Basic Info

Common NameErgine(F04932)
2D Structure
Description

Ergine is an alkaloid of the ergoline family. Like other ergoline alkaloids, it occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi. As the dominant alkaloid in the hallucinogenic seeds of Rivea corymbosa, Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea tricolor (morning glory), it is often stated that ergine and/or isoergine (its epimer) is responsible for the psychedelic activity, though this has not been proven. Long term exposure to some ergoline alkaloids can cause ergotism, a disease causing convulsive and gangrenous symptoms. (L1918, L1919)

FRCD IDF04932
CAS Number478-94-4
PubChem CID442072
FormulaC16H17N3O
IUPAC Name

(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

InChI Key

GENAHGKEFJLNJB-QMTHXVAHSA-N

InChI

InChI=1S/C16H17N3O/c1-19-8-10(16(17)20)5-12-11-3-2-4-13-15(11)9(7-18-13)6-14(12)19/h2-5,7,10,14,18H,6,8H2,1H3,(H2,17,20)/t10-,14-/m1/s1

Canonical SMILES

CN1CC(C=C2C1CC3=CNC4=CC=CC2=C34)C(=O)N

Isomeric SMILES

CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)C(=O)N

WikipediaErgine
Synonyms
        
            073830XH10
        
            LYSERGAMIDE
        
            Ergine
        
            Lysergic acid amide
        
            (+)-Lysergamide
        
            478-94-4
        
            D-Lysergic acid amide
        
            9,10-Didehydro-6-methylergoline-8beta-carboxamide
        
            UNII-073830XH10
        
            CHEBI:4819
        
Classifies
                

                  
                    Fungal Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassAlkaloids and derivatives
ClassErgoline and derivatives
SubclassLysergic acids and derivatives
Intermediate Tree NodesNot available
Direct ParentLysergamides
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsLysergic acid amide - Indoloquinoline - Benzoquinoline - Pyrroloquinoline - Quinoline-3-carboxamide - Quinoline - 3-alkylindole - Indole - Indole or derivatives - Isoindole or derivatives - Aralkylamine - Benzenoid - Heteroaromatic compound - Pyrrole - Tertiary aliphatic amine - Tertiary amine - Primary carboxylic acid amide - Carboxamide group - Amino acid or derivatives - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxygen compound - Amine - Organopnictogen compound - Organonitrogen compound - Carbonyl group - Organic nitrogen compound - Organooxygen compound - Organic oxide - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids.

Properties

Property NameProperty Value
Molecular Weight267.332
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Complexity461
Monoisotopic Mass267.137
Exact Mass267.137
XLogP1.6
Formal Charge0
Heavy Atom Count20
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9715
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2-0.5877
P-glycoprotein SubstrateSubstrate0.7591
P-glycoprotein InhibitorNon-inhibitor0.6792
Non-inhibitor0.6842
Renal Organic Cation TransporterInhibitor0.5813
Distribution
Subcellular localizationMitochondria0.4307
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8573
CYP450 2D6 SubstrateNon-substrate0.7280
CYP450 3A4 SubstrateSubstrate0.6947
CYP450 1A2 InhibitorInhibitor0.6852
CYP450 2C9 InhibitorNon-inhibitor0.8707
CYP450 2D6 InhibitorInhibitor0.5457
CYP450 2C19 InhibitorNon-inhibitor0.8704
CYP450 3A4 InhibitorNon-inhibitor0.6449
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6901
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9739
Non-inhibitor0.5264
AMES ToxicityAMES toxic0.5561
CarcinogensNon-carcinogens0.9542
Fish ToxicityHigh FHMT0.8850
Tetrahymena Pyriformis ToxicityHigh TPT0.6476
Honey Bee ToxicityLow HBT0.7353
BiodegradationNot ready biodegradable0.9587
Acute Oral ToxicityIII0.5182
Carcinogenicity (Three-class)Non-required0.6627

Model Value Unit
Absorption
Aqueous solubility-2.3991LogS
Caco-2 Permeability1.0126LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.8688LD50, mol/kg
Fish Toxicity1.2672pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2580pIGC50, ug/L

References

TitleJournalDatePubmed ID
Indole-diterpenes and ergot alkaloids in Cynodon dactylon (Bermuda grass) infected with Claviceps cynodontis from an outbreak of tremors in cattle.J Agric Food Chem2009 Dec 919891432
Analysis of endophyte toxins: fescue and other grasses toxic to livestock.J Anim Sci1995 Mar7608022

Targets

General Function:
Potassium channel regulator activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular Weight:
50618.91 Da
Mechanism of Action:
Ergine acts as an antagonist at the D2 dopamine receptor, inhibiting cyclic AMP production.
References
  1. Larson BT, Harmon DL, Piper EL, Griffis LM, Bush LP: Alkaloid binding and activation of D2 dopamine receptors in cell culture. J Anim Sci. 1999 Apr;77(4):942-7. [10328360 ]