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

• ChemBase ID: 4439
• Molecular Formular: C14H19NO2
• Molecular Mass: 233.30616
• Monoisotopic Mass: 233.14157885
• SMILES: O(C(=O)[C@@H]([C@@H]1NCCCC1)c1ccccc1)C
• Canonical SMILES: COC(=O)[C@H](c1ccccc1)[C@H]1CCCCN1
• InChI: InChI=1S/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
• InChIKey: DUGOZIWVEXMGBE-CHWSQXEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate
• IUPAC Traditional name: focalin
• Brand Name: Focalin
• Synonyms: Dexmethylphenidate

Database IDs

• CAS Number: 40431-64-9
• PubChem SID: 99443255; 160967871
• PubChem CID: 4158; 154101

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.8258359
• LogD (pH = 7.4): 0.5692904
• Log P: 2.254935
• Molar Refractivity: 66.7282 cm^3
• Polarizability: 26.621723 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.47
• LOG S: -3.11
• Solubility (Water): 1.82e-01 g/l

DETAILS

DrugBank - DB06701

• Drug Groups: approved
• Description: Dexmethylphenidate is the dextrorotary form of methylphenidate. It is a norepinephrine-dopamine reuptake inhibitor (NDRI) and thus a psychostimulant. It is used for treatment of Attention Deficit Hyperactivity Disorder (ADHD).
• Indication: Dexmethylphenidate is used as a treatment for ADHD, ideally in conjunction with psychological, educational, behavioral or other forms of treatment.
• Pharmacology: Methylphenidate is a central nervous system stimulant used most commonly in the treatment of attention-deficit disorders in children and for narcolepsy.
• Toxicity: Insomnia, dizziness, nausea, stomach pain, euphoria, headache, anxiety, anorexia, and weight loss are common side effects.; 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. LD₅₀=190mg/kg (orally in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: epatic, methylphenidate is metabolized primarily by de-esterification to ritalinic acid (α-phenyl-2-piperidine acetic acid, PPAA), which has little to no pharmacologic activity.
• Absorption: 11-52%
• Half Life: 2-4 hours
• Protein Binding: 30%
• Elimination: Renal
• External Links: Wikipedia