Butacaine
{{short description|Chemical compound}}
{{chembox
| ImageFile=Butacaine.svg
| ImageSize=200px
| PIN=3-(Dibutylamino)propyl 4-aminobenzoate
| OtherNames=
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Z84S23CGJJ
| ChemSpiderID = 2386
| ChEMBL = 129529
| InChI = 1/C18H30N2O2/c1-3-5-12-20(13-6-4-2)14-7-15-22-18(21)16-8-10-17(19)11-9-16/h8-11H,3-7,12-15,19H2,1-2H3
| InChIKey = HQFWVSGBVLEQGA-UHFFFAOYAZ
| CASNo=149-16-6
| PubChem=2480
| SMILES = O=C(OCCCN(CCCC)CCCC)c1ccc(N)cc1
}}
|Section2={{Chembox Properties
| C=18 | H=30 | N=2 | O=2
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
}}
Butacaine is a white crystalline ester used as a local anesthetic.{{cite web | url = https://drugs.ncats.io/substance/Z84S23CGJJ | title = Butacaine | work = Inxight Drugs | publisher = National Center for Advancing Translational Sciences }} It was first marketed in 1920.
Synthesis
The addition of metallic sodium is added to a mixture of allyl alcohol (1) and dibutylamine (2){{cite journal | doi = 10.1248/yakushi1947.74.7_763 | title = Synthesis of γ-Alkylaminopropanols | date = 1954 | last1 = Kurihara | first1 = Tozaburo | last2 = Niwa | first2 = Hiroshi | last3 = Chiba | first3 = Katsuichi | journal = Yakugaku Zasshi | volume = 74 | issue = 7 | pages = 763–766 }} gives the conjugate addition product 3-dibutylamino-1-propanol (3). Esterification of this intermediate with para-nitrobenzoyl chloride (4) gives the ester 5. The reduction of the nitro group completes the synthesis of butacaine (6).{{cite journal | doi = 10.1021/ja01290a041 | title = Dialkylaminoalkanol Esters of p-Aminobenzoic Acid | date = 1937 | last1 = Burnett | first1 = W. B. | last2 = Jenkins | first2 = R. L. | last3 = Peet | first3 = C. H. | last4 = Dreger | first4 = E. E. | last5 = Adams | first5 = Roger | journal = Journal of the American Chemical Society | volume = 59 | issue = 11 | pages = 2248–2252 }}{{cite journal | doi = 10.1021/ja01154a084 | title = Dialkylaminoalkyl Esters of 2-Amino-6-carboxybenzothiazole | date = 1951 | last1 = Kaye | first1 = Irving Allan | last2 = Roberts | first2 = I. Melville | journal = Journal of the American Chemical Society | volume = 73 | issue = 10 | pages = 4762–4764 }}Oliver Kamm, Roger Adams, Volwiler Ernest H., {{US patent|1358751}} (1920 to Abbott Lab)Adams Roger, Ernest H Volwiler, {{US patent|1676470}} (1928 to Abbott Lab)Weston Arthur W, {{US patent|2437984}} (1948 to Abbott Lab)Anon., {{Cite patent|GB|191122}} (1922-12-27 to Abbott Lab).
