Cocaine
Cocaine is a tropane alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons. Cocaine binds to the dopamine, serotonin, and norepinephrine transport proteins and inhibits the re-uptake of dopamine, serotonin, and norepinephrine into pre-synaptic neurons. This leads to an accumulation of the respective neurotransmitters in the synaptic cleft and may result in increased postsynaptic receptor activation. The mechanism of action through which cocaine exerts its local anesthetic effects is by binding to and blocking the voltage-gated sodium channels in the neuronal cell membrane. By stabilizing neuronal membranes, cocaine inhibits the initiation and conduction of nerve impulses and produces a reversible loss of sensation. (from PubChem). Cocaine is metabolized by three human enzymes: hCE1 (CE1), intestinal CE (CE2) and serum butyrylcholinesterase (BChE). Cocaine is hydrolized very efficiently by some designed mutants of BChE
General
Type : Natural, Drug, Alkaloid, Benzoate, Azabicyclo
Chemical_Nomenclature : methyl (1S,3S,4R,5R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate
Canonical SMILES : CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC
InChI : InChI=1S\/C17H21NO4\/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11\/h3-7,12-15H,8-10H2,1-2H3\/t12-,13+,14-,15+\/m0\/s1
InChIKey : ZPUCINDJVBIVPJ-LJISPDSOSA-N
Other name(s) : 2beta-carbomethoxy-3beta-benzoyloxytropane hydrochloride || (-)-Cocaine || 3-beta-Hydroxy-, Methyl Ester, Benzoate || Methylbenzoylepgonine || Cocaine Free Base || Benzoylmethylecgonine || Crack || L-Cocain || beta-Cocain || D-cocaine || Cocain || Kokain
Target
Structures : No structure
Families : BCHE, Carb_B_Chordata, Cocaine_esterase
References (64)
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| Gene_locus related to this paper: human-CES1 |
| Title : Catalytic Reaction Mechanism for Drug Metabolism in Human Carboxylesterase-1: Cocaine Hydrolysis Pathway - Yao_2018_Mol.Pharm_15_3871 |
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| Title : Effects of a cocaine hydrolase engineered from human butyrylcholinesterase on metabolic profile of cocaine in rats - Chen_2016_Chem.Biol.Interact_259_104 |
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| Gene_locus related to this paper: human-BCHE |
| Title : Rational design, preparation, and characterization of a therapeutic enzyme mutant with improved stability and function for cocaine detoxification - Fang_2014_ACS.Chem.Biol_9_1764 |
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| Gene_locus related to this paper: rhosm-cocE |
| Title : Preclinical studies on neurobehavioral and neuromuscular effects of cocaine hydrolase gene therapy in mice - Murthy_2014_J.Mol.Neurosci_53_409 |
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| Gene_locus related to this paper: human-BCHE |
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| Gene_locus related to this paper: human-BCHE |
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| Gene_locus related to this paper: human-CES1 |
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| Gene_locus related to this paper: human-BCHE |
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| Gene_locus related to this paper: human-BCHE |
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| Ref : Toxicol Appl Pharmacol , 145 :372 , 1997 |
| Abstract : |
| PubMedSearch : Mattes_1997_Toxicol.Appl.Pharmacol_145_372 |
| PubMedID: 9266811 |
| Title : Overlapping drug interaction sites of human butyrylcholinesterase dissected by site-directed mutagenesis - Loewenstein-Lichtenstein_1996_Mol.Pharmacol_50_1423 |
| Author(s) : Loewenstein-Lichtenstein Y , Glick D , Gluzman N , Sternfeld M , Zakut H , Soreq H |
| Ref : Molecular Pharmacology , 50 :1423 , 1996 |
| Abstract : |
| PubMedSearch : Loewenstein-Lichtenstein_1996_Mol.Pharmacol_50_1423 |
| PubMedID: 8967962 |
| Gene_locus related to this paper: human-BCHE |
| Title : Acetylcholinesterase and butyrylcholinesterase activity in the human term placenta: implications for fetal cocaine exposure - Simone_1994_J.Lab.Clin.Med_123_400 |
| Author(s) : Simone C , Derewlany LO , Oskamp M , Johnson D , Knie B , Koren G |
| Ref : Journal of Laboratory & Clinical Medicine , 123 :400 , 1994 |
| Abstract : |
| PubMedSearch : Simone_1994_J.Lab.Clin.Med_123_400 |
| PubMedID: 8133152 |
| Title : Differential toxicity of cocaine and its isomers, (+)-cocaine and (-)-psi-cocaine, is associated with stereoselective hydrolysis by hepatic carboxylesterases in cultured rat hepatocytes - Melchert_1992_Chem.Biol.Interact_84_243 |
| Author(s) : Melchert RB , Goldlin C , Zweifel U , Welder AA , Boelsterli UA |
| Ref : Chemico-Biological Interactions , 84 :243 , 1992 |
| Abstract : |
| PubMedSearch : Melchert_1992_Chem.Biol.Interact_84_243 |
| PubMedID: 1423743 |
| 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 : Genetic variants of human serum cholinesterase influence metabolism of the muscle relaxant succinylcholine. - Lockridge_1990_Pharmacol.Ther_47_35 |
| Author(s) : Lockridge O |
| Ref : Pharmacol Ther , 47 :35 , 1990 |
| Abstract : |
| PubMedSearch : Lockridge_1990_Pharmacol.Ther_47_35 |
| PubMedID: 2195556 |
| Gene_locus related to this paper: human-BCHE |
| 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 |