Butacaine

Butacaine
Names
	Preferred IUPAC name 3-(Dibutylamino)propyl 4-aminobenzoate
Identifiers
CAS Number	149-16-6;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL129529;
ChemSpider	2386;
ECHA InfoCard	100.005.214
PubChem CID	2480;
UNII	Z84S23CGJJ ;
CompTox Dashboard (EPA)	DTXSID3045300 ;
	InChI 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;
	SMILES O=C(OCCCN(CCCC)CCCC)c1ccc(N)cc1;
Properties
Chemical formula	C18H30N2O2
Molar mass	306.450 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Butacaine is a white crystalline ester used as a local anesthetic.^[1] It was first marketed in 1920.^[1]

Synthesis

The addition of metallic sodium is added to a mixture of allyl alcohol (1) and dibutylamine (2)^[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).^[3]^[4]^[5]^[6]^[7]^[8]

References

^ ^a ^b "Butacaine". Inxight Drugs. National Center for Advancing Translational Sciences.
^ Kurihara, Tozaburo; Niwa, Hiroshi; Chiba, Katsuichi (1954). "Synthesis of γ-Alkylaminopropanols". Yakugaku Zasshi. 74 (7): 763–766. doi:10.1248/yakushi1947.74.7_763.
^ 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.
^ 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.
^ Oliver Kamm, Roger Adams, Volwiler Ernest H., U.S. patent 1,358,751 (1920 to Abbott Lab)
^ Adams Roger, Ernest H Volwiler, U.S. patent 1,676,470 (1928 to Abbott Lab)
^ Weston Arthur W, U.S. patent 2,437,984 (1948 to Abbott Lab)
^ Anon., GB 191122 (1922-12-27 to Abbott Lab).

[ncats-1] "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).

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

Synthesis

See also

References