Butamben

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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
E number{{#property:P628}}
CompTox Dashboard (EPA)
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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
  (verify)

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.

Chemistry

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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

[edit | edit source]
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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  1. ^ drugs.com Butamben
  2. ^ GB 148743, "Manufacture of normal butyl paramino benzoate", issued Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Ste Chim Usines Rhone. 
  3. ^ US 1440652, Adams R, Volwiler E, issued Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Abbott Labs. 
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  8. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).


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