}
2647:{{
2635:.
2601:51
2599:.
2568:.
2556:^
2540:.
2515:21
2513:.
2509:.
2495:^
2481:.
2471:.
2461:30
2459:.
2453:.
2430:.
2420:.
2410:11
2408:.
2402:.
2379:.
2369:13
2367:.
2289:.
2281:.
2269:27
2267:.
2261:.
2236:10
2234:.
2200:.
2190:.
2157:.
2147:.
2114:.
2075:.
2067:.
2057:13
2031:.
1971:.
1963:.
1955:.
1947:.
1909:.
1901:.
1891:.
1879:.
1875:.
1869:.
1854:^
1836:.
1810:.
1786:.
1746:^
1732:.
1722:.
1712:87
1710:.
1704:.
1679:.
1645:.
1635:30
1633:.
1608:.
1589:.
1558:.
1548:.
1540:.
1530:83
1528:.
1524:.
1501:.
1491:.
1483:.
1475:.
1463:.
1457:.
1434:.
1420:15
1418:.
1404:^
1388:.
1357:.
1341:.
1314:NH
1291:25
1263:34
1261:.
1255:.
1243:^
1229:.
1219:.
1211:.
1201:58
1199:.
1193:.
1168:.
1144:^
1066:.
1003:.
975:.
896:,
892:,
888:,
846:.
813:,
809:,
717:.
669:,
665:,
616::
593:.
556:.
501:Mg
486:CO
476:CO
472:.
410:R′
364::
336::
308::
265:2−
166:CO
151:NH
67:NH
2931:e
2924:t
2917:v
2901:.
2879::
2850:.
2840::
2819:.
2807::
2778:.
2754:.
2742::
2736:1
2711:.
2657:)
2643:.
2611:.
2607::
2580:.
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