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Methylphenidate, sold under the brand name Ritalin and Concerta, among others, is a central nervous system (CNS) stimulant used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It may be taken by mouth or applied to the skin, and different formulations have varying durations of effect.[3] For ADHD, the effectiveness of methylphenidate is comparable to atomoxetine[15][16][17][18] but modestly lower than amphetamine.[19][20][21][22] However, methylphenidate is preferred as a first-line treatment in children, while amphetamine is preferred in adults.[23] Methylphenidate reduces core ADHD symptoms and may do so in part by enhancing executive functions, such as working memorysustained attention, and inhibitory control.[24][25][26]

At therapeutic doses, methylphenidate increases alertness and concentration and reduces hyperactivity and impulsive behavior in individuals with ADHD.[27] Common side effects include loss of appetiteweight losstrouble sleeping, and small increases in heart rate and blood pressure.[27][needs update] Long-term treatment in children has been associated with slightly slower growth.[3] Methylphenidate can be misused; dependence and withdrawal are mainly reported with high-dose or non-medical use and are uncommon at therapeutic doses.[28]

Methylphenidate is believed to work by blocking the reuptake of dopamine and norepinephrine by neurons.[29][30] It is a central nervous system (CNS) stimulant of the phenethylamine and piperidine classes. It is available as a generic medication.[31] In 2023, it was the 50th most commonly prescribed medication in the United States, with more than 13 million prescriptions. Buy Methylphenidate (Concerta) Cas 20748-11-2

Uses

Medical

Methylphenidate is most commonly used to treat ADHD and narcolepsy.[34]

Attention deficit hyperactivity disorder

Methylphenidate is used for the treatment of attention deficit hyperactivity disorder (ADHD).[35] The dosage may vary and is titrated to effect, with some guidelines recommending initial treatment with a low dose.[36] Methylphenidate is available in both immediate-release and modified-release formulations.[37][38] Methylphenidate is not approved for children under six years of age. Buy Methylphenidate (Concerta) Cas 20748-11-2

The International Consensus Statement on ADHD shows that the results from systematic reviewsmeta-analyses and large scale studies are clear: methylphenidate is safe and among the most efficacious drugs in all of medicine; treatment in the long-term substantially reduces accidental injuries, traumatic brain injury, substance abuse, cigarette smoking, educational underachievement, bone fractures, sexually transmitted infections, depression, suicide, criminal activity, teenage pregnancy, vehicle crashes, burn injuries and overall-cause mortality, and eliminates the increased risk for obesity. Buy Methylphenidate (Concerta) Cas 20748-11-2

One committee from the World Health Organization (WHO) responsible for the World Health Organization Essential Medicines List rejected an application in 2019, and a second application endorsed by 51 professional medical groups in 2021, for methylphenidate’s inclusion due to uncertainty about its efficacy and safety.[42][43] However, in November 2023, the WHO Mental Health Gap Action Programme Guidelines for mental, neurological, and substance use disorders recommended that methylphenidate should be considered for children aged 6 years and older who have ADHD, noting specifically that, “methylphenidate treatment shows substantial effects on symptom reduction”,[44] in addition to other WHO publications.[45] In 2024, the European Society for Child and Adolescent Psychiatry (ESCAP) and the American Academy of Paediatrics (AAP) endorsed the inclusion of methylphenidate in the WHO EML.[46][47] A new application for methylphenidate’s inclusion is currently pending review,[48] having sparked debate in the comment process among researchers engaged in the evaluation of the evidence-base. Buy Methylphenidate (Concerta) Cas 20748-11-2

Safety and efficacy data have been reviewed extensively by medical regulators (e.g., the US Food and Drug Administration and the European Medicines Agency), the developers of evidence-based national guidelines (e.g., the UK National Institute for Health and Care Excellence and the American Academy of Pediatrics), and government agencies who have endorsed these guidelines (e.g., the Australian National Health and Medical Research Council). These professional groups unanimously conclude, based on the scientific evidence, that methylphenidate is safe and effective and should be considered as a first-line treatment for ADHD. Buy Methylphenidate (Concerta) Cas 20748-11-2

Since the diagnosis of ADHD has increased around the world, methylphenidate may be misused as a “study drug” by students, which may be harmful.[52] This also applies to people who may be experiencing a different issue and are misdiagnosed with ADHD.[52] People in this category are prone to experience the adverse effects of the drug, which can worsen their condition. Buy Methylphenidate (Concerta) Cas 20748-11-2

