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2-methyl pyridine

Chemical Structure

General Material Information

Preferred name 2-methyl pyridine
Trivial Name 2-Methylpyridine
Short Description pyridine, 2-methyl-
Formula C6 H7 N
CAS Number 109-06-8
Flavis Number 14.134
ECHA Number 203-643-7
FDA UNII 3716Q16Q6A
Nikkaji Number J5.087C
Beilstein Number 0104581
MDL MFCD00006332
COE Number 11415
Bio Activity Summary External link
NMR Predictor External link
Synonyms
  • alpha- methyl pyridine
  • o- methyl pyridine
  • ortho- methyl pyridine
  • 2-methylazine
  • 2-methylpyridine
  • alpha- methylpyridine
  • o- methylpyridine
  • ortho- methylpyridine
  • 2-picoline
  • alpha- picoline
  • o- picoline
  • ortho- picoline
  • pyridine, 2-methyl-
  • 2-Picoline
  • 2-Methylpyridine
  • α-Picoline
  • α-Methylpyridine
  • o-Picoline
  • o-Methylpyridine
  • NSC 3409

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

2-methylpyridine
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:109-06-8
Pubchem (cid):7975
Pubchem (sid):134973512
Flavornet:109-06-8
Publications by US Patents
3,931,166 - Certain 2,5-dimethyl-3-thiopyrazines
4,005,227 - Flavoring agent
Publications by PubMed
Structure-Activity Relationship of 3,5-Diaryl-2-aminopyridine ALK2 Inhibitors Reveals Unaltered Binding Affinity for Fibrodysplasia Ossificans Progressiva Causing Mutants.
Syntheses, structures and photocatalytic properties of five new praseodymium-antimony oxochlorides: from discrete clusters to 3D inorganic-organic hybrid racemic compounds.
catena-Poly[2-methyl-pyridinium [tungstate-di-μ-selenido-silver-di-μ-selenido] 2-methyl-pyridine monosolvate].
Discovery of 2-methylpyridine-based biaryl amides as γ-secretase modulators for the treatment of Alzheimer's disease.
A 3D hybrid praseodymium-antimony-oxochloride compound: single-crystal-to-single-crystal transformation and photocatalytic properties.
FT-IR, FT-Raman, UV, NMR spectra, molecular structure, ESP, NBO and HOMO-LUMO investigation of 2-methylpyridine 1-oxide: a combined experimental and DFT study.
Cubane-type Cu(II)4 and Mn(II)2Mn(III)2 complexes based on pyridoxine: a versatile ligand for metal assembling.
Screening of reducing agents for the PEGylation of recombinant human IL-10.
A bromine analogue of picoplatin: a new substance from the group of platinum-based chemotherapeutics.
6-[4-Chloro-2-(trifluoro-meth-yl)phen-yl]-3-fluoro-2-methyl-pyridine.
POM-catalyzed in situ ligand synthesis for the construction of metal complexes and their use in the formation of coordination polymers.
Oxidation of aromatic N-heterocyclic compounds to N-oxides by Verticillium sp. GF39 cells.
A history of the isolation and identification of vitamin B(6).
3-Hydroxy-1-alkyl-2-methylpyridine-4(1H)-thiones: Inhibition of the Pseudomonas aeruginosa Virulence Factor LasB.
The history of cholinesterase reactivation: hydroxylamine and pyridinium aldoximes.
Synthesis and cytotoxicity of three trans-palladium complexes containing planaramine ligands in human ovarian tumor models.
Combining aspects of the platinum anticancer drugs picoplatin and BBR3464 to synthesize a new family of sterically hindered dinuclear complexes; their synthesis, binding kinetics and cytotoxicity.
2-Vinyl-pyridine-tris-(penta-fluoro-phen-yl)borane hexane monosolvate.
Effects of anthropogenic inputs on the organic quality of urbanized streams.
2-Methyl-pyridine-urea (1/1).
Synthesis, characterization and antiproliferative activity on mesothelioma cell lines of bis(carboxylato)platinum(IV) complexes based on picoplatin.
The role of odour quality in the perception of binary and higher-order mixtures.
Rapid determination of pyridine derivatives by dispersive liquid-liquid microextraction coupled with gas chromatography/gas sensor based on nanostructured conducting polypyrrole.
Probing platinum azido complexes by 14N and 15N NMR spectroscopy.
