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Burimamide

Summary

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
Skeletal formula
Ball-and-stick model
Names
IUPAC name
1-[4-(1H-imidazol-5-yl)butyl]-3-methylthiourea
Identifiers
  • 34970-69-9 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL12160 checkY
ChemSpider
  • 2297780 checkY
KEGG
  • C07448 checkY
  • 3032915
UNII
  • TN5A4OD2TV checkY
  • DTXSID00188519 Edit this at Wikidata
  • 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).
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Infobox references

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 edit

References edit

  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. ^ a b "Tagamet: Discovery of Histamine H2-receptor Antagonists". National Historic Chemical Landmarks. American Chemical Society. Archived from the original on December 9, 2012. Retrieved June 25, 2012.