prenalterol prenalterol prenalterol is a cardiac stimulant which acts as a β1 adrenoreceptor agonist. prenalterolclinical dataroutes ofadministrationoral, ivatc codec01ca13 (who) legal statuslegal status in general: ℞ (prescription only) identifiers iupac name 4-phenol cas number57526-81-5 npubchem cid42396iuphar/bps537chemspider38665 yuniim4g34404cxchemblchembl1160714 ycomptox dashboard (epa)dtxsid8023507 echa infocard100.055.246 chemical and physical dataformulac12h19no3molar mass225.288 g·mol−13d model (jsmol)interactive image smiles o(c1ccc(o)cc1)c(o)cnc(c)c inchi inchi=1s/c12h19no3/c1-9(2)13-7-11(15)8-16-12-5-3-10(14)4-6-12/h3-6,9,11,13-15h,7-8h2,1-2h3/t11-/m0/s1 ykey:adukccwbedsmeb-nshdsacasa-n y ny (what is this?) (verify) synthesis stereospecific prenalterol exhibits adrenergic agonist activity in spite of an interposed oxymethylene group. the stereospecific synthesis devised for this molecule relies on the fact that the side chain is very similar in oxidation state to that of a sugar. prenalterol synthesis: condensation of monobenzone (2) with the epoxide derived from α-d-glucofuranose affords the glycosylated derivative (3). hydrolytic removal of the acetonide protecting groups followed by cleavage of the sugar with periodate gives aldehyde (4). this is reduced to the glycol by means of nabh4 and the terminal alcohol is converted to the mesylate (5). displacement of the leaving group with isopropylamine followed by hydrogenolytic removal of the o-benzyl ether affords the β1-adrenergic selective adrenergic agonist prenalterol (6). racemic prepns of the racemic mixture: nl 6409883 corresp to h. köppe et al., u.s. patent 3,637,852 (1965, 1972 both to boehringer ingelheim); nl 301580 corresp to a. f. crowther, l. h. smith, u.s. patent 3,501,769 (1965, 1970 both to ici);