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d bicarbonate 2 synthesis toggle synthesis subsection 2 1 carbamate salts 2 2 carbamate esters 3 natural occurrence toggle natural occurrence subsection 3 1 carbamylated proteins 3 2 co 2 capture by ribulose 1 5 bisphosphate carboxylase 3 3 other biosynthetic pathways 4 applications toggle applications subsection 4 1 polyurethane plastics 4 2 carbamate insecticides 4 2 1 resistance 4 3 carbamate nerve agents 4 4 preservatives 4 5 chemical research 4 6 medicinal uses 4 6 1 ethyl carbamate 4 6 2 carbamate derivatives 5 toxicity 6 sulfur analogues 7 ester terminology 8 see also 9 references toggle the table of contents carbamate 33 languages afrikaans العربية български català čeština dansk deutsch esperanto español euskara فارسی suomi français galego magyar bahasa indonesia italiano 日本語 қазақша 한국어 plattdüütsch nederlands polski português română русский srpskohrvatski српскохрватски simple english српски srpski svenska українська tiếng việt 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical group n c o o chemical structure of carbamates in organic chemistry a carbamate is a category of organic compounds with the general formula r 2 nc o or and structure n c o o formally derived from carbamic acid nh 2 cooh as well as their organic derivatives esters such as ethyl carbamate and chlorphenisin carbamate obtained by replacing one or more of the molecule s hydrogen atoms by other organic functional groups as well as salts with the carbamate anion h 2 ncoo e g ammonium carbamate 1 polymers whose repeat units are joined by carbamate like groups nh c o o are an important family of plastics the polyurethanes properties edit unlike carbamic acids many carbamate esters and salts are stable 2 equilibrium with carbonate and bicarbonate edit in water solutions the carbamate anion slowly equilibrates with the ammonium nh 4 cation and the carbonate co 2 3 or bicarbonate hco 3 anions 3 4 5 h 2 nco 2 2 h 2 o nh 4 hco 3 oh h 2 nco 2 h 2 o nh 4 co 2 3 calcium carbamate is soluble in water whereas calcium carbonate is not adding a calcium salt to an ammonium carbamate carbonate solution will precipitate some calcium carbonate immediately and then slowly precipitate more as the carbamate hydrolyzes 3 synthesis edit carbamate salts edit ammonium carbamate is generated by treatment of ammonia with carbon dioxide 6 2 nh 3 co 2 nh 4 h 2 nco 2 the ammonium carbamate is produced on a large scale as an intermediate in the production of the commodity chemical urea from ammonia and carbon dioxide 1 carbamate esters edit carbamate esters also arise via alcoholysis of carbamoyl chlorides 1 r 2 nc o cl r oh r 2 nco 2 r hcl alternatively carbamates can be formed from chloroformates and amines 7 r oc o cl r 2 nh r 2 nco 2 r hcl carbamates may be formed from the curtius rearrangement where isocyanates formed are reacted with an alcohol 7 rcon 3 rnco n 2 rnco r oh rnhco 2 r natural occurrence edit carbamylated proteins edit within nature carbon dioxide can bind with neutral amine groups to form a carbamate this post translational modification is known as carbamylation and is known to occur on several important proteins 8 the n terminal amino groups of valine residues in the α and β chains of deoxyhemoglobin exist as carbamates they help to stabilise the protein when it becomes deoxyhemoglobin and increases the likelihood of the release of remaining oxygen molecules bound to the protein this stabilizing effect should not be confused with the bohr effect an indirect effect caused by carbon dioxide 9 the ε amino groups of the lysine residues in urease and phosphotriesterase also feature carbamate 10 co 2 capture by ribulose 1 5 bisphosphate carboxylase edit perhaps the most prevalent carbamate is the one involved in the capture of co 2 by plants a process necessary for their growth the enzyme ribulose 1 5 bisphosphate carboxylase oxygenase rubisco fixes a molecule of carbon dioxide as phosphoglycerate in the calvin cycle at the active site of the enzyme a mg 2 ion is bound to glutamate and aspartate residues as well as a lysine carbamate the carbamate is formed when an uncharged lysine side chain near the ion reacts with a carbon dioxide molecule from the air which then renders it charged and therefore able to bind the mg 2 ion 11 carbamate formation is a critical step in the formation of biomass from atmospheric carbon dioxide other biosynthetic pathways edit carbamoyl phosphate is a carbamate mixed anhydride that is an intermediate in the urea cycle and the biosynthesis of pyrimidines 5 carboxyamino 1 5 phospho d ribosyl imidazole wd n 5 cair a carbamate