Norlevorphanol

Base Information

• Chemical Name: Norlevorphanol
• CAS No.: 1531-12-0
• Molecular Formula: C16H21 N O
• Molecular Weight: 243.349
• European Community (EC) Number: 216-236-4
• UNII: IL94262N7K,E4S6LA88PG
• DSSTox Substance ID: DTXSID701018239,DTXSID301336128
• Wikipedia: Norlevorphanol
• Wikidata: Q110184324
• NCI Thesaurus Code: C170233
• ChEMBL ID: CHEMBL3989483
• Mol file: 1531-12-0.mol

Synonyms:3-hydroxymorphinan;norlevorphanol;norlevorphanol hydrobromide;norlevorphanol, 9alpha,13alpha,14alpha-isomer

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Chemical Property of Norlevorphanol

Chemical Property:

• Appearance/Colour: White crystals
• Vapor Pressure: 9.55E-08mmHg at 25°C
• Melting Point: 268-269ºC
• Boiling Point: 422.8 °C at 760 mmHg
• Flash Point: 158.2 °C
• PSA: 32.26000
• Density: 1.19 g/cm³
• LogP: 4.02510
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 243.162314293
• Heavy Atom Count: 18
• Complexity: 331

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC23CCNC(C2C1)CC4=C3C=C(C=C4)O
• Isomeric SMILES: C1CC[C@@]23CCN[C@@H]([C@@H]2C1)CC4=C3C=C(C=C4)O

Technology Process of Norlevorphanol

There total 16 articles about Norlevorphanol 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: 70.0%

(-)-3-Methoxymorphinan (1531-25-5) → norlevorphanol (1531-12-0)

Guidance literature:

With 47 percent aq.;

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

Reference yield:

Levorphanol (77-07-6,125-73-5,297-90-5,2616-02-6,59684-82-1) → norlevorphanol (1531-12-0)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / CHCl₃ / Heating

2: 10 percent aq. NaOH / methanol

3: AcOH; 12 N aq. HCl / Heating

With hydrogenchloride; sodium hydroxide; potassium carbonate; acetic acid; In methanol; chloroform;

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

Reference yield:

C19H25NO3 (58434-39-2) → norlevorphanol (1531-12-0)

Guidance literature:

With hydrogenchloride; acetic acid; Heating;

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

upstream raw materials:

(+)-3-methoxy-N-formylmorphinan

(-)-3-Methoxymorphinan

C₁₉H₂₅NO₃

Levorphanol

Downstream raw materials:

17-(2-cyclohex-1-enyl-ethyl)-morphinan-3-ol

17-(3-phenyl-prop-2-ynyl)-morphinan-3-ol

17-(4-nitro-phenethyl)-morphinan-3-ol

17-(3-phenyl-propyl)-morphinan-3-ol

Refernces

• 1、 Bonn, Britta,Masimirembwa, Collen M.,Castagnoli Jr., Neal. "Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan". experimental part. p. 187 - 199. Retrieved 2010/12/24.
• 2、 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.