ethylphenidate profile

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

ID Source	ID
PubMed CID	3080846
CHEMBL ID	534479
CHEMBL ID	1187932
SCHEMBL ID	727938
MeSH ID	M0125225

Synonym
57413-43-1
ethylphenidate
bdbm50165211
phenyl-piperidin-2-yl-acetic acid ethyl ester; hydrochloride
CHEMBL534479 ,
(2r,2''r)-phenyl-piperidin-2-yl-acetic acid ethyl ester; hydrochloride
(2s,2''s)-phenyl-piperidin-2-yl-acetic acid ethyl ester; hydrochloride
ethyl 2-phenyl-2-piperidin-2-ylacetate
CHEMBL1187932
SCHEMBL727938
AKOS025149438
ethyl phenyl(piperidin-2-yl)acetate
DTXSID60912317
Q5404506

Research Excerpts

Overview

Ethylphenidate is a new potent synthetic psychoactive drug, structurally related to methylphenidate. Methylphenidate (MPH) is a chiral compound with two chiral centers.

Excerpt	Reference	Relevance
"Methylphenidate (MPH) is a chiral compound with two chiral centers."	( Chiral separation and quantitation of methylphenidate, ethylphenidate, and ritalinic acid in blood using supercritical fluid chromatography. Kronstrand, R; Smith, C; Swortwood, MJ; Vikingsson, S, 2023)	1.8
"Ethylphenidate is a psychostimulant and analog of the commonly prescribed compound, methylphenidate (Ritalin®). "	( L- and D-threo ethylphenidate concentrations, pharmacokinetics, and pharmacodynamics in horses. Benson, D; Hartmann, P; Hovda, L; Knych, HK; McKemie, DS; Seminoff, K, 2018)	2.28
"Ethylphenidate is a novel psychoactive substance that is an analogue of methylphenidate. "	( Ethylphenidate: availability, patterns of use, and acute effects of this novel psychoactive substance. Archer, JR; Bailey, GP; Dargan, PI; Ho, JH; Wood, DM, 2015)	3.3
"Ethylphenidate is a psychostimulant and analogue of methylphenidate. "	( A review of ethylphenidate in deaths in east and west Scotland. McKeown, D; Parks, C; Torrance, HJ, 2015)	2.24
"Ethylphenidate is a new potent synthetic psychoactive drug, structurally related to methylphenidate. "	( Identification of in vitro metabolites of ethylphenidate by liquid chromatography coupled to quadrupole time-of-flight mass spectrometry. Covaci, A; Erratico, C; Negreira, N; van Nuijs, AL, 2016)	2.14
"Ethylphenidate is a stimulant novel psychoactive substance that is an analogue of the prescription drug methylphenidate (Ritalin(®)). "	( Seven fatalities associated with ethylphenidate. Cole, R; Hikin, L; Maskell, PD; Morley, SR; Smith, PR, 2016)	2.16

Pharmacokinetics

Methylphenidate concentrations were not markedly affected by ethanol. Ritalinic acid concentrations were lower, especially if ethanol was ingested first.

Excerpt	Reference	Relevance
" Pharmacokinetic parameters were compared."	( Influence of ethanol and gender on methylphenidate pharmacokinetics and pharmacodynamics. DeVane, CL; Herrin, AE; Janis, GC; Malcolm, R; Markowitz, JS; Minhinnett, RR; Patrick, KS; Straughn, AB; Yeatts, SD, 2007)	0.61
" The pharmacokinetic evaluation showed that methylphenidate concentrations were not markedly affected by ethanol, but ritalinic acid concentrations were lower, especially if ethanol was ingested first."	( Influence of ethanol on the pharmacokinetics of methylphenidate's metabolites ritalinic acid and ethylphenidate. Kauert, GF; Koehm, M; Toennes, SW, 2010)	0.87
" The objectives of the current study were to describe drug concentrations, develop an analytical method that could be used to regulate its use, and describe the pharmacodynamic effects of ethylphenidate in horses."	( L- and D-threo ethylphenidate concentrations, pharmacokinetics, and pharmacodynamics in horses. Benson, D; Hartmann, P; Hovda, L; Knych, HK; McKemie, DS; Seminoff, K, 2018)	1.02

Bioavailability

This study explores the hypotheses that: (1) ethanol will interact with dl-Methylphenidate (MPH) to enantioselectively elevate plasma d-MPH. (2) women will exhibit lower relative bioavailability of MPH than men; and (3) sex-dependent differences in subjective effects will exist.

