Phenylacetylrinvanil (IDN-5890) is a synthetic analogue of
capsaicin
Capsaicin (8-methyl-''N''-vanillyl-6-nonenamide) ( or ) is an active component of chili peppers, which are plants belonging to the genus ''Capsicum''. It is a chemical irritant for mammals, including humans, and produces a sensation of burnin ...
which acts as a potent and selective agonist for the
TRPV1
The transient receptor potential cation channel subfamily V member 1 (TrpV1), also known as the capsaicin receptor and the vanilloid receptor 1, is a protein that, in humans, is encoded by the ''TRPV1'' gene. It was the first isolated member of th ...
receptor, with slightly lower potency than
resiniferatoxin
Resiniferatoxin (RTX) is a naturally occurring chemical found in resin spurge (''Euphorbia resinifera''), a cactus-like plant commonly found in Morocco, and in '' Euphorbia poissonii'' found in northern Nigeria. , though still around 300 times the potency of capsaicin. It is an
amide
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it i ...
of
vanillylamine
Vanillylamine is a chemical compound that is an intermediate in the biosynthesis of capsaicin. Vanillylamine is produced from vanillin by the enzyme vanillin aminotransferase. It is then converted with 8-methyl-6-nonenoic acid into capsaicin by ...
and
ricinoleic acid
Ricinoleic acid, formally called 12-hydroxy-9-''cis''-octadecenoic acid is a fatty acid. It is an unsaturated omega-9 fatty acid and a hydroxy acid. It is a major component of the seed oil obtained from mature castor plant (''Ricinus communis' ...
, with the hydroxyl group on ricinoleic acid
esterified with
phenylacetic acid. It is used to study the function of the TRPV1 receptor and its downstream actions, and has also shown anti-cancer effects ''in vitro''.
References
Capsaicinoids
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