Ecgonine methyl ester hydrochloride

Base Information

• Chemical Name: Ecgonine methyl ester hydrochloride
• CAS No.: 38969-40-3
• Deprecated CAS: 335332-48-4
• Molecular Formula: C10H18ClNO3
• Molecular Weight: 235.711
• European Community (EC) Number: 689-136-5
• UNII: VY81V42YYZ
• DSSTox Substance ID: DTXSID10959818
• Wikidata: Q27292094
• Mol file: 38969-40-3.mol

Synonyms:Ecgonine methyl ester hydrochloride;38969-40-3;Methl ester of ecognine hydrochloride;Methylecognine hydrochloride;UNII-VY81V42YYZ;VY81V42YYZ;N 588;Ecognine methyl ester hydrochloride;3-beta-Hydroxy-1-alpha-H,5-alpha-H-tropane-2-beta-carboxylic acid methyl ester hydrochloride;1-alpha-H,5-alpha-H-Tropane-2-beta-carboxylic acid, 3-beta-hydroxy-, methyl ester, hydrochloride;(-)-Ecgonine methyl ester hydrochloride;8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 3-HYDROXY-8-METHYL-, METHYL ESTER, HYDROCHLORIDE (1:1), (1R,2R,3S,5S)-;8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-hydroxy-8-methyl-, methyl ester, hydrochloride (1:1), (1R,2R,3S,5S)-;C10H17NO3.ClH;SCHEMBL3315340;DTXSID10959818;AKOS030254779;ECGONINE METHYLESTER HYDROCHLORIDE;METHYLESTER HYDROCHLORIDE ECGONINE;LS-157767;Q27292094;3.BETA.-HYDROXY-2.BETA.-TROPANECARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE;Methyl 3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate--hydrogen chloride (1/1)

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

Chemical Property of Ecgonine methyl ester hydrochloride

Chemical Property:

• Vapor Pressure: 7.54E-05mmHg at 25°C
• Boiling Point: 305.8°Cat760mmHg
• Flash Point: 138.7°C
• PSA: 49.77000
• Density: g/cm³
• LogP: 0.74290
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 235.0975211
• Heavy Atom Count: 15
• Complexity: 244

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CCC1C(C(C2)O)C(=O)OC.Cl
• Isomeric SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)O)C(=O)OC.Cl
• Uses: (-)-Ecgonine Methyl Ester is the methyl ester derivative of (-)-Ecgonine (E325550) and an important metabolite of Cocaine (C633500). Controlled Substance.

Technology Process of Ecgonine methyl ester hydrochloride

There total 8 articles about Ecgonine methyl ester hydrochloride 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: 100.0%

methanol (67-56-1) + tert-butyl (1R,2S,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate (1393359-56-2) → methyl (1R,2S,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride (38969-40-3,65027-05-6,79735-03-8,93738-78-4,93738-79-5,112574-29-5,112652-63-8,131722-69-5)

Guidance literature:

With thionyl chloride; at 50 ℃; for 5h; Inert atmosphere;

DOI:10.1021/ol3020607

Reference yield:

(-)-cocaine hydrochloride (53-21-4) → Ecgonine methyl ester hydrochloride (38969-40-3)

Guidance literature:

With hydrogenchloride; for 15h; Yield given; Heating;

DOI:10.1111/j.2042-7158.1984.tb06930.x

Reference yield:

(-)-cocaine hydrochloride (53-21-4) → Ecgonine methyl ester hydrochloride (38969-40-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.25M aq. HCl / Heating

2: HCl

With hydrogenchloride;

DOI:10.1016/S0960-894X(00)00659-4

upstream raw materials:

methanol

tert-butyl (1R,2S,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

tert-butyl (1S,2S,7R)-2-hydroxy-7-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}cyclohept-3-ene-1-carboxylate

tert-butyl (1R,2S,3R,4R,5S)-3-hydroxy-4-iodo-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Downstream raw materials:

(+)-Allopseudococaine hydrochloride

(+)-cocaine

ecgonine

(1R,2R,3S,5S)-methyl 3-(((benzyloxy)(phenyl)phosphoryl)oxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Refernces

• 1、 Matsushita, Masayuki,Hoffman, Timothy Z.,Ashley, Jon A.,Zhou, Bin,Wirsching, Peter,Janda, Kim D.. "Cocaine catalytic antibodies: The primary importance of linker effects". . p. 87 - 90. Retrieved 2007/10/03.