Completing data — usually done within a minute
Basic information
- CAS
19262-68-1- Standard SMILES
COC(=O)[C@H](c1ccccc1)[C@H]1CCCCN1.Cl- InChIKey
JUMYIBMBTDDLNG-OJERSXHUSA-N- Molecular formula
- C14H20ClNO2
- Average molar mass
- 269.77 g/mol
- Monoisotopic mass
- 269.11825656
Overview
Dexmethylphenidate Hydrochloride is a synthetic sympathomimetic amine with CNS stimulating properties. Dexmethylphenidate hydrochloride acts by facilitating the release of catecholamines, particularly noradrenaline and dopamine, from nerve terminals in the brain and inhibits their uptake. This leads to an increase in motor activity, causes euphoria, mental alertness and excitement and suppresses appetite. This drug causes dependence and may cause an increase in heart rate and blood pressure. It is used in the treatment of attention deficit hyperactivity disorder. It may also be used in the treatment of fatigue and other nervous system effects seen with chemotherapy.
Names & identifiers
- Preferred name
- Focalin
- IUPAC
- methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate;hydrochloride
Names & synonyms
Dexmethylphenidate hydrochlorideFocalinD-threo-Methylphenidate hydrochloride19262-68-1dex-methylphenidate hydrochloride1678OK0E08Methylphenidate d-threo-form hydrochloride2-Piperidineacetic acid, alpha-phenyl-, methyl ester, hydrochloride, (alphaR,2R)-AZSTARYS COMPONENT DEXMETHYLPHENIDATE HYDROCHLORIDEFocalinxrXR, FocalinRefChem:56470
Show more names
Hydrochloride, DexmethylphenidateDexmethylphenidate Hydrochloride Extended-releaseDexmethylphenidate HCl23655-65-4Focalin XRDexmethylphenidate hydrochloride [USAN]methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate;hydrochloriderac-threo-Methylphenidate Hydrochloride
Database identifiers
- CAS
19262-68-1、23655-65-4- PubChem CID
- 154100
- DTXSID
DTXSID50940927- ChEMBL
CHEMBL904- UNII
- 1678OK0E08、4B3SC438HI
- EC Number
- 111-173-8
Properties
Computed structural propertiesFilling in
- Topological polar surface area
- 38.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 249
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Adrenergic Agents; Central Nervous System Stimulants; Dopamine Agents; Sympathomimetics; Wakefulness-Promoting Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Exposure Routes11-52%
Toxicity Summary
Methylphenidate blocks dopamine uptake in central adrenergic neurons by blocking dopamine transport or carrier proteins. Methylphenidate acts at the brain stem arousal system and the cerebral cortex and causes increased sympathomimetic activity in the central nervous system. Methylphenidate is a catecholamine reuptake inhibitor that indirectly increases catecholaminergic neurotransmission by inhibiting the dopamine transporter (DAT) and norepinephrine transporter (NET), which are responsible for clearing catecholamines from the synapse, particularly in the striatum and meso-limbic system.
Signs and Symptoms
Symptoms of overdose include vomiting, agitation, tremors, hyperreflexia, muscle twitching, convulsions (may be followed by coma), euphoria, confusion, hallucinations, delirium, sweating, flushing, headache, hyperpyrexia, tachycardia, palpitations, cardiac arrhythmias, hypertension, mydriasis, and dryness of mucous membranes.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Dexmethylphenidate hydrochloride
vLess-DILI-concern
7
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataOral, Mouse: LD<sub>50</sub>=190mg/kg
Chemistry & industry
Pharmacology
Metabolism/Metabolitesepatic, methylphenidate is metabolized primarily by de-esterification to ritalinic acid (α-phenyl-2-piperidine acetic acid, PPAA), which has little to no pharmacologic activity.
Route of Elimination: Renal
Half Life: 2-4 hours
FDA Pharmacological Classification
DEXMETHYLPHENIDATE HYDROCHLORIDE
Central Nervous System Stimulation [PE]; Central Nervous System Stimulant [EPC]
MeSH Pharmacological Classification
A loosely defined group of drugs that tend to increase behavioral alertness, agitation, or excitation. They work by a variety of mechanisms, but usually not by direct excitation of neurons. The many drugs that have such actions as side effects to their main therapeutic use are not included here.
Drugs that block the transport of DOPAMINE into axon terminals or into storage vesicles within terminals. Most of the ADRENERGIC UPTAKE INHIBITORS also inhibit dopamine uptake.
Uses & manufacturing
UsesDexmethylphenidate is used as a treatment for ADHD, ideally in conjunction with psychological, educational, behavioral or other forms of treatment.
Related reactions
2 records
Compound notes
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