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Nicotinamide | C6H6N2O - Pubchem 9/29/2020 Nicotinamide | C6H6N2O - PubChem COMPOUND SUMMARY Nicotinamide PubChem CID: 936 Structure: 2D 3D Crystal Find Similar Structures Chemical Safety: Irritant Laboratory Chemical Safety Summary (LCSS) Datasheet Molecular Formula: C6H6N2O nicotinamide niacinamide 98-92-0 Synonyms: 3-Pyridinecarboxamide pyridine-3-carboxamide More... Molecular Weight: 122.12 g/mol Modify: Create: Dates: 2020-09-26 2004-09-16 Niacinamide is the active form of vitamin B3 and a component of the coenzyme nicotinamide adenine dinucleotide (NAD). Niacinamide acts as a chemo- and radio-sensitizing agent by enhancing tumor blood flow, thereby reducing tumor hypoxia. This agent also inhibits poly(ADP-ribose) polymerases, enzymes involved in the rejoining of DNA strand breaks induced by radiation or chemotherapy. NCI Thesaurus (NCIt) Nicotinamide is a pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group. It has a role as an EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor, a metabolite, a cofactor, an antioxidant, a neuroprotective agent, an EC 3.5.1.98 (histone deacetylase) inhibitor, an anti-inflammatory agent, a Sir2 inhibitor, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a pyridinecarboxamide and a pyridine alkaloid. It derives from a nicotinic acid. ChEBI Nicotinamide is a white powder. (NTP, 1992) CAMEO Chemicals https://pubchem.ncbi.nlm.nih.gov/compound/nicotinamide 1/67 9/29/2020 Nicotinamide | C6H6N2O - PubChem 1 Structures 1.1 2D Structure Chemical Structure Depiction PubChem 1.2 3D Conformer PubChem 1.3 Crystal Structures Showing 1 of 6 View More CCDC Number 131756 Crystal Structure Data DOI:10.5517/cc4f36v Crystal Structure Depiction Associated Article DOI:10.1107/S0108768198007848 The Cambridge Structural Database https://pubchem.ncbi.nlm.nih.gov/compound/nicotinamide 2/67 9/29/2020 Nicotinamide | C6H6N2O - PubChem 2 Names and Identifiers 2.1 Computed Descriptors 2.1.1 IUPAC Name pyridine-3-carboxamide Computed by LexiChem 2.6.6 (PubChem release 2019.06.18) PubChem 2.1.2 InChI InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9) Computed by InChI 1.0.5 (PubChem release 2019.06.18) PubChem 2.1.3 InChI Key DFPAKSUCGFBDDF-UHFFFAOYSA-N Computed by InChI 1.0.5 (PubChem release 2019.06.18) PubChem 2.1.4 Canonical SMILES C1=CC(=CN=C1)C(=O)N Computed by OEChem 2.1.5 (PubChem release 2019.06.18) PubChem 2.2 Molecular Formula C6H6N2O ILO International Chemical Safety Cards (ICSC); Wikipedia; PubChem 2.3 Other Identifiers 2.3.1 CAS 98-92-0 CAMEO Chemicals; ChemIDplus; DrugBank; DTP/NCI; EPA Chemicals under the TSCA; EPA DSSTox; European Chemicals Agency (ECHA); Hazardous Substances Data Bank (HSDB); Human Metabolome Database (HMDB); ILO I 11032-50-1 European Chemicals Agency (ECHA) 2.3.2 Deprecated CAS 123574-63-0, 37321-14-5, 78731-47-2 ChemIDplus 2.3.3 European Community (EC) Number 202-713-4 European Chemicals Agency (ECHA) 234-265-0 European Chemicals Agency (ECHA) 2.3.4 ICSC Number 1703 ILO International Chemical Safety Cards (ICSC) 2.3.5 NSC Number 759115 https://pubchem.ncbi.nlm.nih.gov/compound/nicotinamide 3/67 9/29/2020 Nicotinamide | C6H6N2O - PubChem DTP/NCI 27452 DTP/NCI 13128 DTP/NCI 2.3.6 RTECS Number QS3675000 The National Institute for Occupational Safety and Health (NIOSH) 2.3.7 UNII 25X51I8RD4 FDA/SPL Indexing Data 2.3.8 DEA Code Number 1405 Drug Enforcement Administration (DEA) 2.3.9 DSSTox Substance ID DTXSID2020929 EPA DSSTox 2.3.10 Wikipedia Nicotinamide Wikipedia 2.4 Synonyms 2.4.1 MeSH Entry Terms 3 Pyridinecarboxamide Vitamin PP 3-Pyridinecarboxamide B 3, Vitamin B3, Vitamin Enduramide Jenapharm,ph Nicotinsäureamid Niacinamide Nicobion Nicotinamide Nicotinsäureamid Jenapharmph Papulex Vitamin B 3 Vitamin B3 MeSH 2.4.2 Depositor-Supplied Synonyms 3418-EP2311829A1 11783-EP2316828A1 F2173-0513 C00153 AB00373895-13 Niacinamide;Nicotinic acid amide;Vitamin B3; Vitamin PP cifications D00036 AB00373895_15 Nicotinamide, British PharmacopoeiaPh (BP) Reference Standard J10422 AB00373895_16 A186B02E-6C70-4E54-9739-79398D439AAA Nicotinamide (Niacinamide), analytical standard Nicotinamide, Vetec(TM) reagent grade, >=98% Nicotinamide, European PharmacopoeiaPh (EP) Reference Standard W-3583 A845925 Niacinamide, United States PharmacopeiaPh (USP) Reference Standard 11783-EP2269610A2 AC-907/25014114 Niacinamide, PharmaceuticalPh Secondary Standard; Certified Reference Material 11783-EP2289510A1 Q192423 Nicotinamide, BioReagent, suitable for cell culture, suitable for insect cell culture 11783-EP2316457A1 Q-201470 Nicotinamide (Vitamin