[Study On 2-Methylpyridine Initial Catabolic Pathways In Arthrobacter Sp. KM-2MP Strain].
Effect of fluoro substitution on the fragmentation of the K-shell excited/ionized pyridine studied by electron impact.
Molecular clusters in aqueous solutions of pyridine and its methyl derivatives.
Discovery of halopyridines as quiescent affinity labels: inactivation of dimethylarginine dimethylaminohydrolase.
Specific fragmentation of the K-shell excited/ionized pyridine derivatives studied by electron impact: 2-, 3- and 4-methylpyridine.
Syntheses, structures and spectroscopy of uni- and bi-dentate nitrogen base complexes of silver(I) trifluoromethanesulfonate.
2-Cyano-2-isonitrosoacetamide and its Ag(I) complexes. Silver(I) cyanoximate as a non-electric gas sensor.
Photocytotoxic trans-diam(m)ine platinum(IV) diazido complexes more potent than their cis isomers.
Modulation of carcinogen metabolizing enzymes by new fused heterocycles pendant to 5,6,7,8-tetrahydronaphthalene derivatives.
Chemical, structural and biological studies of cis-[Pt(3-Acpy)(2)Cl(2)].
Free energy of mixing of pyridine and its methyl-substituted derivatives with water, as seen from computer simulations.
Effects of alkylation on deviations from Lennard-Jones collision rates for highly excited aromatic molecules: collisions of methylated pyridines with HOD.
Gene identification and characterization of 5-formyl-3-hydroxy-2-methylpyridine 4-carboxylic acid 5-dehydrogenase, an NAD+-dependent dismutase.
Bis(μ-dimesitylborinato-κO:O)bis-[(2-methyl-pyridine-κN)lithium].
Pyridine-N-oxide analogues of DOTA and their gadolinium(III) complexes endowed with a fast water exchange on the square-antiprismatic isomer.
Lanthanide(III) complexes of pyridine-N-oxide analogues of DOTA in solution and in the solid state. A new kind of isomerism in complexes of DOTA-like ligands.
Desensitization of nicotinic acetylcholine receptors as a strategy for drug development.
Microbial degradation of pyridine and alpha-picoline using a strain of the genera Pseudomonas and Nocardia sp.
Heterocyclic compounds: toxic effects using algae, daphnids, and the Salmonella/microsome test taking methodical quantitative aspects into account.
5-Bromo-2-methyl-pyridine N-oxide.
Ethyl 4-hydroxy-methyl-2-methyl-pyridine-5-carboxyl-ate.
Tetra-kis(μ-pivalato-κO:O')bis-[(2-methyl-pyridine-κN)iron(II)](Fe-Fe).
Discovery of sulfonylalkylamides: A new class of orally active factor Xa inhibitors.
Gene identification and structural characterization of the pyridoxal 5'-phosphate degradative protein 3-hydroxy-2-methylpyridine-4,5-dicarboxylate decarboxylase from mesorhizobium loti MAFF303099.
PLP catabolism: identification of the 4-pyridoxic acid dehydrogenase gene in Mesorhizobium loti MAFF303099.
Environmental factors influencing sorption of heterocyclic aromatic compounds to soil.
Alkylation effects on strong collisions of highly vibrationally excited alkylated pyridines with CO2.
A Robust Dimethylgold(III) Complex Stabilized by a 2-Pyridyl-2-pyrrolide Ligand.
Sorption of heterocyclic organic compounds to reference soils: column studies for process identification.
Platinum(IV) analogues of AMD473 (cis-[PtCl2(NH3)(2-picoline)]): preparative, structural, and electrochemical studies.
Boron dipyrromethene dyes: a rational avenue for sensing and light emitting devices.
Synthesis, characterisation, activities, cell uptake and DNA binding of a trinuclear complex: [[trans-PtCl(NH3)]2mu-[trans-Pd(NH3)(2-hydroxypyridine)-(H2)N(CH2)6NH2)2]Cl4.
Design, synthesis, and evaluation of new type of L-amino acids containing pyridine moiety as nitric oxide synthase inhibitor.
Global kinetic model: a case study on the N-oxidation of alkylpyridines.
Oxygen binding and activation by the complexes of PY2- and TPA-appended diphenylglycoluril receptors with copper and other metals.
Identification of genes associated with platinum drug sensitivity and resistance in human ovarian cancer cells.
