101467-40-7

Basic information

• Product Name: (S)-7-METHOXY-1-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL
• Synonyms: SALSOLINE;(S)-7-METHOXY-1-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL;BAS 00867600;BSPBio_002846;CBDivE_000261;DivK1c_006710;EINECS;KBio1_001654
• CAS NO: 101467-40-7
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• EINECS: 201-897-3
• Mol File: 101467-40-7.mol

Chemical Properties

• Melting Point: 221°
• Boiling Point: 336.7°Cat760mmHg
• Flash Point: 157.4°C
• Appearance: /
• Density: 1.106g/cm³
• Vapor Pressure: 5.65E-05mmHg at 25°C
• Refractive Index: 1.542
• CAS DataBase Reference: (S)-7-METHOXY-1-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-7-METHOXY-1-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL(101467-40-7)
• EPA Substance Registry System: (S)-7-METHOXY-1-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL(101467-40-7)

Safety Data

• Hazardous Substances Data: 101467-40-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-7-METHOXY-1-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL is used as an active compound in the development of new pharmaceuticals for various therapeutic applications. Its presence in Tibetan Medicine, as identified by HPLC-Q-TOF/MS, suggests potential traditional uses and therapeutic properties.
Used in Chemical Synthesis:
(S)-7-METHOXY-1-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL can be used as a starting material or intermediate in the synthesis of other complex organic compounds, particularly in the field of medicinal chemistry and drug development.
Used in Analytical Chemistry:
The alkaloid can be employed as an analyte in high-performance liquid chromatography (HPLC) and mass spectrometry (MS) for the identification and quantification of compounds in various samples, including those from traditional medicines and natural sources.
Used in Research and Development:
(S)-7-METHOXY-1-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL serves as a valuable compound for researchers to study its chemical properties, reactivity, and potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.

References

Orekhov, Proskurnina., Ber., 66,841 (1933) Orekhov, Proskurnina., ibid, 67,878 (1934) Spath, Orekhov, Kuffner., ibid, 67, 1214 (1934)

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-/m1/s1

Upstream product

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

Downstream Products

• 89-31-6 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 articles and documents

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