Norcocaine

Base Information

• Chemical Name: Norcocaine
• CAS No.: 18717-72-1
• Deprecated CAS: 887227-42-1
• Molecular Formula: C16H19NO4
• Molecular Weight: 289.331
• European Community (EC) Number: 633-760-2
• UNII: 3SL7BR2M1E
• DSSTox Substance ID: DTXSID80912319
• Nikkaji Number: J54.266K
• Wikipedia: Norcocaine
• Wikidata: Q7050488
• Mol file: 18717-72-1.mol

Synonyms:norcocaine;norcocaine acetate, (1R-(exo,exo))-isomer;norcocaine hydrochloride;norcocaine, (1R-(2-endo,3-exo))-isomer

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Chemical Property of Norcocaine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.11E-06mmHg at 25°C
• Melting Point: 77-82°C
• Boiling Point: 402.2 °C at 760 mmHg
• Flash Point: 197.1 °C
• PSA: 64.63000
• Density: 1.24 g/cm³
• LogP: 1.85430
• Storage Temp.: Controlled Substance, -20?C Freezer, Under Inert Atmosphere
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 289.13140809
• Heavy Atom Count: 21
• Complexity: 405

Purity/Quality:

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 60-26/27/28-43
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C2CCC(N2)CC1OC(=O)C3=CC=CC=C3
• Isomeric SMILES: COC(=O)[C@@H]1[C@H]2CC[C@H](N2)C[C@@H]1OC(=O)C3=CC=CC=C3
• Uses: A minor metabolite of Cocaine. Controlled substance.

Technology Process of Norcocaine

There total 9 articles about Norcocaine 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: 92.0%

Cocaine (50-36-2) → (-)-norcocaine (18717-72-1)

Guidance literature:

With carbonochloridic acid 1-chloro-ethyl ester; potassium carbonate; In methanol; 1,2-dichloro-ethane;

DOI:10.1021/jm0001121

Reference yield: 74.0%

(1R,2R,3S,5S)-3-Benzoyloxy-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester (69610-28-2) → (-)-norcocaine (18717-72-1)

Guidance literature:

With zinc; In acetic acid; for 48h;

DOI:10.1021/jo960373b

Reference yield: 56.0%

aqueous potassium permanganate + Cocaine (50-36-2) → (-)-norcocaine (18717-72-1)

Guidance literature:

With potassium carbonate; acetic acid; In water; acetonitrile;

upstream raw materials:

Cocaine

(1R,2R,3S,5S)-3-Benzoyloxy-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester

methanol

(-)-cocaine hydrochloride

Refernces

• 1、 De Jong, Mats,Sleegers, Nick,Florea, Anca,Van Loon, Joren,Van Nuijs, Alexander L. N.,Samyn, Nele,De Wael, Karolien. "Unraveling the Mechanisms behind the Complete Suppression of Cocaine Electrochemical Signals by Chlorpromazine, Promethazine, Procaine, and Dextromethorphan". . p. 15453 - 15460. Retrieved 2019.
• 2、 -. "Tropane analogs". Page/Page column 21-22; Sheet 3. . Retrieved 2010/02/15.