Methylphenidate
DEXMETHYLPHENIDATE · Rubifen · meridil · Phenidylate · Methylphenidan · Methyl alpha-phenyl-2-piperdine acetate · methyl 2-phenyl-2-(piperidin-2-yl)acetate · alpha-Phenyl-2-piperidineacetic acid methyl ester
Identifikatoren & physikalische Daten
| CAS No. | 113-45-1 |
|---|---|
| Summenformel | C14H19NO2 |
| Durchschnittliche Molmasse | 233,31 g/mol |
| Monoisotopische Masse | 233,14157885 g/mol |
| SMILES | COC(=O)C(c1ccccc1)C1CCCCN1 |
| InChIKey | DUGOZIWVEXMGBE-UHFFFAOYSA-N |
| PubChem CID | 4158 |
| ChEMBL | CHEMBL796 |
| ChEBI | CHEBI:84276 |
| EC No. | 204-028-6 |
| DTXSID | DTXSID5023299 |
Chemische & physikalische Eigenschaften
| XLogP | 0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 38,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 17 |
| Formalladung | 0 |
| Komplexität | 249 |
| Schmelzpunkt | 74.5°C |
| Siedepunkt | 327℃ |
| Dichte | 1.070 |
| Brechungsindex | 1.5110 (estimate) |
| Flammpunkt | 152℃ |
| pKa (Säurekonstante) | 9.51±0.10(Predicted) |
| CAS Datenbank | 113-45-1 |
| EPA chemische Informationen | 2-Piperidineacetic acid, ?-phenyl-, methyl ester (113-45-1) |
Sicherheit & Vorschriften
| Toxizität | LD50 oral in rat: 367mg/kg |
|---|---|
| Gefahrstoffdaten | 113-45-1(Hazardous Substances Data) |
Anwendungen & Verwendung
History
Methylphenidate is a piperidine derivative that is a central nervous system stimulant. Methylphenidate, in its hydrochloride form, is the active ingredient in the common medication Ritalin. Methylphenidate was first synthesized from benzyl cyanide and 2-chloropyridine in Basel, Switzerland in 1944 by Ciba chemist Leandro Panizzon (1907 ).Panizzon named the substance Ritaline after his wife, whose nickname was Rita. Panizzon and Max Hartmann proposed an improved synthesis for methylphenidate and obtained a U.S. patent for its preparation in 1950 (U.S. Patent Number 2507631). In 1954, methylphenidate was patented for use as an agent for treating psychological disorders under the name Ritalin by the Ciba pharmaceutical company.(Ciba subsequently merged with the Geigy company to become Ciba-Geigy, and then Ciba-Geigy merged with Sandoz to form Novartis.) Methylphenidate was first used to reverse drug-induced coma. Ritalin was approved by the Food and Drug Administration (FDA) in 1955 and introduced in the United States in 1956 for several conditions including depression, senile behavior, lethargy, and narcolepsy. Hyperactive children were first treated with stimulants in 1937. Since methylphenidate first appeared on the market, its use for treating ADHD has steadily increased. It is the most commonly used medication for treating children diagnosed with ADHD.
Verwenden
Stimulant.