5796-31-6

Usage

Uses

Used in Pharmaceutical Research:
ECGONIN HCL is used as a research compound for studying the metabolic pathways and mechanisms of cocaine, as well as its potential applications in the development of new pharmaceuticals targeting the tropane alkaloid family.
Used in Forensic Analysis:
In the field of forensic science, ECGONIN HCL is employed as an analytical reference standard to aid in the identification and quantification of cocaine and its metabolites in biological samples, such as blood, urine, or hair.
Used in Drug Metabolism Studies:
ECGONIN HCL serves as a crucial compound in understanding the metabolic processes of cocaine in the human body, which can be valuable for developing strategies to combat drug addiction and its associated health issues.
Used in Drug Synthesis:
As a precursor to cocaine, ECGONIN HCL may also be utilized in the synthesis of other tropane alkaloids or related compounds for various pharmaceutical applications, under strict regulatory control and ethical considerations.
Used in Toxicology:
ECGONIN HCL can be employed in toxicological research to study the effects of cocaine and its metabolites on various organ systems and to develop potential antidotes or treatments for cocaine toxicity.
Used in Drug Testing and Detection:
In the context of drug testing and detection, ECGONIN HCL is used as a reference material to calibrate and validate analytical instruments and methods for the accurate identification and quantification of cocaine and its metabolites in various matrices, such as urine, blood, or hair samples.
Used in Regulatory Compliance:
ECGONIN HCL is utilized by regulatory agencies and organizations to ensure compliance with drug control regulations, by providing a reference standard for the detection and quantification of cocaine and its metabolites in controlled substances.

InChI:InChI=1/C9H15NO3.ClH/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5;/h5-8,11H,2-4H2,1H3,(H,12,13);1H/t5-,6-,7+,8-;/m1./s1

Upstream product

• 53-21-4 (-)-cocaine hydrochloride 
• 50-36-2 Cocaine 

Downstream Products

• 70939-97-8 ecgonine ethyl ester 
• 38969-40-3 Ecgonine methyl ester hydrochloride 
• 173443-25-9 (1R,2R,3S,5S)-3-Hydroxy-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid 5-benzyloxycarbonyl-pentyl ester 
• 173443-27-1 (1R,2R,3S,5S)-3-Benzoyloxy-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid 5-carboxy-pentyl ester 
• 173443-26-0 (1R,2R,3S,5S)-3-Benzoyloxy-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid 5-benzyloxycarbonyl-pentyl ester 
• 843660-60-6 (1R,2R,3S,5S)-3-Benzoyloxy-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid 5-(6-amino-hexylcarbamoyl)-pentyl ester 
• 143966-02-3 RTI 92 
• 706781-11-5 (1R,2S,3S,5S)-8-Methyl-3-(3-trimethylsilanyl-phenyl)-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester 
• 616880-20-7 (1R,2S,7S,9S)-4-ethyl-12-methyl-6-oxa-12-azatricyclo-[7.2.1.0^2,7]dodec-4-en-3-one 
• 616880-20-7 (1R,2R,7S,9S)-4-ethyl-12-methyl-6-oxa-12-azatricyclo-[7.2.1.0^2,7]dodec-4-en-3-one 
• 148562-39-4 3-<(phenylphosphonyl)oxy>-<1R-(exo,exo)>-8-methyl-8-azabicyclo<3.2.1>octane-2-carboxylic acid methyl ester 
• 172954-51-7 3-<(4-aminophenylphosphonyl)oxy>-<1R-(exo,exo)>-8-methyl-8-azabicyclo<3.2.1>octane-2-carboxylic acid methyl ester 
• 172954-49-3 (1R,2R,3S,5S)-3-[Hydroxy-(4-nitro-phenyl)-phosphinoyloxy]-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Method for preparing organoboron derivative containing oxygen and aromatic ring as labeled precursor of dopamine positron emission tomography imaging agent

A method for preparing organoboron derivatives containing oxygen atoms and an aromatic ring as labeled precursors of dopamine positron emission tomography imaging agents is revealed. Hydrochloride salt of cocaine is used as an initiator. Organoboron derivatives containing oxygen atoms are directly produced on an aromatic ring as drug substances and the aromatic ring is directly labeled with radioisotope fluorine-18 (F-18). The method takes only five steps including four steps for preparing organoboron derivatives containing oxygen atoms and an aromatic ring as drug substances and a step of labeling the aromatic ring of the organoboron derivatives with F-18 directly. Not only the process time is significantly reduced, the total yield rate is also improved effectively.