Excerpt	Reference	Relevance
"This study explores the hypotheses that: (1) ethanol will interact with dl-Methylphenidate (MPH) to enantioselectively elevate plasma d-MPH, and primarily yield l-ethylphenidate as a transesterification metabolite; (2) women will exhibit lower relative bioavailability of MPH than men; and (3) sex-dependent differences in subjective effects will exist."	( Influence of ethanol and gender on methylphenidate pharmacokinetics and pharmacodynamics. DeVane, CL; Herrin, AE; Janis, GC; Malcolm, R; Markowitz, JS; Minhinnett, RR; Patrick, KS; Straughn, AB; Yeatts, SD, 2007)	0.84
" Specifically, we asked: (1) will ethanol increase d-MPH biological concentrations, (2) will MTS facilitate the systemic bioavailability of l-MPH, and (3) will l-MPH enantioselectively interact with ethanol to yield l-ethylphenidate (l-EPH)? Mice were dosed with MTS (¼ of a 12."	( Transdermal and oral dl-methylphenidate-ethanol interactions in C57BL/6J mice: transesterification to ethylphenidate and elevation of d-methylphenidate concentrations. Bell, GH; Griffin, WC; Novak, AJ; Patrick, KS, 2011)	0.86

Dosage Studied

Excerpt	Relevance	Reference
" Specifically, we asked: (1) will ethanol increase d-MPH biological concentrations, (2) will MTS facilitate the systemic bioavailability of l-MPH, and (3) will l-MPH enantioselectively interact with ethanol to yield l-ethylphenidate (l-EPH)? Mice were dosed with MTS (¼ of a 12."	( Transdermal and oral dl-methylphenidate-ethanol interactions in C57BL/6J mice: transesterification to ethylphenidate and elevation of d-methylphenidate concentrations. Bell, GH; Griffin, WC; Novak, AJ; Patrick, KS, 2011)	0.86
" A marked individual variability in the dose-response has been observed, and therefore dosage must be titrated for optimal therapeutic effect with minimal toxicity."	( Metabolomics of Methylphenidate and Ethylphenidate: Implications in Pharmacological and Toxicological Effects. Dinis-Oliveira, RJ, 2017)	0.79

