Nonivamide
[CAS# 2444-46-4]

Identification

• Classification: API >> Inhibitor drug
• Name: Nonivamide
• Synonyms: Pelargonic acid vanillylamide; N-Vanillylnonanamide; N-(4-Hydroxy-3-methoxybenzyl)nonanamide
• Molecular Formula: C₁₇H₂₇NO₃
• Molecular Weight: 293.40
• CAS Registry Number: 2444-46-4
• EC Number: 219-484-1
• SMILES: CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC

Properties

• Solubility: 15 mg/ mL (DMSO), <1 mg/ mL (water), <1 mg/ mL (Ethanol )
• Melting point: 54 °C
• Boiling Point: 0.05 °C (200 mmHg)

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08 Danger
• Risk Statements: H301-H315-H317-H319-H334-H335
• Safety Statements: P233-P260-P261-P264-P264+P265-P270-P271-P272-P280-P284-P301+P316-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P342+P316-P362+P364-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	3	H301
Respiratory sensitization	Resp. Sens.	1	H334
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	2	H300

• Transport Information: UN 2811

Discovery and Applications

Nonivamide, also known as pelargonic acid vanillylamide, is a chemical compound recognized for its unique properties and diverse applications. It is a capsaicin analogue, which is a well-known component of chili peppers responsible for their pungent heat. Nonivamide shares structural similarities with capsaicin but differs in its chemical properties and applications.

The discovery of nonivamide emerged from the desire to develop a compound with similar biological activity to capsaicin but with distinct advantages in terms of safety and stability. The compound was first synthesized in the late 20th century as researchers aimed to explore alternatives to capsaicin that could provide similar effects without some of the associated issues, such as irritation or toxicity.

Nonivamide is synthesized through a series of chemical reactions starting with the preparation of pelargonic acid, which is then reacted with vanillylamine to form the final product. This process involves careful control of reaction conditions to ensure the production of high-purity nonivamide.

The compound is primarily known for its use in the field of pest control. Nonivamide acts as a repellent for a variety of pests, including insects and rodents. Its efficacy as a repellent is attributed to its ability to induce a mild, but persistent irritation that deters pests from approaching treated areas. This application is particularly valuable in agriculture and domestic settings, where nonivamide can help manage pest populations without the need for more toxic chemicals.

In addition to its use in pest control, nonivamide is also employed in the cosmetic industry. The compound is used in topical formulations for its potential to promote circulation and provide a warming sensation. It is often included in products designed for muscle and joint pain relief, where it can help enhance blood flow and reduce discomfort through its mild irritant effect. The safety profile of nonivamide in these applications is generally favorable, making it a useful alternative to capsaicin.

Nonivamide is also studied for its potential benefits in therapeutic and pharmacological applications. Research into the compound's effects on sensory nerves and its potential role in modulating pain perception continues to provide insights into its mechanisms of action and possible new uses.

Overall, nonivamide is a versatile compound with applications ranging from pest control to cosmetics and potential therapeutic uses. Its development represents an important step in expanding the range of functional compounds derived from natural sources and exploring their benefits in various fields.

References

2024. Dual Role of TRPV1 Channels in Cerebral Stroke: An Exploration from a Mechanistic and Therapeutic Perspective. Molecular Neurobiology.
DOI: 10.1007/s12035-024-04221-5

2009. Synthesis, photolysis studies and in vitro photorelease of caged TRPV1 agonists and antagonists. Organic & Biomolecular Chemistry, 7(22).
DOI: 10.1039/b914981c

2005. Analysis of Eight Capsaicinoids in Peppers and Pepper-Containing Foods by High-Performance Liquid Chromatography and Liquid Chromatography−Mass Spectrometry. Journal of Agricultural and Food Chemistry, 53(23).
DOI: 10.1021/jf050469j