Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H5NO2.ClH |
| Molecular Weight | 159.57 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.OC(=O)C1=NC=CC=C1
InChI
InChIKey=HFAFXVOPGDBAOK-UHFFFAOYSA-N
InChI=1S/C6H5NO2.ClH/c8-6(9)5-3-1-2-4-7-5;/h1-4H,(H,8,9);1H
| Molecular Formula | C6H5NO2 |
| Molecular Weight | 123.1094 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://en.wikipedia.org/wiki/Picolinic_acid
Curator's Comment: description was created based on several sources, including
https://en.wikipedia.org/wiki/Picolinic_acid
Picolinic acid is an organic compound, is a derivative of pyridine with a carboxylic acid substituent at the 2-position. Picolinic acid is a bidentate chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body. Many of its complexes are charge-neutral and thus lipophilic. After its role in absorption was discovered, zinc dipicolinate dietary supplements became popular as they were shown to be an effective means of introducing zinc into the body. Picolinic Acid is an endogenous metabolite of L-tryptophan (TRP) that has been reported to possess a wide range of neuroprotective, immunological, and anti-proliferative effects within the body. However, the salient physiological function of this molecule is yet to be established. The synthesis of picolinic acid as a product of the kynurenine pathway (KP) suggests that, similar to other KP metabolites, picolinic acid may play a role in the pathogenesis of inflammatory disorders within the CNS and possibly other organs.
Approval Year
Doses
| Dose | Population | Adverse events |
|---|---|---|
10 % 2 times / day multiple, topical Studied dose Dose: 10 %, 2 times / day Route: topical Route: multiple Dose: 10 %, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Burning skin... AEs leading to discontinuation/dose reduction: Burning skin (1 pt) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Burning skin | 1 pt Disc. AE |
10 % 2 times / day multiple, topical Studied dose Dose: 10 %, 2 times / day Route: topical Route: multiple Dose: 10 %, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Direct determination of copper in urine using a sol-gel optical sensor coupled to a multicommutated flow system. | 2004-09 |
|
| Synthesis and characterization of a new family of bi-, tri-, tetra-, and pentanuclear ferric complexes. | 2004-08-09 |
|
| Nikkomycin biosynthesis: formation of a 4-electron oxidation product during turnover of NikD with its physiological substrate. | 2004-07-20 |
|
| Type I methionine aminopeptidase from Saccharomyces cerevisiae is a potential target for antifungal drug screening. | 2004-07 |
|
| A new electrochemical system for stereoselective allylic hydroxylation of cholesteryl acetate with dioxygen induced by iron picolinate complexes. | 2004-06 |
|
| Determining the safety of chromium tripicolinate for addition to foods as a nutrient supplement. | 2004-06 |
|
| Induction of Mycobacterium avium growth restriction and inhibition of phagosome-endosome interactions during macrophage activation and apoptosis induction by picolinic acid plus IFNgamma. | 2004-05 |
|
| Absorption of the biomimetic chromium cation triaqua-mu3-oxo-mu-hexapropionatotrichromium(III) in rats. | 2004-05 |
|
| Relation between electrophoretic behavior and molecular shapes of aromatic anions. | 2004-04 |
|
| Picolinic acid- or desferrioxamine-inducible autocrine activation of macrophages engineered to produce IFNgamma: an approach for gene therapy. | 2004-03 |
|
| Hypoxia selectively inhibits monocyte chemoattractant protein-1 production by macrophages. | 2004-02-01 |
|
| Recent advances in the nutritional biochemistry of trivalent chromium. | 2004-02 |
|
| Alpha-picolinic acid, a fungal toxin and mammal apoptosis-inducing agent, elicits hypersensitive-like response and enhances disease resistance in rice. | 2004-02 |
|
| Dietary L-carnitine increases plasma leptin concentrations of gestating sows fed one meal per day. | 2004-01 |
|
| Recent developments in the biochemistry of chromium(III). | 2004 |
|
| Chromium picolinate supplementation improves insulin sensitivity in Goto-Kakizaki diabetic rats. | 2004 |
|
| Kinetics and mechanistic studies of anticarcinogenic bisperoxovanadium(V) compounds: ligand substitution reactions at physiological pH and relevance to DNA interactions. | 2003-12-01 |
|
| Reactivity of 2-pyridinecarboxylic esters with cadmium(II) halides: study of (113)Cd NMR solid state spectra and crystal structures of hexacoordinated complexes [CdI(2)(C(5)H(4)NCOOMe)(2)] and [CdI(2)(C(5)H(4)NCOOPr(n))(2)]. | 2003-11-17 |
