Nicotinamide

Base Information

• Chemical Name: Nicotinamide
• CAS No.: 98-92-0
• Deprecated CAS: 123574-63-0,37321-14-5,78731-47-2,78731-47-2
• Molecular Formula: C6H6N2O
• Molecular Weight: 122.126
• Hs Code.: 2936.29
• European Community (EC) Number: 202-713-4,234-265-0
• ICSC Number: 1703
• NSC Number: 759115,27452,13128
• UNII: 25X51I8RD4
• DSSTox Substance ID: DTXSID2020929
• Nikkaji Number: J3.988H
• Wikipedia: Nicotinamide
• Wikidata: Q192423
• NCI Thesaurus Code: C2327
• RXCUI: 7405
• Metabolomics Workbench ID: 37778
• ChEMBL ID: CHEMBL1140
• Mol file: 98-92-0.mol

Synonyms:3 Pyridinecarboxamide;3-Pyridinecarboxamide;B 3, Vitamin;B3, Vitamin;Enduramide;Jenapharm, Nicotins?ureamid;Niacinamide;Nicobion;Nicotinamide;Nicotins?ureamid Jenapharm;Papulex;Vitamin B 3;Vitamin B3;Vitamin PP

Chemical Property of Nicotinamide

Chemical Property:

• Appearance/Colour: White to off white powder
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 128-131 °C
• Refractive Index: 1.4660 (estimate)
• Boiling Point: 334.4 °C at 760 mmHg
• PKA: 3.3(at 20℃)
• Flash Point: 156 °C
• PSA: 55.98000
• Density: 1.204 g/cm³
• LogP: 0.88080
• Storage Temp.: 0-6°C
• Solubility.: 691g/l
• Water Solubility.: 1000 g/L (20 ºC)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 122.048012819
• Heavy Atom Count: 9
• Complexity: 114

Purity/Quality:

99%, ^*data from raw suppliers

Nicotinamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T,F
• Statements: 36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-36-37/39-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Vitamins and Derivatives
• Canonical SMILES: C1=CC(=CN=C1)C(=O)N
• Recent ClinicalTrials: Skin Cancer Prevention With Nicotinamide in Transplant Recipients - Pilot Trial
• Recent EU Clinical Trials: A phase II randomized, double-blind, active placebo-controlled parallel group trial to examine the efficacy and safety of psilocybin in treatment-resistant
• Recent NIPH Clinical Trials: Measurement of NAD+ metabolites in blood after oral intake of Vitamin B3
• Inhalation Risk: A nuisance-causing concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is irritating to the eyes.
• Amide Analog of Vitamin B3: Niacinamide, also known as nicotinamide, is an amide form of vitamin B3. It is a precursor of essential coenzymes required for various reactions in the body, including the production of adenosine triphosphate (ATP).
• Management of Skin Disorders: Niacinamide is now explored for its potential in managing various skin disorders. It has been used topically in the treatment of acne vulgaris, melasma, atopic dermatitis, and rosacea.
• Inhibition of Sirtuins: At high doses, niacinamide acts as a dietary supplement that inhibits sirtuins, a class of enzymes involved in cellular regulation.
• Water-Soluble Amide Derivative: Niacinamide is a water-soluble amide derivative of nicotinic acid (niacin), which is one of the major forms of vitamin B3. The recommended dietary allowance for vitamin B3 in adults is typically 14 to 16 mg daily.
• Safety and Tolerance: Niacinamide is generally well-tolerated and has been widely used in cosmetic and personal care formulations for various skin conditions. It is considered an inexpensive dietary supplement that is readily available to the public.
• Topical Formulations: Niacinamide is commonly found in topical formulations for skincare. Studies have confirmed its permeation under certain conditions, indicating its potential effectiveness when applied to the skin.

Technology Process of Nicotinamide

There total 151 articles about Nicotinamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

3-Aminomethylpyridine (3731-52-0) → pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) + nicotinamide (98-92-0,1255150-40-3)

Guidance literature:

With water; oxygen; at 140 ℃; for 24h; under 3800.26 Torr;

DOI:10.1002/anie.200802464

Reference yield: 74.0%

pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) → 3-hydroxymethylpyridin (100-55-0) + nicotinamide (98-92-0,1255150-40-3)

Guidance literature:

With formaldehyd; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In water; toluene; at 90 ℃;

DOI:10.1039/c9cy01484e

Reference yield: 63.0%

N-benzylnicotinamide (2503-55-1) → nicotinamide (98-92-0,1255150-40-3) + benzaldehyde (100-52-7)

Guidance literature:

With N-Bromosuccinimide; In chloroform; at 20 ℃; for 20h; Product distribution;

DOI:10.1055/s-2007-990795

upstream raw materials:

pyridine-3-carbonitrile

nicotinic acid

BIURET

urea

Downstream raw materials:

propyl nicotinamide sulfonate

1,1'-Tetramethylen-bis-<3-carbamoyl-pyridinium-bromid>

1-butyl-3-carbamoylpyridin-1-ium bromide

N-hydroxymethylnicotinamide

Refernces

• 1、 Gómez-Carpintero, Jorge,Sánchez, J. Domingo,González, J. Francisco,Menéndez, J. Carlos. "Mechanochemical Synthesis of Primary Amides". . p. 14232 - 14237. Retrieved 2021/10/20.
• 2、 Long, Xiangdong,Wang, Jia,Gao, Guang,Nie, Chao,Sun, Peng,Xi, Yongjie,Li, Fuwei. "Direct Oxidative Amination of the Methyl C-H Bond in N-Heterocycles over Metal-Free Mesoporous Carbon". . p. 10902 - 10912. Retrieved 2021/09/08.