Pyrazolopyrimidine

Pyrazolopyrimidines are a series of isomeric heterocyclic chemical compounds with the molecular formula C6H5N3. [1] They form the central core of a variety of more complex chemical compounds including some pharmaceuticals and pesticides.

Pyrazolo[1,5-a]pyrimidine
Names
Preferred IUPAC name
Pyrazolo[1,5-a]pyrimidine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.227.461
PubChem CID
UNII
InChI
  • InChI=1S/C6H5N3/c1-3-7-6-2-4-8-9(6)5-1/h1-5H
    Key: LDIJKUBTLZTFRG-UHFFFAOYSA-N
  • InChI=1/C6H5N3/c1-3-7-6-2-4-8-9(6)5-1/h1-5H
    Key: LDIJKUBTLZTFRG-UHFFFAOYAL
SMILES
  • n1cccn2nccc12
Properties
Chemical formula
 C6H5N3
Molar mass 119.127 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Pharmaceuticals

One isomer of pyrazolopyrimidines, known as pyrazolo[1,5-a]pyrimidine, is the basis for a class of sedative and anxiolytic drugs related (in terms of their effect) to benzodiazepines.

Most of the drugs from this class marketed to date are intended to induce sleep, and are prescribed for people suffering insomnia, however some newer compounds produce anxiolytic effects with relatively little sedation, and are being developed for use as non-sedating anti-anxiety drugs.

They include:

As they are not chemically related to the benzodiazepines despite their similar effect, such drugs—as well as the imidazopyridines and cyclopyrrones—are sometimes grouped together and referred to as "nonbenzodiazepines".

Zaleplon

Pesticides

A related use is in pyrazolopyrimidine organothiophosphate pesticides including chlorprazophos (insecticide) and pyrazophos (fungicide, insecticide).

Pyrazophos

See also

References
  1. "Note that according to other sources, the structure is different, and the sum formula is C5H4N4: see pyrazolopyrimidine on". ChemSpider. Retrieved 2018-11-07.
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