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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

WGK

WGK 2

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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W E Glover
European journal of pharmacology, 71(1), 21-31 (1981-04-24)
The effect of 4-aminopyridine (4AP) and 4-methyl-2-aminopyridine (4M2AP), 10(-3) M, was studied on isolated spontaneously beating right atria and electrically driven left atria of the rabbit and the cat. In the rabbit preparations, 4AP had a positive inotropic effect which
Synthesis, spectroscopic and magnetic properties of methoxo-bridged copper (II) complexes with 2-amino-4-methylpyridine as the ligand.
Komaei SA, et al.
Transition Metal Chemistry, 24(1), 104-107 (1999)
M W Fryer et al.
General pharmacology, 29(4), 657-663 (1997-11-14)
1. The effects of 4-methyl-2-aminopyridine (4M2AP) and 4-aminopyridine (4AP) on spontaneous and evoked [3H]-noradrenaline overflow were compared in rabbit ear artery strips. The effects of 4M2AP on smooth muscle contractility were also investigated in isolated perfused ear arteries. 2. Both
F Bergmann et al.
Archives internationales de pharmacodynamie et de therapie, 247(2), 275-282 (1980-10-01)
2-Amino-4-methylpyridine (2-AMP), when implanted into the ventral lateral thalamus of rats, does not cause stereotyped behavior. On the other hand, when compulsive biting and gnawing was evoked by thalamic implants of morphine (via stimulation of type 1 opiate receptors, which
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
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