Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H25NO4 |
Molecular Weight | 355.4275 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(C=C1OC)[C@@H]3CC4=CC=C(OC)C(OC)=C4CN3CC2
InChI
InChIKey=AEQDJSLRWYMAQI-KRWDZBQOSA-N
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
Tetrahydropalmatine is a tetrahydroprotoberberine isoquinoline alkaloid that is a primary active constituent of herbal preparations containing plant species of the genera Stephania and Corydalis. The levo isomer of THP (L-THP) appears to contribute to many of the therapeutic effects of these preparations. The pharmacological profile of L-THP, which includes antagonism of dopamine D1 and D2 receptors and actions at dopamine D3, suggests that it may have utility for treating addiction. Clinical trials where L-THP was used for the treatment of cocaine and heroin addiction have promising results. The clinical trial is planned for the treatment of schizophrenia. L-Tetrahydropalmatine is recorded in the Chinese pharmacopoeia.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28721806 |
|||
Target ID: CHEMBL2056 |
124.0 nM [Ki] | ||
Target ID: CHEMBL217 |
388.0 nM [Ki] | ||
Target ID: CHEMBL3138 |
1.4 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
42.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27363313 |
30 mg 2 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TETRAHYDROPALMATINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
396.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27363313 |
30 mg 2 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TETRAHYDROPALMATINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27363313 |
30 mg 2 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TETRAHYDROPALMATINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
moderate [IC50 20.9 uM] | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
weak [IC50 48.6 uM] | ||||
yes [IC50 2.65 uM] | ||||
yes [Ki 6.42 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
|
HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products. | 1992 May 29 |
|
DL-tetrahydropalmatine-produced hypotension and bradycardia in rats through the inhibition of central nervous dopaminergic mechanisms. | 1995 Oct |
|
Anxiolytic-like action of orally administered dl-tetrahydropalmatine in elevated plus-maze. | 2003 Aug |
|
[Study on extraction conditions for minute powder of processed rhizome of Corydalis with vinegar]. | 2003 Oct |
|
A multidisciplinary approach to the toxicologic problems associated with the use of herbal medicines. | 2005 Feb |
|
[Chemical constituents from Corydalis humosa]. | 2005 Jul |
|
Liquid chromatography-tandem mass spectrometry for the identification of L-tetrahydropalmatine metabolites in Penicillium janthinellum and rats. | 2006 Jan |
|
Enantioseparation of tetrahydropalmatine and Tröger's base by molecularly imprinted monolith in capillary electrochromatography. | 2007 Feb 23 |
|
Characterization of enantioselective binding of racemic natural tetrahydropalmatine to DNA by chromatographic methods. | 2007 Jan 1 |
|
Levo-tetrahydropalmatine attenuates cocaine self-administration and cocaine-induced reinstatement in rats. | 2007 Jul |
|
[Difference absorption of l-tetrahydropalmatine and dl-tetrahydropalmatine in intestine of rats]. | 2007 May |
|
Antimalarial activity of alkaloids isolated from Stephania rotunda. | 2007 May 30 |
|
[Optimal extraction of Dingxiang jiangqi granules]. | 2007 Nov |
|
Levo-tetrahydropalmatine inhibits cocaine's rewarding effects: experiments with self-administration and brain-stimulation reward in rats. | 2007 Nov |
|
Determination of tetrandrine and fangchinoline in plasma samples using hollow fiber liquid-phase microextraction combined with high-performance liquid chromatography. | 2007 Sep 14 |
