Levomethorphan

Base Information

• Chemical Name: Levomethorphan
• CAS No.: 524713-56-2
• Deprecated CAS: 1527-45-3,3894-26-6,5822-42-4,879724-84-2
• Molecular Formula: C18H25NO
• Molecular Weight: 271.3972
• European Community (EC) Number: 208-114-4,204-751-7,803-955-9
• NSC Number: 751452
• UNII: 8YB8F78WM1,7ZZ22K9QE6
• DSSTox Substance ID: DTXSID60872402,DTXSID20872403
• Wikipedia: Methorphan,Levomethorphan
• Wikidata: Q60998690
• NCI Thesaurus Code: C152137,C83875
• Metabolomics Workbench ID: 125301
• ChEMBL ID: CHEMBL1908323
• Mol file: 524713-56-2.mol

Synonyms:d-Methorphan;Delsym;Dextromethorphan;Dextromethorphan Hydrobromide;Dextromethorphan Hydrobromide, (+-)-Isomer;Dextromethorphan Hydrobromide, Monohydrate;Dextromethorphan Hydrochloride;Dextromethorphan, (+-)-Isomer;Hydrobromide, Dextromethorphan;Hydrochloride, Dextromethorphan;l-Methorphan;Levomethorphan;Racemethorphan

Chemical Property of Levomethorphan

Chemical Property:

• Melting Point: 105-110°C
• Flash Point: 9℃
• PSA: 12.47000
• LogP: 3.32130
• Storage Temp.: -20°C Freezer
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 271.193614421
• Heavy Atom Count: 20
• Complexity: 370

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dextromethorphan-d3 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)OC
• Isomeric SMILES: CN1CC[C@]23CCCC[C@H]2[C@H]1CC4=C3C=C(C=C4)OC
• Uses: A labelled Dextromethorphan. An antitussive drug. Orally active synthetic morphine analog. Analgesic (narcotic).

Technology Process of Levomethorphan

There total 3 articles about Levomethorphan 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: 92.0%

dextromethorphan (125-71-3,1453167-99-1) → N-CD3-dextromethorphan (524713-56-2)

Guidance literature:

With deuterium; In tetrahydrofuran; for 36h; regioselective reaction; Glovebox; Inert atmosphere;

DOI:10.1002/anie.201307930

Reference yield: 51.5%

iodomethane-d3 (865-50-9) + (+)-3-methoxymorphinan (1531-23-3,1531-25-5,4163-20-6,28973-47-9,53593-66-1) → N-CD3-dextromethorphan (524713-56-2)

Guidance literature:

(+)-3-methoxymorphinan; With sodium hydride; In tetrahydrofuran; mineral oil; for 0.333333h; Inert atmosphere;

iodomethane-d3; In tetrahydrofuran; mineral oil; at 20 ℃; for 1h;

Reference yield:

(4bS,8aS,9S)-ethyl 3-methoxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate (524713-55-1) → N-CD3-dextromethorphan (524713-56-2)

Guidance literature:

With lithium aluminium deuteride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

upstream raw materials:

(4bS,8aS,9S)-ethyl 3-methoxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate

dextromethorphan

iodomethane-d3

(+)-3-methoxymorphinan

Refernces

• 1、 -. "COMPOSITIONS AND METHODS THEREOF". Paragraph 00536. . Retrieved 2018/03/25.