Page last updated: 2024-11-07

anhydroecgonine methyl ester

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

anhydroecgonine methyl ester: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID119478
CHEMBL ID451136
CHEBI ID191065
SCHEMBL ID1009981
MeSH IDM0187249

Synonyms (30)

Synonym
methylecgonidine
CHEMBL451136
CHEBI:191065
methyl (1r,5s)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
anhydroecgonine methyl ester
43021-26-7
anhydromethylecgonine
AKOS006272123
8-azabicyclo(3.2.1)oct-2-ene-2-carboxylic acid, 8-methyl-, methyl ester, (1r)-
58c337kp3e ,
8-azabicyclo(3.2.1)oct-2-ene-2-carboxylic acid, 8-methyl-, methyl ester, (1r,5s)-
unii-58c337kp3e
bdbm50413637
50373-10-9
methyl ecgonidine
(-)-anhydroecgonine methyl ester
ecgonidine methyl ester [mi]
ecgonidine-methyl-ester
methylesterecgonine
methyl-ecgonidine
anhydroecgonine-methyl-ester
SCHEMBL1009981
ecgonidine methyl ester mesylate
(1r,5s)-methyl 8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
DTXSID20276220
(-)-methylecgonidine
anhydroecgonine methyl ester 1.0 mg/ml in acetonitrile
(1r,5s)-methyl8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
MPSNEAHFGOEKBI-VXNVDRBHSA-N
Q10858037

Research Excerpts

Overview

Anhydroecgonine methyl ester (AEME) is a unique marker following smoked cocaine. AEEE is found in cocaine smokers who also use ethyl alcohol.

ExcerptReferenceRelevance
"Anhydroecgonine methyl ester (AEME) is a unique marker following smoked cocaine, and anhydroecgonine ethyl ester (AEEE) is found in cocaine smokers who also use ethyl alcohol."( Sensitive method for detection of cocaine and associated analytes by liquid chromatography-tandem mass spectrometry in urine.
Bjergum, MW; Crow, FW; Langman, LJ; Williamson, CL, 2009
)
1.07

Toxicity

ExcerptReferenceRelevance
" Since atropine prevented AEME-induced neurotoxicity, it has been suggested that its toxic effects may involve the muscarinic cholinergic receptors (mAChRs)."( M1 and M3 muscarinic receptors may play a role in the neurotoxicity of anhydroecgonine methyl ester, a cocaine pyrolysis product.
Abdalla, FM; Afeche, SC; Camarini, R; Conn, PJ; da Costa, JL; da Silva, MA; Dati, LM; Garcia, RC; Gorjão, R; Marcourakis, T; Niswender, CM; Sandoval, MR; Torres, LH; Udo, MS; Yonamine, M, 2015
)
0.65

Dosage Studied

ExcerptRelevanceReference
" Atropine (10(-6) M) upwardly shifted the dose-response curves of MEG, cocaine, and carbachol but not of procaine."( Effect of cocaine and methylecgonidine on intracellular Ca2+ and myocardial contraction in cardiac myocytes.
Huang, L; Ishiguro, Y; Morgan, JP; Woolf, JH, 1997
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-alkylpyrrolidine
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Potassium voltage-gated channel subfamily H member 2Homo sapiens (human)IC50 (µMol)169.82400.00091.901410.0000AID392051
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
regulation of heart rate by cardiac conductionPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of heart rate by hormonePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of membrane potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
positive regulation of DNA-templated transcriptionPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
potassium ion homeostasisPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
cardiac muscle contractionPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of membrane repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of ventricular cardiac muscle cell membrane repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
cellular response to xenobiotic stimulusPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
potassium ion transmembrane transportPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
ventricular cardiac muscle cell action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane depolarization during action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane repolarization during action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane repolarization during cardiac muscle cell action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of heart rate by cardiac conductionPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
potassium ion export across plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane repolarization during ventricular cardiac muscle cell action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of potassium ion transmembrane transportPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
negative regulation of potassium ion transmembrane transportPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
positive regulation of potassium ion transmembrane transportPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
negative regulation of potassium ion export across plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
potassium ion import across plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
transcription cis-regulatory region bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
inward rectifier potassium channel activityPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
voltage-gated potassium channel activityPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
delayed rectifier potassium channel activityPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
protein bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
ubiquitin protein ligase bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
identical protein bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
protein homodimerization activityPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
C3HC4-type RING finger domain bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
voltage-gated potassium channel activity involved in cardiac muscle cell action potential repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
scaffold protein bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
cell surfacePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
perinuclear region of cytoplasmPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
voltage-gated potassium channel complexPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
inward rectifier potassium channel complexPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID392051Inhibition of human ERG channel in HEK293 cells by voltage-clamp method2008European journal of medicinal chemistry, Nov, Volume: 43, Issue:11
Identification of "toxicophoric" features for predicting drug-induced QT interval prolongation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (49)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's14 (28.57)18.2507
2000's20 (40.82)29.6817
2010's14 (28.57)24.3611
2020's1 (2.04)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.86

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index28.86 (24.57)
Research Supply Index3.97 (2.92)
Research Growth Index4.48 (4.65)
Search Engine Demand Index36.71 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.86)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies3 (5.77%)4.05%
Observational0 (0.00%)0.25%
Other49 (94.23%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]