Ecgonine-methyl-ester
General
Type : Natural, Alkaloid, Benzoate, Azabicyclo
Chemical_Nomenclature : methyl (1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Canonical SMILES : CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)O)C(=O)OC
InChI : 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
InChIKey : QIQNNBXHAYSQRY-UYXSQOIJSA-N
Other name(s) : Ecgonine methyl ester || Methyl ecgonine || Methylecgonine || Y35FJB3QBJ || (-)-Ecgonine methyl ester || CHEBI:31529 || RefChem:905549 || CHEMBL1232472 || DB04688
MW : 199.25
Formula : C10H17NO3
CAS_number : 7143-09-1
PubChem : 104904
UniChem : QIQNNBXHAYSQRY-UYXSQOIJSA-N
Target
Structures : No structure
Families : No family
References (28)
| Title : The Development of Bacterial Carboxylesterase Biological Recognition Elements for Cocaine Detection - Mustafa_2018_Mol.Biotechnol_60_601 |
| Author(s) : Mustafa SA |
| Ref : Mol Biotechnol , 60 :601 , 2018 |
| Abstract : |
| PubMedSearch : Mustafa_2018_Mol.Biotechnol_60_601 |
| PubMedID: 29951737 |
| Title : Effects of a cocaine hydrolase engineered from human butyrylcholinesterase on metabolic profile of cocaine in rats - Chen_2016_Chem.Biol.Interact_259_104 |
| Author(s) : Chen X , Zheng X , Zhou Z , Zhan CG , Zheng F |
| Ref : Chemico-Biological Interactions , 259 :104 , 2016 |
| Abstract : |
| PubMedSearch : Chen_2016_Chem.Biol.Interact_259_104 |
| PubMedID: 27154495 |
| Title : Assessment of Pharmacokinetic and Pharmacodynamic Interactions Between Albumin-Fused Mutated Butyrylcholinesterase and Intravenously Administered Cocaine in Recreational Cocaine Users - Shram_2015_J.Clin.Psychopharmacol_35_396 |
| Author(s) : Shram MJ , Cohen-Barak O , Chakraborty B , Bassan M , Schoedel KA , Hallak H , Eyal E , Weiss S , Gilgun Y , Sellers EM , Faulknor J , Spiegelstein O |
| Ref : J Clin Psychopharmacol , 35 :396 , 2015 |
| Abstract : |
| PubMedSearch : Shram_2015_J.Clin.Psychopharmacol_35_396 |
| PubMedID: 26082975 |
| Title : Reward and Toxicity of Cocaine Metabolites Generated by Cocaine Hydrolase - Murthy_2015_Cell.Mol.Neurobiol_35_819 |
| Author(s) : Murthy V , Geng L , Gao Y , Zhang B , Miller JD , Reyes S , Brimijoin S |
| Ref : Cellular Molecular Neurobiology , 35 :819 , 2015 |
| Abstract : |
| PubMedSearch : Murthy_2015_Cell.Mol.Neurobiol_35_819 |
| PubMedID: 25814464 |
| Title : Modification of pharmacokinetic and abuse-related effects of cocaine by human-derived cocaine hydrolase in monkeys - Schindler_2013_Addict.Biol_18_30 |
| Author(s) : Schindler CW , Justinova Z , Lafleur D , Woods D , Roschke V , Hallak H , Sklair-Tavron L , Redhi GH , Yasar S , Bergman J , Goldberg SR |
| Ref : Addict Biol , 18 :30 , 2013 |
| Abstract : |
| PubMedSearch : Schindler_2013_Addict.Biol_18_30 |
| PubMedID: 22264200 |
| Title : Cocaine hydrolase encoded in viral vector blocks the reinstatement of cocaine seeking in rats for 6 months - Anker_2012_Biol.Psychiatry_71_700 |
| Author(s) : Anker JJ , Brimijoin S , Gao Y , Geng L , Zlebnik NE , Parks RJ , Carroll ME |
| Ref : Biological Psychiatry , 71 :700 , 2012 |
| Abstract : |
| PubMedSearch : Anker_2012_Biol.Psychiatry_71_700 |
| PubMedID: 22209637 |
| Title : Simultaneous analysis of cocaine and its metabolites in urine by capillary electrophoresis-electrospray mass spectrometry using a pressurized liquid junction nanoflow interface - Hezinova_2012_Electrophoresis_33_653 |
| Author(s) : Hezinova V , Aturki Z , Kleparnik K , D'Orazio G , Foret F , Fanali S |
| Ref : Electrophoresis , 33 :653 , 2012 |
| Abstract : |
| PubMedSearch : Hezinova_2012_Electrophoresis_33_653 |
| PubMedID: 22451058 |
| Title : Prolonged toxic effects after cocaine challenge in butyrylcholinesterase\/plasma carboxylesterase double knockout mice: a model for butyrylcholinesterase-deficient humans - Duysen_2011_Drug.Metab.Dispos_39_1321 |
| Author(s) : Duysen EG , Lockridge O |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 39 :1321 , 2011 |
