Aminoaldehydes and aminoketones are

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 ...

s that contain an

amine 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 Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...

functional group as well as either a

aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

functional group. These compounds are important in biology and in chemical synthesis. Because of their bifunctional nature, they have attracted much attention from chemists.

Tertiary amine derivatives

Because primary and secondary amines react with aldehydes and ketones, the most common variety of these aminocarbonyl compounds feature

tertiary amine 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 Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such a ...

s. Such compounds are produced by amination of α-

haloketone In organic chemistry, an α-haloketone is a functional group consisting of a ketone group or more generally a carbonyl group with an α-halogen substituent. α-haloketones are alkylating agents. Prominent α-haloketones include phenacyl bromide ...

s and α- haloaldehydes. Examples include

cathinone Cathinone (also known as benzoylethanamine, or β-keto-amphetamine) is a monoamine alkaloid found in the shrub '' Catha edulis'' (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the m ...

methadone Methadone, sold under the brand names Dolophine and Methadose among others, is a synthetic opioid agonist used for chronic pain and also for opioid dependence. It is used to treat chronic pain, and it is also used to treat addiction to heroin ...

molindone Molindone, sold under the brand name Moban, is an antipsychotic which is used in the United States in the treatment of schizophrenia. It works by blocking the effects of dopamine in the brain, leading to diminished symptoms of psychosis. It is r ...

, pimeclone, ferruginine, and

tropinone Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. I ...

Secondary amine derivatives

Aminoketones containing secondary amines are typically stable when the ketone is located on a ring, e.g.

4-piperidinone 4-Piperidinone is a derivative of piperidine with the molecular formula C5 H9 N O. 4-Piperidone is used as an intermediate in the manufacture of chemicals and pharmaceutical drugs. Piperidones Piperidones are a class of chemical compounds sharin ...

, triacetonamine,

acridone Acridone is an organic compound based on the acridine skeleton, with a carbonyl group at the ''9'' position. It is a yellow solid. Synthesis and structure The molecule is planar. Optical spectra reveal that the keto tautomer predominates in the ga ...

Primary amine derivatives

Most members of this class are unstable towards

self-condensation Self-condensation is an organic reaction in which a chemical compound containing a carbonyl group acts both as the electrophile and the nucleophile in an aldol condensation. It is also called a symmetrical aldol condensation as opposed to a mixed a ...

, however some important examples do exist as intermediates in biosynthetic pathways e.g.

glutamate-1-semialdehyde Glutamate-1-semialdehyde is a molecule formed from by the reduction of tRNA bound glutamate, catalyzed by glutamyl-tRNA reductase. It is isomerized by glutamate-1-semialdehyde 2,1-aminomutase to give aminolevulinic acid in the biosynthesis of por ...

. The acyclic forms of certain

amino sugar In organic chemistry, an amino sugar (or more technically a 2-amino-2-deoxysugar) is a sugar molecule in which a hydroxyl group has been replaced with an amine group. More than 60 amino sugars are known, with one of the most abundant being ''N'' ...

s also qualify, for instance vancosamine.

Aminoacetaldehyde Aminoacetaldehyde is the organic compound with the formula OHCCH2NH2. Under the usual laboratory conditions, it is unstable, tending instead to undergo self-condensation. Aminoacetaldehyde diethylacetal is a stable surrogate. In nature, aminoac ...

, the simplest member of this subclass, is highly reactive toward

. Aminoacetaldehyde diethylacetal, (EtO)₂CHCH₂NH₂, is a stable analogue that is commercially available.

2-Aminobenzaldehyde 2-Aminobenzaldehyde is an organic compound with the formula C6H4(NH2)CHO. It is one of three isomers of aminobenzaldehyde. It is a low-melting yellow solid that is soluble in water. Preparation and reactions It is usually prepared by reduction ...

with the formula C₆H₄(NH₂)CHO is a prominent aromatic aminoaldehyde. The compound is unstable with respect to

Aminoacetone Aminoacetone is the simplest monopeptide with the formula CH3C(O)CH2NH2. Although stable in the gaseous form, once condensed it reacts with itself. The protonated derivative forms stable salts, e.g. aminoacetone hydrochloride ( H3C(O)CH2NH3l)). ...

is a prominent member of this class of compounds. It is unstable under normal laboratory conditions, but the hydrochloride H₃C(O)CH₂NH₃l is readily isolable. Aminoacetone is derived from decarboxylation of alanine. Aminoacetaldehyde is produced by the hydroxylation of

taurine Taurine (), or 2-aminoethanesulfonic acid, is an organic compound that is widely distributed in animal tissues. It is a major constituent of bile and can be found in the large intestine, and accounts for up to 0.1% of total human body weight. It ...

References

{{organic-compound-stub Amines Ketones Aldehydes