Carbamate

	Email		Print
	Bookmark		Link

Carbamate

Carbamates, or urethane

Urethane

Urethane can refer to*Carbamates, compounds with the functional group RONHR'*ethyl carbamate, the trivial name of which is urethane*polyurethane in colloquial usage...
s, are a group of organic compound

Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s sharing a common functional group

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
with the general structure -NH(CO)O-. Carbamates are ester

Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
s of carbamic acid
Carbamic acid

Carbamic acid is a compound that is unstable under normal circumstances. Its importance is due more to its relevance in identifying the names of larger compounds....
, NH₂COOH, an unstable compound. Since carbamic acid contains a nitrogen

Nitrogen

Amide

In chemistry, an amide is one of three kinds of compounds:* the organic chemistry functional group characterized by a carbonyl group linked to a nitrogen atom , or a compound that contains this functional group ; or...
. Therefore, carbamate esters may have alkyl

Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
or aryl

Aryl

In the context of organic molecules, aryl refers to any functional group or substituent derived from a simple aromatic ring, may it be phenyl, thiophene, indole, etc ....
groups substituted on the nitrogen, or the amide function. For example, ethyl carbamate

Ethyl carbamate

Ethyl carbamate is a substance first prepared in the nineteenth century. Structurally it is an ester of carbamate, i. e., ethyl carbamate as shown....
(trivial name "urethane"), is unsubstituted, whereas ethyl N–methylcarbamate has a methyl group attached to the nitrogen (see methyl isocyanate

Methyl isocyanate

Methyl isocyanate is an organic compound with the molecular formula C2H3NO, arranged as H3C-N=C=O. Synonyms are isocyanatomethane, methyl carbylamine, and MIC....
for formation of N-methylcarbamates).

stands for the atoms attached to the other end of the nitrogen

Nitrogen

Discussion

Ask a question about 'Carbamate'

Start a new discussion about 'Carbamate'

Answer questions from other users

Full Discussion Forum

Encyclopedia

Carbamates, or urethane

Urethane

Organic compound

Functional group

Ester

Nitrogen

Amide

Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
or aryl

Aryl

Ethyl carbamate

Methyl isocyanate

Carbamates in biochemistry

A nitrogen-substituted carbamic acid is formed when a carbon dioxide

Carbon dioxide

Carbon dioxide is a chemical compound composed of two oxygen atoms covalent bond to a single carbon atom. It is a gas at standard temperature and pressure and exists in Earth's atmosphere in this state....
molecule reacts with the amino terminus of a peptide

Peptide

Peptides are short polymers formed from the linking, in a defined order, of a-amino acids. The link between one amino acid residue and the next is known as an amide chemical bond or a peptide bond....
chain or an amino group of an amino acid

Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
, adding a COO⁻ group to it and releasing a cation (H⁺ ion) to form a carbamate ion

Ion

An ion is an atom or molecule which has lost or gained one or more electrons, giving it a positive or negative electrical charge. According to the Bohr_model this will be from or in the outer shield 'n'....
.

"R" stands for the atoms attached to the other end of the nitrogen

Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
atom of the amino group. Note that the COO⁻ group is a resonance structure, so the single bonds both show a degree of double-bond character, and the charge is delocalised over the two oxygen atoms. This reaction is reversible

Reversible reaction

A reversible reaction is a chemical reaction that results in an chemical equilibrium mixture of reactants and Product . For a reaction involving two reactants and two products this can be expressed symbolically asA and B can react to form C and D or, in the reverse reaction, C and D can react to form A and B....
(with equilibrium constant K << 1 in the above reaction), as the N–C bond is highly labile.

Some occurrences of carbamate groups in nature

In hemoglobin

Hemoglobin

Hemoglobin is the iron-containing oxygen-transport metalloprotein in the red blood cells of vertebrates, and the tissues of some invertebrates....
, carbamate groups are formed when carbon dioxide molecules bond with the amino termini of the globin

Globin

A globin is a hemeprotein that incorporates the globin fold. Globins are used to transport heme....
chains. This helps to stabilize the protein when it becomes deoxyhemoglobin and increases the likelihood of the release of remaining oxygen

Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
molecules bound to the protein.

Ribulose 1,5-bisphosphate carboxylase/oxygenase

RuBisCO

Ribulose-1,5-bisphosphate carboxylase/oxygenase, most commonly known by the shorter name RuBisCO, is an enzyme that is used in the Calvin cycle to catalyze the first major step of carbon fixation, a process by which the atoms of atmospheric carbon dioxide are made available to organisms in the form of fuel molecules such as sucrose....
(the enzyme required to fix a carbon dioxide molecule at the start of the Calvin cycle

Calvin cycle

The Calvin cycle is a series of biochemistry reactions that take place in the Stroma of chloroplasts in photosynthesis organisms. It was discovered by Melvin Calvin, James Bassham and Andrew Benson at the University of California, Berkeley ....
) also requires the formation of a carbamate to function. At the active site of the enzyme, a Mg²⁺ ion is bound to a glutamate

Glutamic acid

Glutamic acid is one of the 20 proteinogenic amino acids and its codons are GAA and GAG. It is a non-essential amino acid. The carboxylate anions and salt of glutamic acid are known as glutamates....
residue, an aspartate

Aspartic acid

Aspartic acid is an a-amino acid with the chemical formula HO2CCHCH2CO2H. The carboxylate anion of aspartic acid is known as aspartate....
residue and a lysine

Lysine

Lysine is an a-amino acid with the chemical formula HO2CCH4NH2. This amino acid is an essential amino acid, which means that humans cannot synthesize it....
carbamate, which hold the ion in place. The carbamate is formed when an uncharged lysine side-chain near the ion reacts with a carbon dioxide molecule from the air (not the substrate carbon dioxide molecule), which then renders it charged, and, therefore, able to bind the Mg²⁺ ion.

