(+)-Narwedine

HCID 441596CAS 1668-86-6

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Grundinformationen

Standard-SMILES: COc1ccc2c3c1O[C@@H]1CC(=O)C=C[C@]31CCN(C)C2
InChIKey: QENVUHCAYXAROT-RHSMWYFYSA-N
Summenformel: C17H19NO3
Durchschnittliche Molmasse: 285,34 g/mol

Überblick

(+)-narwedine has been reported in Amaryllidaceae, Leucojum aestivum, and other organisms with data available.

Namen und Bezeichner

Bevorzugter Name: (+)-Narwedine
IUPAC: (1R,12R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-one
Englischer Name: (+/-)-Narwedine
Summenformel: C17H19NO3
Molmasse: 285.34

Namen und Synonyme

(+)-NarwedineNarwedine, (+)-7318-55-0UNII-6A3S1D0Z5T6A3S1D0Z5T1668-86-6(4aR,8aR)-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one6H-Benzofuro[3a,3,2-ef][2]benzazepin-6-one, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aR,8aR)-rel-(+/-)-Narwedinerel-(4aR,8aR)-3-Methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one(+) narwedine(+)-GALANTHAMINONE

Weitere Namen anzeigen

(4aR8aR)-rel-DL-Narwedine(+/-) NAWEDINEL(+)-Narwedine(+/-s)Narwedin6H-Benzofuro[3aNarwedine,racemic2-ef][2]benzazepin-6-one

SCHEMBL13993768AKOS015909405(1R,12R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-oneNS00077733H36277Q27264396GALANTHAMINE, 3-DEOXY-3-OXO-, (4A.BETA.,4BS*)-6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-ONE, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-, (4AR,8AR)-

Datenbank-Bezeichner

CAS: 1668-86-6、7318-55-0
PubChem CID: 441596
UNII: 6A3S1D0Z5T
EC Number: 605-454-9
Nikkaji: J977.690G

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,7
Polarare Oberfläche (TPSA): 38,8 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 4
Frei drehbare Bindungen: 1
Schwere Atome: 21
Formalladung: 0
Komplexität: 477

Physikochemische Eigenschaften

Schmelzpunkt: 198 · 198-199 °C(Solv: ethyl acetate (141-78-6))
Siedepunkt: 397.4 · 397.4±42.0 °C(Predicted)
Dichte: 1.28 · 1.28
pka: 7.84 · 7.84±0.20(Predicted)
InChI: InChI=1/C17H19NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,14H,7-10H2,1-2H3/t14-,17-/s3
InChIKey: QENVUHCAYXAROT-OALMKZFLNA-N
SMILES: N1(C)CC2=CC=C(OC)C3O[C@@]4([H])[C@](C=CC(=O)C4)(C2=3)CC1 |&1:11,13,r|
CAS Datenbank: 1668 · 1668-86-6

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P318, P330, P337+P317, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

Gefahrenhinweise

Hazard Classes and Categories · 2 Einträge

Acute Tox. 4 (100%)

Acute toxicity - category 4

Sicherheitsdaten

Alarmwort: Warnung
Gefahrenhinweise: Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302

Chemie und Industrie

Anwendungen · 1 Eintrag

VerwendenNarwedine is the biogenetic precursor of galanthamine, has been studied as a respiratory stimulator. It increases the amplitude and decreases the frequency of cardiac contractions and would therefore be of value in reducing blood loss during surgery. It also inhibits the action of narcotics and hypnotics, and increases the analgesic effect of morphine as well as the pharmacological effects of caffeine, carbazole, arecoline, and nicotine.