Ergine
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Basic Info
Common Name | Ergine(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 ID | F04932 |
CAS Number | 478-94-4 |
PubChem CID | 442072 |
Formula | C16H17N3O |
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 |
Wikipedia | Ergine |
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 Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Alkaloids and derivatives |
Class | Ergoline and derivatives |
Subclass | Lysergic acids and derivatives |
Intermediate Tree Nodes | Not available |
Direct Parent | Lysergamides |
Alternative Parents |
|
Molecular Framework | Aromatic heteropolycyclic compounds |
Substituents | Lysergic 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 |
Description | This compound belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 267.332 |
Hydrogen Bond Donor Count | 2 |
Hydrogen Bond Acceptor Count | 2 |
Rotatable Bond Count | 1 |
Complexity | 461 |
Monoisotopic Mass | 267.137 |
Exact Mass | 267.137 |
XLogP | 1.6 |
Formal Charge | 0 |
Heavy Atom Count | 20 |
Defined Atom Stereocenter Count | 2 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9715 |
Human Intestinal Absorption | HIA+ | 1.0000 |
Caco-2 Permeability | Caco2- | 0.5877 |
P-glycoprotein Substrate | Substrate | 0.7591 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.6792 |
Non-inhibitor | 0.6842 | |
Renal Organic Cation Transporter | Inhibitor | 0.5813 |
Distribution | ||
Subcellular localization | Mitochondria | 0.4307 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8573 |
CYP450 2D6 Substrate | Non-substrate | 0.7280 |
CYP450 3A4 Substrate | Substrate | 0.6947 |
CYP450 1A2 Inhibitor | Inhibitor | 0.6852 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.8707 |
CYP450 2D6 Inhibitor | Inhibitor | 0.5457 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.8704 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.6449 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6901 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9739 |
Non-inhibitor | 0.5264 | |
AMES Toxicity | AMES toxic | 0.5561 |
Carcinogens | Non-carcinogens | 0.9542 |
Fish Toxicity | High FHMT | 0.8850 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.6476 |
Honey Bee Toxicity | Low HBT | 0.7353 |
Biodegradation | Not ready biodegradable | 0.9587 |
Acute Oral Toxicity | III | 0.5182 |
Carcinogenicity (Three-class) | Non-required | 0.6627 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -2.3991 | LogS |
Caco-2 Permeability | 1.0126 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.8688 | LD50, mol/kg |
Fish Toxicity | 1.2672 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.2580 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed 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 Chem | 2009 Dec 9 | 19891432 |
Analysis of endophyte toxins: fescue and other grasses toxic to livestock. | J Anim Sci | 1995 Mar | 7608022 |
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
- 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 ]