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{{Chembox
{{Chembox
| ImageFile = Vomilenine.png
| ImageFile = Vomilenine.svg
| ImageSize = 150px
| ImageSize = 200px
| ImageAlt =
| ImageAlt =
| IUPACName = [(1''R'',10''S'',12''R'',13''E'',14''R'',16''S'',18''R'')-13-Ethylidene-14-hydroxy-8,15-diazahexacyclo[14.2.1.0<sup>1,9</sup>.0<sup>2,7</sup>.0<sup>10,15</sup>.0<sup>12,17</sup>]nonadeca-2,4,6,8-tetraen-18-yl] acetate
| IUPACName =
| OtherNames =
| OtherNames = 21α-Hydroxy-22-norajmala-1,19-dien-17α-yl acetate
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo =
| CASNo = 6880-50-8
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 11953806
| SMILES = }}
| UNII = C9L2GUG8W2
| PubChem = 11953806
| Section2 = {{Chembox Properties
| ChemSpiderID = 10128107
| Formula =
| SMILES = C/C=C/1\[C@@H]2C[C@H]3C4=NC5=CC=CC=C5[C@]46C[C@@H](C2[C@H]6OC(=O)C)N3[C@@H]1O}}
| MolarMass =
|Section2={{Chembox Properties
| Appearance =
| C=21 | H=22 | N=2 | O=3
| Density =
| MeltingPt =
| Appearance =
| BoilingPt =
| Density =
| Solubility = }}
| MeltingPt =
| BoilingPt =
| Section3 = {{Chembox Hazards
| MainHazards =
| Solubility = }}
|Section3={{Chembox Hazards
| FlashPt =
| Autoignition = }}
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
}}


'''Vomilenine''' is an [[alkaloid]] that is an intermediate chemical in the biosynthesis of [[ajmaline]].<ref>{{cite journal |last1=von Schumann |first1=Gerald |last2=Gao |first2=Shujuan |last3=Stöckigt |first3=Joachim |date=2002 |title=Vomilenine reductase--a novel enzyme catalyzing a crucial step in the biosynthesis of the therapeutically applied antiarrhythmic alkaloid ajmaline |journal=Bioorg Med Chem |volume=10 |issue=6 |pages=1913–1918 |doi=10.1016/s0968-0896(01)00435-7 |pmid=11937349}}</ref>
'''Vomilenine''' is an intermediate chemical in the biosynthesis of [[ajmaline]].


==External links==
==References==
{{reflist}}
* [http://www.ncbi.nlm.nih.gov/pubmed/11937349 Vomilenine reductase--a novel enzyme catalyzing a crucial step in the biosynthesis of the therapeutically applied antiarrhythmic alkaloid ajmaline]


[[Category:Tryptamine alkaloids]]
[[Category:Quinolizidine alkaloids]]


{{organic-chem-stub}}
{{alkaloid-stub}}
{{Uncategorized stub|date=October 2013}}

Latest revision as of 18:01, 18 August 2022

Vomilenine
Names
IUPAC name
[(1R,10S,12R,13E,14R,16S,18R)-13-Ethylidene-14-hydroxy-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6,8-tetraen-18-yl] acetate
Other names
21α-Hydroxy-22-norajmala-1,19-dien-17α-yl acetate
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • C/C=C/1\[C@@H]2C[C@H]3C4=NC5=CC=CC=C5[C@]46C[C@@H](C2[C@H]6OC(=O)C)N3[C@@H]1O
Properties
C21H22N2O3
Molar mass 350.418 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vomilenine is an alkaloid that is an intermediate chemical in the biosynthesis of ajmaline.[1]

References

[edit]
  1. ^ von Schumann, Gerald; Gao, Shujuan; Stöckigt, Joachim (2002). "Vomilenine reductase--a novel enzyme catalyzing a crucial step in the biosynthesis of the therapeutically applied antiarrhythmic alkaloid ajmaline". Bioorg Med Chem. 10 (6): 1913–1918. doi:10.1016/s0968-0896(01)00435-7. PMID 11937349.