Galanthaminon
Basic information
- CAS
1668-86-6- Standard SMILES
COc1ccc2c3c1OC1CC(=O)C=CC31CCN(C)C2- InChIKey
QENVUHCAYXAROT-UHFFFAOYSA-N- Molecular formula
- C17H19NO3
- Average molar mass
- 285.34 g/mol
- Monoisotopic mass
- 285.13649347
Overview
Galantaminone has been reported in Galanthus nivalis and Amaryllidaceae with data available.
Names & identifiers
- Preferred name
- Galanthaminon
- IUPAC
- 9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-one
- English name
- (+/-)-Narwedine
- Molecular formula
- C17H19NO3
- Molecular weight
- 285.34
Names & synonyms
(+/-)-NarwedineGalanthaminon1668-86-6orb16616SCHEMBL1719211SCHEMBL10262470QENVUHCAYXAROT-UHFFFAOYSA-NDTXSID801124485AKOS016023722296237-49-5AU-059/43519687(1S,12S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12.0^{6,17]heptadeca-6(17),7,9,15-tetraen-14-one
Show more names
(4aR8aR)-rel-DL-Narwedine(+/-) NAWEDINEL(+)-Narwedine(+/-s)Narwedin6H-Benzofuro[3aNarwedine,racemic2-ef][2]benzazepin-6-one
3-Methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-one3-Methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-one #4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6h-benzofuro[3a,3,2-ef][2]benzazepin-6-one9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0~1,12~.0~6,17~]heptadeca-6(17),7,9,15-tetraen-14-one
Database identifiers
- CAS
1668-86-6、296237-49-5- PubChem CID
- 625124
- DTXSID
DTXSID801124485- EC Number
- 605-454-9、608-383-1
- Nikkaji
- J1.404.117F
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 38.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 477
Physicochemical properties
- Melting point
- 198 · 198-199 °C(Solv: ethyl acetate (141-78-6))
- Boiling point
- 397.4 · 397.4±42.0 °C(Predicted)
- Density
- 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 DataBase Reference
- 1668 · 1668-86-6
- FDA UNII
- 706417 H · ATP706417H
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H319-H412
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501-P264-P280-P305+P351+P338-P337+P313P-P273-P501
- REACH Registrations
- Inactive
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
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]
Hazard information
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute toxicity - category 4
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H319-H412
- REACH Registrations
- Inactive
- Precautionary statements
- P264-P270-P301+P312-P330-P501-P264-P280-P305+P351+P338-P337+P313P-P273-P501
Chemistry & industry
Applications
UsesNarwedine 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.
Additional notes
DefinitionChEBI: Narwedine is a benzazepine.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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