Ecgonine

Identification

Name
Ecgonine
Accession Number
DB01525
Type
Small Molecule
Groups
Experimental, Illicit
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
IDS-NE-001
Categories
UNII
DX2E9E17AV
CAS number
481-37-8
Weight
Average: 185.2203
Monoisotopic: 185.105193351
Chemical Formula
C9H15NO3
InChI Key
PHMBVCPLDPDESM-FKSUSPILSA-N
InChI
InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5-,6+,7-,8+/m0/s1
IUPAC Name
(1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
SMILES
[H][C@]12CC[C@]([H])([C@H]([C@@H](O)C1)C(O)=O)N2C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
BenmoxinThe risk or severity of adverse effects can be increased when Ecgonine is combined with Benmoxin.
CaroxazoneThe risk or severity of adverse effects can be increased when Ecgonine is combined with Caroxazone.
ClorgilineThe risk or severity of adverse effects can be increased when Ecgonine is combined with Clorgiline.
FurazolidoneThe risk or severity of adverse effects can be increased when Ecgonine is combined with Furazolidone.
HarmalineThe risk or severity of adverse effects can be increased when Ecgonine is combined with Harmaline.
HydracarbazineThe risk or severity of adverse effects can be increased when Ecgonine is combined with Hydracarbazine.
IproniazidThe risk or severity of adverse effects can be increased when Ecgonine is combined with Iproniazid.
IsocarboxazidThe risk or severity of adverse effects can be increased when Ecgonine is combined with Isocarboxazid.
LinezolidThe risk or severity of adverse effects can be increased when Ecgonine is combined with Linezolid.
MebanazineThe risk or severity of adverse effects can be increased when Ecgonine is combined with Mebanazine.
Food Interactions
Not Available

References

Synthesis Reference

Lowell M. Somers, James E. Wynn, "Derivatives of benzoylecgonine, ecgonine and ecgonidine and methods for preparing and using same." U.S. Patent US5559123, issued December, 1985.

US5559123
General References
Not Available
External Links
KEGG Compound
C10858
PubChem Compound
91460
PubChem Substance
46506479
ChemSpider
82586
ChEBI
4743
Wikipedia
Ecgonine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)205 °CPhysProp
water solubility1.78E+005 mg/LYALKOWSKY,SH & DANNENFELSER,RM (1992)
logS-0.02ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility1050.0 mg/mLALOGPS
logP-0.69ALOGPS
logP-3.1ChemAxon
logS0.75ALOGPS
pKa (Strongest Acidic)3.48ChemAxon
pKa (Strongest Basic)9.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area60.77 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.57 m3·mol-1ChemAxon
Polarizability18.7 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6852
Blood Brain Barrier+0.5115
Caco-2 permeable+0.664
P-glycoprotein substrateSubstrate0.5177
P-glycoprotein inhibitor INon-inhibitor0.8611
P-glycoprotein inhibitor IINon-inhibitor0.9927
Renal organic cation transporterNon-inhibitor0.5846
CYP450 2C9 substrateNon-substrate0.7356
CYP450 2D6 substrateNon-substrate0.7702
CYP450 3A4 substrateSubstrate0.5536
CYP450 1A2 substrateNon-inhibitor0.8342
CYP450 2C9 inhibitorNon-inhibitor0.9417
CYP450 2D6 inhibitorNon-inhibitor0.937
CYP450 2C19 inhibitorNon-inhibitor0.9417
CYP450 3A4 inhibitorNon-inhibitor0.9904
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9893
Ames testNon AMES toxic0.76
CarcinogenicityNon-carcinogens0.9692
BiodegradationReady biodegradable0.6439
Rat acute toxicity2.5699 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9089
hERG inhibition (predictor II)Non-inhibitor0.9244
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Tropane alkaloids
Sub Class
Not Available
Direct Parent
Tropane alkaloids
Alternative Parents
Piperidinecarboxylic acids / Beta hydroxy acids and derivatives / N-alkylpyrrolidines / Trialkylamines / Secondary alcohols / Cyclic alcohols and derivatives / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds
show 4 more
Substituents
Piperidinecarboxylic acid / Tropane alkaloid / Beta-hydroxy acid / Hydroxy acid / Piperidine / N-alkylpyrrolidine / Cyclic alcohol / Pyrrolidine / Amino acid or derivatives / Amino acid
show 19 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
tropane alkaloid, 2-hydroxy monocarboxylic acid (CHEBI:4743)

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da

Drug created on July 31, 2007 07:10 / Updated on November 02, 2018 05:02