|
Comparative studies on pharmacokinetic fates of tetrahydropalmatine enantiomers in different chemical environments in rats. | 2008 Feb |
|
Simultaneous determination of berberine, palmatine and jatrorrhizine by liquid chromatography-tandem mass spectrometry in rat plasma and its application in a pharmacokinetic study after oral administration of coptis-evodia herb couple. | 2008 Mar 1 |
|
Investigation of modulation of the alpha-2 receptor in tetrahydropalmatine (THP) analgesia in male Sprague-Dawley rats. | 2009 |
|
Amphiphilic poly{[alpha-maleic anhydride-omega-methoxy-poly(ethylene glycol)]-co-(ethyl cyanoacrylate)} graft copolymer nanoparticles as carriers for transdermal drug delivery. | 2009 |
|
Phytochemicals from Flemingia vestita (Fabaceae) and Stephania glabra (Menispermeaceae) alter cGMP concentration in the cestode Raillietina echinobothrida. | 2009 Apr |
|
Simultaneous determination of tetrahydropalmatine, protopine, and palmatine in rat plasma by LC-ESI-MS and its application to a pharmacokinetic study. | 2009 Feb 20 |
|
Levo-tetrahydropalmatine attenuates oxycodone-induced conditioned place preference in rats. | 2009 Jan 14 |
|
[Interaction between four herb compounds and a western drug by CYP3A4 enzyme metabolism in vitro]. | 2009 Jul |
|
[Effects of four components of Rhizoma Corydalis on anoxia and peroxidation injuries in neonatal cardiomyocytes]. | 2010 Jan |
|
Affinity capillary electrophoresis coupling with partial filling technique and field-amplified sample injection for enantioseparation and determination of DL-tetrahydropalmatine. | 2010 Jun |
|
Stereoselective protein binding of tetrahydropalmatine enantiomers in human plasma, HSA, and AGP, but not in rat plasma. | 2010 Jun |
|
Combined comparative and chemical proteomics on the mechanisms of levo-tetrahydropalmatine-induced antinociception in the formalin test. | 2010 Jun 4 |
|
Organic cation transporter 1 mediates the uptake of monocrotaline and plays an important role in its hepatotoxicity. | 2013 Sep 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01631383
30 mg twice daily (7 total doses)
Route of Administration:
Oral
Name | Type | Language | ||
---|---|---|---|---|
|
Preferred Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
483-14-7
Created by
admin on Wed Apr 02 17:57:29 GMT 2025 , Edited by admin on Wed Apr 02 17:57:29 GMT 2025
|
PRIMARY | |||
|
100000127779
Created by
admin on Wed Apr 02 17:57:29 GMT 2025 , Edited by admin on Wed Apr 02 17:57:29 GMT 2025
|
PRIMARY | |||
|
m10630
Created by
admin on Wed Apr 02 17:57:29 GMT 2025 , Edited by admin on Wed Apr 02 17:57:29 GMT 2025
|
PRIMARY | Merck Index | ||
|
SUB33902
Created by
admin on Wed Apr 02 17:57:29 GMT 2025 , Edited by admin on Wed Apr 02 17:57:29 GMT 2025
|
PRIMARY | |||
|
TETRAHYDROPALMATINE
Created by
admin on Wed Apr 02 17:57:29 GMT 2025 , Edited by admin on Wed Apr 02 17:57:29 GMT 2025
|
PRIMARY | |||
|
16563
Created by
admin on Wed Apr 02 17:57:29 GMT 2025 , Edited by admin on Wed Apr 02 17:57:29 GMT 2025
|
PRIMARY | |||
|
DB12093
Created by
admin on Wed Apr 02 17:57:29 GMT 2025 , Edited by admin on Wed Apr 02 17:57:29 GMT 2025
|
PRIMARY | |||
|
72301
Created by
admin on Wed Apr 02 17:57:29 GMT 2025 , Edited by admin on Wed Apr 02 17:57:29 GMT 2025
|
PRIMARY | |||
|
DTXSID701020650
Created by
admin on Wed Apr 02 17:57:29 GMT 2025 , Edited by admin on Wed Apr 02 17:57:29 GMT 2025
|
PRIMARY | |||
|
C014215
Created by
admin on Wed Apr 02 17:57:29 GMT 2025 , Edited by admin on Wed Apr 02 17:57:29 GMT 2025
|
PRIMARY | |||
|
3X69CO5I79
Created by
admin on Wed Apr 02 17:57:29 GMT 2025 , Edited by admin on Wed Apr 02 17:57:29 GMT 2025
|
PRIMARY |
SUBSTANCE RECORD