Long-term meta-analyses and systematic reviews show that the medications used to treat ADHD are not associated with observed deficits in brain structure, but with improved brain development and functioning, most prominently in inferior frontal and striatal regions.[41] The most comprehensive meta-analysis available (19 studies with over 3.9 million participants) found “no statistically significant association between ADHD medications [including methylphenidate] and the risk of cardiovascular event among children and adolescents, young and middle-aged adults, or older adults”;[53] as do other systematic reviews and meta-analyses.[54][55][56]

Narcolepsy

Narcolepsy, a chronic sleep disorder characterized by overwhelming daytime drowsiness and uncontrollable sleep, is treated primarily with stimulants. Methylphenidate is considered effective in increasing wakefulness, vigilance, and performance.[57] Methylphenidate improves measures of somnolence on standardized tests, such as the Multiple Sleep Latency Test (MSLT), but performance does not improve to levels comparable to healthy people.[58]

Other medical uses

Methylphenidate may also be prescribed for off-label use in treatment-resistant cases of bipolar disorder and major depressive disorder.[59] It can also improve depression in several groups, including strokecancer, and HIV-positive patients.[60] There is weak evidence in favor of methylphenidate’s effectiveness for depression,[61] including providing additional benefit in combination with antidepressants.[62] In individuals with terminal cancer, methylphenidate can be used to counteract opioid-induced somnolence, to increase the analgesic effects of opioids, to treat depression, and to improve cognitive function.[63] A 2021 systematic review and meta-analysis found that all studies on geriatric depression reported positive results of methylphenidate use; the review recommended short-term use in combination with citalopram.[64] A 2018 review found low-quality evidence supporting its use to treat apathy as seen in Alzheimer’s disease, in addition to slight benefits for cognition and cognitive performance.[65]

Enhancing performance

Methylphenidate’s efficacy as an athletic performance enhancercognitive enhanceraphrodisiac, and euphoriant is supported by research.[66][67][68][69][70][71][72][73][74] However, the manner in which methylphenidate is used for these purposes (high dosages, alternate routes of administration, during sleep deprivation, etc.) can result in severe unintended side effects.[75][76][74]

A 2015 review found that therapeutic doses of amphetamine and methylphenidate result in modest improvements in cognition, including working memoryepisodic memory, and inhibitory control, in normal healthy adults;[77][a][78][b] the cognition-enhancing effects of these drugs are known to occur through the indirect activation of both dopamine receptor D1 and adrenoceptor α2 in the prefrontal cortex.[77] Methylphenidate and other ADHD stimulants also improve task saliency and increase arousal.[79][80] Stimulants such as amphetamine and methylphenidate can improve performance on difficult and boring tasks,[79][c][80][81] and are used by some students as a study and test-taking aid.[52][82] Based upon studies of self-reported illicit stimulant use, performance-enhancing use rather than use as a recreational drug, is the primary reason that students use stimulants.[83]

Excessive doses of methylphenidate, above the therapeutic range, could interfere with working memory and cognitive control.[79][80] Methylphenidate increases stamina and endurance in humans primarily through reuptake inhibition of dopamine in the central nervous system.[84] Similar to the loss of cognitive enhancement when using large amounts, large doses of methylphenidate could induce side effects that impair athletic performance, such as rhabdomyolysis and hyperthermia.[85] While literature suggests it might improve cognition, there isn’t evidence that its use as a study aid without an ADHD diagnosis improves one’s GPA.[52]

Available forms

The most common formulations of methylphenidate are based on its hydrochloride salt and are available as both immediate-release and extended-release oral dosage forms, as well as transdermal patches. Methylphenidate is a chiral compound with two stereocenters; clinical use overwhelmingly utilizes the racemate threo diastereomer, with the pharmacologically active component being the d-threo-methylphenidate enantiomer. Additionally, dexmethylphenidate (Focalin) is the single d-threo enantiomer formulation approved for medicinal use. There is some evidence that dexmethylphenidate has better bioavailability and a longer duration of action than methylphenidate.[86]

Immediate-release

In the Ritalin tablets series (Ritalin, Ritalin LA, Ritalin SR), the volume of distribution was 2.65±1.11 L/kg for d-methylphenidate and 1.80±0.91 L/kg for l-methylphenidate subsequent to swallowing.[87] Following administration of Concerta, plasma concentrations of the l-isomer were approximately 1/40 the plasma concentrations of the d-isomer.

 

2-Piperidineacetic acid, alpha-phenyl-, methyl ester, stereoisomer is a complex organic compound characterized by a piperidine ring with an alpha-phenyl group and a methyl ester functionality. It is a mixture of stereoisomers, which means it has multiple three-dimensional arrangements of atoms. This unique structure and reactivity make it a valuable building block in the synthesis of various pharmaceuticals and organic compounds.

