pyridine-3-carboxylic acid

• ChemBase ID: 509
• Molecular Formular: C6H5NO2
• Molecular Mass: 123.1094
• Monoisotopic Mass: 123.03202841
• SMILES: OC(=O)c1cccnc1
• Canonical SMILES: OC(=O)c1cccnc1
• InChI: InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
• InChIKey: PVNIIMVLHYAWGP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pyridine-3-carboxylic acid
• IUPAC Systematic name: Pyridine-3-carboxylic acid
• IUPAC Traditional name: niacin
• Brand Name: Akotin; Anti-Pellagra Vitamin; Apelagrin; Bionic; Daskil; Davitamon PP; Diacin; Direktan; Efacin; Kyselina Nikotinova; Linic; NICO; Naotin; Niac; Nicacid; Nicangin; Nico-Span; Nicocidin; Nicocrisina; Nicodan; Nicodelmine; Nicodon; Niconacid; Niconat; Niconazid; Nicorol; Nicosan 3; Nicoside; Nicosyl; Nicotamin; Nicotene; Nicotil; Nicotinipca; Nicotinsaure; Nicovasan; Nicovasen; Nicovel; Nicyl; Nipellen; Nyclin; P.P. Factor; Pellagra Preventive Factor; Pellagramin; Pellagrin; Pelonin; Peviton; PP Factor; Sk-Niacin; Tega-Span; Tinic; Vitaplex N; Niaspan; Simcor
• Synonyms: Acide Nicotinique; Acidum Nicotinicum; M-Pyridinecarboxylic Acid; NAH; Nicotine Acid; Nicotinic Acid; Pyridinecarboxylic Acid; Pyridylcarboxylic Acid; Vitamin B3; 3-Pyridinecarboxylic acid; niacin; Niacin; Niacinamide; Niacin(Nicotinic acid); Pyridine-3-carboxylic acid; 3-Carboxypyridine; Nicotinic acid; Pellagra preventive factor; 3-Carboxylpyridine; Akotin; Apelagrin; Niacor; Niaspan; Nicacid; Pelonin; Vitamin B5; Wampocap; β-Pyridinecarboxylic Acid; Bionic; Nicotinic acid; NICOTINIC ACID FREE ACID; 3-Picolinic acid; Vitamin B₃; 尼可丁酸; 3-吡啶甲酸; 吡啶-3-羧酸; 尼亚生; 抗糙皮病因子; 维生素 B3; 烟酸

Database IDs

• CAS Number: 59-67-6
• EC Number: 200-441-0
• MDL Number: MFCD00006391
• Beilstein Number: 109591
• Merck Index: 146525
• PubChem SID: 24886385; 46507508; 24871534; 24886386; 24897734; 24897668; 24897445; 24897443; 24886384; 160963972
• PubChem CID: 938
• CHEBI ID: 15940
• ATC CODE: C04AC01; C10AD02
• CHEMBL: 573
• Chemspider ID: 913
• DrugBank ID: DB00627
• Gmelin ID: 3340
• IUPHAR ligand ID: 1588
• KEGG ID: D00049
• MeSH Name: Niacin
• Unique Ingredient Identifier: 2679MF687A
• Wikipedia Title: Niacin

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.7856104
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.3303725
• LogD (pH = 7.4): -2.8627489
• Log P: -0.16644564
• Molar Refractivity: 31.1573 cm^3
• Polarizability: 11.793079 Å^3
• Polar Surface Area: 50.19 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.29
• LOG S: -0.17
• Solubility (Water): 8.31e+01 g/l

PROPERTIES

Physical Property

• Solubility: 18 g L^-1 in water; 18 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; DMSO; Methanol; Water
• Apperance: White Solid; White, translucent crystals
• Melting Point: 189-202°C; 233-238 °C; 234-238 °C; 234-238 °C (dec.); 236.6; 236.85°C (510K); 236-239 °C(lit.); 236-239(subl.)°C; 236-239°C
• Flash Point: 193 °C; 193°C; 293°C(559°F); 379.4 °F
• Auto Ignition Point: 365 °C
• Density: 1.4; 1.467; 1.473 g cm^-3
• Refractive Index: 1.4936
• Vapor Pressure: 5.7 x 10-6 mm Hg at 25 °C (estimated)
• Partition Coefficient: 0.219
• Hydrophobicity(logP): 0.4
• pKa: 2.201
• pKb: 11.796
• Isoelectric Point: 4.75
• Dipole Moment: 0.1271305813 D
• Std enthalpy of combustion: -2.73083 MJ mol^-1
• Std enthalpy of formation: -344.9 kJ mol^-1

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• Storage Warning: Irritant/Light Sensitive/Store under Argon
• RTECS: QT0525000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36; R36/37/38
• Safety Statements: 26; S26, S36
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• NFPA704:
  

