275875

4-Aminopyridine

≥99%

• Synonym(s): 4-Pyridinamine, 4-Pyridylamine, 4AP, Fampridine
• Empirical Formula (Hill Notation): C₅H₆N₂
• CAS Number: 504-24-5
• Molecular Weight: 94.11
• Beilstein/REAXYS Number: 105782
• EC Number: 207-987-9
• MDL number: MFCD00006439
• UNSPSC Code: 12352100
• PubChem Substance ID: 24856677
• NACRES: NA.22

Properties

• 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)

Description

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.

Safety Information

• pictograms: GHS06,GHS05,GHS09
• signalword: Danger
• hcodes: H300,H311 + H331,H314,H411
• pcodes: P260 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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_germany: 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