Burimamide

Burimamide

Names
IUPAC name 1-[4-(1H-imidazol-5-yl)butyl]-3-methylthiourea
Identifiers
CAS Number	34970-69-9  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL12160  Y
ChemSpider	2297780  Y
KEGG	C07448  Y
PubChem CID	3032915
UNII	TN5A4OD2TV  Y
CompTox Dashboard (EPA)	DTXSID00188519
InChI 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) Y Key: HXRBAVXGYZUSED-UHFFFAOYSA-N Y 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
SMILES CNC(=S)NCCCCc1c[nH]cn1
Properties
Chemical formula	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). Y  verify  (what is  YN ?) Infobox references

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

• Metiamide
• Cimetidine

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. Archived from the original on December 9, 2012. Retrieved June 25, 2012.