  1

  1

  0
• GHS Hazard statements: H319
• GHS Precautionary statements: P280-P264-P305+P351+P338-P337+P313; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Admin Routes: Intramuscular, Oral
• Half Life: 20-45 min
• Gene Information: human ... CYP1A2(1544)rat ... Chrnb2(54239)

Product Information

• Purity: ≥99%; ≥98%; ≥99.0% (HPLC); ≥99.5%; ≥99.5% (HPLC); 97%; 98%; 99%
• Grade: analytical standard; matrix substance for MALDI-MS; Ph Eur; purum; SAJ special grade
• Salt Data: Free Base
• Packaging: ampule of 1000 mg
• Suitability: meets USP testing specifications; plant cell culture tested; suitable for cell culture; suitable for insect cell culture; suitable for plant cell culture
• Ignition Residue: <0.05%; ≤0.05%
• Impurities: ≤0.2% water
• Cation Traces: Ba: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Loss on Drying: ≤0.2% loss on drying
• Quality Level: PREMIUM
• Feature: standard type water soluble vitamin
• Analyte suitability: oligonucleotides; peptides; proteins
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Empirical Formula (Hill Notation): C6H5NO2

DETAILS

MP Biomedicals - 02194716

Cell Culture Reagent
Purity: 99+%
Crystalline
Free Acid

MP Biomedicals - 02102446

Purity: 99+%
Crystalline
Free Acid

DrugBank - DB00627

• Drug Groups: approved; nutraceutical; investigational
• Description: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has pellagra-curative, vasodilating, and antilipemic properties. [PubChem]
• Indication: For the treatment of type IV and V hyperlipidemia. It is indicated as ajunctive therapy.
• Pharmacology: Niacin and niacinamide are indicated for prevention and treatment of vitamin B3 deficiency states. Vitamin B3 (Niacin) also acts to reduce LDL cholesterol, triglycerides, and HDL cholesterol. The magnitude of individual lipid and lipoprotein responses may be influenced by the severity and type of underlying lipid abnormality. The increase in total HDL is associated with a shift in the distribution of HDL subfractions (as defined by ultra-centrifugation) with an increase in the HDL2:HDL3 ratio and an increase in apolipoprotein A-I content. Vitamin B3 (Niacin) treatment also decreases the serum levels of apolipoprotein B-100 (apo B), the major protein component of the VLDL (very low-density lipoprotein) and LDL fractions, and of lipoprotein-a, a variant form of LDL independently associated with coronary risk.
• Toxicity: Nicotinic acid can cause vasodilation of cutaneous blood vessels resulting in increased blood flow, principally in the face, neck and chest. This produces the niacin- or nicotinic acid-flush. The niacin-flush is thought to be mediated via the prostaglandin prostacyclin. Histamine may also play a role in the niacin-flush. Flushing is the adverse reaction first observed after intake of a large dose of nicotinic acid, and the most bothersome one. LD₅₀ 7000 mg/kg (Rat)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Both nicotinic acid and nicotinamide are efficiently absorbed from the stomach and small intestine.
• Half Life: 20-45 minutes.
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1744

Research Area: Metabolic Disease
Biological Activity:
Niacin(Nicotinic acid) is a water-soluble vitamin belonging to the vitamin B family, which occurs in many animal and plant tissues, with antihyperlipidemic activity. Niacin is converted to its active form niacinamide, which is a component of the coenzymes nicotinamide adenine dinucleotide (NAD) and its phosphate form, NADP. These coenzymes play an important role in tissue respiration and in glycogen, lipid, amino acid, protein, and purine metabolism. [1, 2]

Sigma Aldrich - 72309

Other Notes
Coenzyme and Cofactors, vol 2: Pyridine Nucleotide Coenzymes1,2

Sigma Aldrich - N4126

Biochem/physiol Actions
降低肝脏极低密度脂蛋白和载脂蛋白 B 的产量。
包装
1 kg in poly bottle
5, 100, 500 g in poly bottle

Toronto Research Chemicals - N429250

Nicotinic acid. It is a precursor of the coenzymes NAD and NADP. Widely distributed in nature; appreciable amounts are found in liver , fish, yeast and cereal grains. Dietary deficiency is associated with pellagra. The term “niacin” has also been applied

REFERENCES

• http://www.cancer.gov/drugdictionary/?CdrID=38351
• http://en.wikipedia.org/wiki/Niacin
• Darby, W.J., et al.: Nutr. Rev., 33, 289 (1975)
• Black, A., et al.: Eur. J. Clin. Nutr., 54, 395 (1975)
• Cole, T., et al.: Br. Med. J., 320, 1240 (1975)
• Forshee, R., et al.: J. Nutr., 134, 2733 (1975)