Commercial carbamate compounds

A group of insecticide

Insecticide

An insecticide is a pesticide used against insects in all developmental forms. They include ovicides and larvicides used against the Egg and larvae of insects respectively....
s also contains the carbamate functional group, including aldicarb

Aldicarb

Aldicarb is a carbamate insecticide with structural formula: 2-methyl-2-propanal O-oxime. Aldicarb is the active substance in Temik pesticide, which is effective against thrips, aphids, Red Spider Mites, lygus, fleahoppers, and leafminers but is primarily used as a nematicide....
, carbofuran

Carbofuran

Carbofuran is one of the most toxic carbamate pesticides. It is marketed under the trade names Furadan, by FMC Corporation and Curater, among several others....
, furadan, fenoxycarb

Fenoxycarb

Fenoxycarb is a carbamate insecticide. It has a low toxicity for bees, birds, and humans, but is toxic to fish....
, carbaryl

Carbaryl

Carbaryl is a chemical in the carbamate family used chiefly as an insecticide. It is a colorless white crystalline solid commonly sold under the brand name Sevin, a trademark of the Bayer Company....
(Sevin), ethienocarb, and fenobucarb. These insecticides can cause cholinesterase inhibition poisoning by reversibly inactivating the enzyme acetylcholinesterase

Acetylcholinesterase

Acetylcholinesterase, also known as AChE, is an enzyme that degrades the neurotransmitter acetylcholine, producing choline and an acetate group....
. The organophosphate

Organophosphate

An organophosphate is the general name for esters of phosphoric acid. Phosphates are probably the most pervasive organophosphorus compounds. Many of the most important biochemicals are organophosphates, including DNA and RNA as well as many cofactor s that are essential for life....
pesticides also inhibit this enzyme, though irreversibly, and cause a more severe form of cholinergic poisoning.

Polyurethane

Polyurethane

A polyurethane, commonly abbreviated PU, is any polymer consisting of a chain of organic chemistry units joined by carbamate links. Polyurethane polymers are formed by reacting a monomer containing at least two isocyanate functional groups with another monomer containing at least two alcohol groups in the presence of a catalyst....
s contain multiple carbamate groups as part of their structure, but urethane

Urethane

Polyurethane

Polymer

A polymer is a large molecule composed of repeating structural units typically connected by covalent chemical bonds. While polymer in popular usage suggests plastic, the term actually refers to a large class of natural and synthetic materials with a variety of properties....
s have a wide range of properties and are commercially available as foams, elastomers, and solids.

Urethane

Urethane

Urethane can refer to*Carbamates, compounds with the functional group RONHR'*ethyl carbamate, the trivial name of which is urethane*polyurethane in colloquial usage...
or ethyl carbamate

Ethyl carbamate

Ethyl carbamate is a substance first prepared in the nineteenth century. Structurally it is an ester of carbamate, i. e., ethyl carbamate as shown....
is occasionally used as a veterinary medicine.

In addition, some carbamates are used in human pharmacotherapy, for example, the cholinesterase inhibitors neostigmine

Neostigmine

Neostigmine is a Parasympathomimetic drug, specifically, a reversible cholinesterase inhibitor.Neostigmine is available under several trade names such as Prostigmin and Vagostigmin....
and rivastigmine

Rivastigmine

Rivastigmine is a parasympathomimetics or cholinergic agent for the treatment of mild to moderate Alzheimer's disease and dementia due to Parkinson's disease....
, whose chemical structure

Chemical structure

A Chemical structure includes molecular geometry, electronic structure and crystal structure of a chemical compound. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together....
is based on the natural alkaloid

Alkaloid

Alkaloids are naturally occurring chemical compounds containing base nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base....
physostigmine

Physostigmine

Physostigmine is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor alkaloid of the Calabar bean.The chemical was synthesized for the first time in 1935 by the chemists Percy Lavon Julian and Josef Pikl....
. Other examples are meprobamate

Meprobamate

Meprobamate is a carbamate derivative which is used as an anxiolytic drug. It was the best-selling minor tranquilizer for a time, but has largely been replaced by the benzodiazepines....
and its derivatives, a class of anxiolytic drugs widely used in the 60s before the rise of benzodiazepines, and still used nowadays in some cases.

The insect repellent

Insect repellent

An insect repellent is a substance applied to skin, clothing, or other surfaces which discourages insects from landing or climbing on that surface....
icaridin

Icaridin

Icaridin, also known as picaridine, KBR 3023, under the INCI name hydroxyethyl isobutyl piperidine carboxylate, and under the old trade name Bayrepel and the current trade name Saltidin, is an insect repellent....
is a substituted carbamate.

Carbamate

Carbamates in biochemistry

Some occurrences of carbamate groups in nature

Commercial carbamate compounds

See also