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CAS

  • or

29419-97-4

D-erythro-Methylphenidate Hydrochloride is a pharmaceutical compound that belongs to the class of central nervous system stimulants. It is primarily used for the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. D-erythro-Methylphenidate Hydrochloride is known for its ability to improve focus, attention, and impulse control in individuals with ADHD.

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  • 29419-97-4 Structure

  • Basic information

    1. Product Name: D-erythro-Methylphenidate Hydrochloride
    2. Synonyms: (2R,2'S)-(+)-threo-Methyl α-Phenyl-α-(2-piperidyl)acetate Hydrochloride;(αR,2S)-
    3. CAS NO:29419-97-4
    4. Molecular Formula: C14H19NO2*ClH
    5. Molecular Weight: 269.7671
    6. EINECS: N/A
    7. Product Categories: Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
    8. Mol File: 29419-97-4.mol

  • Chemical Properties

    1. Melting Point: 218-219 °C
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: D-erythro-Methylphenidate Hydrochloride(CAS DataBase Reference)
    10. NIST Chemistry Reference: D-erythro-Methylphenidate Hydrochloride(29419-97-4)
    11. EPA Substance Registry System: D-erythro-Methylphenidate Hydrochloride(29419-97-4)

  • 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: 29419-97-4(Hazardous Substances Data)

29419-97-4 Usage

Uses

Used in Pharmaceutical Industry:
D-erythro-Methylphenidate Hydrochloride is used as a therapeutic agent for the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It works by increasing the levels of certain neurotransmitters in the brain, such as dopamine and norepinephrine, which helps improve focus, attention, and impulse control.
However, it is important to note that the erythro isomers of D-erythro-Methylphenidate Hydrochloride have been shown to exhibit very little therapeutic effect and contribute mainly to the toxic hypertensive effects of the drug. As a result, the dextro isomers are typically preferred for medical use.
Additionally, D-erythro-Methylphenidate Hydrochloride is classified as a controlled substance due to its potential for abuse and dependence. It is crucial to follow the prescribed dosage and administration guidelines to minimize the risk of adverse effects and ensure the safe and effective use of the medication.

Check Digit Verification of cas no

The CAS Registry Mumber 29419-97-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,4,1 and 9 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 29419-97:
(7*2)+(6*9)+(5*4)+(4*1)+(3*9)+(2*9)+(1*7)=144
144 % 10 = 4
So 29419-97-4 is a valid CAS Registry Number.

29419-97-4Relevant articles and documents

Changing stereoselectivity and regioselectivity in copper(i)-catalyzed 5-: Exo cyclization by chelation and rigidity in aminoalkyl radicals: Synthesis towards diverse bioactive N-heterocycles

Sadanandan, Sandhya,Gupta, Dharmendra Kumar

, p. 3350 - 3365 (2020/03/06)

The work reveals that a chelate-Type interaction in the transition state of a β-Aminoalkyl radical in a copper(i)-catalyzed 5-exo-Trig radical cyclization step changes the usual stereochemistry of the NH-pyrrolidine ring predicted by the Beckwith-Houk transition state model. In contrast, the rigidity in the fused β-Aminoalkyl radical changes the Baldwin's predicted 5-exo to 6-endo cyclization mode, preferentially forming a piperidine ring over a pyrrolidine ring via a geometrically constrained transition state. The resultant diverse NH-pyrrolidines, pyrrolines and piperidines are sources of the bioactive natural product roseophilin and the drug Ritalin among others.

IMPROVEMENTS IN OR RELATING TO ORGANIC MATERIAL

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Paragraph 0056; 0057, (2018/04/13)

The invention provides a method for the preparation of an intermediate for use in synthesizing a lower alkyl phenidate compound of formula (I), wherein each R1 independently represents an optionally substituted aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, acyl, carboxyl, hydroxyl, halogen, amino, nitro, sulfo or sulfhydryl group, R2 represents a hydrogen atom or a lower alkyl group, n represents an integer from 1 to 5 and m represents an integer from 1 to 3 or a pharmaceutically acceptable salt thereof; which method comprises the steps of: (a) flowing a tosylhydrazone compound of formula (IV), wherein R1, n and m are as defined above in relation to the methylphenidate of formula (I), an organic base and an organic solvent into a fluidic network; and (b) reacting the tosylhydrazone compound of formula (IV) and the base in the fluidic network under thermal and/or photochemical conditions to form a transient diazoamide compound of formula (V), wherein R1, n and m are as defined above in relation to the methylphenidate of formula (I).

PROCESS FOR THE PREPARATION OF METHYLPHENIDATE AND PHARMACEUTICAL SALTS THEREOF

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Page/Page column 0345-0347, (2015/05/26)

The present invention is directed to an improved process for the preparation of methylphenidate, stereoisomer, mixture of stereoisomers and pharmaceutically acceptable salts thereof, more particularly, the sulfate and hydrochloride salts of methylphenidate, di-threo-methylphenidate and dex-methylphenidate. Methods of removing or reducing the amount of impurities from the above described process are also disclosed.

LOW-TEMPERATURE SYNTHESIS OF METHYLPHENIDATE HYDROCHLORIDE

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Page/Page column 25, (2012/06/30)

The present invention describes a process for the preparation of methylphenidate hydrochloride. The process involves the esterification of ritalinic acid and methanol in the presence of an acid catalyst at a low temperature. The process may optionally involve the addition of an orthoester.

PROCESS FOR PREPARING METHYL PHENIDATE HYDROCHLORIDE

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Page/Page column 6, (2011/06/25)

Disclosed herein is a process for the preparation of methyl phenidate hydrochloride (Formula I), comprising the steps of; hydrolyzing α-phenyl-α-pipyridyl acetamide (Formula II) in presence of mineral acid at reflux temperature and subsequent neutralization to yield threo -α-phenyl-α-pipyridyl-2-acetic acid (Formula III) which in presence of acidic catalyst reacts with methanol followed by treatment with alcoholic hydrochloride solution produces methyl phenidate hydrochloride.

Synthesis of Methylphenidate and Analogs Thereof

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Page/Page column 6-7, (2010/08/03)

A synthetic process for the preparation of amino acid esters such as methylphenidate and analogs thereof is disclosed. The process involves reacting an amino acid such as α-phenyl-α-(2-piperidinyl)acetic acid or an analog thereof with an alcohol such as methanol in the presence of an acid and a water sequestrant such as trimethyl orthoacetate. In some embodiments, the water sequestrant is added to the reaction mixture after an initial period of esterification and then the reaction is allowed to continue. The α-phenyl-α-(2-piperidinyl)acetic acid methyl ester or analog thereof is then isolated from the reaction mixture. In one variation of the process, the supernatant liquid may be recycled in subsequent runs to increase yield and product purity.

Method to separate stereoisomers

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Page/Page column 4, (2010/02/13)

A method to resolve the stereoisomers of an optically active compound comprising an amine moiety. The method provides a mixture comprising two stereoisomers of a compound comprising a amine moiety. The method supplies l-fenchyloxyacetic acid, treats the mixture of stereoisomers with that l-fenchyloxyacetic acid, and collects one of those two stereoisomers having greater than a 99 percent enantiomeric excess.

Process for the preparation of threo-methylphenidate hydrochloride

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Page/Page column 5-6, (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.