This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Tetrahydropalmatine
Accession Number
DB12093
Type
Small Molecule
Groups
Investigational
Description

Tetrahydropalmatine is under investigation in clinical trial NCT02118610 (Treatment of Schizophrenia With L-tetrahydropalmatine (l-THP): a Novel Dopamine Antagonist With Anti-inflammatory and Antiprotozoal Activity).

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Tetrahydropalmatine HydrochlorideRH72T8K75E4880-82-4MGSZZQQRTPWMEI-LMOVPXPDSA-N
Categories
UNII
3X69CO5I79
CAS number
483-14-7
Weight
Average: 355.434
Monoisotopic: 355.178358289
Chemical Formula
C21H25NO4
InChI Key
AEQDJSLRWYMAQI-KRWDZBQOSA-N
InChI
InChI=1S/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3/t17-/m0/s1
IUPAC Name
(12bS)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene
SMILES
COC1=CC=C2C[C@@H]3N(CCC4=CC(OC)=C(OC)C=C34)CC2=C1OC

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UD(1A) dopamine receptor
antagonist
Human
UD(2) dopamine receptor
antagonist
Human
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-ethylamphetamineTetrahydropalmatine may decrease the stimulatory activities of 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineTetrahydropalmatine may decrease the stimulatory activities of 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Tetrahydropalmatine.
4-Bromo-2,5-dimethoxyamphetamineTetrahydropalmatine may decrease the stimulatory activities of 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Tetrahydropalmatine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Tetrahydropalmatine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Tetrahydropalmatine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Tetrahydropalmatine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AbafunginThe therapeutic efficacy of Abafungin can be increased when used in combination with Tetrahydropalmatine.
AcebutololAcebutolol may increase the hypotensive activities of Tetrahydropalmatine.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C02890
PubChem Compound
72301
PubChem Substance
347828397
ChemSpider
65252
BindingDB
50424077
ChEBI
16563
ChEMBL
CHEMBL487182
Wikipedia
Tetrahydropalmatine

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
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0246 mg/mLALOGPS
logP3.09ALOGPS
logP3.15ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)5.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.16 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity101.36 m3·mol-1ChemAxon
Polarizability39.97 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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 protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Protoberberine alkaloids and derivatives
Sub Class
Not Available
Direct Parent
Protoberberine alkaloids and derivatives
Alternative Parents
Tetrahydroisoquinolines / Anisoles / Aralkylamines / Alkyl aryl ethers / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Protoberberine skeleton / Tetrahydroprotoberberine skeleton / Tetrahydroisoquinoline / Anisole / Alkyl aryl ether / Aralkylamine / Benzenoid / Tertiary amine / Tertiary aliphatic amine / Ether
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heterotetracyclic compound, berberine alkaloid (CHEBI:16563) / Isoquinoline alkaloids (C02890)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name
DRD1
Uniprot ID
P21728
Uniprot Name
D(1A) dopamine receptor
Molecular Weight
49292.765 Da
References
  1. Mantsch JR, Li SJ, Risinger R, Awad S, Katz E, Baker DA, Yang Z: Levo-tetrahydropalmatine attenuates cocaine self-administration and cocaine-induced reinstatement in rats. Psychopharmacology (Berl). 2007 Jul;192(4):581-91. Epub 2007 Mar 15. [PubMed:17361394]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Mantsch JR, Li SJ, Risinger R, Awad S, Katz E, Baker DA, Yang Z: Levo-tetrahydropalmatine attenuates cocaine self-administration and cocaine-induced reinstatement in rats. Psychopharmacology (Berl). 2007 Jul;192(4):581-91. Epub 2007 Mar 15. [PubMed:17361394]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [PubMed:22039822]

Drug created on October 20, 2016 15:20 / Updated on August 26, 2018 02:06