38969-40-3

Usage

Uses

Used in Pharmaceutical Industry:
ECGONINE METHYL ESTER HYDROCHLORIDE is used as an intermediate compound for the synthesis of various pharmaceutical products. Its role in the synthesis process is crucial for developing medications with potential therapeutic applications.
Used in Research and Development:
In the field of research and development, ECGONINE METHYL ESTER HYDROCHLORIDE serves as a valuable compound for studying the properties and effects of its parent compound, cocaine, and its derivatives. This helps in understanding the mechanisms of action, potential risks, and benefits associated with cocaine and its related substances.
Used in Forensic Science:
ECGONINE METHYL ESTER HYDROCHLORIDE is utilized as a reference material in forensic science for the identification and analysis of cocaine and its metabolites in biological samples. This aids in the investigation of drug-related crimes and the assessment of drug use in individuals.
Used in Controlled Substance Regulation:
As a controlled substance, ECGONINE METHYL ESTER HYDROCHLORIDE is subject to strict regulations and monitoring by authorities. Its use is limited to specific applications, such as research and pharmaceutical development, to prevent misuse and ensure the safety of the public.

InChI:InChI=1/C10H17NO3.ClH/c1-11-6-3-4-7(11)9(8(12)5-6)10(13)14-2;/h6-9,12H,3-5H2,1-2H3;1H/t6-,7+,8-,9+;/m0./s1

Synthetic route

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

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

methanol (67-56-1) + ecgonine hydrochloride (5796-31-6) → Ecgonine methyl ester hydrochloride (38969-40-3)

Conditions	Yield
With hydrogenchloride

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

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.25M aq. HCl / Heating 2: HCl View Scheme

Ecgonine methyl ester hydrochloride (38969-40-3) → ecgonine (481-37-8)

Conditions	Yield
With phosphate buffer In water at 30℃; Kinetics; other reagents;

diazomethane (186581-53-3, 908094-01-9) + Ecgonine methyl ester hydrochloride (38969-40-3) → methyl ecgonine (7143-09-1)

Conditions	Yield
In methanol; diethyl ether Yield given;

C13H12ClO2P (50972-25-3) + Ecgonine methyl ester hydrochloride (38969-40-3) → (1R,2R,3S,5S)-methyl 3-(((benzyloxy)(phenyl)phosphoryl)oxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate (148533-52-2)

Conditions	Yield
Stage #1: Ecgonine methyl ester hydrochloride With lithium diisopropyl amide Stage #2: C13H12ClO2P

Ecgonine methyl ester hydrochloride (38969-40-3) → (1R,2R,3S,5S)-methyl 3-(((benzyloxy)(phenyl)phosphoryl)oxy)-8-azabicyclo[3.2.1]octane-2-carboxylate (148533-51-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: LDA 2.1: Troc-Cl; Et3N 2.2: Zn; HCO2H View Scheme

Ecgonine methyl ester hydrochloride (38969-40-3) → (1R,2R,3S,5S)-3-(Benzyloxy-phenyl-phosphinoyloxy)-8-(5-carboxy-pentyl)-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1.1: LDA 2.1: Troc-Cl; Et3N 2.2: Zn; HCO2H 3.1: Et3N / acetonitrile 4.1: TFA View Scheme

Ecgonine methyl ester hydrochloride (38969-40-3) → (1R,2R,3S,5S)-8-[5-(2-Carboxy-ethylcarbamoyl)-pentyl]-3-(hydroxy-phenyl-phosphinoyloxy)-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester

Conditions	Yield
Multi-step reaction with 6 steps 1.1: LDA 2.1: Troc-Cl; Et3N 2.2: Zn; HCO2H 3.1: Et3N / acetonitrile 4.1: TFA 5.1: EDC; HOBt 6.1: H2 / Pd/C View Scheme

Ecgonine methyl ester hydrochloride (38969-40-3) → (1R,2R,3S,5S)-3-(Benzyloxy-phenyl-phosphinoyloxy)-8-(5-tert-butoxycarbonyl-pentyl)-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester (148533-53-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: LDA 2.1: Troc-Cl; Et3N 2.2: Zn; HCO2H 3.1: Et3N / acetonitrile View Scheme

Ecgonine methyl ester hydrochloride (38969-40-3) → (1R,2R,3S,5S)-8-[5-(2-Benzyloxycarbonyl-ethylcarbamoyl)-pentyl]-3-(benzyloxy-phenyl-phosphinoyloxy)-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester

