bezitramide bezitramide bezitramide is an opioid analgesic. bezitramide itself is a prodrug which is readily hydrolyzed in the gastrointestinal tract to its active metabolite, despropionyl-bezitramide. bezitramide was discovered at janssen pharmaceutica in 1961. it is most commonly marketed under the trade name burgodin. bezitramideclinical dataroutes ofadministrationoralatc coden02ac05 (who) legal statuslegal status ca: schedule i de: anlage i (authorized scientific use only) us: schedule ii identifiers iupac name 4--2,2-diphenylbutanenitrile cas number15301-48-1pubchem cid61791drugbankdb01459 ychemspider55675 yunii3kxw0y310ichemblchembl2104149comptox dashboard (epa)dtxsid90165197 echa infocard100.035.744 chemical and physical dataformulac31h32n4o2molar mass492.623 g·mol−13d model (jsmol)interactive image smiles o=c(n2c1ccccc1n(c2=o)c5ccn(ccc(c#n)(c3ccccc3)c4ccccc4)cc5)cc inchi inchi=1s/c31h32n4o2/c1-2-29(36)35-28-16-10-9-15-27(28)34(30(35)37)26-17-20-33(21-18-26)22-19-31(23-32,24-11-5-3-6-12-24)25-13-7-4-8-14-25/h3-16,26h,2,17-22h2,1h3 ykey:flkwnffcssjanb-uhfffaoysa-n y (verify) the drug was pulled from the shelves in the netherlands in 2004 after fatal overdose cases, including one where a five-year-old child took one tablet from his mother's purse, ate it, and promptly died. bezitramide is regulated much the same as morphine in all known jurisdictions and is a schedule ii substance under the united states' controlled substances act of 1970, with an acscn of 9800 and zero annual manufacturing quota. however, as of may 2021, it has never been marketed in the united states. synthesis synthesis: patent: prec: the sn2 alkylation between 4-bromo-2,2-diphenylbutyronitrile (1) and 4-(2-oxo-1-benzimidazolinyl)-piperidine (2) with affords depropionylbezitramide (3). acylation with propanoic anhydride then completed the synthesis of bezitramide (4).