7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline

Identification

Name
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline
Accession Number
DB08550
Type
Small Molecule
Groups
Experimental
Description

Potent reversible inhibitor of phenylethanolamine N-methyltransferase.

Structure
Thumb
Synonyms
Not Available
External IDs
SKF-64139 FREE BASE
Categories
UNII
A0EP5O913J
CAS number
61563-24-4
Weight
Average: 202.08
Monoisotopic: 201.011204707
Chemical Formula
C9H9Cl2N
InChI Key
WFPUBEDBBOGGIQ-UHFFFAOYSA-N
InChI
InChI=1S/C9H9Cl2N/c10-8-2-1-6-3-4-12-5-7(6)9(8)11/h1-2,12H,3-5H2
IUPAC Name
7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
SMILES
ClC1=CC=C2CCNCC2=C1Cl

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPhenylethanolamine N-methyltransferaseNot AvailableHuman
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
2,5-Dimethoxy-4-ethylamphetamine7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypertensive activities of 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
3,4-Methylenedioxyamphetamine7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypertensive activities of 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamine7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypertensive activities of 4-Bromo-2,5-dimethoxyamphetamine.
4-Methoxyamphetamine7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypertensive activities of 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AbediterolThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Abediterol.
AlaproclateThe risk or severity of adverse effects can be increased when Alaproclate is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
Albiglutide7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypoglycemic activities of Albiglutide.
Alfentanil7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the central nervous system depressant (CNS depressant) and hypertensive activities of Alfentanil.
Food Interactions
Not Available

References

Synthesis Reference

Kenneth G. Holden, Carl D. Perchonock, "Method for preparing 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline." U.S. Patent US4200754, issued February, 1976.

US4200754
General References
Not Available
External Links
PubChem Compound
123920
PubChem Substance
99445021
ChemSpider
110451
BindingDB
13014
ChEBI
160129
ChEMBL
CHEMBL287837
HET
SKA
PDB Entries
1yz3

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.139 mg/mLALOGPS
logP2.68ALOGPS
logP2.78ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)8.35ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity52.23 m3·mol-1ChemAxon
Polarizability19.82 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9946
Blood Brain Barrier+0.9774
Caco-2 permeable+0.6236
P-glycoprotein substrateSubstrate0.7056
P-glycoprotein inhibitor INon-inhibitor0.6028
P-glycoprotein inhibitor IINon-inhibitor0.879
Renal organic cation transporterInhibitor0.6923
CYP450 2C9 substrateNon-substrate0.8528
CYP450 2D6 substrateNon-substrate0.6446
CYP450 3A4 substrateNon-substrate0.6057
CYP450 1A2 substrateInhibitor0.7823
CYP450 2C9 inhibitorNon-inhibitor0.7498
CYP450 2D6 inhibitorInhibitor0.7316
CYP450 2C19 inhibitorNon-inhibitor0.6595
CYP450 3A4 inhibitorNon-inhibitor0.7796
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5249
Ames testNon AMES toxic0.7517
CarcinogenicityNon-carcinogens0.9147
BiodegradationNot ready biodegradable0.9727
Rat acute toxicity2.9080 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6871
hERG inhibition (predictor II)Inhibitor0.6952
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 tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Tetrahydroisoquinolines
Sub Class
Not Available
Direct Parent
Tetrahydroisoquinolines
Alternative Parents
Aralkylamines / Benzenoids / Aryl chlorides / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
Tetrahydroisoquinoline / Aralkylamine / Aryl chloride / Aryl halide / Benzenoid / Secondary aliphatic amine / Secondary amine / Azacycle / Organonitrogen compound / Organochloride
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, isoquinolines (CHEBI:160129)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Phenylethanolamine n-methyltransferase activity
Specific Function
Converts noradrenaline to adrenaline.
Gene Name
PNMT
Uniprot ID
P11086
Uniprot Name
Phenylethanolamine N-methyltransferase
Molecular Weight
30854.745 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:32 / Updated on August 02, 2018 06:06