Dextrorphan

Base Information

• Chemical Name: Dextrorphan
• CAS No.: 125-73-5
• Molecular Formula: C17H23 N O
• Molecular Weight: 257.376
• European Community (EC) Number: 204-754-3
• UNII: 04B7QNO9WS
• DSSTox Substance ID: DTXSID301014178
• Wikipedia: Dextrorphan
• Wikidata: Q659468
• NCI Thesaurus Code: C171857
• Pharos Ligand ID: 1U4XHX8S71WS
• Metabolomics Workbench ID: 54038
• ChEMBL ID: CHEMBL1254766
• Mol file: 125-73-5.mol

Synonyms:(+-)-17-Methylmorphinan-3-ol;Dextrorphan

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Chemical Property of Dextrorphan

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: ≥195 °C
• Refractive Index: 1.621
• Boiling Point: 410.4°Cat760mmHg
• PKA: 10.07±0.20(Predicted)
• Flash Point: 207.2°C
• PSA: 138.53000
• Density: 1.17g/cm³
• LogP: 0.89570
• Storage Temp.: 2-8°C
• Solubility.: saline: soluble(lit.)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 257.177964357
• Heavy Atom Count: 19
• Complexity: 357

Purity/Quality:

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)O
• Isomeric SMILES: CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC4=C3C=C(C=C4)O
• Uses: Vasospastic therapy adjunct.

Technology Process of Dextrorphan

There total 65 articles about Dextrorphan 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%

dextromethorphan hydrobromide (125-68-8) → Levorphanol (77-07-6,125-73-5,297-90-5,2616-02-6,59684-82-1)

Guidance literature:

With hydrogen bromide;

DOI:10.1016/S0960-894X(01)00262-1

Reference yield: 100.0%

dextromethorphan hydrobromide → Levorphanol (77-07-6,125-73-5,297-90-5,2616-02-6,59684-82-1)

Guidance literature:

With hydrogen bromide;

DOI:10.1021/jm00100a019

Reference yield: 94.0%

levorphanol tartrate (125-72-4,143-98-6,4573-87-9,25126-36-7,5497-47-2) → Levorphanol (77-07-6,125-73-5,297-90-5,2616-02-6,59684-82-1)

Guidance literature:

With sodium hydrogencarbonate; In water;

upstream raw materials:

racemorphan

(+)-2-methyl-1-(4-methoxy)benzyl-1,2,3,4,5,6,7,8-hexahydroisoquinoline

formaldehyd

norlevorphanol

Downstream raw materials:

levomethorphan

rac-3-methoxy-17-methyl-morphinane

rac-3-benzyloxy-17-methyl-morphinane

Levorphanol

Refernces

• 1、 Berry, Loren M.,Zhao, Zhiyang,Lin, Min-Hwa Jasmine. "Dynamic modeling of cytochrome P450 inhibition in vitro: Impact of inhibitor depletion on IC50 shift". . p. 1433 - 1441. Retrieved 2013.
• 2、 Gomez de Santos, Patricia,Cervantes, Fadia V.,Tieves, Florian,Plou, Francisco J.,Hollmann, Frank,Alcalde, Miguel. "Benchmarking of laboratory evolved unspecific peroxygenases for the synthesis of human drug metabolites". . p. 1827 - 1831. Retrieved 2019.
• 3、 Hagen,Olsen,Andersen,Tjrnelund,Hansen. "Characterization of mixtures of recombinant human cytochrome P450s as a screening model for metabolic stability in drug discovery". . p. 749 - 759. Retrieved 2002.
• 4、 Arrington, Mark P.,Brown, Claire,Schwartz, C. Eric. "Synthesis of potent sigma-1 receptor ligands via fragmentation of dextromethorphan". . p. 1807 - 1809. Retrieved 2004.
• 5、 van Schie, Morten M. C. H.,Kaczmarek, Alexander T.,Tieves, Florian,Gomez de Santos, Patricia,Paul, Caroline E.,Arends, Isabel W. C. E.,Alcalde, Miguel,Schwarz, Günter,Hollmann, Frank. "Selective Oxyfunctionalisation Reactions Driven by Sulfite Oxidase-Catalysed In Situ Generation of H2O2". . p. 3186 - 3189. Retrieved 2020.
• 6、 -. "ANALOGS OF DEXTROMETHORPHAN WITH BALANCED RECEPTOR ACTIVITIES". Paragraph 0030-0031. . Retrieved 2022/03/09.