B3) solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material 11783-EP2316458A1 SR-01000721872-3 11783-EP2316825A1 SR-01000721872-4 11783-EP2316826A1 SR-01000721872-5 11783-EP2316827A1 Z33546463 PubChem https://pubchem.ncbi.nlm.nih.gov/compound/nicotinamide 4/67 9/29/2020 Nicotinamide | C6H6N2O - PubChem https://pubchem.ncbi.nlm.nih.gov/compound/nicotinamide 5/67 9/29/2020 Nicotinamide | C6H6N2O - PubChem 3 Chemical and PhysicalPh Properties 3.1 Computed Properties Property Name Property Value Reference Molecular Weight 122.12 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18) XLogP3 -0.4 Computed by XLogP3 3.0 (PubChem release 2019.06.18) Hydrogen Bond Donor Count 1 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Hydrogen Bond Acceptor Count 2 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Rotatable Bond Count 1 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Exact Mass 122.048013 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18) Monoisotopic Mass 122.048013 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18) Topological Polar Surface Area 56 Ų Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Heavy Atom Count 9 Computed by PubChem Formal Charge 0 Computed by PubChem Complexity 114 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Isotope Atom Count 0 Computed by PubChem Defined Atom Stereocenter Count 0 Computed by PubChem Undefined Atom Stereocenter Count 0 Computed by PubChem Defined Bond Stereocenter Count 0 Computed by PubChem Undefined Bond Stereocenter Count 0 Computed by PubChem Covalently-Bonded Unit Count 1 Computed by PubChem Compound Is Canonicalized Yes Computed by PubChem (release 2019.01.04) PubChem 3.2 Experimental Properties 3.2.1 PhysicalPh Description Nicotinamide is a white powder. (NTP, 1992) National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina. CAMEO Chemicals DryPowder; OtherSolid EPA Chemicals under the TSCA Solid FooDB; Human Metabolome Database (HMDB) WHITE CRYSTALLINE POWDER. ILO International Chemical Safety Cards (ICSC) 3.2.2 Color/Form White, powder, needles from benzene Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics.Ph 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-474 Hazardous Substances Data Bank (HSDB) Colorless crystalline solid Van Arnum SD; Niacin, Nicotinamide, and Nicotinic Acid. Kirk-Othmer Encyclopedia of Chemical Technology. (1999-2018). New York, NY: John Wiley & Sons. Online Posting Date: 4 Dec 2000 Hazardous Substances Data Bank (HSDB) White, crystalline powder Chase et al; Remington's PharmaceuticalPh Sciences 14th ed. Mack Publ Co. Easton, PA p. 1039 (1970) Hazardous Substances Data Bank (HSDB) Colorless needles Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 966 Hazardous Substances Data Bank (HSDB) 3.2.3 Odor Odorless Osol, A. and J.E. Hoover, et al. (eds.). Remington's PharmaceuticalPh Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 950 https://pubchem.ncbi.nlm.nih.gov/compound/nicotinamide 6/67 9/29/2020 Nicotinamide | C6H6N2O - PubChem Hazardous Substances Data Bank (HSDB) 3.2.4 Taste Bitter taste Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 966 Hazardous Substances Data Bank (HSDB) 3.2.5 Boiling Point 302 to 320 °F at 760 mm Hg (NTP, 1992) National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina. CAMEO Chemicals 157 °C at 5.00E-04 mm Hg PhysPropPh DrugBank 3.2.6 Melting Point 264 to 268 °F (NTP, 1992) National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina. CAMEO Chemicals 130 °C PhysPropPh DrugBank 130.0 °C EPA DSSTox Mp 129-130 ° DFC FooDB 128.8 °C Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics.Ph 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-474 Hazardous Substances Data Bank (HSDB) 130°C Human Metabolome Database (HMDB) 127-131 °C ILO International Chemical Safety Cards (ICSC) 3.2.7 Flash Point 182 °C ILO International Chemical Safety Cards (ICSC) 3.2.8 Solubility greater than or equal to 100 mg/mL at 70° F (NTP, 1992) National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina. CAMEO Chemicals 500000 mg/L (at 25 °C) MERCK INDEX (1996) DrugBank 4.09 M MERCK INDEX (1996) EPA DSSTox 500 mg/mL at 25 °C MERCK INDEX (1996) https://pubchem.ncbi.nlm.nih.gov/compound/nicotinamide 7/67 9/29/2020 Nicotinamide | C6H6N2O - PubChem FooDB; Human Metabolome Database (HMDB) In water, 5X10+5 mg/L at 25 °C Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1114 Hazardous Substances Data Bank (HSDB) Very soluble in water; 1 g is soluble in 1 mL water Van Arnum SD; Niacin, Nicotinamide, and Nicotinic Acid.
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