Azocine
Encyclopedia
Azocine is a 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....

 organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the molecular formula C7H7N. It consists of an unsaturated
Saturation (chemistry)
In chemistry, saturation has six different meanings, all based on reaching a maximum capacity...

 eight-membered ring having seven carbon atoms, one nitrogen atom and four double bonds.

Saturated or partially saturated azocine rings form the core structure of a group of opioid
Opioid
An opioid is a psychoactive chemical that works by binding to opioid receptors, which are found principally in the central and peripheral nervous system and the gastrointestinal tract...

 compounds sometimes known as azocines. These include cyclazocine
Cyclazocine
Cyclazocine is a mixed opioid agonist/antagonist related to dezocine, pentazocine and phenazocine. This family of opioid drugs is called the benzomorphans or benzazocines.- Use :...

, pentazocine
Pentazocine
Pentazocine is a synthetically prepared prototypical mixed agonist-antagonist narcotic drug of the benzomorphan class of opioids used to treat moderate to moderately severe pain...

, and phenazocine
Phenazocine
Phenazocine is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects....

.

The fully saturated analog of azocine is azocane
Azocane
Azocane is a heterocyclic organic compound with the molecular formula C7H15N. It consists of a saturated eight-membered ring having seven carbon atoms and one nitrogen atom attached to a single hydrogen atom. The fully unsaturated analog of azocane is azocine....

.

Azocine rings are found in many natural products, including the manzamine family of marine alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...

s. One such compound is nakadomarin A, which contains a partially saturated azocine within its hexacyclic fused ring system.

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