Butamben

Chemical compound From Wikipedia, the free encyclopedia

Butamben is a local anesthetic. Proprietary names includes Alvogil in Spain and Alvogyl in Switzerland. It is one of three components in the topical anesthetic Cetacaine.

Other namesn-butyl p-aminobenzoate
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administrationTopical
ATC code
  • none
Quick facts Clinical data, Other names ...
Butamben
Clinical data
Other namesn-butyl p-aminobenzoate
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		Topical
ATC code
  • none
Identifiers
  • Butyl 4-aminobenzoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.002.107 Edit this at Wikidata
Chemical and physical data
FormulaC11H15NO2
Molar mass193.246 g·mol−1
3D model (JSmol)
Melting point58 °C (136 °F)
  • O=C(OCCCC)c1ccc(N)cc1
  • InChI=1S/C11H15NO2/c1-2-3-8-14-11(13)9-4-6-10(12)7-5-9/h4-7H,2-3,8,12H2,1H3 checkY
  • Key:IUWVALYLNVXWKX-UHFFFAOYSA-N checkY
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Chemistry

It is the ester of 4-aminobenzoic acid and butanol.[1] A white, odourless, crystalline powder. that is mildly soluble in water (1 part in 7000) and soluble in alcohol, ether, chloroform, fixed oils, and dilute acids. It slowly hydrolyses when boiled with water. Synonyms include Butamben, Butilaminobenzoato, and Butoforme.

Synthesis

Patents:[2][3] ~97%:[4] ~94%:[5] ~88%:[6] NA:[7][8]

The Fischer esterification of 4-Nitrobenzoic acid [62-23-7] (1) and 1-Butanol [71-36-3] (2) gives n-Butyl 4-Nitrobenzoate [120-48-9] (3). Bechamp reduction then gives Butamben (4).

Alternatively, 4-aminobenzoic acid can be used directly.

References

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