(-)-Salsoline

Base Information

• Chemical Name: (-)-Salsoline
• CAS No.: 89-31-6
• Molecular Formula: C11H15 N O2
• Molecular Weight: 193.246
• Hs Code.: 2933499090
• European Community (EC) Number: 201-897-3
• UNII: T246JT0V8K
• Nikkaji Number: J4.300A
• Wikidata: Q27105241
• Metabolomics Workbench ID: 42013
• ChEMBL ID: CHEMBL1187592
• Mol file: 89-31-6.mol

Synonyms:(+)-salsoline;(-)-salsoline;(S)-salsoline;1(R),2(N)-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline;7-O-methylsalsolinol;D-salosine;methylsalsolinol;N-methyl-(R)-salsolinol;salsoline;salsoline (-)-form;salsoline hydrochloride;salsoline hydrochloride, (R)-isomer;salsoline hydrochloride, (S)-isomer;salsoline hydrochloride, hydrate (4:4:1)

Chemical Property of (-)-Salsoline

Chemical Property:

• Vapor Pressure: 5.65E-05mmHg at 25°C
• Melting Point: 214-215°
• Refractive Index: 1.5041 (estimate)
• Boiling Point: 336.7°C at 760 mmHg
• Flash Point: 157.4°C
• PSA: 41.49000
• Density: 1.106g/cm³
• LogP: 1.93630
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 193.110278721
• Heavy Atom Count: 14
• Complexity: 198

Purity/Quality:

99% ^*data from raw suppliers

Salsoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2=CC(=C(C=C2CCN1)O)OC
• Isomeric SMILES: C[C@H]1C2=CC(=C(C=C2CCN1)O)OC
• Uses: antihypertensive, antihistamine

Technology Process of (-)-Salsoline

There total 15 articles about (-)-Salsoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

benzyl (6-benzyloxy-7-methoxy-1-methyl-3,4-dihydro-1H-isoquinoline)-2-carboxylate (350586-92-4) → rac-salsoline (89-31-6,20405-58-7,76419-97-1,101467-40-7)

Guidance literature:

With formic acid; hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 30h; under 760 Torr;

Reference yield: 89.0%

(+/-)-6-benzyloxy-1,2,3,4-tetrahydro-7-methoxy-1-methylisoquinoline (51745-26-7,123438-47-1) → rac-salsoline (89-31-6,20405-58-7,76419-97-1,101467-40-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 0.666667h;

Reference yield:

6-benzyloxy-7-methoxy-1-methyl-3,4-dihydroisoquinoline (6857-58-5) → rac-salsoline (89-31-6,20405-58-7,76419-97-1,101467-40-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / NaBH₄ / ethanol / 3 h / 0 °C

2: 89 percent / H₂ / 10percent Pd-C / ethanol / 0.67 h / 20 °C

With sodium tetrahydroborate; hydrogen; palladium on activated charcoal; In ethanol;

upstream raw materials:

rac-salsoline

N-{2-[3-(benzyloxy)-4-methoxyphenyl]ethyl}acetamide

3-hydroxy-4-methoxy-β-phenethylamine hydrochloride

acetaldehyde

Downstream raw materials:

(R)-(+)-salsoline

6-methyl-8-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

rac-bernumicine

Refernces

• 1、 Iwasa, K.,Kamigauchi, M.,Takao, N.. "METABOLISM OF SALSOLINOL BY TISSUE CULTURES OF SOME PAPAVERACEAE". . p. 2973 - 2976. Retrieved 2007/10/02.