derivative of aminoimidazole is an intermediate in the biosynthesis of inosine both carbamates are produced via reaction of nh 2 groups with carboxyphosphate ho c o opo 2 3 10 applications edit polyurethane plastics edit main article polyurethane polyurethanes contain multiple urethane carbamate groups as part of their structure and i are usually formed by reaction of an alcohol with an isocyanate commonly urethanes made by a non isocyanate route are called carbamates citation needed polyurethane polymers have a wide range of properties and are commercially available as foams elastomers and solids typically polyurethane polymers are made by combining diisocyanates e g toluene diisocyanate and diols where the carbamate groups are formed by reaction of the alcohols with the isocyanates 12 rn c o r oh rnhc o or carbamate insecticides edit the carbamate insecticide carbaryl the so called carbamate insecticides feature the carbamate ester functional group roc o nhr included in this group are aldicarb temik carbofuran furadan carbaryl sevin ethienocarb fenobucarb oxamyl and methomyl they are synthetic analogues of the toxic alkaloid physostigmine the study of which led to this class of insecticides an estimated 25m kg of carbaryl were produced in 1971 13 these insecticides kill insects by reversibly inactivating the enzyme acetylcholinesterase ache inhibition 14 irac mode of action 1a 15 fenoxycarb has a carbamate group but acts as a juvenile hormone mimic rather than inactivating acetylcholinesterase 16 the insect repellent icaridin is a substituted carbamate 17 besides their common use as arthropodocides insecticides they are also nematicidal 18 with one such example being oxamyl 18 the journal pesticide biochemistry and physiology reported in 2020 that sales clarification needed have declined dramatically over recent decades 18 resistance edit among insecticide resistance mutations in esterases carbamate resistance most commonly involves acetylcholinesterase ache desensitization while organophosphate resistance most commonly is carboxylesterase metabolization 19 carbamate nerve agents edit 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 aldicarb and carbofuran 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 higher toxicity to humans and some such as t 1123 and ea 3990 were investigated for potential military use as nerve agents however since all compounds of this type have a quaternary ammonium group with a permanent positive charge they have poor blood brain barrier penetration and also are only stable as crystalline salts or aqueous solutions and so were not considered to have suitable properties for weaponisation 20 21 preservatives edit iodopropynyl butylcarbamate is a wood and paint preservative and also used in cosmetics 22 chlorphenisin is an antifungal agent used medicinally as well as among cosmetics and foods while its ester chlorphenisin carbamate has skeletal muscle relaxant properties chemical research edit some of the most common amine protecting groups such as boc 23 fmoc 24 benzyl chloroformate 25 and trichloroethyl chloroformate 26 are carbamates medicinal uses edit ethyl carbamate edit urethane or ethyl carbamate was once used in the united states as a chemotherapy agent and for other medicinal purposes clarification needed but was later found to be toxic and relatively ineffective 27 as of 2013 it is occasionally used in veterinary medicine in combination with other drugs to produce anesthesia 28 carbamate derivatives edit this section is in list format but may read better as prose you can help by converting this section if appropriate editing help is available october 2026 several carbamate derivatives have seen use in human pharmacotherapy the acetylcholinesterase inhibitor chemical class includes neostigmine and rivastigmine both of which have a chemical structure based on the natural alkaloid physostigmine citation needed in 1955 the united states food and drug administration approved ethinamate as a prescription nonbarbiturate soporific under the trade name valmid followed by meprobamate marketed primarily as miltown quickly became ubiquitous as a prescription nerve pill minor tranquilizer or daytime anxiolytic and myorelaxant and sedative hypnotic 29 failed verification meprobamate is almost entirely discontinued globally in 2026 carisoprodol is a cns depressant and a prodrug of meprobamate initially acting primarily as a muscle relaxant and muscle pain reliever after 2 3 hours 20 30 of initial dose converts into active metabolite meprobamate synergistically working together to potentiate or increase the existing sedation and muscle