| Abstract : |
| PubMedSearch : Duysen_2011_Drug.Metab.Dispos_39_1321 |
| PubMedID: 21540357 |
| Title : The ability of bacterial cocaine esterase to hydrolyze cocaine metabolites and their simultaneous quantification using high-performance liquid chromatography-tandem mass spectrometry - Brim_2011_Mol.Pharmacol_80_1119 |
| Author(s) : Brim RL , Noon KR , Collins GT , Nichols J , Narasimhan D , Sunahara RK , Woods JH |
| Ref : Molecular Pharmacology , 80 :1119 , 2011 |
| Abstract : |
| PubMedSearch : Brim_2011_Mol.Pharmacol_80_1119 |
| PubMedID: 21885621 |
| Gene_locus related to this paper: rhosm-cocE |
| Title : The effect of ethanol on oral cocaine pharmacokinetics reveals an unrecognized class of ethanol-mediated drug interactions - Parker_2010_Drug.Metab.Dispos_38_317 |
| Author(s) : Parker RB , Laizure SC |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 38 :317 , 2010 |
| Abstract : |
| PubMedSearch : Parker_2010_Drug.Metab.Dispos_38_317 |
| PubMedID: 19920055 |
| Title : The effect of lovastatin and thioridazine on the degradation of cocaine in human serum in vitro - Bailey_2005_Ther.Drug.Monit_27_168 |
| Author(s) : Bailey DN , Briggs JR |
| Ref : Ther Drug Monit , 27 :168 , 2005 |
| Abstract : |
| PubMedSearch : Bailey_2005_Ther.Drug.Monit_27_168 |
| PubMedID: 15795647 |
| Title : Ecgonine methyl ester protects against cocaine lethality in mice - Hoffman_2004_J.Toxicol.Clin.Toxicol_42_349 |
| Author(s) : Hoffman RS , Kaplan JL , Hung OL , Goldfrank LR |
| Ref : J Toxicol Clinical Toxicology , 42 :349 , 2004 |
| Abstract : |
| PubMedSearch : Hoffman_2004_J.Toxicol.Clin.Toxicol_42_349 |
| PubMedID: 15461242 |
| Title : Mechanism-based discovery of small molecules that prevent noncompetitive inhibition by cocaine and MK-801 mediated by two different sites on the nicotinic acetylcholine receptor - Chen_2004_Biochemistry_43_10149 |
| Author(s) : Chen Y , Banerjee A , Hess GP |
| Ref : Biochemistry , 43 :10149 , 2004 |
| Abstract : |
| PubMedSearch : Chen_2004_Biochemistry_43_10149 |
| PubMedID: 15287742 |
| Title : Butyrylcholinesterase accelerates cocaine metabolism: in vitro and in vivo effects in nonhuman primates and humans - Carmona_2000_Drug.Metab.Dispos_28_367 |
| Author(s) : Carmona GN , Jufer RA , Goldberg SR , Gorelick DA , Greig NH , Yu QS , Cone EJ , Schindler CW |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 28 :367 , 2000 |
| Abstract : |
| PubMedSearch : Carmona_2000_Drug.Metab.Dispos_28_367 |
| PubMedID: 10681384 |
| Title : Catalytic antibodies that hydrolyze (-)-cocaine obtained by a high-throughput procedure - Cashman_2000_J.Pharmacol.Exp.Ther_293_952 |
| Author(s) : Cashman JR , Berkman CE , Underiner GE |
| Ref : Journal of Pharmacology & Experimental Therapeutics , 293 :952 , 2000 |
| Abstract : |
| PubMedSearch : Cashman_2000_J.Pharmacol.Exp.Ther_293_952 |
| PubMedID: 10869397 |
| Title : Gene cloning and nucleotide sequencing and properties of a cocaine esterase from Rhodococcus sp. strain MB1 - Bresler_2000_Appl.Environ.Microbiol_66_904 |
| Author(s) : Bresler MM , Rosser SJ , Basran A , Bruce NC |
| Ref : Applied Environmental Microbiology , 66 :904 , 2000 |
| Abstract : |
| PubMedSearch : Bresler_2000_Appl.Environ.Microbiol_66_904 |
| PubMedID: 10698749 |
| Gene_locus related to this paper: rhosm-cocE |
| Title : Attenuation of cocaine-induced locomotor activity by butyrylcholinesterase - Carmona_1998_Exp.Clin.Psychopharmacol_6_274 |
| Author(s) : Carmona GN , Schindler CW , Shoaib M , Jufer R , Cone EJ , Goldberg SR , Greig NH , Yu QS , Gorelick DA |
| Ref : Experimental & Clinical Psychopharmacology , 6 :274 , 1998 |
| Abstract : |
| PubMedSearch : Carmona_1998_Exp.Clin.Psychopharmacol_6_274 |
| PubMedID: 9725111 |
| Title : Butyrylcholinesterase: an enzyme antidote for cocaine intoxication - Mattes_1998_Addict.Biol_3_171 |
| Author(s) : Mattes CE , Belendiuk GW , Lynch TJ , Brady RO , Dretchen KL |