Conditions	Yield
Multi-step reaction with 5 steps 1.1: LDA 2.1: Troc-Cl; Et3N 2.2: Zn; HCO2H 3.1: Et3N / acetonitrile 4.1: TFA 5.1: EDC; HOBt View Scheme

Ecgonine methyl ester hydrochloride (38969-40-3) → 4-hydroxy-benzoylecgonine

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol; diethyl ether 2: Na2CO3 / benzene / 16 h / Heating 3: 0.1 M aq. NaOH / 12 h / Heating View Scheme

Ecgonine methyl ester hydrochloride (38969-40-3) → p-Acetoxycocaine (90899-21-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol; diethyl ether 2: Na2CO3 / benzene / 16 h / Heating View Scheme

Upstream product

• 67-56-1 methanol 
• 1393359-56-2 tert-butyl (1R,2S,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate 
• 1393359-52-8 tert-butyl (1S,2S,7R)-2-hydroxy-7-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}cyclohept-3-ene-1-carboxylate 
• 1393359-57-3 tert-butyl (1R,2S,3R,4R,5S)-3-hydroxy-4-iodo-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate 
• 1393359-48-2 tert-butyl (2S,3R)-2-[(1S)-1-hydroxyprop-2-en-1-yl]-3-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}hept-6-enoate 
• 270901-71-8 tert-butyl (E)-hepta-2,6-dienoate 
• 53-21-4 (-)-cocaine hydrochloride 
• 5796-31-6 ecgonine hydrochloride 

Downstream Products

• 131829-34-0 (+)-Allopseudococaine hydrochloride 
• 47195-07-3 (+)-cocaine 
• 478-73-9 (+)-pseudococaine 
• 53-21-4 Pseudococaine hydrochloride 
• 148533-52-2 (1R,2R,3S,5S)-methyl 3-(((benzyloxy)(phenyl)phosphoryl)oxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate 
• 148533-53-3 (1R,2R,3S,5S)-3-(Benzyloxy-phenyl-phosphinoyloxy)-8-(5-tert-butoxycarbonyl-pentyl)-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester 
• 90899-21-1 p-Acetoxycocaine 
• 481-37-8 ecgonine 

Relevant academic research and scientific papers

Asymmetric synthesis of the tropane alkaloid (+)-pseudococaine via ring-closing iodoamination

Ring-closing iodoamination of tert-butyl 2-hydroxy-7-[N-methyl-N-(α- methyl-p-methoxybenzyl)amino]cyclohept-3-ene-1-carboxylates proceeds with concomitant loss of the N-α-methyl-p-methoxybenzyl group to give the corresponding 8-azabicyclo[3.2.1]octane sca

Cocaine catalytic antibodies: The primary importance of linker effects

Current treatments for cocaine addiction are not effective. The development of a catalytic monoclonal antibody (mAb) provides a strategy for not only binding, but also degrading cocaine, which offers a broad-based therapy. Hapten design is the central element for programming antibody catalysis. The characteristics of the linker used in classic transition-state analogue phosphonate haptens were shown to be important for obtaining mAbs that hydrolyze the benzoate ester of cocaine.

Radioimmunoassay of benzoylecgonine in samples of forensic interest

A simple and economical radioimmunoassay for benzoylecgonine in blood or urine is described. Haemolysis, decomposition, common anticoagulants and sodium fluoride do not affect the results. A commercially available antiserum is used at a dilution of 1 : 600. The tracer is radioiodinated p-hydroxybenzoylecgonine. It is prepared by reacting p-acetoxy-benzoic anhydride with methyl ecgonine followed by mild hydrolysis and radioiodination by the Iodo-gen method. The product is purified on a disposable silica cartridge and has a specific activity of about 30 TBq mmol-1. Polyethylene glycol is used to separate the bound and free fractions in the assay. The range of the dose-response curve is 0-400 ng ml-1 benzoylecgonine. The assay is largely specific for benzoylecgonine. Cocaine, ecgonine, methylecgonine and cinnamoyl cocaine have slight or negligible cross-reactivities. The inter-assay coefficient of variation is 7.5% and the recovery of benzoylecgonine from 'spiked' blood is 103%. The 'cut-off' is 20 ng ml-1 benzoylecgonine for both blood and urine. Radioimmunoassay and high-performance liquid chromatography results agree well.