Diaminomaleonitrile (DAMN) is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

composed of two

amino In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent s ...

groups and two

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix ''cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including met ...

groups bonded to a central

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...

unit. The

systematic name A systematic name is a name given in a systematic way to one unique group, organism, object or chemical substance, out of a specific population or collection. Systematic names are usually part of a nomenclature. A semisystematic name or semitrivial ...

reflects its relationship to

maleic acid Maleic acid or ''cis''-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Its chemical formula is HO2CCH=CHCO2H. Maleic acid is the ''cis''-isomer of butenedioic acid, whereas fumaric acid ...

. The chemical can be formed by

polymerization In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer, monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are ...

hydrogen cyanide Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structure . It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at . HCN is produced on an ...

and can be used as the starting point for the synthesis of several classes of

heterocyclic compound A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...

s. Therefore, it has been considered as a possible organic chemical present in prebiotic conditions.

History

Diaminomaleonitrile was first isolated in 1873 as a black solid, when it was recognized as a polymer of hydrogen cyanide with the formula (HCN)_x. It was identified as the tetramer (HCN)₄ by

ebullioscopy An ebullioscope (from the Latin ''ēbullīre'' (to boil) + -scope) is an instrument for measuring the boiling point of a liquid. This can be used for determining the alcoholic strength of a mixture, or for determining the molecular weight of a non- ...

in 1923. The ''cis''-configuration of the amino groups was shown in 1928 through reaction with

glyoxal Glyoxal is an organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of ...

to give 2,3-diaminopyrazine, and the full structure was shown in 1955 to be diaminomaleonitrile, as opposed to the

isomeric In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...

aminoiminosuccinonitrile (AISN). :

Role in abiogenesis

Diaminomaleonitrile has been proposed since the 1960s as a key substance for the prebiotic synthesis of

nucleobases Nucleobases, also known as ''nitrogenous bases'' or often simply ''bases'', are nitrogen-containing biological compounds that form nucleosides, which, in turn, are components of nucleotides, with all of these monomers constituting the basic b ...

. Photochemical rearrangement of DAMN under UV light gives 4-aminoimidazole-5-carbonitrile (AICN), which can react further to form various nucleobases. : Early experiments have also suggested that certain amino acids, such as

aspartic acid Aspartic acid (symbol Asp or D; the ionic form is known as aspartate), is an α-amino acid that is used in the biosynthesis of proteins. Like all other amino acids, it contains an amino group and a carboxylic acid. Its α-amino group is in the pro ...

alanine Alanine (symbol Ala or A), or α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the central carbon atom which also carries a methyl group side c ...

, and

glycine Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid (carbamic acid is unstable), with the chemical formula NH2‐ CH2‐ COOH. Glycine is one of the proteinogeni ...

, may have their probiotic origins in the acidic hydrolysis of diaminomaleonitrile. Due to the ubiquity of hydrogen cyanide and its oligomers in space, it has been proposed that the dark material found in comets may consist of diaminomaleonitrile and higher oligomers, and that such polymers of HCN may have covered the surface of the early Earth.

References

{{organic-compound-stub Nitriles Diamines Enamines