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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

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
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
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
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
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