Sydnone
Encyclopedia
Mesoionic
Mesoionic chemical compounds are dipolar five- or six- membered heterocyclic compounds in which both the negative and the positive charges are delocalized...
heterocyclic
Heterocyclic compound
A heterocyclic compound is a cyclic compound which has atoms of at least two different elements as members of its ring. The counterparts of heterocyclic compounds are homocyclic compounds, the rings of which are made of a single element....
aromatic chemical compound
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
. A sydnone imine
Sydnone imine
Sydnone imine is a mesoionic heterocyclic aromatic chemical compound. Sydnone imine is the imine of sydnone where the keto functional group of sydnone has been replaced with an imine group. A sydnone imine substructure can be found in the stimulant drugs feprosidnine and mesocarb and the...
in which the keto
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...
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. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
of sydnone (=O) has been replaced with an imino
Imine
An imine is a functional group or chemical compound containing a carbon–nitrogen double bond, with the nitrogen attached to a hydrogen atom or an organic group. If this group is not a hydrogen atom, then the compound is known as a Schiff base...
(=NH) group can be found as a substructure in the stimulant drugs feprosidnine
Feprosidnine
Feprosidnine is a stimulant drug which was developed in the USSR in the 1970s. It is structurally related to another Russian drug mesocarb but unlike mesocarb it has not been developed for medical use in humans....
and mesocarb
Mesocarb
Mesocarb is a stimulant drug which was developed in the USSR in the 1970s. It has been shown to act as a dopamine reuptake inhibitor which is slower acting but longer lasting and less neurotoxic than dextroamphetamine....
.
Discovery
Sydnone was first prepared in 1935 by Earl & Mackney by cyclodehydration of N-Nitroso-N-phenylglycine with acetic anhydrideAcetic anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula 2O. Commonly abbreviated Ac2O, it is the simplest isolatable acid anhydride and is a widely used reagent in organic synthesis...
.