関: ethylcocaine

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/12/27 06:37:45」(JST)

wiki en

Cocaethylene (ethylbenzoylecgonine) is the ethyl ester of benzoylecgonine. It is structurally similar to cocaine, which is the methyl ester of benzoylecgonine. Cocaethylene is formed in vivo when cocaine and ethyl alcohol have been ingested simultaneously.^[1]

Normally cocaine's metabolism produces two major and biologically inactive metabolites, benzoylecogonine and ecgonine methyl ester. Carboxylesterase is an important part of cocaine's metabolism because it acts as the catalyst for the hydrolysis of cocaine which produces the inactive metabolites. If ethanol is present during the metabolism of cocaine, a portion of the cocaine undergoes transesterification with ethanol, instead of undergoing hydrolysis with water, which results in cocaethylene.^[2]

Cocaethylene is a recreational drug with stimulant, euphoriant, anorectic, sympathomimetic and local anesthetic properties. Three monoamine neurotransmitters known as serotonin (5-HT), norepinephrine (NE), and dopamine (DA) play an important role in cocaethylene's action. Cocaethylene increases the level of serotonergic, noradrenergic, and dopaminergic neurotransmission by inhibiting the action of the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT) which makes cocaethylene a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI).^{[Note 1]}

Cocaethylene appears to, in most users, produce more euphoria and possess a longer duration of action than cocaine. Some studies suggest that it may be more cardiotoxic than cocaine. Cocaethylene is more potent than cocaine at binding to the dopamine transporter, however it is less potent at binding to the serotonin transporter and norepinephrine transporter.^[3]^[4]

Notes

Footnotes

^ Serotonin-norepinephrine-dopamine reuptake inhibitors are also known as triple reuptake inhibitor which is abbreviated TRI

References

^ S. Casey Laizure, Timothy Mandrell, Naomi M. Gades, and Robert B. Parker (2003). "Cocaethylene Metabolism and Interaction with Cocaine and Ethanol: Role of Carboxylesterases". Drug Metabolism and Disposition 31 (1): 16–20. doi:10.1124/dmd.31.1.16. PMID 12485948.
^ Cocaethylene metabolism : interaction with cocaine and ethanol Cocaethylene metabolism and interaction with cocaine and ethanol: role of carboxylesterases by Laizure SC, Mandrell T, Gades NM, Parker RB (January 31st, 2003).
^ Jatlow, Peter; McCance, Elinore F.; Bradberry, Charles W.; Elsworth, John D.; Taylor, Jane R.; Roth, Robert H. (1996). noradrenaline transporter(NAT) 00026&type=abstract "Alcohol plus Cocaine: The Whole Is More Than the Sum of Its Parts". Therapeutic Drug Monitoring 18 (4): 460–4. doi:10.1097/00007691-199608000-00026. PMID 8857569. http://jousrnals.lww.com/drug-monitoring/pages/articleviewer.aspx?year=1996&issue=08000&article=the noradrenaline transporter(NAT) 00026&type=abstract.
^ M. Perez et al. (1994). "Cocaine and cocaethylene: microdialysis comparison of brain drug levels and effects on dopamine and serotonin". Psychopharmacology (Berl.) 116 (4): 428–32. doi:10.1111/j.1471-4159.1993.tb03305.x. PMID 8455033.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 成人におけるコカイン使用障害：病態、薬理学、臨床症状、医学的転帰、および診断 cocaine use disorder in adults epidemiology pharmacology clinical manifestations medical consequences and diagnosis
2. コカイン：急性中毒 cocaine acute intoxication

English Journal

Specificity and Ligand Affinities of the Cocaine Aptamer: Impact of Structural Features and Physiological NaCl.

Sachan A1, Ilgu M1, Kempema A1, Kraus GA1, Nilsen-Hamilton M1.
Analytical chemistry.Anal Chem.2016 Jul 11. [Epub ahead of print]
The cocaine aptamer has been seen as a good candidate for development as a probe for cocaine in many contexts. Here, we demonstrate that the aptamer binds cocaine, norcocaine, and cocaethylene with similar affinities and aminoglycosides with similar or higher affinities in a mutually exclusive manne
PMID 27348073

Determination of cocaine and its metabolites in plasma by porous membrane-protected molecularly imprinted polymer micro-solid-phase extraction and liquid chromatography-tandem mass spectrometry.

Sánchez-González J1, García-Carballal S1, Cabarcos P2, Tabernero MJ2, Bermejo-Barrera P1, Moreda-Piñeiro A3.
Journal of chromatography. A.J Chromatogr A.2016 Jun 17;1451:15-22. doi: 10.1016/j.chroma.2016.05.003. Epub 2016 May 3.
A selective molecularly imprinted polymer synthesized for the selective retention of cocaine (COC) and its metabolites [benzoylecgonine (BZE), ecgonine methyl ester (EME), and cocaethylene (CE)] was used as a solid adsorbent for assessing cocaine abuse by plasma analysis. The MIP beads (50mg) were l
PMID 27207577

Screening for illicit drugs in pooled human urine and urinated soil samples and studies on the stability of urinary excretion products of cocaine, MDMA, and MDEA in wastewater by hyphenated mass spectrometry techniques.

Mardal M1, Kinyua J2, Ramin P3, Miserez B4, van Nuijs AL2, Covaci A2, Meyer MR1,5.
Drug testing and analysis.Drug Test Anal.2016 Feb 17. doi: 10.1002/dta.1957. [Epub ahead of print]
Monitoring population drug use through wastewater-based epidemiology (WBE) is a useful method to quantitatively follow trends and estimate total drug consumption in communities. Concentrations of drug biomarkers might be low in wastewater due to dilution; and therefore analysis of pooled urine (PU)
PMID 26888521

Japanese Journal

Determination of cocaine, benzoylecgonine, cocaethylene and norcocaine in human hair using solid-phase extraction and liquid chromatography with tandem mass spectrometric detection

MOORE Christine,COULTER Cynthia,CROMPTON Katherine
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 859(2), 208-212, 2007-11-15
NAID 10027466337

Determination of cocaine and cocaethylene in plasma by solid-phase microextraction and gas chromatography-mass spectrometry

ALVAREZ Ivan,BERMEJO Ana Maria,TABERNERO Maria Jesus,FERNANDEZ Purificacion,LOPEZ Patricia
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 845(1), 90-94, 2007-01-01
NAID 10019944177

Detection of cocaine and cocaethylene in sweat by solid-phase microextraction and gas chromatography/mass spectrometry

FOLLADOR Maria Jose Damas,YONAMINE Mauricio,DE MORAES MOREAU Regina Lucia,SILVA Ovandir Alves
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 811(1), 37-40, 2004-11-05
NAID 10016557263

「コカエチレン」

Cocaethylene
Systematic (IUPAC) name
	ethyl (2R,3S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Clinical data
Pregnancy cat.	C
Legal status	CD (UK) Not scheduled specifically, could be prosecuted as an analogue of a scheduled substance.
Dependence liability	Moderate to High
Routes	Produced from ingestion of cocaine and ethanol
Identifiers
CAS number	529-38-4
ATC code	None
PubChem	CID 65034
ChemSpider	559082
ChEMBL	CHEMBL608806
Synonyms	benzoylecgonine ethyl ester, ethylbenzoylecgonine,
Chemical data
Formula	C18H23NO4
Mol. mass	317.38 g/mol
	SMILES O=C(O[C@H]1C[C@H]2N(C)[C@@H]([C@H]1C(=O)OCC)CC2)c3ccccc3;