Methyl nicotinate
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Methyl nicotinate
structure -
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CAS No:
93-60-7
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Formula:
C7H7NO2
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Chemical Name:
Methyl nicotinate
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Synonyms:
3-Pyridinecarboxylic acid,methyl ester;Nicotinic acid,methyl ester;Methyl nicotinate;Nicometh;3-(Carbomethoxy)pyridine;Methyl 3-pyridinecarboxylate;3-(Methoxycarbonyl)pyridine;m-(Methoxycarbonyl)pyridine;NSC 13126;NSC 403799;123574-61-8
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CAS No:
Description
Methyl nicotinate, the methyl ester of Niacin found in alcoholic beverages, that is used as an active ingredient as a rubefacient in over-the-counter topical preparations indicated for muscle and joint pain[1].
Solid|White crystalline solid; Fresh caramelic nutty, mild tobacco aroma
Methyl nicotinate is a member of pyridines and an aromatic carboxylic acid.|Methyl nicotinate is the methyl ester of [DB00627] that is used as an active ingredient as a rubefacient in over-the-counter topical preparations indicated for muscle and joint pain. 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 Basic Attributes
137.14
137.14
113951
202-261-8
7B1AVU9DJN
403799|13126
DTXSID7044471
29333999
Characteristics
39.2
0.8
White to brownish Crystals or Crystalline Powder
1.1±0.1 g/cm3
42.5 °C
204 °C
204 °F
1.511
H2O: negligible soluble
Store below +30°C.
0.4 hPa (25 °C)
LD50 orally in Rabbit: > 2000 mg/kg
Safety Information
NONH for all modes of transport
3
36/37/38-36/38
26-36-37/39
QT1925000
Xi
Stable under normal temperatures and pressures.
P305 + P351 + P338
H315-H319-H335
|Warning|H315 (99.25%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|Aggregated GHS information provided by 1621 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
The acute subcutaneous LD50 of structurally-related nicotinamide and nicotinic acid in rats were 1.68 and 5.0 g/kg bw, respectively. In humans, oral ingestion of 3-9 g of nicotinic acid per day resulted in "niacin hepatitis", gout, and impaired glucose intolerance within a short period of time.
No pharmacokinetic data available.
Drug Information
Indicated for the temporary relief of aches and pains in muscles, tendons, and joints.
Following topical administration, methyl nicotinate acts as a peripheral vasodilator to enhance local blood flow at the site of application. It induced vasodilation of the peripheral blood capillaries which are located in the dermal papillae of upper dermis layers adjacent to the epidermis–dermis junction. During tissue penetration at the dermis, methyl nicotinate is hydrolyzed to nicotinic acid. In human volunteers, topical administration of methyl nicotinate caused vasodilation-induced generalized cutaneous erythema.
The presence of methyl group facilitates the penetration of methyl nicotinate through the skin with good lipophilicity, allowing rapid absorption following topical administration. _In vitro_, about 80-90% of the polar compounds methyl nicotinate rapidly penetrated the skin. It was demonstrated in excised skin of hairless mice that methyl nicotinate can effectively bypass the stratum corneum layer of the skin. In humans, nicotinic acid and nicotinamide were shown to be rapidly absorbed from the stomach and intestine via a sodium carrier-mediated mechanism at low concentrations.|Following epicutaneous administration of small radiolabelled dose of methyl nicotinate in human volunteers, approximately 15% of the dose was recovered in the urine within 108 hours after treatment. The excretion of nicotinic acid mainly takes place in the kidneys.|According to the animal studies, nicotinic acid is mainly concentrated in the liver, kidneys, and adipose tissue.|No pharmacokinetic data available.
Methyl nicotinate undergoes ester hydrolysis to form nicotinic acid and methanol. The hydrolysis is thought to be mediated by nonspecific α-naphthylacetate-esterase at the dermis layer of the skin.
_In vitro_, the half-life of methyl nicotinate in the dermis was 3 to 10 minutes.
While the mechanism of action of methyl nicotinate and other topically-administered nicotinic acid esters is not clear, it is thought that methyl nicotinate promotes the release of prostaglandin D2 that is strictly locally-acting due to its short half-life. It was demonstrated in human subjects that the local cutaneous vascular response to methyl nicotinic was suppressed by inhibitors of prostaglandin biosynthesis, indicating that the effect of methyl nicotinate on vascular smooth muscles may be mediated by the release of local prostaglandins. Prostaglandins released from the skin and blood vessels induce cutaneous vasodilation.
methyl nicotinate
Methyl nicotinate Use and Manufacturing
Vasodilator.
3-Pyridinecarboxylic acid, methyl ester: ACTIVE
Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Soothing; Tonic
Flavoring Agents
Computed Properties
Molecular Weight:137.14
XLogP3:0.8
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:137.047678466
Monoisotopic Mass:137.047678466
Topological Polar Surface Area:39.2
Heavy Atom Count:10
Complexity:125
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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