Grundinformationen
- Standard-SMILES
COC(=O)C(c1ccccc1)C1CCCCN1- InChIKey
DUGOZIWVEXMGBE-UHFFFAOYSA-N- Summenformel
- C14H19NO2
- Durchschnittliche Molmasse
- 233,31 g/mol
- Monoisotopische Masse
- 233,14157885
Namen und Bezeichner
- Bevorzugter Name
- Methylphenidate
- IUPAC
- methyl 2-phenyl-2-piperidin-2-ylacetate
- Englischer Name
- Ritalin
- Summenformel
- C14H19NO2
- Molmasse
- 233.31
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
113-45-1- PubChem CID
- 4158
- DTXSID
DTXSID5023299- ChEMBL
CHEMBL796- ChEBI
CHEBI:84276- EC Number
- 204-028-6
- Nikkaji
- J5.133K
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,2
- Polarare Oberfläche (TPSA)
- 38,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 17
- Formalladung
- 0
- Komplexität
- 249
Physikochemische Eigenschaften
- Schmelzpunkt
- 74.5 °C · 74.5°C
- Siedepunkt
- 327 ℃ · 327℃
- Dichte
- 1.07 · 1.070
- Brechungsindex
- 1.511 · 1.5110 (estimate)
- Flammpunkt
- 152 ℃ · 152℃
- pka
- 9.51 · 9.51±0.10(Predicted)
- CAS Datenbank
- 113 · 113-45-1
- EPA chemische Informationen
- 2 · 2-Piperidineacetic acid, ?-phenyl-, methyl ester (113-45-1)
Sicherheit und Regulatorisches
Sicherheitsdaten
- Toxizität
- LD50 oral in rat: 367mg/kg
- Giftige Stoffe Daten
- 113-45-1(Hazardous Substances Data)
Chemie und Industrie
Anwendungen
HistoryMethylphenidate 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.
VerwendenStimulant.
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