thionicotinamide
amino-3-pyridylmethane-1-thione
Identification
| Name | thionicotinamide |
| IUPAC | pyridine-3-carbothioamide |
| CAS Number | 4621-66-3 |
| EINECS | 225-036-6 |
| FDA UNII | 6A0HXX0753 |
| Molecular Formula | C6 H6 N2 S |
| Molecular Weight | 138.19282000 |
| MDL Number | MFCD00006399 |
| Nikkaji Number | J124.097H |
| Beilstein | 0109593 |
| XlogP3 | 0.70 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 278.87 °C. @ 760.00 mm Hg (est) |
| Vapor Pressure | 0.004000 mmHg @ 25.00 °C. (est) |
| Flash Point | 252.00 °F. TCC ( 122.50 °C. ) (est) |
| logP (o/w) | 0.670 |
| Soluble in | water, 2.324e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD25 105 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | pharmaceuticals / chemical synthisis |
| Recommendation for thionicotinamide usage levels up to | not for fragrance use. |
| Recommendation for thionicotinamide flavor usage levels up to | not for flavor use. |
Endeavour Specialty Chemicals Ltd
Expertise in high impact aroma chemicals
Endeavour Speciality Chemicals offers high-impact aroma chemicals, at small to medium scale.
Robinson Brothers Limited
Providing Excellence in Chemistry
Award-winning UK chemical manufacturer of chemical intermediates and high-impact aroma chemicals.
Potential Uses
Natural Occurrence
Synonyms
amino-3-pyridylmethane-1-thione
nicotinamide, thio-
nicotinothioamide
pyridine-3-carbothioamide
pyridine-3-carbothioic acid amide
pyridine-3-thiocarboxamide
3-
pyridinecarbothioamide
3-
pyridinethiocarboxamide
3-
pyridylthiocarboxamide
thio-3-pyridinecarboxamide
3-
thioamidopyridine
3-
thiocarbamoylpyridine
PubMed:
Suppression of Cytosolic NADPH Pool by Thionicotinamide Increases Oxidative Stress and Synergizes with Chemotherapy.
PubMed:
Boronic acid-containing CXCR1/2 antagonists: Optimization of metabolic stability, in vivo evaluation, and a proposed receptor binding model.
PubMed:
Electrochemistry, surface plasmon resonance, and quartz crystal microbalance: an associative study on cytochrome c adsorption on pyridine tail-group monolayers on gold.
PubMed:
Spectrophotometric method for the assay of steroid 5α-reductase activity of rat liver and prostate microsomes.
PubMed:
[Development of super high-sensitive measurement of proteins by combination of ELISA and enzyme cycling methods].
PubMed:
Enhanced degradation of dihydrofolate reductase through inhibition of NAD kinase by nicotinamide analogs.
PubMed:
Thermodynamic, kinetic, surface pKa, and structural aspects of self-assembled monolayers of thio compounds on gold.
PubMed:
Ascorbic acid reduction of compound I of mammalian catalases proceeds via specific binding to the NADPH binding pocket.
PubMed:
Structural and kinetic isotope effect studies of nicotinamidase (Pnc1) from Saccharomyces cerevisiae.
PubMed:
Elucidating the structure-activity relationships of the vasorelaxation and antioxidation properties of thionicotinic acid derivatives.
PubMed:
Novel bUT-B2 urea transporter isoform is constitutively activated.
PubMed:
Transhydrogenation reactions catalyzed by mitochondrial NADH-ubiquinone oxidoreductase (Complex I).
PubMed:
Determinants of substrate specificity for saccharopine dehydrogenase from Saccharomyces cerevisiae.
PubMed:
Molecular cloning and characterization of a novel lactate dehydrogenase gene from Clonorchis sinensis.
PubMed:
Electron transfer kinetics and mechanistic study of the thionicotinamide coordinated to the pentacyanoferrate(III)/(II) complexes: a model system for the in vitro activation of thioamides anti-tuberculosis drugs.
