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Elymoclavine information


Elymoclavine
Names
IUPAC name
(6-Methyl-8,9-didehydroergolin-8-yl)methanol
Systematic IUPAC name
[(6aR,10aR)-7-Methyl-4,6,6a,7,8,10a-hexahydroindolo[4,3-fg]quinolin-9-yl]methanol
Identifiers
CAS Number
  • 548-43-6 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 389734
ECHA InfoCard 100.008.136 Edit this at Wikidata
PubChem CID
  • 440904
UNII
  • 5LR46DLO0D checkY
CompTox Dashboard (EPA)
  • DTXSID70970145 Edit this at Wikidata
InChI
  • InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,13,15,17,19H,6,8-9H2,1H3/t13-,15-/m1/s1
    Key: DAVNRFCJMIONPO-UKRRQHHQSA-N
  • InChI=1/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,13,15,17,19H,6,8-9H2,1H3/t13-,15-/m1/s1
    Key: DAVNRFCJMIONPO-UKRRQHHQBW
SMILES
  • OCC\2=C\[C@@H]3c4cccc1c4c(c[nH]1)C[C@H]3N(C/2)C
Properties
Chemical formula
 C16H18N2O
Molar mass 254.327
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Elymoclavine is an ergot alkaloid (ergoline alkaloid). It can be produced from C. fusiformis from Pennisetum typhoideum. It is a precursor in the biosynthesis of D-(+)-lysergic acid. Ergot alkaloids are natural products derived from L-tryptophan. They are often toxic for humans and animals. Despite that they are also well known for their pharmacological activities.[1][2]

  1. ^ Ahimsa-Müller, M. A.; Markert A.; Hellwig S.; Knoop V.; Steiner U.; Drewke C.; Leistner E. (2007). "Clavicipitaceous fungi associated with ergoline alkaloid-containing convolvulaceae". J. Nat. Prod. 70 (12): 1955–1960. doi:10.1021/np070315t. PMID 18031017.
  2. ^ Komarova, E. L.; Tolkachev O. N. (2001). "The Chemistry of Peptide Ergot Alkaloids. Part 2. Analytical Methods for Determining Ergot Alkaloids". Pharm. Chem. J. 35 (10): 542–549. doi:10.1023/A:1014706301632. S2CID 2721387.

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Elymoclavine

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Elymoclavine is an ergot alkaloid (ergoline alkaloid). It can be produced from C. fusiformis from Pennisetum typhoideum. It is a precursor in the biosynthesis...

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Ergine

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monooxygenases (CYP450) are then thought to catalyze the formation of elymoclavine from argoclavine via a 2 electron oxidation. This is further converted...

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Argyreia nervosa

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Ergometrine 0.049% Lysergic acid hydroxyethylamide 0.035% Isolysergic acid hydroxyethylamide 0.024% Elymoclavine 0.022% Ergometrinine 0.011% Chanoclavine 0.016%...

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C16H18N2O

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C16H18N2O (molar mass: 254.33 g/mol) may refer to: Amphenone B, or amphenone Elymoclavine Epoxyagroclavine Lysergol Setoclavine This set index page lists chemical...

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Ergoline

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modifications to the basic ergoline are seen in nature, for example agroclavine, elymoclavine, lysergol. Those deriving from dimethylergoline are referred to as clavines...

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Agroclavine

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in the synthesis of ergot-based drugs; agroclavine can be oxidized to elymoclavine, which then undergoes further processing. Bhattacharji, S., Birch, A...

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Ergocryptine

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oxidation of agroclavne to the corresponding primary alcohol, elymoclavine. Elymoclavine is then oxidized by four electrons by a P450 monooxygenase to...

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Indole alkaloid

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biosynthesis are chanoclavine-I and agroclavine – the latter is hydroxylated to elymoclavine, which in turn oxidizes into paspalic acid. In the process of allyl rearrangement...

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