Butacaine

In today's world, Butacaine has become a relevant and influential topic in society. Its impact can be felt in different areas, from politics to popular culture, and has generated an open debate in public opinion. With the rapid advancement of technology, globalization and sociocultural changes, Butacaine has positioned itself as a point of interest for experts in various disciplines. In this article, we will thoroughly explore the meaning and importance of Butacaine, as well as its influence on our daily lives.
Butacaine
Names
Preferred IUPAC name
3-(Dibutylamino)propyl 4-aminobenzoate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.214 Edit this at Wikidata
UNII
  • 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
    Key: HQFWVSGBVLEQGA-UHFFFAOYAZ
  • O=C(OCCCN(CCCC)CCCC)c1ccc(N)cc1
Properties
C18H30N2O2
Molar mass 306.450 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).

Butacaine is a white crystalline ester used as a local anesthetic. It was first marketed in 1920.

Synthesis

The addition of metallic sodium is added to a mixture of allyl alcohol (1) and dibutylamine (2) 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).

Synthesis of butacaine

See also

References

  1. ^ a b "Butacaine". Inxight Drugs. National Center for Advancing Translational Sciences.
  2. ^ Kurihara, Tozaburo; Niwa, Hiroshi; Chiba, Katsuichi (1954). "Synthesis of γ-Alkylaminopropanols". Yakugaku Zasshi. 74 (7): 763–766. doi:10.1248/yakushi1947.74.7_763.
  3. ^ Burnett, W. B.; Jenkins, R. L.; Peet, C. H.; Dreger, E. E.; Adams, Roger (1937). "Dialkylaminoalkanol Esters of p-Aminobenzoic Acid". Journal of the American Chemical Society. 59 (11): 2248–2252. doi:10.1021/ja01290a041.
  4. ^ Kaye, Irving Allan; Roberts, I. Melville (1951). "Dialkylaminoalkyl Esters of 2-Amino-6-carboxybenzothiazole". Journal of the American Chemical Society. 73 (10): 4762–4764. doi:10.1021/ja01154a084.
  5. ^ Oliver Kamm, Roger Adams, Volwiler Ernest H., U.S. patent 1,358,751 (1920 to Abbott Lab)
  6. ^ Adams Roger, Ernest H Volwiler, U.S. patent 1,676,470 (1928 to Abbott Lab)
  7. ^ Weston Arthur W, U.S. patent 2,437,984 (1948 to Abbott Lab)
  8. ^ Anon., GB 191122  (1922-12-27 to Abbott Lab).
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