PubMed:
Kinetic study of the enzymatic cycling reaction conducted with 3alpha-hydroxysteroid dehydrogenase in the presence of excessive thio-NAD(+) and NADH.
PubMed:
Urea transport in MDCK cells that are stably transfected with UT-A1.
PubMed:
Interactions between transhydrogenase and thio-nicotinamide Analogues of NAD(H) and NADP(H) underline the importance of nucleotide conformational changes in coupling to proton translocation.
PubMed:
EPYLRFamide-mediated reduction of acetylcholine-induced inward currents in Helix lucorum-identified neurones: role of NAADP-dependent and IP3-dependent Ca2+ release from internal stores, calmodulin and Ca2+/calmodulin-dependent protein kinase II.
PubMed:
Tartrate dehydrogenase catalyzes the stepwise oxidative decarboxylation of D-malate with both NAD and thio-NAD.
PubMed:
Structures of D-glyceraldehyde-3-phosphate dehydrogenase complexed with coenzyme analogues.
PubMed:
The determination of ketone bodies: preanalytical, analytical and physiological considerations.
PubMed:
Mycobacterium tuberculosis lipoamide dehydrogenase is encoded by Rv0462 and not by the lpdA or lpdB genes.
PubMed:
Interaction of NADP(H) with oxidized and reduced P450 reductase during catalysis. Studies with nucleotide analogues.
PubMed:
UT-A urea transporter protein expressed in liver: upregulation by uremia.
PubMed:
InsP3, but not novel Ca2+ releasers, contributes to agonist-initiated contraction in rabbit airway smooth muscle.
PubMed:
Thio-NADP is not an antagonist of NAADP.
PubMed:
Azotobacter vinelandii glucose 6-phosphate dehydrogenase properties of NAD- and NADP-linked reactions.
PubMed:
Nicotinate-adenine dinucleotide phosphate-induced Ca(2+)-release does not behave as a Ca(2+)-induced Ca(2+)-release system.
PubMed:
Palmitoyl-CoA potentiates the Ca2+ release elicited by cyclic ADP-ribose.
PubMed:
Purification and characterization of Azotobacter vinelandii glucose-6-phosphate dehydrogenase: dual coenzyme specificity.
PubMed:
Nicotinate adenine dinucleotide phosphate (NAADP) triggers a specific calcium release system in sea urchin eggs.
PubMed:
The urease inhibitor acetohydroxamic acid is transported by the urea pathway in rat terminal IMCD.
PubMed:
Crystal structures of chicken liver dihydrofolate reductase: binary thioNADP+ and ternary thioNADP+.biopterin complexes.
PubMed:
Selectivity in the binding of NAD(P)+ analogues to NAD- and NADP-dependent pig heart isocitrate dehydrogenases. A nuclear magnetic resonance study.
PubMed:
The effect of methimazole on thioamide bioactivation and toxicity.
PubMed:
Multiple isotope effects with alternative dinucleotide substrates as a probe of the malic enzyme reaction.
PubMed:
Analogues of NADP(+) as inhibitors and coenzymes for NADP(+) malic enzyme from maize leaves.
PubMed:
The S-oxidation of thioamides by rat liver microsomes.
PubMed:
Kinetic mechanism of the endogenous lactate dehydrogenase activity of duck epsilon-crystallin.
PubMed:
The metabolism of thionicotinamide in the rat.
PubMed:
Clinical usefulness of malate dehydrogenase and its mitochondrial isoenzyme in comparison with aspartate aminotransferase and its mitochondrial isoenzyme in sera of patients with liver disease.
PubMed:
In vitro evaluation of nicotinamide riboside analogs against Haemophilus influenzae.
PubMed:
Distance between the substrate and regulatory reduced coenzyme binding sites of bovine liver glutamate dehydrogenase by resonance energy transfer.
