7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline
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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
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UPhenylethanolamine N-methyltransferase Not Available Humans - 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 outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with 1,2-Benzodiazepine. Abaloparatide 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the orthostatic hypotensive activities of Abaloparatide. Abciximab The risk or severity of bleeding and hemorrhage can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Abciximab. Acarbose 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypoglycemic activities of Acarbose. Acebutolol 7,8-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
- External Links
- PubChem Compound
- 123920
- PubChem Substance
- 99445021
- ChemSpider
- 110451
- BindingDB
- 13014
- ChEBI
- 160129
- ChEMBL
- CHEMBL287837
- ZINC
- ZINC000024714117
- PDBe Ligand
- SKA
- PDB Entries
- 1yz3
Clinical Trials
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
Property Value Source Water Solubility 0.139 mg/mL ALOGPS logP 2.68 ALOGPS logP 2.78 Chemaxon logS -3.2 ALOGPS pKa (Strongest Basic) 8.06 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 12.03 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 52.23 m3·mol-1 Chemaxon Polarizability 19.82 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9946 Blood Brain Barrier + 0.9774 Caco-2 permeable + 0.6236 P-glycoprotein substrate Substrate 0.7056 P-glycoprotein inhibitor I Non-inhibitor 0.6028 P-glycoprotein inhibitor II Non-inhibitor 0.879 Renal organic cation transporter Inhibitor 0.6923 CYP450 2C9 substrate Non-substrate 0.8528 CYP450 2D6 substrate Non-substrate 0.6446 CYP450 3A4 substrate Non-substrate 0.6057 CYP450 1A2 substrate Inhibitor 0.7823 CYP450 2C9 inhibitor Non-inhibitor 0.7498 CYP450 2D6 inhibitor Inhibitor 0.7316 CYP450 2C19 inhibitor Non-inhibitor 0.6595 CYP450 3A4 inhibitor Non-inhibitor 0.7796 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5249 Ames test Non AMES toxic 0.7517 Carcinogenicity Non-carcinogens 0.9147 Biodegradation Not ready biodegradable 0.9727 Rat acute toxicity 2.9080 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.6871 hERG inhibition (predictor II) Inhibitor 0.6952
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0gi0-1910000000-71ff04dd939b70be80ab Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0090000000-f22f160174099740b5a0 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0190000000-e6213d43838bafdd3db7 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0090000000-8db907ea0185b3c48c5a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-053s-0900000000-f217f10a03869d0cd747 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-1190000000-6feb0473585587f2872f Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9700000000-03fa69d930d060fbeab1 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 135.23584 predictedDeepCCS 1.0 (2019) [M+H]+ 138.28302 predictedDeepCCS 1.0 (2019) [M+Na]+ 147.3233 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsPhenylethanolamine N-methyltransferase
- 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
- 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