Butyrophenones

Butyrophenone
Names
	Preferred IUPAC name 1-Phenylbutan-1-one
Identifiers
CAS Number	495-40-9 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL193524 ;
ChemSpider	9893 ;
ECHA InfoCard	100.007.091
PubChem CID	10315;
UNII	186I11WB5B ;
CompTox Dashboard (EPA)	DTXSID3047059 ;
	InChI InChI=1S/C10H12O/c1-2-6-10(11)9-7-4-3-5-8-9/h3-5,7-8H,2,6H2,1H3 Key: FFSAXUULYPJSKH-UHFFFAOYSA-N ; InChI=1/C10H12O/c1-2-6-10(11)9-7-4-3-5-8-9/h3-5,7-8H,2,6H2,1H3 Key: FFSAXUULYPJSKH-UHFFFAOYAC;
	SMILES O=C(c1ccccc1)CCC; CCCC(=O)c1ccccc1;
Properties
Chemical formula	C10H12O
Molar mass	148.20 g/mol
Appearance	clear liquid
Melting point	12 °C (54 °F; 285 K)
Boiling point	229 °C (444 °F; 502 K)
Solubility in water	poor
log P	2.77
Refractive index (nD)	1.520
Hazards
NFPA 704 (fire diamond)	1 1 1
Flash point	99 °C (210 °F; 372 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). verify (what is ?) Infobox references

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.^[1]

Examples of butyrophenone-derived pharmaceuticals include:

Haloperidol, the most widely used classical antipsychotic drug in this class^[1]
Benperidol, the most potent commonly used antipsychotic (200 times more potent than chlorpromazine)^[1]^[2]
Lumateperone, an atypical antipsychotic used for schizophrenia and bipolar depression
Droperidol, Antiemetic for postoperative nausea and vomiting

References

^ ^a ^b ^c Keith Parker; Laurence Brunton Goodman; Louis Sanford; Lazo, John S.; Gilman, Alfred (2006). Goodman & Gilman's The Pharmacological Basis of Therapeutics (11th ed.). New York: McGraw-Hill. ISBN 0071422803.
^ Grogan, Charles H.; Rice, Leonard M. (1967). "Ω-Azabicyclic Butyrophenones". Journal of Medicinal Chemistry. 10 (4): 621–623. doi:10.1021/jm00316a022. PMID 6037051.

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[Goodman_Gilman-1] Keith Parker; Laurence Brunton Goodman; Louis Sanford; Lazo, John S.; Gilman, Alfred (2006). Goodman & Gilman's The Pharmacological Basis of Therapeutics (11th ed.). New York: McGraw-Hill. ISBN 0071422803.

[2] Grogan, Charles H.; Rice, Leonard M. (1967). "Ω-Azabicyclic Butyrophenones". Journal of Medicinal Chemistry. 10 (4): 621–623. doi:10.1021/jm00316a022. PMID 6037051.

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