Identification

Generic Name
Ecgonine
DrugBank Accession Number
DB01525
Background

Not Available

Type
Small Molecule
Groups
Experimental, Illicit
Structure
Thumb
Weight
Average: 185.2203
Monoisotopic: 185.105193351
Chemical Formula
C9H15NO3
Synonyms
Not Available
External IDs
  • IDS-NE-001

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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.
Methylene blueThe risk or severity of adverse effects can be increased when Ecgonine is combined with Methylene blue.
MetoclopramideThe therapeutic efficacy of Metoclopramide can be decreased when used in combination with Ecgonine.
MinaprineThe risk or severity of adverse effects can be increased when Ecgonine is combined with Minaprine.
MoclobemideThe risk or severity of adverse effects can be increased when Ecgonine is combined with Moclobemide.
NialamideThe risk or severity of adverse effects can be increased when Ecgonine is combined with Nialamide.
PargylineThe risk or severity of adverse effects can be increased when Ecgonine is combined with Pargyline.
PhenelzineThe risk or severity of adverse effects can be increased when Ecgonine is combined with Phenelzine.
ProcaineThe risk or severity of adverse effects can be increased when Ecgonine is combined with Procaine.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Aliphatic heteropolycyclic compound / Amine / Amino acid / Amino acid or derivatives / Azacycle / Beta-hydroxy acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative
show 19 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
tropane alkaloid, 2-hydroxy monocarboxylic acid (CHEBI:4743)
Affected organisms
Not Available

Chemical Identifiers

UNII
DX2E9E17AV
CAS number
481-37-8
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

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
KEGG Compound
C10858
PubChem Compound
91460
PubChem Substance
46506479
ChemSpider
82586
ChEBI
4743
ZINC
ZINC000004098901
Wikipedia
Ecgonine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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

Drug created at July 31, 2007 13:10 / Updated at June 12, 2020 16:51