Methyl nicotinate Chemical Properties

Melting point:

42-44 °C (lit.)

Boiling point:

204 °C (lit.)

Density 

1.2528 (rough estimate)

vapor pressure 

0.4 hPa (25 °C)

FEMA 

3709 | METHYL NICOTINATE

refractive index 

1.5323 (estimate)

Flash point:

204 °F

storage temp. 

Store below +30°C.

solubility 

H₂O: 0.1 g/mL, clear

form 

Crystals or Crystalline Powder

pka

pKa 3.1 (Uncertain)

color 

White to brownish

Odor

at 10.00 % in dipropylene glycol. warm herbal tobacco

Odor Type

herbal

Water Solubility 

NEGLIGIBLE

JECFA Number

1320

Merck 

14,6100

BRN 

113951

InChIKey

YNBADRVTZLEFNH-UHFFFAOYSA-N

LogP

0.68 at 25℃

CAS DataBase Reference

93-60-7(CAS DataBase Reference)

NIST Chemistry Reference

Methyl nicotinate(93-60-7)

EPA Substance Registry System

Methyl nicotinate (93-60-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

QT1925000

TSCA 

Yes

HS Code 

29333999

Toxicity

LD50 orally in Rabbit: > 2000 mg/kg

MSDS

• Language:English Provider:Methyl nicotinate
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Methyl nicotinate Usage And Synthesis

Description

Methyl nicotinate is a skin irritant in man, in particular producing vasodilatation, which is used on purpose in “rubefacient”, to produce a redness or inflammation for a short period of time, often in lip plumper or other lip products. Methyl nicotinate is also an active ingredient of a number of veterinary preparations intended for topical application as a rubefacient for the treatment of a variety of diseases, such as respiratory diseases, vascular disorders (oedema, haematoma), and rheumatoid disorders in cattle and horses (doses not stated; the concentration in the formulated veterinary medicinal product is 2%).

Chemical Properties

Methyl nicotinate is white to brownish crystals or crystalline powder and has a fresh, caramellic, nutty and mild tobacco odor.

Occurrence

Reported found in ground coffee, roasted filberts, guanabana (Annona muicata L.), roasted peanuts, wild strawberries, vanilla bean, papaya, guava, plum, beer cognac, soursop, malt, wort, Bourbon vanilla and mountain papaya.

Uses

Methyl nicotinate (MN) is the methyl ester of nicotinic acid that is used as an active ingredient, a rubefacient and counter-irritant in over-the-counter topical preparations indicated for the temporary relief of aches and pains in muscles,tendons, and joints. The action of methyl nicotinate as a rubefacient is thought to involve peripheral vasodilation.For veterinary purposes，methyl nicotinate is used to treat respiratory diseases, vascular disorders, rheumatoid arthritis, and muscle and joint pains.Methyl nicotinate can be found in in guava fruit, papaya, strawberry, soursop(Annona muricata), beer, grape brandy, coffee, roasted filbert, roasted peanut and Bourbon vanilla.

Definition

ChEBI: Methyl nicotinate is a member of pyridines and an aromatic carboxylic acid.

Application

Methyl nicotinate can be employed as a precursor in the synthesis:
Di-3-pyridyl ketone ligand, which is used in the preparation of silver(I) complexes for the derivation of coordination polymeric chains.
5-arylnicotinates , ±-sesbanine , and 1,4-dihydropyridine derivatives.

Preparation

Methyl nicotinate was prepared by esterification of nicotinic acid by refluxing with methanol in the presence of concentrated sulphuric acid, esterification product obtained was extracted into organic solvent (chloroform) after neutralization of the reaction mixture with 10% sodium bicarbonate.
Synthesis and antinociceptive activity of methyl nicotinate
DOI:10.4314/jpb.v12i1.8

General Description

Methyl nicotinate (or nicotinic acid methyl ester) is used as a rubefacient for the relief of pains in muscles, tendons, and joints. It is also used in food as a flavoring agent.

Side effects

There is presently no side effect information available for Methyl nicotinate(MN) itself. a few patients who applied a medicated topical preparation containing MN (and other components) suffered adverse reactions including faintness, nausea, pain and skin rashes.

Safety

No data are available for chronic toxicity of Methyl nicotinate(MN) in humans. No adverse effects were reported for nicotinamide in clinical studies, whereas high doses of NA (3000 mg/day) are associated with considerable toxicity. In one third to one half of the 1119 patients taking 3000 mg NA /day for at least five years (to reduce the incidence of a second myocardial infarction), side effects included gastrointestinal and urinary tract problems, as well as dermatological problems of flushing, itching and rash ("The Coronary Drug Project", 1975, cited in "monograph of methyl nicotinate", Council of Europe, 2008, pp. 248).

Synthesis

Methyl nicotinate is synthesized from Nicotinyl chloride hydrochloride and and Methanol in presence of Pyridine.

Carcinogenicity

No data on the mutagenic or carcinogenic potential of methyl nicotinate were presented. However life-time studies in mice employing doses of 2 to 3 mg nicotinamide/kg bw/day gave no indication of carcinogenic potential.

Methyl nicotinate(93-60-7)Related Product Information

• Paraquat dichloride
• Nicotinic acid
• Acetonitrile
• Methyl acrylate
• Basic Violet 1
• Methylparaben
• Kresoxim-methyl
• Methanol
• Methyl acetate
• N-BUTYL NICOTINATE
• Ethyl nicotinate
• Nicotinamide
• Hexyl nicotinate
• METHYLENEDIPHOSPHONIC ACID
• NICOTINIC ACID MONONUCLEOTIDE
• Methyl
• Topiroxostat Impurity 6
• 2-CYANO-4-PYRIDINE CARBOXYLIC ACID