Aspidospermine
Completing data — refresh the page later to see the latest
Basic information
- CAS
1935-07-5- Standard SMILES
CC[C@@]12CCCN3CC[C@]4(c5cccc(OC)c5N(C(C)=O)[C@@H]4CC1)[C@H]32- InChIKey
ARQOGCYMPUOVHK-ZHHKINOHSA-N- Molecular formula
- C22H30N2O2
- Average molar mass
- 354.5 g/mol
- Monoisotopic mass
- 354.2307282
Overview
Aspidospermine is an indole alkaloid having the structure of aspirospermidine methoxylated at C-17 and acetylated at N-1. It derives from a hydride of an aspidospermidine.
Names & identifiers
- Preferred name
- Aspidospermine
- IUPAC
- 1-[(1R,9R,12R,19R)-12-ethyl-6-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5-trien-8-yl]ethanone
- English name
- ASPIDOSPERMINE
- Molecular formula
- C22H30N2O2
- Molecular weight
- 354.49
Names & synonyms
ASPIDOSPERMINEAspidospermin(-)-Aspidospermine466-49-9NSC-19508NSC-61811U1475W62Q5CHEBI:28463DTXSID701968831-(17-methoxyaspidospermidin-1-yl)ethanone1-((1R,9R,12R,19R)-12-ethyl-6-methoxy-8,16-diazapentacyclo(10.6.1.0^(1,9).0^(2,7).0^(16,19))nonadeca-2(7),3,5-trien-8-yl)ethan-1-one1-((1R,9R,12R,19R)-12-ethyl-6-methoxy-8,16-diazapentacyclo(10.6.1.01,9.02,7.016,19)nonadeca-2(7),3,5-trien-8-yl)ethanone
Show more names
1-acetyl-17-methoxy-aspidospermidinEthanone, 1-(17-methoxyaspidospermidin-1-yl)-
1-[(1R,9R,12R,19R)-12-ethyl-6-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5-trien-8-yl]ethan-1-one1-[(1R,9R,12R,19R)-12-ethyl-6-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5-trien-8-yl]ethanoneRefChem:916386DTXCID10119374207-376-71-Acetyl-17-methoxyaspidospermidineCHEMBL519457NSC61811
Database identifiers
Properties
Computed structural propertiesFilling in
- XLogP
- 3.4
- Topological polar surface area
- 32.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 595
Experimental & physicochemical properties
SpringerMaterials PropertiesCrystal structure
Melting Point208 - 209 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 208 ° · 208°
- alpha
- 15 · D15 -100.2° (alc); D -93° (chloroform)
- Boiling point
- 2 · bp2 220°
- Density
- 1.0938 · 1.0938 (rough estimate)
- refractive index
- 1.63 · 1.6300 (estimate)
- pka
- 1 · pK1: 7.65 (25°C)
- optical activity
- -100.215 · -100.215 (ethanol)
- Water Solubility
- 166.6 mg/L · 166.6mg/L(cold water)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1475 W62Q5 · U1475W62Q5
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- LD50 i.p. in mice: 40 mg/kg (Plzak, Doull)
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
UsesMedicine (respiratory stimulant).
Additional notes
DefinitionChEBI: An indole alkaloid having the structure of aspirospermidine methoxylated at C-17 and acetylated at N-1.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…