20748-11-2

  • 20748-11-2 Structure
  • Basic information

    1. Product Name: 2-Piperidineacetic acid, alpha-phenyl-, methyl ester, stereoisomer
    2. Synonyms:
    3. CAS NO:20748-11-2
    4. Molecular Formula: C14H19NO2
    5. Molecular Weight: 233.31
    6. EINECS: N/A
    7. Product Categories: N/A
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 2-Piperidineacetic acid, alpha-phenyl-, methyl ester, stereoisomer(CAS DataBase Reference)
    10. NIST Chemistry Reference: 2-Piperidineacetic acid, alpha-phenyl-, methyl ester, stereoisomer(20748-11-2)
    11. EPA Substance Registry System: 2-Piperidineacetic acid, alpha-phenyl-, methyl ester, stereoisomer(20748-11-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 20748-11-2(Hazardous Substances Data)

20748-11-2 Suppliers

This product is a nationally controlled contraband or patented product, and the Lookchem platform doesn’t provide relevant sales information.

20748-11-2 Usage

Uses

Used in Pharmaceutical Industry:
2-Piperidineacetic acid, alpha-phenyl-, methyl ester, stereoisomer is used as a key intermediate in the synthesis of various pharmaceuticals for its unique structural and reactive properties. It contributes to the development of new drugs and medicinal compounds, enhancing their therapeutic potential.
Used in Organic Chemistry Research:
In the field of organic chemistry, 2-Piperidineacetic acid, alpha-phenyl-, methyl ester, stereoisomer serves as a versatile building block for the synthesis of complex organic molecules. Its unique structure allows for further functionalization and modification, facilitating the exploration of new chemical reactions and the discovery of novel compounds with potential applications.
Used in Drug Development:
2-Piperidineacetic acid, alpha-phenyl-, methyl ester, stereoisomer plays a crucial role in drug development, where it is utilized to create new drug candidates with improved pharmacological properties. Its presence in the molecular structure can influence the drug’s efficacy, selectivity, and safety profile, making it an essential component in the design and optimization of new therapeutic agents.
It is important to handle and use 2-Piperidineacetic acid, alpha-phenyl-, methyl ester, stereoisomer with caution due to potential hazards and risks associated with its use. Proper safety measures and guidelines should be followed to ensure the safe application of 2-Piperidineacetic acid, alpha-phenyl-, methyl ester, stereoisomer in various industries.

Check Digit Verification of cas no

The CAS Registry Mumber 20748-11-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,7,4 and 8 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 20748-11:
(7*2)+(6*0)+(5*7)+(4*4)+(3*8)+(2*1)+(1*1)=92
92 % 10 = 2
So 20748-11-2 is a valid CAS Registry Number.

20748-11-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) – Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name dl-threo-methylphenidate

1.2 Other means of identification

Product number
Other names

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier’s details

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More Details:20748-11-2 SDS

20748-11-2Relevant academic research and scientific papers

α-C-H Bond Functionalization of Unprotected Alicyclic Amines: Lewis-Acid-Promoted Addition of Enolates to Transient Imines

Kim, Jae Hyun,Paul, Anirudra,Ghiviriga, Ion,Seidel, Daniel

, p. 797 – 801 (2021/02/06)

Enolizable cyclic imines, obtained in situ from their corresponding lithium amides by oxidation with simple ketone oxidants, are readily alkylated with a range of enolates to provide mono- and polycyclic β-aminoketones in a single operation, including the natural product (±)-myrtine. Nitrile anions also serve as competent nucleophiles in these transformations, which are promoted by BF3 etherate. β-Aminoesters derived from ester enolates can be converted to the corresponding β-lactams.

Methylphenidate, right pai methyl ester preparation method, intermediate and preparation method

, (2019/04/30)

The invention discloses preparation methods of methylphenidate and dexmethylphenidate, intermediates and preparation methods of the intermediates. The invention provides the preparation method of the methylphenidate, wherein the preparation method is any one of the following methods: a first method comprises the following steps of in a solvent, carrying out an amino protecting group removal reaction of a compound 4 with an amino de-protection reagent, and thus obtaining the methylphenidate 5; a second method comprises the following steps of under the action of an alkali, carrying out an intramolecular nucleophilic substitution reaction of a compound 11 to obtain the methylphenidate 5; and a third method comprises the following steps of in a closed system, in a solvent, under a palladium on carbon or palladium carbon hydroxide catalytic condition, carrying out a reaction of a compound 9 with hydrogen, to obtain the methylphenidate 5. The synthesis method has the advantages of short steps, cheap and easily obtained raw materials, high product yield, good chiral purity, low production cost, and good atomic economy, and is suitable for industrialized production.

