| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2007-05-22 23:46:51 -0600 |
| Update Date |
2013-05-29 13:43:42 -0600 |
| HMDB ID |
HMDB06406 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Ecgonine methyl ester |
| Description |
Ecgonine methyl ester is a major metabolite of cocaine. It is generally not measured by HPLC because it is poorly detectable by UV, and its water solubility makes recovery from urine difficult. Using modified solid-phase extraction procedures, recoveries of 85% for ecgonine methyl ester could be obtained from urine. (PMID:1298401  ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- Methyl ecgonine
|
| Chemical Formula |
C10H17NO3 |
| Average Molecular Weight |
199.2469 |
| Monoisotopic Molecular Weight |
199.120843415 |
| IUPAC Name |
methyl (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate |
| Traditional IUPAC Name |
methyl (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate |
| CAS Registry Number |
7143-09-1 |
| SMILES |
COC(=O)[C@@H]1C2CCC(C[C@@H]1O)N2C |
| InChI Identifier |
InChI=1S/C10H17NO3/c1-11-6-3-4-7(11)9(8(12)5-6)10(13)14-2/h6-9,12H,3-5H2,1-2H3/t6?,7?,8-,9+/m0/s1 |
| InChI Key |
QIQNNBXHAYSQRY-ABIFROTESA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Aliphatic Heteropolycyclic Compounds |
| Class |
Piperidines |
| Sub Class |
Piperidinecarboxylic Acids and Derivatives |
| Other Descriptors |
- Aliphatic Heteropolycyclic Compounds
- Tropane alkaloids(KEGG)
- Tropanes
|
| Substituents |
- Beta Hydroxy Acid
- Carboxylic Acid Ester
- Cyclic Alcohol
- Pyrrolidine
- Secondary Alcohol
- Tertiary Aliphatic Amine (Trialkylamine)
|
| Direct Parent |
Piperidinecarboxylic Acids and Derivatives |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
Not Available
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| Application |
Not Available
|
| Cellular locations |
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
|
| Tissue Location |
Not Available
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.237 +/- 0.0150 uM |
Adult (>18 years old) |
Both |
Normal
|
|
|
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB023911 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
391939 |
| KEGG Compound ID |
C12448 |
| BioCyc ID |
Not Available |
| BiGG ID |
2267774 |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB06406 |
| Metagene Link |
HMDB06406 |
| METLIN ID |
Not Available |
| PubChem Compound |
443844 |
| PDB ID |
Not Available |
| ChEBI ID |
708640 |
| References |
|---|
| Synthesis Reference |
Kline, Richard Harry, Jr. The synthesis and pharmacological activity of 3-arylecgonine methyl ester and 3-carbamoyloxyecgonine methyl ester analogs: probes for the characterization of the dopaminergic cocaine receptor. (1991), 127 pp. CAN 116:21292 AN 1992:21292 |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- Roy IM, Jefferies TM, Threadgill MD, Dewar GH: Analysis of cocaine, benzoylecgonine, ecgonine methyl ester, ethylcocaine and norcocaine in human urine using HPLC with post-column ion-pair extraction and fluorescence detection. J Pharm Biomed Anal. 1992 Oct-Dec;10(10-12):943-8.
Pubmed: 1298401
|
