Laudanosine

Base Information

• Chemical Name: Laudanosine
• CAS No.: 1699-51-0
• Molecular Formula: C21H27 N O4
• Molecular Weight: 357.45
• Hs Code.: 2933499090
• European Community (EC) Number: 220-253-2,216-923-9
• NSC Number: 331268,94267,35045
• DSSTox Substance ID: DTXSID00871873
• Nikkaji Number: J10.989D
• Wikipedia: Laudanosine
• Wikidata: Q27163429
• Metabolomics Workbench ID: 123449
• ChEMBL ID: CHEMBL1407
• Mol file: 1699-51-0.mol

Synonyms:laudanosine

Chemical Property of Laudanosine

Chemical Property:

• Vapor Pressure: 6.19E-09mmHg at 25°C
• Melting Point: 115°C
• 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
• 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:

98%min ^*data from raw suppliers

DL-Laudanosine ^*data from reagent suppliers

Safty Information:

• Statements: 26/28-40
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)OC)OC)OC
• Description: This opium alkaloid occurs in the liquor following precipitation of Thebaine (q.v.) and is purified by extraction with small quantities of Et20, followed by precipitation with potassium iodide. The base crystallizes from hot C6H6 in small, colourless needles and has [α]15D+ 103.23° (EtOH). It is freely soluble in CHCI3, EtOH, Et20 or hot C6H6 but insoluble in H20 or alkalies. No colour is produced with FeCl 3 but with Fe203 and H2S04, a brown colour is formed, changing to green when warmed to ISOoC. With concentrated H2S04 alone, the alkaloid gives a rose-red colour, changing to deep violet at ISO°C. The solution of the alkaloid in EtOH is alkaline to litmus and both it, and its salts, are bitter to the taste. The crystalline methiodide has m.p. 218-221°C; [α]D + 120°. The oxidation products with Mn02 and H2S04 are veratraldehyde, 2:3:6:7- tetramethoxy-9: I O-dihydroanthracene and laudaline (4: S-dimethoxy-2: - methylaminoethylbenzaldehyde, m.p. 123-4°C. On exhaustive methylation it yields trimethylamine and laudanosene (tetramethoxy-o-vinylstilbene). Laudanosine is one of the most convulsant of the opium alkaloids but possesses only a slight analgesic action.

Technology Process of Laudanosine

There total 62 articles about 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: 91.0%

(+/-)-1-(3,4-dimethoxybenzyl)-2-ethoxycarbonyl-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline (50461-24-0) → laudanosine (1699-51-0,20412-65-1)

Guidance literature:

With lithium aluminium tetrahydride;

DOI:10.1016/j.tetlet.2007.09.073

Reference yield: 89.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + Tetrahydropapaverine (13074-31-2) → laudanosine (1699-51-0,20412-65-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; water; Ambient temperature; 1) 1 h 2) 18 h;

DOI:10.1002/jhet.5570280720

Reference yield: 89.0%

cis-(+/-)laudanosine N-oxide (74904-62-4,74904-66-8,81872-02-8,106488-66-8,112531-10-9,112531-11-0) → laudanosine (1699-51-0,20412-65-1)

Guidance literature:

With hydrogenchloride; zinc; for 2h; Heating;

DOI:10.1071/CH9800379c

upstream raw materials:

Papaverine

2-Methylpapaverinium iodide

2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

4-chloromethyl-1,2-dimethoxy-benzene

Downstream raw materials:

(R)-laudanosine

2-(β-N-Benzyloxycarbonyl-N-methyl-aminoethyl)-4,5,3',4'-tetramethoxystilbene

2-(β-N-2,2,2-Trichloroethoxycarbonyl-N-methyl-aminoethyl)-4,5,3',4'-tetramethoxystilbene

2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Refernces

• 1、 Arndt,Baarschers. "-". . p. 2244,2247. Retrieved 1964.
• 2、 Groenewoud,Robinson. "-". . p. 199,201. Retrieved 1936.
• 3、 Tomita et al.. "-". . . Retrieved 1958.
• 4、 Jangir, Ravi,Argade, Narshinha P.. "Total Synthesis of Tetrahydroisoquinoline-Based Bioactive Natural Products Laudanosine, Romneine, Glaucine, Dicentrine, and Their Unnatural Analogues Isolaudanosine and Isoromneine". . p. 1655 - 1663. Retrieved 2017/03/21.
• 5、 Li, Xiabing,Leonori, Daniele,Sheikh, Nadeem S.,Coldham, Iain. "Synthesis of 1-substituted tetrahydroisoquinolines by lithiation and electrophilic quenching guided by in situ IR and NMR spectroscopy and application to the synthesis of salsolidine, carnegine and laudanosine". supporting information. p. 7724 - 7730. Retrieved 2013/07/19.