ABUSE DETERRENT AND ANTI-DOSE DUMPING PHARMACEUTICAL SALTS USEFUL FOR THE TREATMENT OF ATTENTION DEFICIT/HYPERACTIVITY DISORDER

Page/Page column 23, (2012/02/06)

A pharmaceutical composition comprising a drug substance consisting essentially of a pharmaceutically acceptable organic acid addition salt of an amine containing pharmaceutically active compound wherein the amine containing pharmaceutical active compound is selected from the group consisting of racemic or single isomer ritalinic acid or phenethylamine derivatives and the drug substance has a physical form selected from amorphous and polymorphic.

Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids

Neto, Brenno A.D.,Lapis, Alexandre A.M.,Bernd, Alinne B.,Russowsky, Dennis

experimental part, p. 2484 – 2496 (2009/08/07)

The conditions of the Eschenmoser coupling reaction were studied. The formation of the α-thioiminium ion was achieved faster in the presence of an additive (NaI) and dry chloroform as the preferred solvent. The developed conditions were used for the second part of the reaction (the sulfur extrusion itself). The present protocol avoids the formation of byproducts, which were previously described as a major drawback to be overcome. Electrospray ionization tandem mass spectrometry was used to characterize some aspects (intermediates) of the first step of the reaction mechanism. Some reduction conditions were properly tested and the selected conditions were applied to the synthesis of the natural alkaloid Norallosedamine and other derivatives.

Process for the preparation of threo-methylphenidate hydrochloride

Page/Page column 5, (2008/06/13)

The present invention provides a process for the preparation of threo-methylphenidate hydrochloride. According to a preferred embodiment, the process comprises the following steps: (a) contacting 1-(phenylglyoxylyl)piperidine arenesulfonylhydrazone of the formula wherein Ar denotes an aryl group, where the aryl group may be substituted by a C1-C6 alkyl, halo or nitro group; with an inorganic base in the presence of a water immiscible organic solvent and a phase transfer catalyst to obtain (R*,R*)-enriched 7-phenyl-1-azabicyclo[4.2.0]octan-8-one of the formula: (b) reacting the (R*,R*)-enriched 7-phenyl-1-azabicyclo[4.2.0]octan-8-one prepared in step (a) with a solution of hydrogen chloride in methanol to obtain threo-enriched methylphenidate hydrochloride; (c) crystallizing the threo-enriched methylphenidate hydrochloride prepared in step (b) to give the desired threo-methylphenidate hydrochloride. Preferably, the threo-methylphenidate hydrochloride produced by the process of the present invention contains no more than 1% of the erythro-isomer.

Process for the preparation of dexmethylphenidate hydrochloride

Page 6; 8, (2008/06/13)

The present invention provides a new and efficient process for the preparation of the dexmethylphenidate hydrochloride with high optical purity, the process comprising: (a) reacting a solution of threo-N-Boc-ritalinic acid with (S)-1-phenylethylamine, separating precipitated solid salt of (R,R)-enriched N-Boc-ritalinic acid with (S)-1-phenylethylamnine from the reaction mixture and recrystallizing, reslurring and/or trituring of said salt; (b) mixing the solid salt of (R,R)-N-Boc-ritalinic acid and (S)-1-phenylethylamine obtained in step (a) with aqueous acid and separating (R,R)-N-Boc-ritalinic acid from the mixture; and (c) reacting the (R,R)-N-Boc-ritalinic acid prepared in step (b) with hydrogen chloride and methanol to give dexmethylphenidate hydrochloride with optical purity of at least 99% ee. The present invention further provides salt of (R,R)-N-Boc-ritalinic acid with (S)-1-phenylethylamine as new intermediate in the preparation of dexmethylphenidate hydrochloride.

Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites

Davies, Huw M. L.,Hopper, Darrin W.,Hansen, Tore,Liu, Quixu,Childers, Steven R.

, p. 1799 – 1802 (2007/10/03)

The rhodium(II)-catalyzed intermolecular C-H insertion of methyl aryldiazoacetates with either N-Boc-piperidine or N-Boc-pyrrolidine followed by deprotection with trifluoroacetic acid is a very direct method for the synthesis of methylphenidate analogues. By using either dirhodium tetraacetate or dirhodium tetraprolinate derivatives as catalyst, either the racemic or enantioenriched methylphenidate analogues can be prepared. The binding affinities of the methylphenidate analogues to both the dopamine and the serotonin transporters are described. The most notable compounds are the erythro-(2-naphthyl) analogues which display high binding affinity and selectivity for the serotonin transporter.

