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275875

4-Aminopyridine

≥99%

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:
24856677
EC Number:
207-987-9
Beilstein/REAXYS Number:
105782
MDL number:
MFCD00006439
Assay:
≥99%
Form:
solid
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Quality Level

100

assay

≥99%

form

solid

bp

273 °C (lit.)

mp

155-158 °C (lit.)

solubility

DMF: soluble(lit.), DMSO: soluble(lit.), THF: soluble(lit.), acetone: soluble(lit.), acetonitrile: soluble(lit.), ethanol: soluble(lit.), isopropanol: soluble(lit.), methanol: soluble(lit.), water: soluble(lit.)

SMILES string

Nc1ccncc1

InChI

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

InChI key

NUKYPUAOHBNCPY-UHFFFAOYSA-N

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)

General description

4-Aminopyridine (4-AP) blocks the voltage-dependent potassium channels in other nerve membranes. 4-AP is a K+ channel blocker and causes epileptiform activity in in vitro preparations and is a potent convulsant in animals and man.

Application

4-Aminopyridine can be used as:
  • A reactant to prepare pharmacologically important 4-amino-N-pyridin-4-yl-butyramide hydrochloride.
  • A reactant to prepare cinnamic acid derivatives as potent cholinesterase inhibitors.
  • A starting material to prepare aza analogs of batracylin, a topoisomerase II inhibitor.

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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

Regulatory Information

危险化学品

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ3794
MKCJ2184
MKBW8059V
MKBN8495V
MKBF7199

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Design, synthesis and evaluation of novel cinnamic acid derivatives bearing N-benzyl pyridinium moiety as multifunctional cholinesterase inhibitors for Alzheimer′s disease
Lan J-S, et al.
Journal of Enzyme Inhibition and Medicinal Chemistry, 32(1), 776-788 (2017)
H Bostock et al.
The Journal of physiology, 313, 301-315 (1981-01-01)
1. 4-Aminopyridine (4AP) and tetraethylammonium ions (TEA), which block voltage-dependent potassium channels in other nerve membranes, have been used to study nerve conduction in fibres of normal rat spinal roots and those demyelinated with diphtheria toxin. The pharmacological actions have
M B Gill et al.
British journal of pharmacology, 160(6), 1417-1429 (2010-07-02)
A new class of heterotricyclic glutamate analogues recently was generated by incorporating structural elements of two excitotoxic marine compounds, kainic acid and neodysiherbaine A. Rather than acting as convulsants, several of these 'IKM' compounds markedly depressed CNS activity in mice.
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Global Trade Item Number

SKUGTIN
275875-1G04061826177662
275875-5G04061835554867