ritalinic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID Source	ID
PubMed CID	86863
CHEBI ID	83481
SCHEMBL ID	1462581
MeSH ID	M0053672

Synonyms (44)

Synonym
ritalinic acid ,
ritalinic acid, 99% (cp)
19395-41-6
FT-0653505
phenyl(piperidin-2-yl)acetic acid
2-phenyl-2-piperidin-2-ylacetic acid
phenyl(2-piperidinyl)acetic acid;2-phenyl-2-piperidineacetic acid
A19443
2-piperidineacetic acid, alpha-phenyl-
einecs 243-020-7
alpha-phenylpiperidine-2-acetic acid
alpha-phenyl-2-piperidineacetic acid
SCHEMBL1462581
2-phenyl-2-piperidineacetic acid
2-phenyl-2-(piperidin-2-yl)acetic acid
phenyl(2-piperidinyl)acetic acid
FS-3198
AKOS015892837
S5251
CHEBI:83481
mfcd06200695
SY030346
2-phenyl-2-(2-piperidyl)acetic acid
2-phenyl-2-(2-piperidyl) acetic acid
phenyl(2-piperidinyl)acetic acid #
R0111
2-phenyl-2-piperidineacetic acid, 98%
ritalinic acid, analytical standard
AC-8122
ritalinic acid; methylphenidate related compound a
CS-W022954
FT-0674441
FT-0674440
FT-0674442
FT-0674439
FT-0674435
BCP07811
DTXSID20864888
FT-0674443
Q17052328
l-threo-ritalinic acid;(2s)-2-phenyl-2-[(s)-2-piperidinyl]acetic acid
BCP26035
FT-0674438
EN300-7375458

Research Excerpts

Effects

Excerpt	Reference	Relevance
"Ritalinic acid has further been detected in German rivers at concentrations of 4-23 ngL(-1) and in bank filtrate samples in 100-850 m distance from the river up to 5 ngL(-1) demonstrating the widespread occurrence of this stable metabolite in the aquatic environment."	( Occurrence and fate of the human pharmaceutical metabolite ritalinic acid in the aquatic system. Letzel, M; Schüssler, W; Sengl, M; Weiss, K, 2010)	1.33

Pharmacokinetics

Methylphenidate concentrations were not markedly affected by ethanol, but ritalinic acid concentrations were lower. For the first time a physiologically based pharmacokinetic (PBPK) model has been developed.

Excerpt	Reference	Relevance
" MPH and RA were both detected in oral fluid with a pharmacokinetic profile similar to that in plasma."	( Pharmacokinetics of methylphenidate in oral fluid and sweat of a pediatric subject. Farrè, M; García-Algar, O; Marchei, E; Pacifici, R; Pellegrini, M; Pichini, S; Vall, O, 2010)	0.36
" 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)	0.8
" For the first time a physiologically based pharmacokinetic (PBPK) model has been developed in juvenile and adult humans and nonhuman primates to quantitatively evaluate species- and age-dependent enantiomer specific pharmacokinetics of MPH and its primary metabolite ritalinic acid."	( Development of a physiologically based model to describe the pharmacokinetics of methylphenidate in juvenile and adult humans and nonhuman primates. Doerge, DR; Fisher, JW; Gearhart, JM; Mattison, DR; Morris, SM; Paule, MG; Ruark, CD; Slikker, W; Twaddle, NC; Vitiello, B; Yang, X; Young, JF, 2014)	0.58
" 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)	0.48

Bioavailability

Excerpt	Reference	Relevance
"The pharmacokinetics and bioavailability of methylphenidate (MPH) and a metabolite, ritalinic acid (RA), were studied in normal adults, children with hyperactivity, monkeys and rats."	( Pharmacokinetics of methylphenidate in man, rat and monkey. Breese, GR; Ellington, K; Gualtieri, CT; Kilts, C; Kraemer, G; Mueller, RA; Patrick, K; Wargin, W, 1983)	0.49
" In summary, food had no substantial effect on the bioavailability of d-MPH, with an equivalent rate and extent of exposure obtained."	( A single-dose, two-way crossover, bioequivalence study of dexmethylphenidate HCl with and without food in healthy subjects. Khetani, VD; Scheffler, MR; Stirling, DI; Stypinski, D; Teo, SK; Thomas, SD; Wu, A, 2004)	0.32
" An important assumption in the animal models that have been employed to study methylphenidate's effects on the brain and behavior is that bioavailability of methylphenidate in the animal models reflects that in human subjects."	( Plasma and brain concentrations of oral therapeutic doses of methylphenidate and their impact on brain monoamine content in mice. Balcioglu, A; Bhide, PG; Biederman, J; McCarthy, D; Ren, JQ; Spencer, TJ, 2009)	0.35
" Metabolism of MPH in the small intestine was assumed to account for the low oral bioavailability of MPH."	( Development of a physiologically based model to describe the pharmacokinetics of methylphenidate in juvenile and adult humans and nonhuman primates. Doerge, DR; Fisher, JW; Gearhart, JM; Mattison, DR; Morris, SM; Paule, MG; Ruark, CD; Slikker, W; Twaddle, NC; Vitiello, B; Yang, X; Young, JF, 2014)	0.4

