4-aminopyridine

4-Aminopyridine

Names
Preferred IUPAC name Pyridin-4-amine
Other names 4-Pyridinamine 4-Pyridylamine Fampridine
Identifiers
CAS Number	504-24-5 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:34385 Y
ChemSpider	1664 Y
ECHA InfoCard	100.007.262
IUPHAR/BPS	2416
KEGG	D04127 Y
MeSH	4-Aminopyridine
PubChem CID	1727
UNII	BH3B64OKL9 Y
InChI InChI=1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7) Y Key: NUKYPUAOHBNCPY-UHFFFAOYSA-N Y InChI=1/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7) Key: NUKYPUAOHBNCPY-UHFFFAOYAH
SMILES n1ccc(N)cc1
Properties
Chemical formula	C5H6N2
Molar mass	94.1146 g/mol
Appearance	colourless solid
Melting point	155 to 158 °C (311 to 316 °F; 428 to 431 K)
Boiling point	273 °C (523 °F; 546 K)
Solubility in water	polar organic solvents
Pharmacology
ATC code	N07XX07 (WHO)
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Oral
Pharmacokinetics:
Bioavailability	96%
Legal status	US: ℞-only
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

4-Aminopyridine (4-AP, INN fampridine, USAN dalfampridine) is an organic compound with the chemical formula C₅H₄N–NH₂. The molecule is one of the three isomeric amines of pyridine. It is used as a research tool in characterizing subtypes of the potassium channel. It has also been used as a drug, to manage some of the symptoms of multiple sclerosis, and is indicated for symptomatic improvement of walking in adults with several variations of the disease. It was undergoing Phase III clinical trials as of 2008^[update], and the U.S. Food and Drug Administration (FDA) approved the compound on January 22, 2010. Fampridine is also marketed as Ampyra (pronounced "am-PEER-ah," according to the maker's website) in the United States by Acorda Therapeutics and as Fampyra in Europe. In Canada, the medication has been approved for use by Health Canada since February 10, 2012.

4-Aminopyridine is prepared by the decarbonylation of pyridine-4-carboxamide using sodium hypochlorite via the Hofmann rearrangement. The pyridine carboxamide is generated from the corresponding nitrile, which in turn is obtained from ammoxidation of 4-methylpyridine.

The largest scale industrial application of 4-aminopyridine is as a precursor to the drug pinacidil, which affects potassium ion channels. The sequel to pinacidil, Naminidil was also derived from 4-aminopyridine. This is used as a hair growth stimulant.