(S)-Laudanosine

Base Information

• Chemical Name: (S)-Laudanosine
• CAS No.: 2688-77-9
• Molecular Formula: C21H27 N O4
• Molecular Weight: 357.45
• European Community (EC) Number: 220-253-2
• UNII: DA7R5WVN48
• DSSTox Substance ID: DTXSID30878577
• Nikkaji Number: J14.884I
• Wikipedia: Laudanosine
• Wikidata: Q408074
• Metabolomics Workbench ID: 67914
• ChEMBL ID: CHEMBL519894
• Mol file: 2688-77-9.mol

Synonyms:laudanosine

Chemical Property of (S)-Laudanosine

Chemical Property:

• Vapor Pressure: 6.19E-09mmHg at 25°C
• Melting Point: 89°
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 468.1°Cat760mmHg
• PKA: 7.80±0.40(Predicted)
• Flash Point: 131.2°C
• PSA: 40.16000
• Density: 1.111g/cm³
• LogP: 3.43060
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 357.19400834
• Heavy Atom Count: 26
• Complexity: 434

Purity/Quality:

99% ^*data from raw suppliers

(S)-Laudanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)OC)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)OC)OC)OC
• Uses: Laudanosine is a metabolite of the neuromuscular-blocking drugs Atracurium (A794500) and Cisatracurium (C496700) with potentially toxic systemic effects. It crosses the blood-brain barrier and may cause excitement and seizure activity.

Technology Process of (S)-Laudanosine

There total 66 articles about (S)-Laudanosine 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: 95.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + S-(-)-Norlaudanosine (4747-98-2) → (S)-laudanosine (2688-77-9,20412-65-1)

Guidance literature:

formaldehyd; S-(-)-Norlaudanosine; In methanol; at 20 ℃; for 0.5h; Inert atmosphere;

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 0.666667h; Inert atmosphere;

DOI:10.1021/jo201871c

Reference yield: 80.0%

(S)-1-<(3,4-Dimethoxyphenyl)methyl>-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (57651-56-6) → (S)-laudanosine (2688-77-9,20412-65-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 0.333333h; Heating;

DOI:10.1021/jo00081a007

Reference yield: 70.0%

(+)-O,O,O-Trimethylvateamine (87183-78-6) → (S)-(+)-1-(3-hydroxy-4-methoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (3122-95-0) + (S)-laudanosine (2688-77-9,20412-65-1)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; 1) -78 degC, 0.5-2 h, 2) warm to room temp.;

DOI:10.1021/jo00170a016

upstream raw materials:

laudanosine

diazomethane

(S)-(+)-1-(3',4'-dimethoxybenzyl)-6-hydroxy-7-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline

(+)-O,O,O-Trimethylvateamine

Downstream raw materials:

laudanosine

(R)-laudanosine

(+/-)-N-ethyl-Laudanosine iodide

2,3,6,7-tetramethoxy-9,10-dihydro-anthracene

Refernces

• 1、 Ruiz-Olalla, Andrea,Würdemann, Martien A.,Wanner, Martin J.,Ingemann, Steen,Van Maarseveen, Jan H.,Hiemstra, Henk. "Organocatalytic Enantioselective Pictet-Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids". . p. 5125 - 5132. Retrieved 2015/05/27.
• 2、 Ogata, Tokutaro,Kimachi, Tetsutaro,Yamada, Ken-Ichi,Yamamoto, Yasutomo,Tomioka, Kiyoshi. "Catalytic asymmetric synthesis of (S)-laudanosine by hydroamination". . p. 469 - 485. Retrieved 2013/08/23.