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A78403

Sigma-Aldrich

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
Beilstein:
105782
EC Number:
207-987-9
MDL number:
MFCD00006439
UNSPSC Code:
12352100
PubChem Substance ID:
24891285
NACRES:
NA.22

Quality Level

200

Assay

98%

form

crystals

bp

273 °C (lit.)

mp

155-158 °C (lit.)

solubility

H2O: 50 mg/mL, clear, colorless

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)

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General description

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

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.

Signal Word

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 Code

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

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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4-Aminopyridine derivatives with antiamnesic activity
Aldo A et al.
European Journal of Medicinal Chemistry, 35, 77-82 (2000)
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)
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)
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)
4-Aminopyridine catalyzed direct and regioselective acylation of N-tosylhydrazide
Namba K, et al.
Organic Letters, 11(21), 4970-4973 (2009)
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