Aminoaldehydes and aminoketones are

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

s that contain an

amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

functional group as well as either a

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

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 organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

s. Such compounds are produced by amination of α- haloketones and α- haloaldehydes. Examples include

cathinone Cathinone (; also known as β-ketoamphetamine) 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 main contributor to t ...

methadone Methadone, sold under the brand names Dolophine and Methadose among others, is a synthetic opioid used medically to treat chronic pain and opioid use disorder. Prescribed for daily use, the medicine relieves cravings and opioid withdrawal sym ...

, molindone, 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-Piperidone is an organic compound with the molecular formula . It can be viewed as a derivative of piperidine. 4-Piperidone is used as an intermediate in the manufacture of chemicals and pharmaceutical drugs. Substituted and dehydro derivatives ...

, triacetonamine,

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

Primary amine derivatives

Most members of this class are unstable towards

self-condensation In organic chemistry, 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 condensat ...

, 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 po ...

. The acyclic forms of certain

amino sugar In organic chemistry, an amino sugar 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-Acetylglucosamine, ''N''-acetyl--glucosamine (a 2- ...

s also qualify, for instance vancosamine. Aminoacetaldehyde, 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 organic compound with the formula CH3C(O)CH2NH2. Although stable in the gaseous form, once condensed it reacts with itself. The protonated derivative forms isolable salts, e.g. aminoacetone hydrochloride ( H3C(O)CH2NH3l)). The ...

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 a naturally occurring amino sulfonic acid that is widely distributed in animal tissues. It is a major constituent of bile and can be found in the large intestine. It is named after Latin (cogna ...

References

{{Reflist Ketones Aldehydes Amines