relaxation and analgesia citation needed valmid or valamin was a carbamate derivative chemically named ethinamate it was withdrawn from the market in the u s and netherlands around 1990 30 the protease inhibitor darunavir for hiv treatment also contains a carbamate functional group 31 ephedroxane an aminorex analogue used as a stimulant also falls into the carbamate category 32 felbamate is an anticonvulsant 33 used in the treatment of epilepsy with high risk of potentially fatal aplastic anemia and or liver failure limiting the drug s usage to severe refractory epilepsy toxicity edit main article carbamate poisoning besides inhibiting human acetylcholinesterase 34 although to a lesser degree than the insect enzyme carbamate insecticides also target human melatonin receptors 35 the human health effects of carbamates are well documented in the list of known endocrine disruptor compounds 36 clinical effects of 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 36 these clinical manifestations of carbamate intoxication are muscarinic signs nicotinic signs and in rare cases central nervous system signs 36 sulfur analogues edit there are two oxygen atoms in a carbamate 1 roc o nr 2 and either or both of them can be conceptually replaced by sulfur analogues of carbamates with only one of the oxygens replaced by sulfur are called thiocarbamates 2 and 3 carbamates with both oxygens replaced by sulfur are called dithiocarbamates 4 rsc s nr 2 37 there are two different structurally isomeric types of thiocarbamate o thiocarbamates 2 roc s nr 2 where the carbonyl group c o is replaced with a thiocarbonyl group c s 38 s thiocarbamates 3 rsc o nr 2 where the r o group is replaced with an r s group 38 o thiocarbamates can isomerise to s thiocarbamates for example in the newman kwart rearrangement 39 ester terminology edit iupac states normatively that carbamate esters are often called urethanes or urethans a usage that is strictly correct only for the ethyl esters 40 however as a descriptive matter the iupac recognizes that an alternative term for the compounds r 2 nc o or r not h esters of carbamic acids r 2 nc o oh in strict use limited to the ethyl esters but widely used in the general sense 41 see also edit methyl carbamate ethyl carbamate polyurethane cholinesterase inhibitor references edit 1 2 3 jäger peter rentzea costin n kieczka heinz 2000 carbamates and carbamoyl chlorides ullmann s encyclopedia of industrial chemistry weinheim wiley vch doi 10 1002 14356007 a05_051 isbn 3 527 30673 0 ghosh arun k brindisi margherita 2015 04 09 organic carbamates in drug design and medicinal chemistry journal of medicinal chemistry 58 7 2895 2940 bibcode 2015jmedc 58 2895g doi 10 1021 jm501371s issn 0022 2623 pmc 4393377 pmid 25565044 1 2 burrows george h lewis gilbert n 1912 the equilibrium between ammonium carbonate and ammonium carbamate in aqueous solution at 25 journal of the american chemical society 34 8 993 995 bibcode 1912jachs 34 993b doi 10 1021 ja02209a003 clark k g gaddy v l rist c e 1933 equilibria in the ammonium carbamate urea water system ind eng chem 25 10 1092 1096 doi 10 1021 ie50286a008 mani fabrizio peruzzini maurizio stoppioni piero 2006 co2 absorption by aqueous nh 3 solutions speciation of ammonium carbamate bicarbonate and carbonate by a 13 c nmr study green chemistry 8 11 royal society of chemistry 995 doi 10 1039 b602051h issn 1463 9262 brooks l a audrieta l f bluestone h jofinsox w c 1946 ammonium carbamate inorganic syntheses vol 2 pp 85 86 doi 10 1002 9780470132333 ch23 isbn 978 0 470 13233 3 cite book isbn date incompatibility help 1 2 chaturvedi devdutt 1 may 2011 recent developments on the carbamation of amines current organic chemistry 15 10 bentham science publishers ltd 1593 1624 doi 10 2174 138527211795378173 issn 1385 2728 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 the identification of carbon dioxide mediated protein post translational modifications nature communications 9 1 3092 bibcode 2018natco 9 3092l doi 10 1038 s41467 018 05475 z issn 2041 1723 pmc 6078960 pmid 30082797 ferguson j k w roughton f j w 1934 12 14 the direct chemical estimation of carbamino compounds of co2 with hæmoglobin the journal of physiology 83 1 68 86 doi 10 1113 jphysiol 1934 sp003212 issn 0022 3751 pmc 1394306 pmid 16994615 1 2 bartoschek s vorholt j a thauer r k geierstanger b h griesinger c 2001 n carboxymethanofuran carbamate formation from methanofuran and co 2 in methanogenic archaea thermodynamics and kinetics of the spontaneous reaction eur j biochem 267 11 3130 3138 doi 10 1046 j 1432 1327 2000 01331 x pmid 10824097 t lundqvist g schneider 1991 0...