Design, synthesis, and biological activity of non-amidine factor Xa inhibitors containing pyridine N-oxide and 2-carbamoylthiazole units.
Unconventional density dependence of the stochastic dynamics in an organic liquid.
Synthesis and structure of selected quaternary N-(1,4-anhydro-5-deoxy-2,3-O-isopropylidene-D,L-ribitol-5-yl)ammonium salts.
Antiproliferative effects of ZD0473 (AMD473) in combination with 5-fluorouracil or SN38 in human colorectal cancer cell lines.
New class of quaternary ammonium salts, derivatives of methyl D-glucopyranosides.
Adenosylcobinamide plus exogenous, sterically hindered, putative axial bases: a reinvestigation into the cause of record levels of Co-C heterolysis.
Determination of the platinum drug cis-amminedichloro(2-methylpyridine)platinum(II) in human urine by liquid chromatography-tandem mass spectrometry.
In vitro effects of combinations of cis-amminedichloro (2-methylpyridine) platinum (II) (ZD0473) with other novel anticancer drugs on the growth of SBC-3, a human small cell lung cancer cell line.
AMD473 (ZD0473) exhibits marked in vitro anticancer activity in human tumor specimens taken directly from patients.
A Phase I clinical and pharmacological study of cis-diamminedichloro(2-methylpyridine) platinum II (AMD473).
A comparison of the quantitative methods for the analysis of the platinum-containing anticancer drug [cis-[amminedichloro(2-methylpyridine)]platinum(II)] (ZD0473) by HPLC coupled to either a triple quadrupole mass spectrometer or an inductively coupled plasma mass spectrometer.
Pyridines in cigarette smoke inhibit hamster oviductal functioning in picomolar doses.
Determination and quantification of clonidine in human blood serum.
The copper transporter CTR1 regulates cisplatin uptake in Saccharomyces cerevisiae.
Transition metal complexes with thiosemicarbazide-based ligands. XLIV. Aqua(3-hydroxy-5-hydroxymethyl-2-methylpyridine-4-carboxaldehyde 3-methylisothiosemicarbazone-kappa(3)O,N1,N4)nitratocopper(II) nitrate.
Out-of-center distortions in d(0) transition metal oxide fluoride anions.
Identification of aroma compounds in Parmigiano-Reggiano cheese by gas chromatography/olfactometry.
DNA-binding and cleavage studies of macrocyclic copper(II) complexes.
Simultaneous separation of common mono- and divalent cations on a calcinated silica gel column by ion chromatography with indirect photometric detection and aromatic monoamines-oxalic acid, containing crown ethers, used as eluent.
Catalytic hydrophosphination of styrenes.
A validated liquid chromatography/tandem mass spectrometry assay for cis-amminedichloro(2-methylpyridine)platinum(II) in human plasma ultrafiltrate.
Coenzyme B(12) Axial-Base Chemical Precedent Studies. Adenosylcobinamide Plus Sterically Hindered Axial-Base Co-C Bond Cleavage Product and Kinetic Studies: Evidence for the Dominance of Axial-Base Transition-State Effects and for Co-N(Axial-Base) Distance-Dependent, Competing sigma and pi Effects.
Mass spectrometric studies on pyridine-piperazine-containing ligands and their complexes with transition metals formed in solution.
Structural basis of the synergistic inhibition of glycogen phosphorylase a by caffeine and a potential antidiabetic drug.
Pyrone and pyridone compounds in the liquid culture of Physisporinus sanguinolentus.
Influence of DNA on the rate of ligand substitution in platinum(II) terpyridine complexes.
Dimeric copper(II) trimethylsilylacetate adducts with pyridine, 2-methylpyridine, 3-methylpyridine and quinoline, and a polymeric copper(II) trimethylsilylacetate
Dimeric copper(II) 3,3-dimethylbutyrate adducts with ethanol, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine and 3,3-dimethylbutyric acid
Mini-review: discovery and development of platinum complexes designed to circumvent cisplatin resistance.
