Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H5NO2 |
| Molecular Weight | 123.1094 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=NC=CC=C1
InChI
InChIKey=SIOXPEMLGUPBBT-UHFFFAOYSA-N
InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
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 (unknown) Studied dose Dose: 10 %, 2 times / day Route: topical Route: multiple Dose: 10 %, 2 times / day Sources: |
unhealthy n = 20 Health Status: unhealthy Condition: acne vulgaris Sex: M+F Food Status: UNKNOWN Population Size: 20 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 (unknown) Studied dose Dose: 10 %, 2 times / day Route: topical Route: multiple Dose: 10 %, 2 times / day Sources: |
unhealthy n = 20 Health Status: unhealthy Condition: acne vulgaris Sex: M+F Food Status: UNKNOWN Population Size: 20 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Regulation of prostaglandin synthesis and cell adhesion by a tryptophan catabolizing enzyme. | 2001 |
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| Effect of chromium picolinate and chromium propionate on glucose and insulin kinetics of growing barrows and on growth and carcass traits of growing-finishing barrows. | 2001 Aug |
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| Enzyme activities involved in tryptophan metabolism along the kynurenine pathway in rabbits. | 2001 Aug 15 |
|
| [Bimodal physiological effect of picolinic acid derivatives is determined by the zwitterion structure characteristics]. | 2001 Mar-Apr |
|
| Seizure activity and unresponsiveness after hydroxycut ingestion. | 2001 May |
|
| Methyloxorhenium(V) complexes with two bidentate ligands: syntheses and reactivity studies. | 2002 Dec 30 |
|
| Molecular characterization of NikD, a new flavoenzyme important in the biosynthesis of nikkomycin antibiotics. | 2002 Dec 31 |
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| Effect of chromium tripicolinate supplementation on porcine immune response during the postweaning period. | 2002 Feb |
|
| In vivo distribution of chromium from chromium picolinate in rats and implications for the safety of the dietary supplement. | 2002 Feb |
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| Concurrent quantification of quinolinic, picolinic, and nicotinic acids using electron-capture negative-ion gas chromatography-mass spectrometry. | 2002 Feb 1 |
|
| Structure-dependent metallokinetics of antidiabetic vanadyl-picolinate complexes in rats: studies on solution structure, insulinomimetic activity, and metallokinetics. | 2002 Jul 25 |
|
| The clinical significance of cerebrospinal fluid levels of kynurenine pathway metabolites and lactate in severe malaria. | 2002 Mar 1 |
|
| Determination of bopindolol in pharmaceuticals by capillary isotachophoresis. | 2002 May 15 |
|
| Cytotoxicity and oxidative mechanisms of different forms of chromium. | 2002 Oct 30 |
|
| Self-assembly of polymer and sheet structures in palladium(II) complexes containing carboxylic acid substituents. | 2002 Oct 7 |
|
| Drug targeting to the brain: transfer of picolinic acid along the olfactory pathways. | 2002 Sep |
|
| Assessment of chromium tripicolinate supplementation and dietary protein level on growth, carcass, and blood criteria in growing pigs. | 2002 Sep |
|
| 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 compounds: cytotoxicity and carcinogenesis. | 2003 Apr 15 |
|
| Effectiveness of chromium in atypical depression: a placebo-controlled trial. | 2003 Feb 1 |
|
| Cationic sigma-phenylplatinum(II) complexes with carboxylic acid functionality: pK(a) determinations and x-ray structures. | 2003 Feb 24 |
|
| The preparation of (S)-aspartate semi-aldehyde appropriate for use in biochemical studies. | 2003 Jan 20 |
|
| Study of the mechanism of the cytostatic effect of picolinic acid on proliferating Tetrahymena pyriformis cells. | 2003 Jul-Aug |
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| Effect of chromium picolinate on histopathological alterations in STZ and neonatal STZ diabetic rats. | 2003 Jul-Sep |
|
| Antioxidant properties of chromium and zinc: in vivo effects on digestibility, lipid peroxidation, antioxidant vitamins, and some minerals under a low ambient temperature. | 2003 May |
|
| 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 Nov 17 |
|
| Turning off phototriggered linkage isomerizations in ruthenium dimethyl sulfoxide complexes. | 2003 Nov 17 |
|
| A new family of insulin-mimetic vanadium complexes derived from 5-carboalkoxypicolinates. | 2003 Oct 17 |
|
| Synthesis of alpha-amino acids via asymmetric phase transfer-catalyzed alkylation of achiral nickel(II) complexes of glycine-derived Schiff bases. | 2003 Oct 22 |
|
| Effects of treatment with chromium picolinate on peripheral amino acid availability and brain monoamine function in the rat. | 2003 Sep |
|
| Chromium picolinate supplementation improves insulin sensitivity in Goto-Kakizaki diabetic rats. | 2004 |
|
| Dietary L-carnitine increases plasma leptin concentrations of gestating sows fed one meal per day. | 2004 Jan |
|
| Type I methionine aminopeptidase from Saccharomyces cerevisiae is a potential target for antifungal drug screening. | 2004 Jul |
|
| A new electrochemical system for stereoselective allylic hydroxylation of cholesteryl acetate with dioxygen induced by iron picolinate complexes. | 2004 Jun |
|
| Absorption of the biomimetic chromium cation triaqua-mu3-oxo-mu-hexapropionatotrichromium(III) in rats. | 2004 May |
Patents
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171
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m8785
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SUB35118
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QZV2W997JQ
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DTXSID7031903
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C030614
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1018
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28747
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33684
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PICOLINIC ACID
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98-98-6
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202-719-7
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100000128279
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
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