Copper-mediated nucleophilic radiofluorination of [18F]β-CFT for positron emission tomography imaging of dopamine transporter

[18F]β-CFT is a positron emission tomography (PET) ligand for imaging of dopamine transporter. It was proved to be a sensitive PET marker to detect presynaptic dopaminergic hypofunction in Parkinson's disease. In recent years, copper-mediated 18F-fluorination of aryl boronic esters has been successful in some molecules containing aromatic groups. In this study, we describe the novel synthetic strategy of [18F]β-CFT by copper-mediated nucleophilic radiofluorination with pinacol-derived aryl boronic esters upon reaction with [18F]KF/K222 and Cu (OTf)2(py)4. The radiolabeling protocol was optimized with [18F]fluoride elution method and amount of copper catalyst used. [18F]β-CFT is obtained from boronic ester precursors in 2.2% to 10.6% non-isolated radiochemical yield (RCY). Purified [18F]β-CFT with >99% radiochemical purity (RCP) and high molar activity was obtained in validation runs. The radiolabeling procedure is straightforward and can easily be adapted for clinical use.

Fluorescent cocaine probes: A tool for the selection and engineering of therapeutic antibodies

Cocaine is a highly addictive drug, and despite intensive efforts, effective therapies for cocaine craving and addiction remain elusive. In recent years, we and others have reported advances in anti-cocaine immunopharmacotherapy based on specific antibodi

Synthesis and monoamine transporter affinity of 3′-analogs of 2-β-carbomethoxy-3-β-(4′-iodophenyl)tropane (β-CIT)

The 3′-iodo positional isomer of 2-β-carbomethoxy-3-β- (4′-iodophenyl)tropane (β-CIT) and other 3′-substituted analogs were synthesized and evaluated for binding to monoamine transporters in rat forebrain and membranes of cell lines selectively expressing human transporter genes. All 3′-substituted compounds displayed affinity for both serotonin (SERT) and dopamine (DAT), but much less for norepinephrine transporters (NET), with selectivity for rat (r) or human (h) SERT over NET, but only 3′-iodo-substituted phenyltropanes showed selectivity for SERT versus DAT. The 3′-iodo, N-methyl analog of β-CIT (7) displayed 29-fold selectivity and high affinity for hSERT (Ki=9.6nM) over hDAT (K i=279nM), and its nor-congener (8) showed even higher hSERT potency (Ki=1.2nM) and selectivity over DAT (415-fold).

NOVEL TROPANE ESTERS AND METHODS FOR PRODUCING AND USING THEM

This invention relates to novel primary diol tropane esters and related compounds, including methods for making and using those compounds. The compounds of this invention are those of formula (I), (II) or (III): wherein A, B and Rl are as defined herein. These compounds may be used as therapeutic and prophylactic agents against diseases such as immunoregulatory disorders, neuromuscular disorders, joint disorders, connective tissue disorders, circulatory disorders and pain.

Synthesis and nicotinic binding studies on enantiopure pinnamine variants with an 8-azabicyclo[3.2.1]octane moiety

Bioisosteric replacement of the 9-azabicyclo[4.2.1]nonane pharmacophoric element of the novel alkaloidal marine toxine pinnamine (5) by the 8-azabicyclo[3.2.1]octane moiety resulted in conformationally restricted analogues 6a and 6c of (-)-ferruginine (4). Key step in the diastereoselective synthesis of these pyranotropanes was the condensation of enantiopure ecgonine methyl ester (9) from the "chiral pool" with the lithium anion of N-tert-butylbutyraldimin and subsequent cyclisation with TFA. The potential nAChR ligands were tested for their in vitro affinity for the (α4)2(β2)3 and the α7* nAChR subtypes. Despite obvious structural similarities with the potent alkaloids pinnamine (5) and (-)-ferruginine (4) the pyranotropanes 6a and 6c exhibited distinctly lower nAChR affinities.

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.

Synthesis and dopamine transporter binding of 2'-substituted cocaine analogs

A series of 2'-substituted cocaine analogs (4-8) was synthesized and evaluated in an in vitro dopamine transporter (DAT) system. Compounds 4-7 were prepared by esterifying the 3β-hydroxyl group of ecgonine methyl ester (3) using the appropriate acid chloride in the presence of NEt3 and benzene. Compound 3 was obtained from cocaine (1) by hydrolysis using lN HCl to afford ecgonine HCl which was subjected to acid catalyzed esterification using MeOH saturated with HCl gas. Compound 8 was obtained from 5 by selective trans- esterification with MeOH and HCl gas. The binding affinities of these compounds were determined at DAT for the displacement of [3H]WIN-35428 (2). The 2'-substituted acetoxy and hydroxy analogs exhibited high binding potency for the DAT compared to cocaine (3.5- and 10-fold respectively).

The synthesis of deuterium-labelled cocaine, cocaethylene and metabolites

We describe the syntheses of benzoylecgonine (1,1,1-2H3)methyl ester [(2H3) cocaine], (2H5)benzoylecgonine, (2H5)benzoylecgonine methyl ester [(2H5/su

A convenient synthesis of 2'- or 4'-hydroxycocaine

A short, convenient and efficient synthesis of 2'- or 4'-hydroxycocaine is described. The key step involved selective hydrolysis/transesterification of the acetoxy group of 2'- or 4'-acetoxycocaine in methanol saturated with dry HCl gas.