levallorphan

Base Information

• Chemical Name: levallorphan
• CAS No.: 152-02-3
• Molecular Formula: C19H25 N O
• Molecular Weight: 283.414
• European Community (EC) Number: 205-799-1
• UNII: 353613BU4U
• DSSTox Substance ID: DTXSID9023205
• Wikipedia: Levallorphan
• Wikidata: Q6534827
• NCI Thesaurus Code: C66004
• Pharos Ligand ID: NDSKXMKUM7QA
• Metabolomics Workbench ID: 42848
• ChEMBL ID: CHEMBL1254682
• Mol file: 152-02-3.mol

Synonyms:2H-10,4a-Iminoethanophenanthren-6-ol,11-allyl-1,3,4,9,10,10a-hexahydro- (6CI); Morphinan-3-ol, 17-(2-propenyl)-(9CI); Morphinan-3-ol, 17-allyl- (8CI); (-)-3-Hydroxy-N-allylmorphinan;17-Allylmorphinan-3-ol; Levallorphan; MCL 113; N-Allyl-3-hydroxymorphinan;l-N-Allyl-3-hydroxymorphinan

Chemical Property of levallorphan

Chemical Property:

• Vapor Pressure: 4.02E-08mmHg at 25°C
• Melting Point: 180-182°
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 433.5°Cat760mmHg
• Flash Point: 214.2°C
• PSA: 23.47000
• Density: 1.14g/cm³
• LogP: 3.57450
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 283.193614421
• Heavy Atom Count: 21
• Complexity: 408

Purity/Quality:

98%min ^*data from raw suppliers

LEVALLORPHAN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCN1CCC23CCCCC2C1CC4=C3C=C(C=C4)O
• Isomeric SMILES: C=CCN1CC[C@]23CCCC[C@H]2[C@H]1CC4=C3C=C(C=C4)O

Technology Process of levallorphan

There total 24 articles about levallorphan 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: 82.0%

4-((S)-2-allyl-1,2,3,4,5,6,7,8-octahydro-[1]isoquinolylmethyl)-phenol → levallorphan (152-02-3)

Guidance literature:

With trifluorormethanesulfonic acid; acetic anhydride; at 35 - 40 ℃; for 6h; Inert atmosphere;

Reference yield: 61.0%

allyl bromide (106-95-6) + norlevorphanol (1531-12-0) → levallorphan (152-02-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00543-1

Reference yield:

Levorphanol (77-07-6,125-73-5,297-90-5,2616-02-6,59684-82-1) → levallorphan (152-02-3)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃ / CHCl₃ / Heating

2: 10 percent aq. NaOH / methanol

3: AcOH; 12 N aq. HCl / Heating

4: 61 percent / K₂CO₃ / dimethylformamide

With hydrogenchloride; sodium hydroxide; potassium carbonate; acetic acid; In methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00543-1

upstream raw materials:

allyl bromide

norlevorphanol

17-allyl-3-methoxy-morphinane

Levorphanol

Downstream raw materials:

C₁₆H₁₉NO₂

C₁₉H₂₅NO₂

C₁₉H₂₅NO₃

norlevorphanol

Refernces

• 1、 Neumeyer, John L,Gu, Xiao-Hui,Van Vliet,DeNunzio, Nicholas J,Rusovici, Daniela E,Cohen, Dana J,Negus,Mello, Nancy K,Bidlack, Jean M. "Mixed κ agonists and μ agonists/antagonists as potential pharmacotherapeutics for cocaine abuse: Synthesis and opioid receptor binding affinity of N-substituted derivatives of morphinan". . p. 2735 - 2740. Retrieved 2007/10/03.