Dosage Studied

Excerpt	Relevance	Reference
" An essential component of such studies is the determination of MP plasma levels under chronic and acute dosing conditions."	( Analysis of methylphenidate and its metabolite ritalinic acid in monkey plasma by liquid chromatography/electrospray ionization mass spectrometry. Bajic, S; Doerge, DR; Fogle, CM; McCullagh, M; Paule, MG, 2000)	0.56

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

Roles (2)

Role	Description
marine xenobiotic metabolite	Any metabolite produced by metabolism of a xenobiotic compound in marine macro- and microorganisms.
drug metabolite	null
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

Class	Description
monocarboxylic acid	An oxoacid containing a single carboxy group.
piperidines
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (54)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	11 (20.37)	18.7374
1990's	5 (9.26)	18.2507
2000's	8 (14.81)	29.6817
2010's	25 (46.30)	24.3611
2020's	5 (9.26)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 46.80

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	46.80 (24.57)
Research Supply Index	4.16 (2.92)
Research Growth Index	4.80 (4.65)
Search Engine Demand Index	69.38 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (46.80)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	5 (8.62%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	2 (3.45%)	4.05%
Observational	0 (0.00%)	0.25%
Other	51 (87.93%)	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
carbamazepine Carbamazepine: A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.. carbamazepine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.	2.05	1	0	dibenzoazepine; ureas	analgesic; anticonvulsant; antimanic drug; drug allergen; EC 3.5.1.98 (histone deacetylase) inhibitor; environmental contaminant; glutamate transporter activator; mitogen; non-narcotic analgesic; sodium channel blocker; xenobiotic
chlorpheniramine Chlorpheniramine: A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than PROMETHAZINE.. chlorphenamine : A tertiary amino compound that is propylamine which is substituted at position 3 by a pyridin-2-yl group and a p-chlorophenyl group and in which the hydrogens attached to the nitrogen are replaced by methyl groups. A histamine H1 antagonist, it is used to relieve the symptoms of hay fever, rhinitis, urticaria, and asthma.	7.03	1	0	monochlorobenzenes; pyridines; tertiary amino compound	anti-allergic agent; antidepressant; antipruritic drug; H1-receptor antagonist; histamine antagonist; serotonin uptake inhibitor
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.	2.59	2	0	primary amine
ketamine Ketamine: A cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE) and may interact with sigma receptors.. ketamine : A member of the class of cyclohexanones in which one of the hydrogens at position 2 is substituted by a 2-chlorophenyl group, while the other is substituted by a methylamino group.	7.46	2	0	cyclohexanones; monochlorobenzenes; secondary amino compound	analgesic; environmental contaminant; intravenous anaesthetic; neurotoxin; NMDA receptor antagonist; xenobiotic
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.	8.08	53	5	beta-amino acid ester; methyl ester; piperidines
phenmetrazine Phenmetrazine: A sympathomimetic drug used primarily as an appetite depressant. Its actions and mechanisms are similar to DEXTROAMPHETAMINE.. phenmetrazine : A member of the class of morpholines that is morpholine substituted with a phenyl group at position 2 and a methyl group at position 3.	2.6	1	0	morpholines	metabolite; sympathomimetic agent
zolpidem Zolpidem: An imidazopyridine derivative and short-acting GABA-A receptor agonist that is used for the treatment of INSOMNIA.. zolpidem : An imidazo[1,2-a]pyridine compound having a 4-tolyl group at the 2-position, an N,N-dimethylcarbamoylmethyl group at the 3-position and a methyl substituent at the 6-position.	2.6	1	0	imidazopyridine	central nervous system depressant; GABA agonist; sedative
ephedrine Ephedrine: A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.. (-)-ephedrine : A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.	2.6	1	0	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
du-21220 Ritodrine: An adrenergic beta-2 agonist used to control PREMATURE LABOR.. 4-[2-[[1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenol : A secondary amino compound that is 4-(2-amino-1-hydroxypropyl)phenol in which one of the hydrogens attached to the nitrogen is replaced by a 2-(4-hydroxyphenyl)ethyl group.	1.96	1	0	benzyl alcohols; polyphenol; secondary alcohol; secondary amino compound
tramadol Tramadol: A narcotic analgesic proposed for severe pain. It may be habituating.. tramadol : A racemate consisting of equal amounts of (R,R)- and (S,S)-tramadol. A centrally acting synthetic opioid analgesic, used (as the hydrochloride salt) to treat moderately severe pain. The (R,R)-enantiomer exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer. Originally developed by Gruenenthal GmbH and launched in 1977, it was subsequently isolated from the root bark of the South African tree Nauclea latifolia.. (R,R)-tramadol : A 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol in which both stereocentres have R-configuration; the (R,R)-enantiomer of the racemic opioid analgesic tramadol, it exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer.	2.6	1	0	2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol	adrenergic uptake inhibitor; antitussive; capsaicin receptor antagonist; delta-opioid receptor agonist; kappa-opioid receptor agonist; metabolite; mu-opioid receptor agonist; muscarinic antagonist; nicotinic antagonist; NMDA receptor antagonist; opioid analgesic; serotonergic antagonist; serotonin uptake inhibitor
cathinone cathinone: alkaloid from khat shrub, Catha edulis; RN given refers to parent cpd without isomeric designation. cathinone : The S stereoisomer of 2-aminopropiophenone.	2.1	1	0	2-aminopropiophenone; monoamine alkaloid	central nervous system stimulant; psychotropic drug
peroxyoxalate [no description available]	7.06	1	0
dexmethylphenidate hydrochloride Dexmethylphenidate Hydrochloride: A methylphenidate derivative, DOPAMINE UPTAKE INHIBITOR and CENTRAL NERVOUS SYSTEM STIMULANT that is used in the treatment of ATTENTION DEFICIT HYPERACTIVITY DISORDER.	3.4	1	1
quinidine Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.	3.39	1	1	cinchona alkaloid	alpha-adrenergic antagonist; anti-arrhythmia drug; antimalarial; drug allergen; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; muscarinic antagonist; P450 inhibitor; potassium channel blocker; sodium channel blocker
tempo TEMPO: structure. TEMPO : A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.	7.17	1	0	aminoxyls; piperidines	catalyst; ferroptosis inhibitor; radical scavenger
laccase Laccase: A copper-containing oxidoreductase enzyme that catalyzes the oxidation of 4-benzenediol to 4-benzosemiquinone. It also has activity towards a variety of O-quinols and P-quinols. It primarily found in FUNGI and is involved in LIGNIN degradation, pigment biosynthesis and detoxification of lignin-derived products.	7.17	1	0
ethylphenidate ethylphenidate: structure given in first source	4.57	5	1
oxalates Oxalates: Derivatives of OXALIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are derived from the ethanedioic acid structure.	2.06	1	0