A concise and stereoselective synthesis of (+/-)-erythro-methylphenidate

Russowsky, Dennis,Da Silveira Neto, Brenno Amaro

, p. 2923 – 2926 (2007/10/03)

A concise and stereoselective synthesis of racemic erythro-methylphenidate (1) is described. The coupling reaction between piperidine-2-thione (3) and 2-bromo-2-phenylmethylacetate (4) afforded the β-enaminocarbonyl compound 2 in 60% yield by a modified Eschenmoser sulfide contraction reaction. In most cases the bicyclic thiazolidinone 5 was produced. Diastereoselective reduction of 2 in the presence of borohydrydes furnished the (+/-)-erythro-methylphenidate in good yields with dr >95%.

Conformational analysis and stereochemical assignments of products derived from C-H activation at secondary sites

Davies, Huw M.L,Ren, Pingda

, p. 3149 – 3151 (2007/10/03)

The products derived from C-H activation of secondary sites by rhodium-carbenoids exist in a well-defined conformation. Consequently, their stereochemical assignment can be readily determined on the basis of chemical shift arguments.

Synthesis and pharmacology of site specific cocaine abuse treatment agents: A new synthetic methodology for methylphenidate analogs based on the Blaise reaction

Deutsch, Howard M,Ye, Xiaocong,Shi, Qing,Liu, Zhanzhu,Schweri, Margaret M

, p. 303 – 311 (2007/10/03)

In order to make new analogs of the dopamine (DA) uptake inhibitor methylphenidate, a synthetic methodology based on the Blaise reaction was developed. The reaction between α-bromophenylacetic acid esters, zinc and α-cyano-ω-mesylates gave stable primary enamines. After reduction of the enamines with cyanoborohydride, the amines could be cyclized to methylphenidate analogs in which the amine ring size and aromatic ring were varied. These compounds were tested for inhibitory potency against [3H]WIN 35,428 binding to the cocaine recognition site and [3H]DA uptake using rat striatal tissue. When the heterocyclic ring size was varied, the six-membered ring of methylphenidate appeared to be the optimum ring size. When the aryl ring was varied the 4-trifluoromethylphenyl analog was less potent than methylphenidate, the β-naphthyl congener was considerably more potent, whereas the α-naphthyl congener was less potent. Most of the compounds tested had ratios of uptake to binding inhibition (discrimination ratio) that were similar to cocaine and were therefore not lead compounds for the development of cocaine antagonists.

methyl (S)-phenyl[(S)-piperidin-2-yl]acetate

Base Information
  • Chemical Name:methyl (S)-phenyl[(S)-piperidin-2-yl]acetate
  • CAS No.:20748-11-2
  • Deprecated CAS:52760-39-1,73790-87-1
  • Molecular Formula:C14H19NO2
  • Molecular Weight:233.31
  • Hs Code.:
  • UNII:207ZZ9QZ49,IS6UTS8ES9
  • DSSTox Substance ID:DTXSID501312263
  • Nikkaji Number:J343.158D
  • Wikidata:Q27122839
  • NCI Thesaurus Code:C62045
  • RXCUI:6901
  • Pharos Ligand ID:AS1ZHKH1VYVD
  • Metabolomics Workbench ID:57929
  • ChEMBL ID:CHEMBL290634
methyl (S)-phenyl[(S)-piperidin-2-yl]acetate

Synonyms:Centedrin;Concerta;Daytrana;Equasym;Hydrochloride, Methylphenidate;Metadate;Methylin;Methylphenidate;Methylphenidate Hydrochloride;Phenidylate;Ritalin;Ritalin SR;Ritalin-SR;Ritaline;Tsentedrin

 This product is a nationally controlled contraband, and the Lookchem platform doesn’t provide relevant sales information.

Chemical Property of methyl (S)-phenyl[(S)-piperidin-2-yl]acetate
Chemical Property:
  • XLogP3:0.2
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:3
  • Rotatable Bond Count:4
  • Exact Mass:233.141578849
  • Heavy Atom Count:17
  • Complexity:249
Purity/Quality:
Safty Information:
  • Pictogram(s): 
  • Hazard Codes: 
MSDS Files:
SDS file from LookChem
Useful:
  • Canonical SMILES:COC(=O)C(C1CCCCN1)C2=CC=CC=C2
  • Isomeric SMILES:COC(=O)[C@H]([C@@H]1CCCCN1)C2=CC=CC=C2
Technology Process of methyl (S)-phenyl[(S)-piperidin-2-yl]acetate

There total 59 articles about methyl (S)-phenyl[(S)-piperidin-2-yl]acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

 

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