Allosteric inhibition of glycogen phosphorylase a by the potential antidiabetic drug 3-isopropyl 4-(2-chlorophenyl)-1,4-dihydro-1-ethyl-2-methyl-pyridine-3,5,6-tricarbo xylate.
Biodegradation of 2-methyl, 2-ethyl, and 2-hydroxypyridine by an Arthrobacter sp. isolated from subsurface sediment.
cis-Amminedichloro(2-methylpyridine) platinum(II) (AMD473), a novel sterically hindered platinum complex: in vivo activity, toxicology, and pharmacokinetics in mice.
Lack of a role for MRP1 in platinum drug resistance in human ovarian cancer cell lines.
The structure of glycogen phosphorylase b with an alkyldihydropyridine-dicarboxylic acid compound, a novel and potent inhibitor.
Chemical, biochemical and pharmacological activity of the novel sterically hindered platinum co-ordination complex, cis-[amminedichloro(2-methylpyridine)] platinum(II) (AMD473).
In vitro circumvention of cisplatin resistance by the novel sterically hindered platinum complex AMD473.
Analogues of methotrexate in rheumatoid arthritis. 1. Effects of 10-deazaaminopterin analogues on type II collagen-induced arthritis in mice.
Absorption spectral studies on heme ligand interactions of P-450nor.
Measurement of the turnover of glycogen phosphorylase by GC/MS using stable isotope derivatives of pyridoxine (vitamin B6).
Synthesis and biological activity of 3- and 5-amino derivatives of pyridine-2-carboxaldehyde thiosemicarbazone.
Use of borinium ions as probes of steric effects in gas-phase ion-molecule complexes.
Effects of Maillard reaction products on mutagen formation in boiled pork juice.
Characterization of the mutagen 2-amino-3-methylimidazo[4,5-f]quinoline prepared from a 2-methylpyridine/creatinine/acetylformaldehyde model system.
Application of gas chromatography-mass spectrometry with selected ion monitoring to the urinanalysis of 4-pyridoxic acid.
Steric factors affecting the discrimination of isomeric and structurally related olefin gases and vapors with a reagent-coated surface acoustic wave sensor.
Intracellular glutathione levels in human colon cancer cells naturally resistant to cross-linking agents.
Comparison of cellular basis of drug sensitivity of human colon, pancreatic, and renal carcinoma cell lines with that of leukemia cell lines.
Enzymes of vitamin B6 degradation. Purification and properties of 5-pyridoxic-acid oxygenase from Arthrobacter sp.
Enzymes of vitamin B6 degradation. Purification and properties of isopyridoxal dehydrogenase and 5-formyl-3-hydroxy-2-methylpyridine-4-carboxylic-acid dehydrogenase.
Pyridinium- and quinolinium-2-dithioacetic acid zwitterions: antiradiation and anticancer activities.
Structure-activity relationships in reactivators of organophosphorus-inhibited acetylcholinesterase. 10. Hydroxyiminomethylarylethenylpyridine methiodides.
Spectroscopic properties of ferrous heme complexes of sterically hindered ligands.
Out-of-Plane Interactions in Parallel-Planar Copper(II) Dimers. The Structure and Magnetic Properties of Dobromobis(2-methylpyridine)copper(II).
Synthesis of a pyridoxal analog, 4,5-diformyl-3-hydroxy-2-methylpyridine.
Contributions to the chemistry of pyridine; 3- and 5-hydroxy-2-methylpyridine, and the condensation of 5-hydroxy-2-methylpyridine with formaldehyde in alkaline medium.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C14447
HMDB (The Human Metabolome Database):HMDB61888
FooDB:FDB004399
YMDB (Yeast Metabolome Database):YMDB01458
Export Tariff Code:2933.39.1000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 93.128791809082
Specific gravity @ 25 °C
Pounds per Gallon 7.83 to 7.88
Refractive Index 1.494 to 1.5 @ 20 °C
Boiling Point 128 to 130°C @ 760 mm Hg
Vapor Pressure 13.468 mmHg @ 25 °C
Vapor Density 3.2
Flash Point TCC Value 26.11 °C TCC
logP (o/w) 1.11
Solubility
alcohol Yes
water, 2.749e+005 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Sweaty
General comment Sweat
Flavor Type: Astringent
astringent, hazelnut, nutty
General comment Astringent hazelnut nutty

