Levomethorphan

Base Information

• Chemical Name: Levomethorphan
• CAS No.: 510-53-2
• Deprecated CAS: 1527-45-3,3894-26-6,5822-42-4,879724-84-2
• Molecular Formula: C₁₈H₂₅NO
• Molecular Weight: 271.403
• 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: 510-53-2.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

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Chemical Property of Levomethorphan

Chemical Property:

• Boiling Point: 394.9°Cat760mmHg
• Flash Point: 116.2°C
• Density: 1.11g/cm³
• 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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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

Technology Process of Levomethorphan

There total 13 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: 95.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 3-Hydroxy-N-methylmorphinan (888939-18-2) → dextromethorphan (125-70-2,125-71-3,510-53-2,3561-92-0,1453167-99-1)

Guidance literature:

In methanol; chloroform; water; for 15h; Ambient temperature;

DOI:10.1002/ardp.19853180804

Reference yield:

1-(4-Methoxybenzyl)-2-methyl-5,6,7,8-tetrahydroisochinoliniumiodide (98237-33-3) → dextromethorphan (125-70-2,125-71-3,510-53-2,3561-92-0,1453167-99-1)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄, NaOH / aq. ethanol / 15 h / Ambient temperature

2: 79 percent / 48percent aq. HBr / 40 h / 140 °C

3: 95 percent / CHCl₃; methanol; H₂O / 15 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; hydrogen bromide; In methanol; ethanol; chloroform; water;

DOI:10.1002/ardp.19853180804

Reference yield:

1-(p-methoxybenzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline (38969-65-2,31414-58-1) → dextromethorphan (125-70-2,125-71-3,510-53-2,3561-92-0,1453167-99-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / 48percent aq. HBr / 40 h / 140 °C

2: 95 percent / CHCl₃; methanol; H₂O / 15 h / Ambient temperature

With hydrogen bromide; In methanol; chloroform; water;

DOI:10.1002/ardp.19853180804

upstream raw materials:

diazomethane

racemorphan

trimethylphenylammonium hydroxide

1-(p-methoxybenzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline

Downstream raw materials:

levomethorphan

dextromethorphan

rac-(17Ξ)-3-methoxy-17-methyl-morphinane-17-oxide

C₁₇H₂₃NO

Refernces