Nordihydrocapsaicin

Nordihydrocapsaicin

0Nordihydrocapsaicin is a capsaicinoid and minor component of capsicum plants. It is an analog of capsaicin, but is less potent, with a Scoville scale rating of 9,100,000.

Chemistry

Nordihydrocapsaicin is a fatty acid amide of vanillylamine and pelargonic acid. It is structurally similar to capsaicin, but lacks the 9-methyl group on its side chain. This results in a lower lipophilicity and thus a lower potency as a TRPV1 agonist.

Biosynthesis

Nordihydrocapsaicin is biosynthesized in the fruit of capsicum plants, alongside other capsaicinoids. The biosynthesis involves the condensation of vanillylamine with pelargonic acid, catalyzed by the enzyme capsaicin synthase.

Pharmacology

Like other capsaicinoids, nordihydrocapsaicin acts as an agonist at the TRPV1 receptor. This receptor is a non-selective cation channel that is expressed in nociceptors, which are sensory neurons that respond to damaging or potentially damaging stimuli. Activation of TRPV1 by nordihydrocapsaicin leads to the sensation of heat and pain, and subsequent desensitization of the neuron to other forms of painful stimuli.

Uses

Nordihydrocapsaicin is used in the production of capsaicin cream and capsaicin patch, which are topical analgesics used to treat neuropathic pain. It is also used in the production of pepper spray, where it contributes to the overall potency of the product.

Safety

The LD50 of nordihydrocapsaicin in mice is 118.8mg/kg when administered intraperitoneally. It is therefore considered to be less toxic than capsaicin, which has an LD50 of 47.2mg/kg under the same conditions.

See also

• Capsaicin
• Capsaicinoid
• Scoville scale
• TRPV1