19262-68-1 Usage
Description
Dexmethylphenidate, the pharmacologically effective enantiomer of d,l-methyl
phenidate (Ritalin?) was developed as an improved treatment for attention deficit
hyperactivity disorder (ADHD) in children. Dexmethylphenidate acts via the inhibition of
reuptake of dopamine (by binding to dopamine transporter) and nor-adrenaline. It is thought
to block dopamine and noradrenaline reuptake into the presynaptic neuron and increase
neurotmnsmitter release into the extraneuronal space. Dexmethytphenidate, at half the
usual dose of racemic methylphenidate, improved the symptoms of attention deficit
hyperactivity disorder to a similar extent to methylphenidate in both home and school
settings (SNAP-ADHD scores) at 3 h post dosing. Moreover, some studies showed that
dexmethylphenidate has a statistically significant longer duration of action than the racemic
form as measured by a behavioral scale at 6 h post dosing compared to placebo. In
patients with ADHD, plasma dexmethylphenidate concentrations increased rapidly,
reaching a maximum in the fasted state at approximately l-l.5 h post-dose. The mean
plasma half-life for dexmethylphenidate is approximately 2.2 h. Dexmethylphenidate is
metabolized to d-α-phenyl-piperidine acetic acid, its main urinary metabolite which has
negligible pharmacological activity. In vitro studies showed that dexmethylphenidate did
not inhibit cytochrome P450 isozymes. Dexmethylphenidate was well tolerated; the most
commonly reported adverse events (abdominal pain, headache, anorexia, insomnia) were
mild in severity and consistent with those known to be associated with agents containing
methylphenidate. Current labeling states that dexmethylphenidate should be administered
twice daily with an interval of at least 4 hours between doses. Stimulant medications have
been used for over sixty years and remain, until now, the first line pharmacological therapy
for children with ADHD, demonstrating effectiveness in roughly 70% of patients.
Chemical Properties
White Solid
Originator
Celgene (USA)
Uses
Different sources of media describe the Uses of 19262-68-1 differently. You can refer to the following data:
1. Controlled substance. CNS stimulant. More potent enantiomer
2. Controlled substance. CNS stimulant. The more potent isomers of Methylphenidate. The threo enantomers have shown that the pharmacological activity residues predominantly in the d-threo enantiomer.
Brand name
Focalin (Novartis).
Check Digit Verification of cas no
The CAS Registry Mumber 19262-68-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,2,6 and 2 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 19262-68:
(7*1)+(6*9)+(5*2)+(4*6)+(3*2)+(2*6)+(1*8)=121
121 % 10 = 1
So 19262-68-1 is a valid CAS Registry Number.
InChI:InChI=1/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3/t12-,13-/m1/s1
19262-68-1Relevant articles and documents
Enantioselective synthesis of D-threo-methylphenidate [8]
Axten, Jeffrey M.,Ivy, Robert,Krim, Lori,Winkler, Jeffrey D.
, p. 6511 - 6512 (1999)
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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.
Preparation method of dexmethylphenidate
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Paragraph 0022; 0025; 0030, (2019/10/01)
The invention relates to a new synthetic route of dexmethylphenidate. Methyl phenylacetate serves as a raw material, and the dexmethylphenidate is synthesized at high yield through four steps of an amidation reaction, a diazotization reaction, a cyclization reaction and a rearrangement reaction. The preparation method of the dexmethylphenidate is high in yield, low in cost, environmentally friendly, easy to operate and suitable for industrialization.
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