Butamben

Chemical compound

none

Identifiers

IUPAC name

Butyl 4-aminobenzoate

CAS Number

94-25-7^Y

PubChem CID

2482

ChemSpider

2388^Y

UNII

EFW857872Q

KEGG

D00730

ChEBI

CHEBI:3231

ChEMBL

ChEMBL127516^Y

CompTox Dashboard (EPA)

DTXSID7022417

ECHA InfoCard100.002.107

Chemical and physical dataFormulaC₁₁H₁₅NO₂Molar mass193.246 g·mol⁻¹3D model (JSmol)

Interactive image

Melting point58 °C (136 °F)

SMILES

O=C(OCCCC)c1ccc(N)cc1

InChI

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^Y
Key:IUWVALYLNVXWKX-UHFFFAOYSA-N^Y

(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

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

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

Alternatively, 4-aminobenzoic acid can be used directly.

References

^ drugs.com Butamben
^ GB 148743, "Manufacture of normal butyl paramino benzoate", issued 1920, assigned to Ste Chim Usines Rhone.
^ US 1440652, Adams R, Volwiler E, issued 1923, assigned to Abbott Labs.
^ Morogina OK, Nasibulin AA, Klyuev MV (1998). "Liquid-Phase Hydrogenation of p-Nitrobenzoic Acid Esters on Palladium Catalysts". Petroleum Chemistry. 38 (4): 251–255.
^ Hosangadi BD, Dave RH (August 1996). "An efficient general method for esterification of aromatic carboxylic acids". Tetrahedron Letters. 37 (35): 6375–6378. doi:10.1016/0040-4039(96)01351-2.
^ Gök Y, Alici B, Cetinkaya E, Özdemir İ, Özeroğlu Ö (2010). "Ionic liquids as solvent for efficient esterification of carboxylic acids with alkyl halides". Turkish Journal of Chemistry. 34 (2): 187–192. doi:10.3906/kim-0904-39. S2CID 93020800.
^ Matsunaga Y, Sakamoto S, Togashi A, Tsujimoto M (July 1994). "Smectogenic Salts Formed by Combination of Alkyl p-Aminobenzoates and p-Ethyl-or p-Chlorobenzenesulfonic Acid". Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals. 250 (1): 161–166. doi:10.1080/10587259408028202.
^ Brill HC (June 1921). "Esters of Aminobenzoic Acids". Journal of the American Chemical Society. 43 (6): 1320–1323. doi:10.1021/ja01439a014.

Local anesthetics (primarily sodium channel blockers) (N01B)

Esters by acid

Aminobenzoic	Benzocaine Benzonatate Butacaine Butamben Chloroprocaine Dimethocaine Lucaine Meprylcaine Metabutethamine Metabutoxycaine Nitracaine Orthocaine Propoxycaine Procaine (Novocaine) Proxymetacaine Risocaine Tetracaine
Benzoic	Amylocaine Cocaine Cyclomethycaine α-Eucaine β-Eucaine Hexylcaine Isobucaine Piperocaine
ArCO2- (not para-amino or Ph)	Amoproxan (3,4,5-Trimethoxybenzoyl) 3-(p-Fluorobenzoyloxy)tropane