Burimamide

{{chembox

| Watchedfields = changed

| verifiedrevid = 443491066

| ImageFile = Burimamide.svg

| ImageSize = 222

| ImageAlt = Skeletal formula

| ImageFile1 = File:Burimamide-from-xtal-3D-bs.png

| ImageSize1 = 220

| ImageAlt1 = Ball-and-stick model

| IUPACName = 1-[4-(1H-imidazol-5-yl)butyl]-3-methylthiourea

| OtherNames =

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2297780

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C07448

| 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)

| InChIKey = HXRBAVXGYZUSED-UHFFFAOYAJ

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 12160

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HXRBAVXGYZUSED-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 34970-69-9

| PubChem = 3032915

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = TN5A4OD2TV

| SMILES = CNC(=S)NCCCCc1c[nH]cn1

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| Section2 = {{Chembox Properties

| Formula = C₉H₁₆N₄S

| MolarMass = 212.32 g/mol

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| Section3 = {{Chembox Hazards

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Burimamide is an antagonist at the H₂ and H₃ histamine receptors. At physiological pH, it is largely inactive as an H₂ antagonist,{{Clayden|page=205}} 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.{{cite web |url = http://portal.acs.org/portal/PublicWebSite/education/whatischemistry/landmarks/cimetidinetagamet/ |title = Tagamet: Discovery of Histamine H₂-receptor Antagonists |publisher = American Chemical Society |work = National Historic Chemical Landmarks |access-date = June 25, 2012 |url-status = dead |archive-url = https://archive.today/20121209003707/http://portal.acs.org/portal/PublicWebSite/education/whatischemistry/landmarks/cimetidinetagamet/ |archive-date = December 9, 2012 }} The discovery of burimamide ultimately led to the development of cimetidine (Tagamet).