Ecgonine methyl ester

Base Information

• Chemical Name: Ecgonine methyl ester
• CAS No.: 7143-09-1
• Molecular Formula: C10H17NO3
• Molecular Weight: 199.25
• UNII: Y35FJB3QBJ
• DSSTox Substance ID: DTXSID00891435
• Nikkaji Number: J276.362A,J501.766A
• Wikipedia: Methylecgonine
• Wikidata: Q27095434
• Metabolomics Workbench ID: 54416
• ChEMBL ID: CHEMBL1232472
• Mol file: 7143-09-1.mol

Synonyms:ecgonine methyl ester;ecgonine methyl ester hydrochloride, (1R-(exo,exo))-isomer;ecgonine methyl ester, (1R-(2-endo,3-exo))-isomer;ecgonine methyl ester, (1R-(2-exo,3-endo))-isomer;ecgonine methyl ester, (1R-(endo,endo))-isomer;ecgonine methyl ester, (1S-(endo,endo))-isomer;methyl ecgonine

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Ecgonine methyl ester

Chemical Property:

• Vapor Pressure: 7.54E-05mmHg at 25°C
• Refractive Index: 1.518
• Boiling Point: 305.8 °C at 760 mmHg
• PKA: pKa 9.16(H2O t=25c=0.02) (Uncertain)
• Flash Point: 138.7 °C
• PSA: 49.77000
• Density: 1.181 g/cm³
• LogP: -0.05910
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 199.12084340
• Heavy Atom Count: 14
• Complexity: 244

Purity/Quality:

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CCC1C(C(C2)O)C(=O)OC
• Isomeric SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)O)C(=O)OC

Technology Process of Ecgonine methyl ester

There total 21 articles about Ecgonine methyl ester 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: 10.0%

methyl 8-methyl-3-oxo-8-azabicyclo<3.2.1>octan-2-carboxylate (36127-17-0,53955-90-1,85506-18-9,112574-77-3,112652-64-9,145414-58-0,149197-42-2) → methyl (endo, endo)-3-hydroxy-8-methyl-8-azabicyclo<3.2.1>octan-2-carboxylate (46255-79-2) + methyl (2-endo, 3-exo)-3-hydroxy-8-methyl-8-azabicyclo<3.2.1>octan-2-carboxylate (7143-09-1,46255-78-1,46255-79-2,50373-09-6,53955-92-3,65027-04-5,65913-90-8,67844-05-7,74562-04-2,106293-60-1,112574-75-1,112574-76-2,145414-57-9,149110-83-8)

Guidance literature:

With sodium tetrahydroborate; ammonium chloride; In ethanol; 1.) -60 deg C, 3 h, 2.) RT, overnight;

Reference yield:

(+/-)-cocaine (21206-60-0) → (+)-cocaine (47195-07-3) + S-(+)-ecgonine methyl ester (112574-76-2) + methyl ecgonine (7143-09-1) + Cocaine (50-36-2)

Guidance literature:

Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/0960-894X(96)00037-6

Reference yield:

(+/-)-cocaine (21206-60-0) → S-(+)-ecgonine methyl ester (112574-76-2) + methyl ecgonine (7143-09-1) + Cocaine (50-36-2)

Guidance literature:

With sodium hydroxide; pig liver esterase; water; at 37 ℃; for 7h; pH=7;

DOI:10.1016/S0014-827X(99)00027-0

upstream raw materials:

Cocaine

(+/-)-cocaine

(-)-cocaine hydrochloride

methanol

Downstream raw materials:

3-iodo-cocaine

3-<(2-iodobenzoyl)oxy>-8-methyl-<1R-(exo,exo)>-8-azabicyclo<3.2.1>octane-2-carboxylic acid methyl ester

3-hydroxy-cocaine

3-[(4-iodobenzoyl)oxy]-8-methyl-[1R-(exo,exo)]-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester

Refernces

• 1、 Isomura, Shigeki,Hoffman, Timothy Z.,Wirsching, Peter,Janda, Kim D.. "Synthesis, properties, and reactivity of cocaine benzoylthio ester possessing the cocaine absolute configuration". . p. 3661 - 3668. Retrieved 2007/10/03.
• 2、 Li, Pan,Zhao, Kang,Deng, Shixian,Landry, Donald W.. "Nonenzymatic hydrolysis of cocaine via intramolecular acid catalysis". . p. 85 - 89. Retrieved 2007/10/03.