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=C₁₀H₁₂O

| 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 C₆H₅C(O)C₃H₇. It is a colorless liquid.

The butyrophenone structure—a ketone flanked by a phenyl ring and a butyl chain—forms the basis for many other chemicals containing various substituents. Some of these butyrophenones are used to treat various psychiatric disorders such as schizophrenia, as well as acting as antiemetics.{{GoodmanGilman11th}}

Examples of butyrophenone-derived pharmaceuticals include:

• Benperidol‡‡ 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. (200 times more potent than chlorpromazine){{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.}}
• Bromperidol†† indicates drugs that are no longer (or were never) marketed in English-speaking countries.
• Droperidol‡, Antiemetic for postoperative nausea and vomiting
• Haloperidol, the most widely used classical antipsychotic drug in this class
• Lumateperone, an atypical antipsychotic used for schizophrenia and bipolar depression
• Moperone (discontinued)†
• Pipamperone (discontinued)†
• Timiperone†
• Lenperone
• Melperone