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Merck

A78403

4-Aminopyridine

98%

Synonym(s):

4-Pyridinamine, 4-Pyridylamine, 4AP, Fampridine

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About This Item

Empirical Formula (Hill Notation):
C5H6N2
CAS Number:
504-24-5
Molecular Weight:
94.11
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24891285
EC Number:
207-987-9
Beilstein/REAXYS Number:
105782
MDL number:
MFCD00006439

Product Name

4-Aminopyridine, 98%

InChI key

NUKYPUAOHBNCPY-UHFFFAOYSA-N

InChI

1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)

SMILES string

Nc1ccncc1

assay

98%

form

crystals

bp

273 °C (lit.)

mp

155-158 °C (lit.)

solubility

H2O: 50 mg/mL, clear, colorless

Quality Level

200

Gene Information

human ... KCNA1(3736), KCNA10(3744), KCNA2(3737), KCNA3(3738), KCNA4(3739), KCNA5(3741), KCNA6(3742), KCNA7(3743), KCNB1(3745), KCNB2(9312), KCNC1(3746), KCNC2(3747), KCNC3(3748), KCNC4(3749), KCND1(3750), KCND2(3751), KCND3(3752), KCNF1(3754), KCNG1(3755), KCNG2(26251), KCNG3(170850), KCNG4(93107), KCNH1(3756), KCNH2(3757), KCNH3(23416), KCNH4(23415), KCNH5(27133), KCNH6(81033), KCNH7(90134), KCNH8(131096), KCNQ1(3784), KCNQ2(3785), KCNQ3(3786), KCNQ4(9132), KCNQ5(56479), KCNS1(3787), KCNS2(3788), KCNS3(3790), KCNV1(27012), KCNV2(169522)
mouse ... Kcna3(16491)
rat ... Grin2a(24409)

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Application

4-Aminopyridine (4-AP) can be used as a:
  • Catalyst in the regioselective acylation of N-tosylhydrazide.
  • Starting material in the synthesis of 4-aminopyridine derivatives for neurological disorder studies.
  • Precursor for the synthesis of enantiomerically pure 4-(pyrrolidino)pyridine (PPY) derivatives by cyclocondensation reaction.

General description

4-aminopyridine is a ligand and an ion channel modulator used as an acetylcholine release enhancing agent.

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Aquatic Chronic 2 - Eye Dam. 1 - Skin Corr. 1B

Storage Class

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

wgk

WGK 3

flash_point_f

312.8 °F

flash_point_c

156 °C

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ1308
MKCV6115
MKCV0742
MKCR0614
MKCQ6276

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Effect of protonated aminopyridines on the structural divergences of M (II)--malonate complexes (M= Cu, Ni, Co)
Amrita D et al.
Polyhedron, 29, 1317-1325 (2010)
Development of novel 4-aminopyridine derivatives as potential treatments for neurological injury and disease
Smith DT, et al.
European Journal of Medicinal Chemistry, 40(9), 908-917 (2005)
4-Aminopyridine derivatives with antiamnesic activity
Aldo A et al.
European Journal of Medicinal Chemistry, 35, 77-82 (2000)
4-Aminopyridine catalyzed direct and regioselective acylation of N-tosylhydrazide
Namba K, et al.
Organic Letters, 11(21), 4970-4973 (2009)
Synthesis of C 2-symmetric analogues of 4-(pyrrolidino) pyridine: new chiral nucleophilic catalysts
Spivey AC, et al.
Journal of the Chemical Society, Part 1, 1(20), 3460-3468 (2000)
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