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 burning ...
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 is ...
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
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fa ...
with
phenylacetic acid
Phenylacetic acid (PAA; conjugate base phenylacetate), also known by various synonyms, is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a strong honey-like odor. Endogen ...
. 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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