1,4-Dihydropyridine
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| Preferred IUPAC name
1,4-Dihydropyridine[1] | |||
| Identifiers | |||
3D model (JSmol)
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| MeSH | 1,4-dihydropyridine | ||
PubChem CID
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| UNII | |||
CompTox Dashboard (EPA)
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| Properties | |||
| 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).
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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. Dihydropyridine calcium channel blockers are a class of L-type calcium channel blockers used in the treatment of hypertension. 1,2-Dihydropyridines are also known.[3][4]
Properties and reactions
[edit | edit source]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
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See also
[edit | edit source]References
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External links
[edit | edit source]- Dihydropyridines at the U.S. National Library of Medicine Medical Subject Headings (MeSH)