Butyrophenone
|
| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name
1-Phenylbutan-1-one | |||
| Identifiers | |||
3D model (JSmol)
|
|||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.007.091 | ||
PubChem CID
|
|||
| UNII | |||
CompTox Dashboard (EPA)
|
|||
| |||
| |||
| Properties | |||
| 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) | ||
| poor | |||
| log P | 2.77 | ||
Refractive index (nD)
|
1.520 | ||
| Hazards | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 99 °C (210 °F; 372 K) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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:
- Benperidol‡[2] (200 times more potent than chlorpromazine)[1][3]
- Bromperidol†[4]
- Droperidol‡,[2] Antiemetic for postoperative nausea and vomiting
- Haloperidol, the most widely used classical antipsychotic drug in this class[1]
- Lumateperone, an atypical antipsychotic used for schizophrenia and bipolar depression
- Moperone (discontinued)†[4]
- Pipamperone (discontinued)†[4]
- Timiperone†[4]
- Lenperone
- Melperone
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.
- ^ a b ‡ 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.
- ^ Grogan, Charles H.; Rice, Leonard M. (1967). "Ω-Azabicyclic Butyrophenones". Journal of Medicinal Chemistry. 10 (4): 621–623. doi:10.1021/jm00316a022. PMID 6037051.
- ^ a b c d † indicates drugs that are no longer (or were never) marketed in English-speaking countries.