Norbuprenorphine

Base Information

• Chemical Name: Norbuprenorphine
• CAS No.: 78715-23-8
• Molecular Formula: C25H35 N O4
• Molecular Weight: 413.557
• UNII: 7E53B4O073
• DSSTox Substance ID: DTXSID60891436
• Wikipedia: Norbuprenorphine
• Wikidata: Q63396332
• ChEMBL ID: CHEMBL1743323
• Mol file: 78715-23-8.mol

Synonyms:des(cyclopropylmethyl)buprenorphine;N-desalkylbuprenorphine;norbuprenorphine

Chemical Property of Norbuprenorphine

Chemical Property:

• Vapor Pressure: 1.68E-13mmHg at 25°C
• Melting Point: 221-224°C
• Boiling Point: 562.7°C at 760 mmHg
• PKA: 9.14±0.60(Predicted)
• Flash Point: 294.1°C
• PSA: 70.95000
• Density: 1.27g/cm³
• LogP: 3.62020
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 413.25660860
• Heavy Atom Count: 30
• Complexity: 752

Purity/Quality:

99.9% ^*data from raw suppliers

Norbuprenorphine solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? ^*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: 16-36/37-45-7

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(C)(C1CC23CCC1(C4C25CCNC3CC6=C5C(=C(C=C6)O)O4)OC)O
• Isomeric SMILES: C[C@]([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN[C@@H]3CC6=C5C(=C(C=C6)O)O4)OC)(C(C)(C)C)O
• Description: Norbuprenorphine (CRM) (Item No. 20127) is a certified reference material categorized as an opioid. It is a major active metabolite of buprenorphine (Item Nos. 14025 | ISO60178). This product is intended for research and forensic applications.

Technology Process of Norbuprenorphine

There total 21 articles about Norbuprenorphine 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: 97.19%

N-cyano-7α-(1--hydroxy-1,2,2-trimethylpropyl)-6,14-endo-ethano-6,7,8,14-tetrahydronorthebaine → norbuprenorphine (78715-23-8)

Guidance literature:

With water; potassium hydroxide; In diethylene glycol; at 185 ℃; Product distribution / selectivity; Inert atmosphere;

Reference yield: 80.0%

(S)-2-((4R,4aS,6R,7R,7aR,12bS)-7,9-dimethoxy-1,2,3,4,5,6,7,7a-octahydro-4a,7-ethano-4,12-methanobenzofuro[3,2-e]isoquinolin-6-yl)-3,3-dimethylbutan-2-ol (22151-78-6,136232-87-6,16614-59-8) → norbuprenorphine (78715-23-8)

Guidance literature:

(S)-2-((4R,4aS,6R,7R,7aR,12bS)-7,9-dimethoxy-1,2,3,4,5,6,7,7a-octahydro-4a,7-ethano-4,12-methanobenzofuro[3,2-e]isoquinolin-6-yl)-3,3-dimethylbutan-2-ol; With water; potassium hydroxide; In diethylene glycol; at 185 ℃; for 5.25h;

With sulfuric acid; In water; diethylene glycol; at 90 ℃; pH=8.6;

Reference yield: 49.0%

(4R,4aR,7R,7aR,12bS,14R)-3-benzyl-14-((S)-2-hydroxy-3,3-dimethylbutan-2-yl)-7-methoxy-1,2,3,4,7,7a-hexahydro-7,4a-etheno-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol → norbuprenorphine (78715-23-8)

Guidance literature:

(4R,4aR,7R,7aR,12bS,14R)-3-benzyl-14-((S)-2-hydroxy-3,3-dimethylbutan-2-yl)-7-methoxy-1,2,3,4,7,7a-hexahydro-7,4a-etheno-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol; With palladium 10% on activated carbon; hydrogen; acetic acid; In water; isopropyl alcohol; at 60 ℃; for 72h;

With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; water; at 60 ℃; for 72h; under 760.051 Torr;

upstream raw materials:

[5α,7α]-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-α,17-dimethyl-6,14-ethenomorphinan-7-methanol

(S)-2-((4R,4aS,6R,7R,7aR,12bS)-7,9-dimethoxy-1,2,3,4,5,6,7,7a-octahydro-4a,7-ethano-4,12-methanobenzofuro[3,2-e]isoquinolin-6-yl)-3,3-dimethylbutan-2-ol

1-[(5α,7α)-3-methoxy-4,5-epoxy-18,19-dihydro-7-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-6,14-ethenomorphinan-17-yl]ethanone

[5α,7α]-17-acetyl-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-6-methoxy-α-methyl-6,14-ethenomorphinan-7-methanolamide

Downstream raw materials:

Buprenorphine

buprenorphine hydrochloride

(2S)-2-[(5R,6R,7R,14S)-N-cyclopropanoyl-4,5-epoxy-6,14-ethano-3-hydroxy-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol

Refernces

• 1、 -. "Demethylation of Reticuline and Derivatives Thereof with Fungal Cytochrome P450". Paragraph 0801; 0802; 0803; 0804. . Retrieved 2021/07/31.
• 2、 -. "PREPARATION OF BUPRENORPHINE". Paragraph 00374; 00375. . Retrieved 2018/12/13.