| Ref : Addict Biol , 3 :171 , 1998 |
| Abstract : |
| PubMedSearch : Mattes_1998_Addict.Biol_3_171 |
| PubMedID: 26734822 |
| Title : The influence of plasma butyrylcholinesterase concentration on the in vitro hydrolysis of cocaine in human plasma - Browne_1998_Biopharm.Drug.Dispos_19_309 |
| Author(s) : Browne SP , Slaughter EA , Couch RA , Rudnic EM , McLean AM |
| Ref : Biopharmaceutics & Drug Disposition , 19 :309 , 1998 |
| Abstract : |
| PubMedSearch : Browne_1998_Biopharm.Drug.Dispos_19_309 |
| PubMedID: 9673783 |
| Title : Cocaine benzoyl thioester: synthesis, kinetics of base hydrolysis, and application to the assay of cocaine esterases - Cashman_1998_Chem.Res.Toxicol_11_895 |
| Author(s) : Cashman JR , Berkman CE , Underiner G , Kolly CA , Hunter AD |
| Ref : Chemical Research in Toxicology , 11 :895 , 1998 |
| Abstract : |
| PubMedSearch : Cashman_1998_Chem.Res.Toxicol_11_895 |
| PubMedID: 9705751 |
| Title : Stereoselective inhibition of human butyrylcholinesterase by phosphonothiolate analogs of (+)- and (-)-cocaine - Berkman_1997_Biochem.Pharmacol_54_1261 |
| Author(s) : Berkman CE , Underiner GE , Cashman JR |
| Ref : Biochemical Pharmacology , 54 :1261 , 1997 |
| Abstract : |
| PubMedSearch : Berkman_1997_Biochem.Pharmacol_54_1261 |
| PubMedID: 9416977 |
| Title : Administration of purified human plasma cholinesterase protects against cocaine toxicity in mice - Hoffman_1996_J.Toxicol.Clin.Toxicol_34_259 |
| Author(s) : Hoffman RS , Morasco R , Goldfrank LR |
| Ref : Journal of Toxicology Clinical Toxicology , 34 :259 , 1996 |
| Abstract : |
| PubMedSearch : Hoffman_1996_J.Toxicol.Clin.Toxicol_34_259 |
| PubMedID: 8667461 |
| Title : A new placental enzyme in the metabolism of cocaine: an in vitro animal model - Little_1995_Am.J.Obstet.Gynecol_172_1441 |
| Author(s) : Little BB , Roe DA , Stettler RW , Bohman VR , Westfall KL , Sobhi S |
| Ref : American Journal of Obstetrics & Gynecology , 172 :1441 , 1995 |
| Abstract : |
| PubMedSearch : Little_1995_Am.J.Obstet.Gynecol_172_1441 |
| PubMedID: 7755051 |
| Title : The effect of hepatectomy and plasma cholinesterase inhibition on cocaine metabolism and cardiovascular responses in pigs - Kambam_1994_J.Lab.Clin.Med_124_715 |
| Author(s) : Kambam JR , Franks JJ , Mets B , Janicki PK , Hickman R , van der Watt M |
| Ref : Journal of Laboratory & Clinical Medicine , 124 :715 , 1994 |
| Abstract : |
| PubMedSearch : Kambam_1994_J.Lab.Clin.Med_124_715 |
| PubMedID: 7964130 |
| Title : Activities of the enantiomers of cocaine and some related compounds as substrates and inhibitors of plasma butyrylcholinesterase - Gatley_1991_Biochem.Pharmacol_41_1249 |
| Author(s) : Gatley SJ |
| Ref : Biochemical Pharmacology , 41 :1249 , 1991 |
| Abstract : |
| PubMedSearch : Gatley_1991_Biochem.Pharmacol_41_1249 |
| PubMedID: 2009099 |
| Title : Rapid stereoselective hydrolysis of (+)-cocaine in baboon plasma prevents its uptake in the brain: implications for behavioral studies - Gatley_1990_J.Neurochem_54_720 |
| Author(s) : Gatley SJ , MacGregor RR , Fowler JS , Wolf AP , Dewey SL , Schlyer DJ |
| Ref : Journal of Neurochemistry , 54 :720 , 1990 |
| Abstract : |
| PubMedSearch : Gatley_1990_J.Neurochem_54_720 |
| PubMedID: 2299363 |
| Title : Cocaine metabolism: cocaine and norcocaine hydrolysis by liver and serum esterases - Stewart_1979_Clin.Pharmacol.Ther_25_464 |
| Author(s) : Stewart DJ , Inaba T , Lucassen M , Kalow W |
| Ref : Clinical Pharmacology & Therapeutics , 25 :464 , 1979 |
| Abstract : |
| PubMedSearch : Stewart_1979_Clin.Pharmacol.Ther_25_464 |
| PubMedID: 428191 |
| Title : Metabolism of cocaine in man - Inaba_1978_Clin.Pharmacol.Ther_23_547 |
| Author(s) : Inaba T , Stewart DJ , Kalow W |
| Ref : Clinical Pharmacology & Therapeutics , 23 :547 , 1978 |
| Abstract : |
| PubMedSearch : Inaba_1978_Clin.Pharmacol.Ther_23_547 |
| PubMedID: 639429 |