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 10 - Flammable.
R 20/21/22 - Harmful by inhalation, in contact with skin and if swallowed.
R 36/37 - Irritating to eyes and respiratory system.
S 01/02 - Keep locked up and out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 [sex: M] > 950 mg/kg
(Dow Chemical Company, 1976)

oral-rat LD50 400 - 800 mg/kg
(Eastman Kodak Co., 1980b)

oral-rat LD50 1410 mg/kg
(Smyth et al., 1951a)

oral-rat LD50 [sex: M,F] 810 mg/kg
(Birch, 1972a)

oral-guinea pig LD50 900 mg/kg
Hygiene and Sanitation Vol. 33(10-12), Pg. 341, 1968.

intraperitoneal-mouse LD50 529 mg/kg
Toxicon. Vol. 23, Pg. 815, 1985.

oral-mouse LD50 674 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: EXCITEMENT BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(12), Pg. 62, 1980.

intraperitoneal-rat LD50 200 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Fundamental and Applied Toxicology. Vol. 5, Pg. 920, 1985.

oral-rat LD50 790 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(12), Pg. 62, 1980.

Dermal Toxicity:
skin-rabbit LD50 410 ul/kg
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(12), Pg. 62, 1980.

skin-rabbit LD50 410 uL/kg
AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.

Inhalation Toxicity:
inhalation-mouse LC50 9000 mg/m3
AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.

inhalation-mouse LC50 9000 mg/m3
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(9-10), Pg. 64, 1992.

inhalation-rat LCLo 4000 ppm/4H
AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.

Safety in use information

Category:
flavoring agents
Recommendation for 2-methyl pyridine usage levels up to:
not for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.21 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 400 (μg/person/day)
Threshold of Concern:540 (μg/person/day)
Structure Class: II
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 0.400002.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 0.200001.00000
Edible ices, including sherbet and sorbet (03.0): 0.400002.00000
Processed fruit (04.1): 0.400002.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 1.000005.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 0.200001.00000
Bakery wares (07.0): 2.0000010.00000
Meat and meat products, including poultry and game (08.0): 0.200001.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 0.200001.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 0.100000.50000
Foodstuffs intended for particular nutritional uses (13.0): 0.200001.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.200001.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): --
Ready-to-eat savouries (15.0): 1.000005.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 0.200001.00000

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 24 (FGE.24): Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28 Flavouring Group Evaluation 24, Revision 1 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 77 (FGE77) [1] - Consideration of Pyridine, Pyrrole and Quinoline Derivatives evaluated by JECFA (63rd meeting) structurally related to Pyridine, Pyrrole, Indole and Quinoline Derivatives evaluated by EFSA in FGE.24Rev1 (2008)
View page or View pdf

Scientific opinion on Flavouring Group Evaluation 24, Revision 2 (FGE.24Rev2): Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28
View page or View pdf

EPI System: View
NIOSH International Chemical Safety Cards:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):109-06-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7975
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 2313
WGK Germany:1
2-methylpyridine
Chemidplus:0000109068
EPA/NOAA CAMEO:hazardous materials
RTECS:109-06-8