Condition	Relationship Strength	Studies	Trials
ADDH [description not available]	5.09	5	2
Attention Deficit Disorder with Hyperactivity A behavior disorder originating in childhood in which the essential features are signs of developmentally inappropriate inattention, impulsivity, and hyperactivity. Although most individuals have symptoms of both inattention and hyperactivity-impulsivity, one or the other pattern may be predominant. The disorder is more frequent in males than females. Onset is in childhood. Symptoms often attenuate during late adolescence although a minority experience the full complement of symptoms into mid-adulthood. (From DSM-V)	5.09	5	2
Chemical Dependence [description not available]	2.21	1	0
Substance-Related Disorders Disorders related to substance use or abuse.	2.21	1	0
Ache [description not available]	2.1	1	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.1	1	0
Daytime Sleepiness [description not available]	2.1	1	0
Disorders of Excessive Somnolence Disorders characterized by hypersomnolence during normal waking hours that may impair cognitive functioning. Subtypes include primary hypersomnia disorders (e.g., IDIOPATHIC HYPERSOMNOLENCE; NARCOLEPSY; and KLEINE-LEVIN SYNDROME) and secondary hypersomnia disorders where excessive somnolence can be attributed to a known cause (e.g., drug affect, MENTAL DISORDERS, and SLEEP APNEA SYNDROME). (From J Neurol Sci 1998 Jan 8;153(2):192-202; Thorpy, Principles and Practice of Sleep Medicine, 2nd ed, p320)	2.1	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.04	1	0
Hiccough [description not available]	1.93	1	0
Hyperactivity, Motor [description not available]	2.64	3	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	2	1	0
Drug Overdose Accidental or deliberate use of a medication or street drug in excess of normal dosage.	2	1	0
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.	2.36	2	0

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