View source for Pyrazolopyrimidine

{{Chembox
| Name = Pyrazolo[1,5-''a'']pyrimidine
| ImageFile = pyrazolopyrimidine.svg
| ImageSize = 150px
| PIN = Pyrazolo[1,5-''a'']pyrimidine
| OtherNames = 
|Section1={{Chembox Identifiers
| CASNo = 274-71-5
| CASNo_Ref = {{cascite|correct|}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = NX2KR7M4A4
| PubChem = 11636795
| ChemSpiderID = 9811537
| SMILES = n1cccn2nccc12
| InChI = 1/C6H5N3/c1-3-7-6-2-4-8-9(6)5-1/h1-5H
| InChIKey = LDIJKUBTLZTFRG-UHFFFAOYAL
| StdInChI = 1S/C6H5N3/c1-3-7-6-2-4-8-9(6)5-1/h1-5H
| StdInChIKey = LDIJKUBTLZTFRG-UHFFFAOYSA-N
  }}
|Section2={{Chembox Properties
| C=6 | H=5 | N=3
| Appearance = 
| Density = 
| MeltingPt = 
| BoilingPt = 
| Solubility =
  }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt =
  }}
}}

'''Pyrazolopyrimidines''' are a series of [[isomer]]ic [[heterocyclic]] [[chemical compound]]s with the molecular formula C<sub>6</sub>H<sub>5</sub>N<sub>3</sub>. <!-- Note that according to other sources, the structure is different, and the sum formula is C5H4N4. --><ref>{{Cite web|url=http://www.chemspider.com/Chemical-Structure.10466972.html|title=Note that according to other sources, the structure is different, and the sum formula is C5H4N4: see pyrazolopyrimidine on|website=ChemSpider|access-date=2018-11-07}}</ref>  They form the central core of a variety of more complex chemical compounds including some pharmaceuticals and pesticides.

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

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:

* [[Zaleplon]] - hypnotic (trade name '''Sonata''')
* [[Indiplon]] - hypnotic
* [[Ocinaplon]] - anxiolytic
* [[Lorediplon]] - hypnotic

As they are not chemically related to the benzodiazepines despite their similar effect, such drugs—as well as the [[imidazopyridine]]s and [[cyclopyrrone]]s—are sometimes grouped together and referred to as "[[nonbenzodiazepine]]s".
[[File:zaleplon skeletal.svg|thumb|left|100px|Zaleplon]]{{clear-left}}

== Pesticides ==
A related use is in pyrazolopyrimidine [[organothiophosphate]] [[pesticide]]s including chlorprazophos ([[insecticide]]) and [[pyrazophos]] (fungicide, insecticide).
[[File:pyrazophos.svg|thumb|left|Pyrazophos]]{{clear-left}}

== See also ==
* [[Nonbenzodiazepine]]

== References ==
{{Reflist}}


{{Chemical classes of psychoactive drugs}}

[[Category:Pyrazolopyrimidines| ]]
[[Category:Chemical classes of psychoactive drugs]]