View source for Butyrophenone

{{Chembox
| Watchedfields = changed
| verifiedrevid = 414039216
| ImageFileL1 = Butyrophenone.svg
| ImageFileR1 = Butyrophenone3d.png
| PIN = 1-Phenylbutan-1-one
| OtherNames =
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9893
| InChI = 1/C10H12O/c1-2-6-10(11)9-7-4-3-5-8-9/h3-5,7-8H,2,6H2,1H3
| InChIKey = FFSAXUULYPJSKH-UHFFFAOYAC
| SMILES1 = CCCC(=O)c1ccccc1
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 193524
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H12O/c1-2-6-10(11)9-7-4-3-5-8-9/h3-5,7-8H,2,6H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FFSAXUULYPJSKH-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=495-40-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 186I11WB5B
| PubChem=10315
| SMILES = O=C(c1ccccc1)CCC
}}
|Section2={{Chembox Properties
| Formula=C<sub>10</sub>H<sub>12</sub>O
| MolarMass=148.20 g/mol
| Appearance= clear liquid
| Density=
| MeltingPtC= 12
| BoilingPtC= 229
| Solubility= poor
| RefractIndex = 1.520
| LogP = 2.77
  }}
|Section7={{Chembox Hazards
| MainHazards=
| FlashPtC= 99
| AutoignitionPt =
| NFPA-H = 1
| NFPA-F = 1
| NFPA-R = 1
  }}
}}

'''Butyrophenone''' is an [[organic compound]] with the formula C<sub>6</sub>H<sub>5</sub>C(O)C<sub>3</sub>H<sub>7</sub>.  It is a colorless liquid.

The butyrophenone structure—a [[ketone]] flanked by a [[phenyl ring]] and a [[butyl group|butyl chain]]—forms the basis for many other chemicals containing various [[substituent]]s. Some of these butyrophenones are used to treat various psychiatric disorders such as [[schizophrenia]], as well as acting as [[antiemetics]].<ref name="Goodman_Gilman">{{GoodmanGilman11th}}</ref>

Examples of butyrophenone-derived pharmaceuticals include:
* [[Benperidol]]‡<ref name="‡">‡ denotes drugs that are no longer (or were never to begin with) marketed in the United States. Some antipsychotics are not firmly placed in either first-generation or second-generation classes.</ref> (200 times more potent than [[chlorpromazine]])<ref name="Goodman_Gilman" /><ref>{{cite journal|doi=10.1021/jm00316a022|pmid=6037051|title=Ω-Azabicyclic Butyrophenones|journal=Journal of Medicinal Chemistry|volume=10|issue=4|pages=621–623|year=1967|last1=Grogan|first1=Charles H.|last2=Rice|first2=Leonard M.}}</ref>
* [[Bromperidol]]†<ref name="†">† indicates drugs that are no longer (or were never) marketed in English-speaking countries.</ref>
* [[Droperidol]]‡,<ref name="‡"/> [[Antiemetic]] for [[postoperative nausea and vomiting]]
* [[Haloperidol]], the most widely used classical antipsychotic drug in this class<ref name="Goodman_Gilman" />
* [[Lumateperone]], an atypical antipsychotic used for schizophrenia and bipolar depression
* [[Moperone]] (''discontinued'')†<ref name="†"/>
* [[Pipamperone]] (''discontinued'')†<ref name="†"/>
* [[Timiperone]]†<ref name="†"/>
* [[Lenperone]]
* [[Melperone]]

== References ==
{{Reflist|2}}

{{Chemical classes of psychoactive drugs}}

[[Category:Aromatic ketones]]
[[Category:Phenyl compounds]]


{{Ketone-stub}}