PubMed:
Regulation of coenzyme utilization by mitochondrial NAD(P)-dependent malic enzyme.
PubMed:
Assay of creatine kinase in microtiter plates using thio-NAD to allow monitoring at 405 nM.
PubMed:
ALT reagent with thionicotinamide adenine dinucleotide.
PubMed:
Isolation, characterization, and biological activity of ferredoxin-NAD+ reductase from the methane oxidizer Methylosinus trichosporium OB3b.
PubMed:
Substrate specificity of nicotinamide methyltransferase isolated from porcine liver.
PubMed:
The mechanism of peroxidase-mediated cytotoxicity. II. Role of the heme moiety.
PubMed:
Inhibitory effects of niacin and its analogues on induction of ornithine decarboxylase activity by diethylnitrosamine in rat liver.
PubMed:
Distances among coenzyme and metal sites of NADP+-dependent isocitrate dehydrogenase using resonance energy transfer.
PubMed:
Interactions of nicotinamide-adenine dinucleotide phosphate analogues and fragments with pigeon liver malic enzyme. Synergistic effect between the nicotinamide and adenine moieties.
PubMed:
[Simultaneous assay of serum lactate dehydrogenase activities depending on NAD (N) and thio-NAD (T), and the clinical significance of N/T values].
PubMed:
A one-step enzymatic assay for the measurement of 17 beta-hydroxy- and 17-oxo-steroid profiles in biological samples.
PubMed:
Simultaneous determination of multiple forms of lactate dehydrogenase based on NAD and thio-NAD.
PubMed:
Studies on NADH(NADPH)-cytochrome c reductase (FMN-containing) from yeast: steady-state kinetic properties of the flavoenzyme from top-fermenting ale yeast.
PubMed:
Protonation mechanism and location of rate-determining steps for the Ascaris suum nicotinamide adenine dinucleotide-malic enzyme reaction from isotope effects and pH studies.
PubMed:
Cytochemical localization of nicotinamide adenine dinucleotide phosphatase (NADPase) in bovine Leydig cells.
PubMed:
The redox state of activated bleomycin.
PubMed:
Kinetic and spectroscopic studies of transhydrogenase activity and nucleotide site of lipoamide dehydrogenase.
PubMed:
Variation of transition-state structure as a function of the nucleotide in reactions catalyzed by dehydrogenases. 2. Formate dehydrogenase.
PubMed:
Synthesis and properties of (4-13C)NAD+. Observation of its binding to yeast alcohol dehydrogenase by 13C-NMR spectroscopy.
PubMed:
Bovine lens aldehyde dehydrogenase. Kinetics and mechanism.
PubMed:
Adenosine diphosphoribose transfer reactions catalyzed by Bungarus fasciatus venom NAD glycohydrolase.
PubMed:
Use of transferred nuclear Overhauser effect measurements to compare binding of coenzyme analogues to dihydrofolate reductase.
PubMed:
Oxidation of the 17-aldol (20 beta hydroxy-21-aldehyde) intermediate of corticosteroid metabolism to hydroxy acids by homogeneous human liver aldehyde dehydrogenases.
PubMed:
Regulation of coenzyme utilization by bovine liver glutamate dehydrogenase: investigations using thionicotinamide analogues of NAD and NADP in a dual wavelength assay.
PubMed:
Negative cooperativity between folinic acid and coenzyme in their binding to Lactobacillus casei dihydrofolate reductase.
PubMed:
Effects of coenzyme binding on histidine residues of Lactobacillus casei dihydrofolate reductase.
PubMed:
Dual nucleotide specificity of bovine glutamate dehydrogenase. The role of negative co-operativity.
PubMed:
Energy-linked mitochondrial transhydrogenation from NADPH to NADP analogs.
PubMed:
Effect of pH on the mitochondrial energy-linked and non-energy-linked transhydrogenation reactions.
