89-31-6

Usage

Uses

antihypertensive, antihistamine

InChI:InChI=1/C11H15NO2/c1-7-9-6-11(14-2)10(13)5-8(9)3-4-12-7/h5-7,12-13H,3-4H2,1-2H3/t7-/m0/s1

Upstream product

• 645-33-0 3-hydroxy-4-methoxy-β-phenethylamine hydrochloride 
• 75-07-0 acetaldehyde 
• 525-72-4 (+/-)-salsolinol 
• 36455-21-7 3-benzyloxy-4-methoxyphenylethylamine 
• 6857-58-5 6-benzyloxy-7-methoxy-1-methyl-3,4-dihydroisoquinoline 
• 350586-97-9 [2-(3-benzyloxy-4-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester 
• 350586-92-4 benzyl (6-benzyloxy-7-methoxy-1-methyl-3,4-dihydro-1H-isoquinoline)-2-carboxylate 
• 51745-26-7 (+/-)-6-benzyloxy-1,2,3,4-tetrahydro-7-methoxy-1-methylisoquinoline 
• 186581-53-3 diazomethane 
• 55161-43-8 N-{2-[3-(benzyloxy)-4-methoxyphenyl]ethyl}acetamide 
• 89-31-6 rac-salsoline 
• 63909-29-5 3-benzyloxy-4-methoxy-β-nitrostyrene 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 

Downstream Products

• 101467-40-7 (R)-(+)-salsoline 
• 1607833-80-6 6-methyl-8-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one 
• 350586-87-7 rac-bernumicine 

Relevant academic research and scientific papers

Total synthesis of bernumicine and bernumidine, two alkaloids from Berberis nummularia

Bernumicine and bernumidine are two alkaloids extracted from Berberis nummularia. Their total synthesis has been completed and it has been shown that the configuration of the stereogenic carbon of both is (R).

METABOLISM OF SALSOLINOL BY TISSUE CULTURES OF SOME PAPAVERACEAE

(+/-)-Salsolinol, a substance possibly inducing Parkinsonism and alcoholism, was transformed into the 6- and 7-O-monomethylated salsolinols by various plant tissue cultures of Papaveraceae.Only 6-O-methylsalsolinol was further N-methylated to provide N-methylisosalsoline.Key Word Index - Corydalis ochotensis; C. opliocarpa; Macleaya cordata; Papaveraceae; tissue cultures; metabolism; isoquinoline alkaloid; salsolinol.

Quinolizidines. VIII. Structure and Synthesis of the Alangium Alkaloid Alangicine: Syntheses of (+/-)- and (+)-Alangicines

The first total synthesis of alangicine (3), an Alangium lamarckii alkaloid, has been achieved in the form of a racemic modification by means of an initial alkaline hydrolysis of the (+/-)-tricyclic ester 6 and succeeding steps proceeding through the intermediates (+/-)-7, (+/-)-10, and (+/-)-9.A parallel synthetic route starting with the (-)-tricyclic ester 6, derived from (+)-cincholoipon ethyl ester (8), produced the chiral target molecule (+)-3 via the intermediates (-)-7, (-)-10, and 9.The identity of the synthetic (+)-3 with alangicine unequivocally established the structure and absolute stereochemistry of this alkaloid.The (13)C nuclear magnetic resonance spectra of (+/-)-alangicine (3) and the ipecac and Alangium alkaloid psychotrine (18) confirmed their endocyclic double bond structures in the dihydroisoquinoline moiety.Catalytic reductions of 11, (+/-)-12, and 15 using hydrogen and Pd-C were investigated, and the results have shown that hydrogenolysis of the benzyloxy group proceeds much faster than saturation of the endocyclic C=N bond.Keywords - alangicine; psychotrine; structure; absolute configuration; stereoselective synthesis; (13)C NMR; CD; benzyl ether; hydrogenolysis