U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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
Structure of TETRAHYDROPALMATINE

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

HIDE SMILES / InChI
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.

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
42.8 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
396.1 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
13.3 h
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
Doses

Doses

DosePopulationAdverse events​
30 mg 2 times / day multiple, oral
Studied dose
Dose: 30 mg, 2 times / day
Route: oral
Route: multiple
Dose: 30 mg, 2 times / day
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
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

Patents

Sample Use Guides

30 mg twice daily (7 total doses)
Route of Administration: Oral
Co-incubation with L-THP (0.01-1ug/ml) did not produce significant effects on 500 uM cocaine-inhibited neurite growth in PC12 cells either at low or high doses.
Name Type Language
(-)-CORYDALIS B
Preferred Name English
TETRAHYDROPALMATINE
WHO-DD  
INCI  
Official Name English
LEVO-TETRAHYDROPALMATINE
Common Name English
5,8,13,13A-TETRAHYDRO-(S)-2,3,9,10-TETRAMETHOXY-6H-DIBENZO(A,G)QUINOLIZINE
Common Name English
(-)-ROTUNDINE
Common Name English
ROTUNDINE
Common Name English
TETRAHYDROPALMATINE, L-
Common Name English
CASEANINE
Common Name English
(-)-TETRAHYDROPALMATINE
Common Name English
GINDARINE
Common Name English
TETRAHYDROPALMATINE, (-)-
Common Name English
(-)-2,3,9,10-TETRAMETHOXYBERBINE
Systematic Name English
TETRAHYDROPALMATINE L-FORM [MI]
Common Name English
HYNDARINE
Common Name English
Tetrahydropalmatine [WHO-DD]
Common Name English
2,3,9,10-TETRAMETHOXYBERBINE
Systematic Name English
Code System Code Type Description
CAS
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
SMS_ID
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
MERCK INDEX
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
EVMPD
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
WIKIPEDIA
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
CHEBI
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
DRUG BANK
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
PUBCHEM
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
EPA CompTox
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
MESH
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
FDA UNII
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