|
| Turning off phototriggered linkage isomerizations in ruthenium dimethyl sulfoxide complexes. | 2003-11-17 |
|
| Effect of chromium picolinate on histopathological alterations in STZ and neonatal STZ diabetic rats. | 2003-11-05 |
|
| Harnessing chromium in the fight against diabetes. | 2003-11-01 |
|
| Synthesis of alpha-amino acids via asymmetric phase transfer-catalyzed alkylation of achiral nickel(II) complexes of glycine-derived Schiff bases. | 2003-10-22 |
|
| [Chromium (III)-ion enhances the utilization of glucose in type-2 diabetes mellitus]. | 2003-10-19 |
|
| A new family of insulin-mimetic vanadium complexes derived from 5-carboalkoxypicolinates. | 2003-10-17 |
|
| Study of the mechanism of the cytostatic effect of picolinic acid on proliferating Tetrahymena pyriformis cells. | 2003-10-15 |
|
| Regulation of geometry around the ruthenium center of bis(2-pyridinecarboxylato) complexes by the nitrosyl moiety: syntheses, structures, and theoretical studies. | 2003-10-06 |
|
| Synthesis of a pyridinium bis[citrato(2-)]oxochromate(V) complex and its ligand-exchange reactions. | 2003-10-06 |
|
| Diuretics vs. ACE inhibitors. | 2003-10 |
|
| Conformational changes combined with charge-transfer interactions are essential for reduction in catalysis by p-hydroxybenzoate hydroxylase. | 2003-09-30 |
|
| Reactions of the dirhenium(II) complex Re2Cl4(mu-dppm)2 with pyridinecarboxylic acids. Examples of bidentate O,O versus N,O coordination and tridentate O,N,O coordination and structural isomers that contain the pyridine-2,6-dicarboxylate ligand. | 2003-09-22 |
|
| Metabolites of the kynurenine pathway of tryptophan metabolism in the cerebrospinal fluid of Malawian children with malaria. | 2003-09-15 |
|
| Effects of treatment with chromium picolinate on peripheral amino acid availability and brain monoamine function in the rat. | 2003-09 |
|
| Cellular antiendotoxin activities of lung surfactant protein C in lipid vesicles. | 2003-08-01 |
|
| Membrane differential filtration is safe and effective for the long-term treatment of Refsum syndrome--an update of treatment modalities and pathophysiological cognition. | 2003-08 |
|
| Ruthenium(III) triazacyclononane dithiocarbamate, pyridinecarboxylate, or aminocarboxylate complexes as scavengers of nitric oxide. | 2003-06-30 |
|
| Discovery and structural modification of inhibitors of methionine aminopeptidases from Escherichia coli and Saccharomyces cerevisiae. | 2003-06-19 |
|
| Antioxidant properties of chromium and zinc: in vivo effects on digestibility, lipid peroxidation, antioxidant vitamins, and some minerals under a low ambient temperature. | 2003-05 |
|
| Antifungal activity of macrophages engineered to produce IFNgamma: inducibility by picolinic acid. | 2003-05 |
|
| Chromium compounds: cytotoxicity and carcinogenesis. | 2003-04-15 |
|
| Formation, preservation, and cleavage of the disulfide bond by vanadium. | 2003-04-14 |
|
| Chromium picolinate for reducing body weight: meta-analysis of randomized trials. | 2003-04 |
|
| Synthesis of 6-formyl-pyridine-2-carboxylate derivatives and their telomerase inhibitory activities. | 2003-02-24 |
|
| Tissue and subcellular distribution of chromium picolinate with time after entering the bloodstream. | 2003-02-01 |
|
| Dipicolinic acid prevents the copper-dependent oxidation of low density lipoprotein. | 2003-02 |
|
| ECNI GC-MS analysis of picolinic and quinolinic acids and their amides in human plasma, CSF, and brain tissue. | 2003 |
|
| Macrophage activating properties of the tryptophan catabolite picolinic acid. | 2003 |
|
| [Chromium as an essential element]. | 2003 |
|
| The potential value and toxicity of chromium picolinate as a nutritional supplement, weight loss agent and muscle development agent. | 2003 |
|
| Antagonistic effect of picolinic acid and interferon-gamma on macrophage inflammatory protein-1alpha/beta production. | 2002-11 |
|
| Blood glucose lowering and toxicological effects of zinc (II) complexes with maltol, threonine, and picolinic acid. | 2002 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Apr 01 17:40:38 GMT 2025
by
admin
on
Tue Apr 01 17:40:38 GMT 2025
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| Record UNII |
8HE8GCH2RD
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| Record Status |
Validated (UNII)
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| Record Version |
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PARENT -> SALT/SOLVATE |
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