PubMed:
Energy-linked transhydrogenation from NADPH to [14C]NADP.
PubMed:
Phosphorus-31 nuclear magnetic resonance studies of the binding of oxidized coenzymes to Lactobacillus casei dihydrofolate reductase.
PubMed:
Proton nuclear magnetic resonance saturation transfer studies of coenzyme binding to Lactobacillus casei dihydrofolate reductase.
PubMed:
Binding of coenzyme analogues to Lactobacillus casei dihydrofolate reductase: binary and ternary complexes.
PubMed:
Self-inactivation of an erythrocyte NAD glycohydrolase.
PubMed:
Kinetic studies of multifunctional reactions catalysed by lipoamide dehydrogenase.
PubMed:
Simultaneous analysis of NAD- and NADP-linked activities of dual nucleotide-specific dehydrogenases. Application to Leuconostoc mesenteroides glucose-6-phosphate dehydrogenase.
PubMed:
Mercury complexes of thionicotinamide adenine dinucleotide.
PubMed:
Fluorescence properties of reduced thionicotinamide--adenine dinucleotide and of its complex with octopine dehydrogenase.
PubMed:
Circular dichroic properties and conformation of thionicotinamide dinucleotides bound to horse-liver alcohol dehydrogenase.
PubMed:
Circular dichroic properties and conformation of thionicotinamide dinucleotides.
PubMed:
Further studies on the properties of glucose 6-phosphate dehydrogenase from the coccidium Eimeria stiedai (Protozoa).
PubMed:
Fluorescence energy transfer between heterologous active sites of affinity-labeled aspartokinase of Escherichia coli.
PubMed:
Application of nicotin amide-adenine dinucleotide analogs for clinical enzymology: alcohol dehydrogenase activity in liver injury.
PubMed:
Application of nicotinamide-adenine dinucleotide analogs for clinical enzymology: a spectrophotometric method for clinical analysis of lactate dehydrogenase patterns with the use of a nicotinamide-adenine dinucleotide analog.
PubMed:
Demonstration and possible function of NADH:NAD+ transhydrogenase from ascaris muscle mitochondria.
PubMed:
Human liver akdehyde dehydrogenase. Kinetics of aldehyde oxidation.
PubMed:
Treatment of psoriasis with 6-aminonicotinamide.
PubMed:
Separation behaviour of nicotinamide and thionicotinamide derivatives on Dowex 1-X8.
PubMed:
Covalent binding of 3-pyridinealdehyde nicotinamide adenine dinucleotide and substrate to glyceraldehyde 3-phosphate dehydrogenase.
PubMed:
3Alpha-hydroxysteroid dehydrogenase from Pseudomonas testosteroni: kinetic properties with NAD and its thionicotinamide analogue.
PubMed:
Thionicotinamide-NADP, a nucleotide analog interfering with ferredoxin-NADP reductase-ferredoxin interaction.
PubMed:
Carbohydrate metabolism during morphogenesis of Coprinus lagopus (sensu Buller).
PubMed:
[Pharmacologic and biochemical properties of thionicotinamide (thio-NA) and its NAD (P)-analogues].
PubMed:
CO(2) Metabolism in Corn Roots. II. Intracellular Distribution of Enzymes.
PubMed:
Nicotinamide-adenine dinucleotide pyrophosphatase in the growing and aging mosquito.
PubMed:
Comparative aspects of some bacterial dehydrogenases and transhydrogenases.
PubMed:
THE THIONICOTINAMIDE ANALOGS OF DPN AND TPN. II. ENZYME STUDIES.
PubMed:
THE THIONICOTINAMIDE ANALOGS OF DPN AND TPN. I. PREPARATION AND ANALYSIS.
PubMed:
Coenzyme analogs. II. Photochemical inactivation of reducd thionicotinamide adenine dinucleotide.
PubMed:
Coenzyme analogs. I. Preparation and properties of thionicotinamide methiodide.