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123080

Sigma-Aldrich

2-Amino-4-methylpyridine

99%

Synonym(s):

2-Amino-4-picoline

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About This Item

Empirical Formula (Hill Notation):
C6H8N2
CAS Number:
695-34-1
Molecular Weight:
108.14
Beilstein:
107066
EC Number:
211-780-9
MDL number:
MFCD00006321
UNSPSC Code:
12352100
PubChem Substance ID:
24847520
NACRES:
NA.22

Quality Level

100

Assay

99%

bp

230 °C (lit.)

mp

96-99 °C (lit.)

solubility

DMF: freely soluble
H2O: freely soluble
aliphatic hydrocarbons: slightly soluble
coal tar bases: freely soluble
lower alcohols: freely soluble
petroleum ether: slightly soluble

SMILES string

Cc1ccnc(N)c1

InChI

1S/C6H8N2/c1-5-2-3-8-6(7)4-5/h2-4H,1H3,(H2,7,8)

InChI key

ORLGLBZRQYOWNA-UHFFFAOYSA-N

Gene Information

human ... NOS1(4842) , NOS2(4843) , NOS3(4846)
rat ... Nos1(24598)

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General description

2-Amino-4-methylpyridine acts as ligand and forms methoxo-bridged copper(II) complexes.

Application

2-Amino-4-methylpyridine has been used in the synthesis of 2-amino-4-methyl­pyridinium 2-hy­droxy­benzoate.

Biochem/physiol Actions

2-Amino-4-methylpyridine inhibits the activity of inducible NO synthase isolated from mouse RAW 264.7 cells in vitro.

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 2

Flash Point(F)

244.4 °F - closed cup

Flash Point(C)

118 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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W S Faraci et al.
British journal of pharmacology, 119(6), 1101-1108 (1996-11-01)
1. The ability of 2-amino-4-methylpyridine to inhibit the catalytic activity of the inducible NO synthase (NOS II) enzyme was characterized in vitro and in vivo. 2. In vitro, 2-amino-4-methylpyridine inhibited NOS II activity derived from mouse RAW 264.7 cells with
Madhukar Hemamalini et al.
Acta crystallographica. Section E, Structure reports online, 66(Pt 8), o2151-o2152 (2010-01-01)
The asymmetric unit of the title mol-ecular salt, C(6)H(9)N(2) (+)·C(7)H(5)O(3) (-), contains two cations and two anions. Both the salicylate anions contain an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) ring. Both the 2-amino-4-methyl-pyridine mol-ecules are protonated at their
N Kiloh et al.
European journal of pharmacology, 70(1), 53-57 (1981-03-05)
4-Methyl-2-aminopyridine (4M2AP) increased responses of isolated rat diaphragm and chick biventer cervicis nerve-muscle preparations to nerve stimulation but depressed responses to direct stimulation. Responses to acetylcholine were also increased while responses to carbachol were depressed. When tested after inhibition of
R Boer et al.
Molecular pharmacology, 58(5), 1026-1034 (2000-10-20)
We have investigated various nitric oxide (NO) synthase inhibitors for their affinity and selectivity toward the three human isoenzymes in radioligand binding experiments. Therefore, we developed the new radioligand [(3)H]2-amino-4-picoline to measure binding of these compounds to the three human
Ravil R Petrov et al.
Bioorganic & medicinal chemistry letters, 16(18), 4946-4950 (2006-07-11)
An enkephalin analogue coupled to 'aminofentanyl' has been synthesized and tested for biological activities at the mu and delta opioid receptors. Aminofentanyl which represents a structural derivative of fentanyl has been synthesized by acylation of 1-(2-phenethyl)-4-(N-anilino)piperidine with phthaloyl protected beta-alaninyl
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