1,4-Dihydropyridine

1,4-Dihydropyridine (DHP) is an organic compound with the formula CH₂(CH=CH)₂NH. The parent compound is uncommon,^[2] but derivatives of 1,4-dihydropyridine are important commercially and biologically. The pervasive cofactors NADH and NADPH are derivatives of 1,4-dihydropyridine. 1,4-Dihydropyridine-based drugs are L-type calcium channel blockers, used in the treatment of hypertension. 1,2-Dihydropyridines are also known.^[3][4]

1,4-Dihydropyridine

Names
Preferred IUPAC name 1,4-Dihydropyridine[1]
Identifiers
CAS Number	3337-17-5 Y
3D model (JSmol)	Interactive image
ChemSpider	94619 Y
MeSH	1,4-dihydropyridine
PubChem CID	104822
UNII	7M8K3P6I89 Y
CompTox Dashboard (EPA)	DTXSID20274185
InChI InChI=1S/C5H7N/c1-2-4-6-5-3-1/h2-6H,1H2 Y Key: YNGDWRXWKFWCJY-UHFFFAOYSA-N Y
SMILES C1C=CNC=C1
Properties
Chemical formula	C 5H 7N
Molar mass	81.1158 g mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Properties and reactions

A recurring feature of 1,4-dihydropyridines is the presence of substituents at the 2- and 6-positions. Dihydropyridines are enamines, which otherwise tend to tautomerize or hydrolyze.^{[citation needed]}

The dominant reaction of dihydropyridines is their ease of oxidation. In the case of dihydropyridines with hydrogen as the substituent on nitrogen, oxidation yields pyridines:

CH₂(CH=CR)₂NH → C₅H₃R₂N + H₂

The naturally-occurring dihydropyridines NADH and NADPH contain N-alkyl groups. Therefore, their oxidation does not yield pyridine, but N-alkylpyridinium cations:

CH₂(CH=CR)₂NR' → C₅H₃R₂NR' + H⁻

Hantzsch ester

Chemical structure of Hantzsch's ethyl ester, a well-known dihydropyridine.

Hantzsch ester^[5]

See also

• Dihydropyridine calcium channel blockers
• Dihydropyridine receptor
• Ryanodine receptor