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (3.33)	18.7374
1990's	1 (3.33)	18.2507
2000's	4 (13.33)	29.6817
2010's	21 (70.00)	24.3611
2020's	3 (10.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	2 (6.45%)	5.53%
Reviews	3 (9.68%)	6.00%
Case Studies	7 (22.58%)	4.05%
Observational	1 (3.23%)	0.25%
Other	18 (58.06%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
amphetamine Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.	7.41	1	0	primary amine
methylphenidate Methylphenidate: A central nervous system stimulant used most commonly in the treatment of ATTENTION DEFICIT DISORDER in children and for NARCOLEPSY. Its mechanisms appear to be similar to those of DEXTROAMPHETAMINE. The d-isomer of this drug is referred to as DEXMETHYLPHENIDATE HYDROCHLORIDE.. methylphenidate : A racemate comprising equimolar amounts of the two threo isomers of methyl phenyl(piperidin-2-yl)acetate. A central stimulant and indirect-acting sympathomimetic, is used (generally as the hydrochloride salt) in the treatment of hyperactivity disorders in children and for the treatment of narcolepsy.. methyl phenyl(piperidin-2-yl)acetate : A amino acid ester that is methyl phenylacetate in which one of the hydrogens alpha to the carbonyl group is replaced by a piperidin-2-yl group.	8.71	30	2	beta-amino acid ester; methyl ester; piperidines
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2.1	1	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.57	2	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	2.15	1	0	indazole
benzofuran benzofuran: RN & structure given in first source. 1-benzofuran : A benzofuran consisting of fused benzene and furan rings. It is the parent compound of the class of 1-benzofurans.	7.15	1	0	1-benzofurans; benzofuran
adamantane Adamantane: A tricyclo bridged hydrocarbon.	2.15	1	0	adamantanes; polycyclic alkane
methamphetamine Methamphetamine: A central nervous system stimulant and sympathomimetic with actions and uses similar to DEXTROAMPHETAMINE. The smokable form is a drug of abuse and is referred to as crank, crystal, crystal meth, ice, and speed.. methamphetamine : A member of the class of amphetamines in which the amino group of (S)-amphetamine carries a methyl substituent.	2.89	3	0	amphetamines; secondary amine	central nervous system stimulant; environmental contaminant; neurotoxin; psychotropic drug; xenobiotic
ritalinic acid [no description available]	4.57	5	1	monocarboxylic acid; piperidines	drug metabolite; marine xenobiotic metabolite
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	7.52	2	0
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.1	1	0	cyclodextrin
cocaine Cocaine: An 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; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.	2.02	1	0	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
6-(2-aminopropyl)benzofuran 6-(2-aminopropyl)benzofuran: do not confuse with 1-(2, 3-dihydro-1-benzofuran-6-yl)propan-2-amine, which is also known as 6-APB	2.1	1	0
lisdexamfetamine dimesylate Lisdexamfetamine Dimesylate: A dextroamphetamine drug precursor that also functions as a CENTRAL NERVOUS SYSTEM STIMULANT and DOPAMINE UPTAKE INHIBITOR and is used in the treatment of ATTENTION DEFICIT HYPERACTIVITY DISORDER.	2.41	1	0
mephedrone mephedrone: a beta-keto (bk) designer drug; Central Nervous System Stimulants. mephedrone : An aromatic ketone that is propiophenone substituted at C-4 and at C-beta with methyl and methylamino groups respectively. It is a synthetic stimulant and entactogen drug of the amphetamine and cathinone classes.	7.31	1	0	amphetamines; aromatic ketone; secondary amino compound	environmental contaminant; xenobiotic
n-(1-adamantyl)-1-(5-fluoropentyl)-1h-indazole-3-carboxamide N-(1-adamantyl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide: a cannabinoid receptor agonist; structure in first source	2.15	1	0	aromatic amide; indazoles

Condition	Relationship Strength	Studies
Amphetamine Abuse [description not available]	2.15	1
Infections, Staphylococcal [description not available]	2.15	1
Drug Abuse, Intravenous [description not available]	2.54	2
Group A Strep Infection [description not available]	2.15	1
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	2.15	1
Streptococcal Infections Infections with bacteria of the genus STREPTOCOCCUS.	2.15	1
Amphetamine-Related Disorders Disorders related or resulting from use of amphetamines.	2.15	1
Chemical Dependence [description not available]	3.03	4
Substance-Related Disorders Disorders related to substance use or abuse.	3.03	4
Drug Bombing [description not available]	2.17	1
Infective Endocarditis [description not available]	2.1	1
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	2.1	1
Endocarditis Inflammation of the inner lining of the heart (ENDOCARDIUM), the continuous membrane lining the four chambers and HEART VALVES. It is often caused by microorganisms including bacteria, viruses, fungi, and rickettsiae. Left untreated, endocarditis can damage heart valves and become life-threatening.	2.1	1
Pneumonia Infection of the lung often accompanied by inflammation.	2.1	1
Arrhythmia [description not available]	2.11	1
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	2.11	1
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	2.11	1
Drug Overdose Accidental or deliberate use of a medication or street drug in excess of normal dosage.	2.44	2
Adipocere [description not available]	2.13	1
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	2.13	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.06	1
Child Behavior Disorders Disturbances considered to be pathological based on age and stage appropriateness, e.g., conduct disturbances and anaclitic depression. This concept does not include psychoneuroses, psychoses, or personality disorders with fixed patterns.	1.96	1
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	2.4	2

ethylphenidate

Description

Cross-References

Synonyms (14)

Research Excerpts

Overview

Pharmacokinetics

Bioavailability

Dosage Studied

Research

Studies (30)

Market Indicators

Research Demand Index: 46.46

Study Types

ethylphenidate

Description

Cross-References

Synonyms (14)

Research Excerpts

Overview

Pharmacokinetics

Bioavailability

Dosage Studied

Research

Studies (30)

Market Indicators

Research Demand Index: 46.46

Study Types

Related Drugs (16)

Related Conditions (23)