Levomethorphan

Base Information

• Chemical Name: Levomethorphan
• CAS No.: 125-71-3
• Deprecated CAS: 1527-45-3,3894-26-6,5822-42-4,879724-84-2
• Molecular Formula: C18H25NO
• Molecular Weight: 271.403
• Hs Code.: 2933492250
• 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: 125-71-3.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:

• Vapor Pressure: 1.92E-06mmHg at 25°C
• Melting Point: 80 °C
• Refractive Index: 1.585
• Boiling Point: 394.9 °C at 760 mmHg
• PKA: pKa 8.3 (Uncertain)
• Flash Point: 116.2 °C
• PSA: 12.47000
• Density: 1.11 g/cm³
• LogP: 3.32130
• Storage Temp.: ?20°C
• Water Solubility.: 12mg/L(temperature not stated)
• 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:

99% , ^*data from raw suppliers

Dextromethorphan ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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
• Description: Dextromethorphan is an over-the-counter drug that is sold alone and in combination with other products as a cough suppressant for children and adults. We have previously recommended dextromethorphan as a safe and effective cough suppressant for both children and adults. However, the weight of the evidence now suggests that dextromethorphan is no more effective than an inactive placebo syrup in suppressing a nighttime cough in children. It is the disomer of the potent opiate analgesic 3-methoxyN-methylmorphine (levorphanol). Although dextromethorphan is structurally related to opioids, it is devoid of analgesic or sedative effects at therapeutic doses. Dextromethorphan is metabolized by CYP2D6 to a more potent metabolite, dextrorphan. Dextrorphan is a stronger noncompetitive antagonist than dextromethorphan for the N-methyl-D-aspartate (NMDA) glutamate receptor.These properties promote its use in treatment of neuropathic and postoperative pain management.
• Uses: Dextromethorphan is used therapeutically as an over-thecounter cough suppressant and antitussive. It is also commonly abused particularly by adolescents because of its relative ease of availability.
• Indications: Dextromethorphan is used in treating nonproductive cough. It is available widely in a variety of nonprescription forms, such as capsules, lozenges, syrups, extended-release oral suspension, and chewable tablets. This drug possesses a pronounced anticough effect and minimal action on the CNS. It is not addictive.
• Biological Functions: Dextromethorphan hydrobromide is the D-isomer of levorphanol. It lacks CNS activity but acts at the cough center in the medulla to produce an antitussive effect. It is half as potent as codeine as an antitussive. Anecdotal reports of abuse exist, but studies of abuse potential are lacking. It has few side effects but does potentiate the activity of monoamine oxidase inhibitors, leading to hypotension and infrequently coma. Dextromethorphan is often combined in lozenges with the local anesthetic benzocaine, which blocks pain from throat irritation due to coughing.

Technology Process of Levomethorphan

There total 29 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: 100.0%

dextromethorphan hydrobromide → dextromethorphan (125-71-3,1453167-99-1)

Guidance literature:

With sodium hydroxide; In water; pH=10; Inert atmosphere;

DOI:10.1021/jacs.6b09690

Reference yield: 97.98%

dextromethorphan hydrobromide, monohydrate (6700-34-1) → dextromethorphan (125-71-3,1453167-99-1)

Guidance literature:

With sodium hydroxide; In chloroform; water; for 0.5h;

DOI:10.1016/j.bmc.2014.10.036

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

upstream raw materials:

rac-3-methoxy-17-methyl-morphinane

(9α,13α,14α)-3-methoxy-17-methylmorphinan-10-one

(+)-3-methoxy-N-formylmorphinan

trimethylphenylammonium hydroxide

Downstream raw materials:

ent-(17Ξ)-17-benzyl-3-methoxy-17-methyl-morphinanium; bromide

(9α,13α,14α)-3-methoxy-17-methylmorphinan-10-one

dextromethorphan N-oxide

levomethorphan

Refernces

• 1、 -. "A process for preparing dextromethorphan method". . . Retrieved 2018/02/04.
• 2、 Barham, Joshua P.,John, Matthew P.,Murphy, John A.. "Contra-thermodynamic Hydrogen Atom Abstraction in the Selective C-H Functionalization of Trialkylamine N-CH3 Groups". supporting information. p. 15482 - 15487. Retrieved 2016/12/09.