Article · Wikipedia archive · Last revised Jul 18, 2026

Burimamide

Burimamide is an antagonist at the H2 and H3 histamine receptors. At physiological pH, it is largely inactive as an H2 antagonist, but its H3 affinity is 100x higher. It is a thiourea derivative.

Last revised
Jul 18, 2026
Read time
≈ 1 min
Length
206 w
Citations
3
Source
Wikipedia ↗
Burimamide
Skeletal formula
source ↗
Ball-and-stick model
source ↗
Names
IUPAC name
1-[4-(1H-imidazol-5-yl)butyl]-3-methylthiourea
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C9H16N4S/c1-10-9(14)12-5-3-2-4-8-6-11-7-13-8/h6-7H,2-5H2,1H3,(H,11,13)(H2,10,12,14) checkY
    Key: HXRBAVXGYZUSED-UHFFFAOYSA-N checkY
  • InChI=1/C9H16N4S/c1-10-9(14)12-5-3-2-4-8-6-11-7-13-8/h6-7H,2-5H2,1H3,(H,11,13)(H2,10,12,14)
    Key: HXRBAVXGYZUSED-UHFFFAOYAJ
  • CNC(=S)NCCCCc1c[nH]cn1
Properties
C9H16N4S
Molar mass 212.32 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkYX markN ?)

Burimamide is an antagonist at the H2 and H3 histamine receptors. At physiological pH, it is largely inactive as an H2 antagonist,1 but its H3 affinity is 100x higher. It is a thiourea derivative.

Burimamide was first developed by scientists at Smith, Kline & French (SK&F; now GlaxoSmithKline) in their intent to develop a histamine antagonist for the treatment of peptic ulcers.2 The discovery of burimamide ultimately led to the development of cimetidine (Tagamet).2

See also

See also

References

References

  1. Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. p. 205. ISBN 978-0-19-850346-0.
  2. "Tagamet: Discovery of Histamine H2-receptor Antagonists". National Historic Chemical Landmarks. American Chemical Society. Retrieved June 25, 2012.{{cite web}}: CS1 maint: deprecated archival service (link)