Butamben: Difference between revisions

{{Short description|Chemical compound}}

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| StdInChI = 1S/C11H15NO2/c1-2-3-8-14-11(13)9-4-6-10(12)7-5-9/h4-7H,2-3,8,12H2,1H3

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| C=11 | H=15 | N=1 | O=2

'''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]].<ref>drugs.com [https://www.drugs.com/international/butamben.html Butamben]</ref> 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==

[[File:Butamben synthesis.svg|thumb|center|500px|Patents:<ref>{{cite patent | country = GB | number = 148743 | title = Manufacture of normal butyl paramino benzoate | assign1 = Ste Chim Usines Rhone | gdate = 1920 | postscript = . }}</ref><ref>{{cite patent | inventor = Adams R, Volwiler E | country = US | number = 1440652 | gdate = 1923 | assign1 = Abbott Labs | postscript = . }}</ref> ~97%:<ref>{{cite journal | vauthors = Morogina OK, Nasibulin AA, Klyuev MV | title = Liquid-Phase Hydrogenation of p-Nitrobenzoic Acid Esters on Palladium Catalysts. | journal = Petroleum Chemistry | date = 1998 | volume = 38 | issue = 4 | pages = 251–255 | doi = }}</ref> ~94%:<ref>{{cite journal | vauthors = Hosangadi BD, Dave RH | title = An efficient general method for esterification of aromatic carboxylic acids. | journal = Tetrahedron Letters | date = August 1996 | volume = 37 | issue = 35 | pages = 6375–6378 | doi = 10.1016/0040-4039(96)01351-2 }}</ref> ~88%:<ref>{{cite journal | vauthors = Gök Y, Alici B, Cetinkaya E, Özdemir İ, Özeroğlu Ö | title = Ionic liquids as solvent for efficient esterification of carboxylic acids with alkyl halides. | journal = Turkish Journal of Chemistry | date = 2010 | volume = 34 | issue = 2 | pages = 187–192 | doi = 10.3906/kim-0904-39 | s2cid = 93020800 }}</ref> NA:<ref>{{cite journal | vauthors = Matsunaga Y, Sakamoto S, Togashi A, Tsujimoto M | title = Smectogenic Salts Formed by Combination of Alkyl p-Aminobenzoates and p-Ethyl-or p-Chlorobenzenesulfonic Acid. | journal = Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals. | date = July 1994 | volume = 250 | issue = 1 | pages = 161–166 | doi = 10.1080/10587259408028202 }}</ref><ref>{{cite journal | vauthors = Brill HC | title = Esters of Aminobenzoic Acids | journal = Journal of the American Chemical Society | date = June 1921 | volume = 43 | issue = 6 | pages = 1320–1323 | doi = 10.1021/ja01439a014 }}</ref>]]

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==

{{reflist}}

{{Local anesthetics}}

{{Analgesic-stub}}