Nonivamide Property

Melting point:

54°C

Boiling point:

200-210 °C(Press: 0.05 Torr)

Density 

1,1 g/cm³

FEMA 

2787 | NONANOYL 4-HYDROXY-3-METHOXYBENZYLAMIDE

Flash point:

190°C

storage temp. 

Sealed in dry,2-8°C

solubility 

methanol: 100 mg/mL, clear to slightly hazy

form 

powder

pka

9.76±0.20(Predicted)

color 

white to off-white

Odor

bland odorless

Odor Type

bland

JECFA Number

1599

BRN 

2144300

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

RGOVYLWUIBMPGK-UHFFFAOYSA-N

LogP

3.43

CAS DataBase Reference

2444-46-4(CAS DataBase Reference)

EPA Substance Registry System

Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]- (2444-46-4)

Safety

Hazard Codes 

T,Xi

Risk Statements 

25-36/37/38-43

Safety Statements 

26-45-37/39-36/37

RIDADR 

UN 3462 6.1/PG 2

WGK Germany 

3

RTECS 

RA5998000

F 

19

HazardClass 

6.1

PackingGroup 

II

HS Code 

29242990

Toxicity

mouse,LD50,intraperitoneal,8mg/kg (8mg/kg),Journal of Medicinal Chemistry. Vol. 36, Pg. 2595, 1993.

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H318Causes serious eye damage

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Nonivamide Chemical Properties,Usage,Production

Description

Nonivamide is also called pelargonic acid vanillylamide or PAVA. It is a capsaicinoid. Nonivamide, isolated from peppers, is a naturally occurring analog of capsaicin (sc-3577). Similar to capsaicin, nonivamide can activate the TRPV1 receptor, thus, stimulate the firing rate of dopaminergic neurons in the ventral tegmental area of the brain and to increase the expression of the serotonin receptor gene HTR2A. Nonivamide is with lower TRPV1 binding affinity, thus, a reduced pungency (9 200 000 scoville heat units) compared to capsaicin (16 000 000 scoville heat units).
Nonivamide is used in the food production to add a hot sensation to flavoring agents and spice mixtures. It is also used in the sweets and confectionary industries to add hot sensation into products. In pharmaceutical industries, nonivamide is used as a cheaper alternative for capsaicin. Warming or heating ointment of nonivamide is used for temporary relief of pain from conditions such as rheumatism, arthritis, lumbao, muscular aches, sprains and strains, sporting injuries and other conditions where local warmth is beneficial. Finalgon is one of the common product utilizing nonivamide for this purpose. Nonivamide is also used as an incapacitant spray, affecting the assailed person’s eyes, causing intense pain and swelling.

References

[1] https://www.scbt.com/scbt/product/nonivamide-2444-46-4
[2] https://pubchem.ncbi.nlm.nih.gov/compound/N-Vanillylnonanamide#section=Clinical-Trials
[3] https://cot.food.gov.uk/sites/default/files/cot/cotsection.pdf

Description

Nonanoyl-4-hydroxy-3-methoxybenzylamide is odorless with a pungent, burning taste. Synthesized from nonanyl chloride and vanillylamine.

Chemical Properties

n-Nonanyl-4-hydroxy-3-methoxybenzyl-amide is an odorless compound, but has a pungent, burning taste

Chemical Properties

solid

Uses

analgesic (topical), depletes Substance P

Uses

N-Vanillylnonanamide is a synthetic analogue of Capsaicin (175680) with similar bioactivity.

Definition

ChEBI: A capsaicinoid that is the carboxamide resulting from the formal condensation of the amino group of 4-hydroxy-3-methoxybenzylamine with the carboxy group of nonanoic acid. It is the active ingredient in many pepper sprays.

Preparation

From nonanyl chloride and vanillylamine.

References

1. m. j. caterina, m. a. schumacher, m. tominaga, t. a. rosen, j. d. levine and d. julius, nature 1997, 389, 816-824. 2. y. g. gil and m. k. kang, life sci 2008, 82, 997-1003. 3. y. s. lee, d. h. nam and j. a. kim, cancer lett 2000, 161, 121-130. 4. h. c. chang, s. t. chen, s. y. chien, s. j. kuo, h. t. tsai and d. r. chen, hum exp toxicol 2011, 30, 1657-1665. 5. k. c. brown, t. r. witte, w. e. hardman, h. luo, y. c. chen, a. b. carpenter, j. k. lau and p. dasgupta, plos one 2010, 5, e10243.>