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

Identification

Generic Name
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline
DrugBank Accession Number
DB08550
Background

Potent reversible inhibitor of phenylethanolamine N-methyltransferase.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 202.08
Monoisotopic: 201.011204707
Chemical Formula
C9H9Cl2N
Synonyms
Not Available
External IDs
  • SKF-64139 FREE BASE

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPhenylethanolamine N-methyltransferaseNot AvailableHumans
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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with 1,2-Benzodiazepine.
Abaloparatide7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the orthostatic hypotensive activities of Abaloparatide.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Abciximab.
Acarbose7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypoglycemic activities of Acarbose.
Acebutolol7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Acebutolol.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Hydrocarbon derivative / Organic nitrogen compound / Organochloride
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, isoquinolines (CHEBI:160129)
Affected organisms
Not Available

Chemical Identifiers

UNII
A0EP5O913J
CAS number
61563-24-4
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

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
PubChem Compound
123920
PubChem Substance
99445021
ChemSpider
110451
BindingDB
13014
ChEBI
160129
ChEMBL
CHEMBL287837
ZINC
ZINC000024714117
PDBe Ligand
SKA
PDB Entries
1yz3

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.139 mg/mLALOGPS
logP2.68ALOGPS
logP2.78Chemaxon
logS-3.2ALOGPS
pKa (Strongest Basic)8.06Chemaxon
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-MSsplash10-0gi0-1910000000-71ff04dd939b70be80ab
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-f22f160174099740b5a0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0190000000-e6213d43838bafdd3db7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-8db907ea0185b3c48c5a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-053s-0900000000-f217f10a03869d0cd747
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-1190000000-6feb0473585587f2872f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9700000000-03fa69d930d060fbeab1
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-135.23584
predicted
DeepCCS 1.0 (2019)
[M+H]+138.28302
predicted
DeepCCS 1.0 (2019)
[M+Na]+147.3233
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:32 / Updated at June 12, 2020 16:52