Lochnerine
Grundinformationen
- CAS
522-47-4- Standard-SMILES
C/C=C1/CN2[C@H]3C[C@@H]1[C@@H](CO)[C@@H]2Cc1c3[nH]c2ccc(OC)cc12- InChIKey
YTIVOMMYBBBYFH-BOPWJTLDSA-N- Summenformel
- C20H24N2O2
- Durchschnittliche Molmasse
- 324,4 g/mol
- Monoisotopische Masse
- 324,18377801
Überblick
[(1S,12S,13R,14R,15E)-15-ethylidene-7-methoxy-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol has been reported in Rauvolfia biauriculata, Rauvolfia sprucei, and other organisms with data available.
Namen und Bezeichner
- Bevorzugter Name
- Lochnerine
- IUPAC
- [(1S,12S,13R,14R,15E)-15-ethylidene-7-methoxy-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4(9),5,7-tetraen-13-yl]methanol
- Englischer Name
- LOCHNERINE
- Summenformel
- C20H24N2O2
- Molmasse
- 324.42
Namen und Synonyme
Lochnerine(+)-Lochnerine522-47-4Sarpagan-17-ol, 10-methoxy-[(1S,12S,13R,14R,15E)-15-ethylidene-7-methoxy-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4(9),5,7-tetraen-13-yl]methanol((1S,12S,13R,14R,15E)-15-ethylidene-7-methoxy-3,17-diazapentacyclo(12.3.1.02,10.04,9.012,17)octadeca-2(10),4(9),5,7-tetraen-13-yl)methanolRefChem:153912YTIVOMMYBBBYFH-JYOAFUTRSA-NCHEMBL484153DTXSID601318507HY-N3374BDBM50480330
Weitere Namen anzeigen
LochenerineLuo Ke alkali(+)-Lochenerine10-O-Methylsarpagine10-Methoxynormacusine B10-Methoxysarpagan-17-ol6,10-Methanoindolo[3,2-b]quinolizine-11-methanol,9-ethylidene-5,6,8,9,10,11,11a,12-octahydro-2-methoxy-,(6S,7R,9E,10R,11R,11aS)-
AKOS040744703(4R,19E)-10-Methoxysarpagan-17-ol[(E)-ethylidene(methoxy)[?]yl]methanolCS-0024033
Datenbank-Bezeichner
- CAS
522-47-4- PubChem CID
- 6436184
- DTXSID
DTXSID601318507- ChEMBL
CHEMBL484153- Nikkaji
- J147.587H、J3.799.551G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,1
- Polarare Oberfläche (TPSA)
- 48,5 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 536
Physikochemische Eigenschaften
- Schmelzpunkt
- 202.5 · 202.5-203.5°C
- Siedepunkt
- 503.817 · 503.817±50.00 °C(Press: 760.00 Torr)(predicted)
- Dichte
- 1.307 · 1.307±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 14.762 · 14.762±0.10(predicted)
Chemie und Industrie
Anwendungen
BeschreibungThis carboline alkaloid has been obtained from Lochnera rosea and is also present in curare (Strychnos toxifera). Early preparations have been designated Alkaloid 'C' and C-Alkaloid T. It has [α]D + 56° (pyridine) or + n° (EtOH) and forms a crystalline picrate with a double melting point of 177-9°C and 243-5°C (dec.). The methiodide is identical with lochneram iodide, m.p. 235-8°C. A characteristic p-toluenesulphonyl derivative has been prepared, m.p. 153-4°C. One primary alcoholic hydroxyl is present and the alkaloid yields the O-acetate as colourless needles, m.p. 243°C; [α]D - 5.6° ± 3.0° (c 0.36, pyridine). The structure is that of O-methylsarpagine.
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