Rolipram (HCID 5092)

Überblick

Rolipram is a member of the lclass of pyrrolidin-2-ones that is pyrrolidin-2-one bearing a 3-(cyclopentyloxy)-4-methoxyphenyl substituent at the 4-position. It is a type IV-specific phosphodiesterase (PDE4) inhibitor. It has a role as an antidepressant and an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor.

Namen und Bezeichner

Bevorzugter Name: Rolipram
IUPAC: 4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one
Lokaler Name: Rolipram
Englischer Name: ROLIPRAM
Summenformel: C16H21NO3
Molmasse: 275.34

Namen und Synonyme

rolipram61413-54-5(R,S)-rolipram4-(3-(cyclopentyloxy)-4-methoxyphenyl)pyrrolidin-2-oneZK 62711RolipramumZK-627114-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-oneNSC-7601254-(3-(Cyclopentyloxy)-4-methoxyphenyl)-2-pyrrolidinoneZK 62 711

Weitere Namen anzeigen

SB 95952Roliprame(¨¤)-RoliprRolipram >(±)-RolipramROLIPRAM 98+%

SB-95952ZK-62771K676NL63N7CHEBI:104872(+-)-rolipramPyrrolidone, 4-(3-cyclopentyloxy-4-methoxyphenyl)-2-ZK62711RefChem:389268

Datenbank-Bezeichner

CAS: 61413-54-5
PubChem CID: 5092
DTXSID: DTXSID3044124
ChEMBL: CHEMBL63
ChEBI: CHEBI:104872
UNII: K676NL63N7
EC Number: 262-771-1
Nikkaji: J18.478K

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,2
Polarare Oberfläche (TPSA): 47,6 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 4
Schwere Atome: 20
Formalladung: 0
Komplexität: 341

Experimentelle und physikochemische Eigenschaften

LogP2.17

Endocrine DisruptorsPotential endocrine disrupting compound

Collision Cross Section174.11 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt: 127 · 127-133 °C
Siedepunkt: 418.29 °C · 418.29°C (rough estimate)
Dichte: 1.0677 · 1.0677 (rough estimate)
Brechungsindex: 1.55 · 1.5500 (estimate)
storage temp.: -20 °C · Sealed in dry,Store in freezer, under -20°C
Löslichkeit: 2 O: · H2O: 0.2 mg/mL
Aggregatzustand: solid
pka: 16.02 · 16.02±0.40(Predicted)
Farbe: white to off-white
Biologische Quelle: synthetic (organic)
Wasserlöslichkeit: 2 O: · H2O: 0.2mg/mLethanol: 7mg/mLDMSO: 7.3mg/mL
Merck: 14 · 14,8251
Stabilität: 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
InChI: InChI=1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)
InChIKey: HJORMJIFDVBMOB-UHFFFAOYSA-N
SMILES: O(C1CCCC1)C1C=C(C2CC(NC2)=O)C=CC=1OC

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (37.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 64 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (37.5%)

Sicherheitsdaten

wgk: 3
ridadr: 3249
hs_code: 29337900
RTECS-Nr.: UY5749237
risk_code: 36/37/38-11
Toxizität: LD50 oral in mouse: > 300mg/kg
hazard_code: Xi
safety_code: 26-36
hazard_class: 6.1(b)
packing_group: III
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 2 Einträge

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems.

Compounds that specifically inhibit PHOSPHODIESTERASE 4.