Fenilpropilcetona

Fenilpropilcetona
Alerta sobre risco à saúde
Nome IUPAC 1-Fenilbutan-1-one
Identificadores
Número CAS 495-40-9
PubChem 10315
Número EINECS 207-799-7
SMILES
InChI
1/C10H12O/c1-2-6-10(11)9-7-4-3-5-8-9/h3-5,7-8H,2,6H2,1H3
Propriedades
Fórmula química C10H12O
Massa molar 148.2 g mol-1
Aparência líquido incolor[1]
Densidade 0,99 g cm-3[1]
Ponto de fusão

11-13 °C[1]

Ponto de ebulição

229 °C (502 K)[1]

Solubilidade em água praticamente insolúvel [1]
Índice de refracção (nD) 1.520 (20 °C)[2]
Riscos associados
Frases R R41 R43
Frases S S26 S36/37/39
Ponto de fulgor 99 °C (vaso fechado)[1]
Compostos relacionados
Cetonas relacionados 2-Pentanona
Propiofenona (feniletilcetona ou 1-fenil-1-propanona)
Valerofenona (fenilbutilcetona ou 1-fenil-1-pentanona)
Haloperidol (antipsicótico baseado na fenilpropilcetona)
Compostos relacionados Fenilpropilcarbinol (reduzido a álcool)
Página de dados suplementares
Estrutura e propriedades n, εr, etc.
Dados termodinâmicos Phase behaviour
Solid, liquid, gas
Dados espectrais UV, IV, RMN, EM
Exceto onde denotado, os dados referem-se a
materiais sob condições normais de temperatura e pressão
Referências e avisos gerais sobre esta caixa.
Alerta sobre risco à saúde.

Fenilpropilcetona, também chamado 1-fenilbutan-1-ona, 1-fenil-1-butanona ou n-butirofenona, é um composto químico orgânico de fórmula química C10H12O, SMILES c1ccccc1C(=O)CCC, classificado com o número CAS 495-40-9.[3] Apresenta massa molecular de 148,2017 g/mol, ponto de fusão de 12 °C (285 K), ponto de ebulição de 229 °C (502 K).[4]

Aplicações

Alguns dos seus derivados (chamados comumente butirofenonas) são utilizados para tratar vários distúrbios psiquiátricos, tais como a esquizofrenia, bem como na qualidade de antieméticos.[5]

A classe de fármacos das butirofenonas incluem:

  • Haloperidol, o fármaco antipsicótico mais utilizado nesta classe.[5]
  • Droperidol, frequentemente usado para anestesia neuroleptanalgésica e sedação em cuidados de tratamento intensivo.
  • Benperidol, o antipsicótico mais potente usado (200 vezes mais potente do que a clorpromazina)[5]
  • Triperidol, um antipsicótico altamente potente (100 vezes mais potente do que a clorpromazina).
  • Melperona, um antipsicótico fracamente potente, na Europa, geralmente utilizado para o tratamento da insônia, estados confusionais, agitação psicomotora, delírio e, em particular, em pacientes geriátricos.
  • Lenperona
  • Azaperona, utilizada em medicina veterinária.
  • Domperidona, um antagonista antiemético da dopamina, derivados posteriores da butirofenona (não sendo uma butirofenona em si).

O antipsicótico atípico risperidona, embora não uma butirofenona, foi desenvolvido com as estruturas do benperidol e lenperona como base.

Referências

  1. ↑ a b c d e f Registo de CAS RN 495-40-9 na Base de Dados de Substâncias GESTIS do IFA
  2. ↑ Fiche Sigma Aldrich, consultée le 3 juin 2011
  3. ↑ 1-phenylbutan-1-one - www.chemindustry.com
  4. ↑ 1-Phénylbutan-1-one - chem-file.sourceforge.net
  5. ↑ a b c Keith Parker; Laurence Brunton; Goodman, Louis Sanford; Lazo, John S.; Gilman, Alfred (2006). Goodman & Gilman's The Pharmacological Basis of Therapeutics (11 ed.). New York: McGraw-Hill. ISBN 0071422803.

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