U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

[H][C@@]12CC3=C(CN1CCC4=C2C=C(OC)C(OC)=C4)C(OC)=C(OC)C=C3

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: Page: p.7, 8
healthy, ADULT
n = 11
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources: Page: p.7, 8
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
DL-tetrahydropalmatine-produced hypotension and bradycardia in rats through the inhibition of central nervous dopaminergic mechanisms.
1995 Oct
[Study on extraction conditions for minute powder of processed rhizome of Corydalis with vinegar].
2003 Oct
Effects of L-tetrahydropalmatine on the expressions of bcl-2 and bax in rat after acute global cerebral ischemia and reperfusion.
2004
[Effects of L-tetrahydropalmatine on concentrations of neurotransmitter amino acids in mice with cerebral ischemia].
2004 Apr
The combination of rat mast cell and rabbit aortic smooth muscle is the simple bioassay for the screening of anti-allergic ingredient from methanolic extract of Corydalis tuber.
2004 Aug
[Resource investigation and quality evaluation on wild Corydalis yanhusuo].
2004 May
[Stereoselective pharmacokinetics of tetrahydropalmatine in rats].
2005 Aug
A multidisciplinary approach to the toxicologic problems associated with the use of herbal medicines.
2005 Feb
[Chemical constituents from Corydalis humosa].
2005 Jul
[Effect of l-tetrahydropalmatine on expression of adhesion molecules induced by lipopolysaccharides in human umbilical vein endothelium cell].
2005 Jun
Effects of l-tetrahydropalmatine on locomotor sensitization to oxycodone in mice.
2005 May
Stereoselective pharmacokinetics of tetrahydropalmatine after oral administration of (-)-enantiomer and the racemate.
2005 May 15
[Studies on the alkaloids from herb of Corydalis adunca].
2005 Nov
Asymmetric synthesis of tetrahydropalmatine via tandem 1,2-addition/cyclization.
2005 Nov 11
Chiral liquid chromatography resolution and stereoselective pharmacokinetic study of tetrahydropalmatine enantiomers in dogs.
2005 Nov 5
Brain pharmacokinetics and tissue distribution of tetrahydropalmatine enantiomers in rats after oral administration of the racemate.
2006 Apr
Anxiolytic-Like Effect of baicalin and its additivity with other anxiolytics.
2006 Feb
Liquid chromatography-tandem mass spectrometry for the identification of L-tetrahydropalmatine metabolites in Penicillium janthinellum and rats.
2006 Jan
[Effects of different types and standard of processing vinegaron inherent constituents in rhizoma of Corydalis yanhusuo].
2006 Mar
[Comparison of pharmacokinetics of tetrahydropalmatine monomer and extractive of corydalis and corydalis processed with vinegar].
2007 Dec
Levo-tetrahydropalmatine attenuates cocaine self-administration and cocaine-induced reinstatement in rats.
2007 Jul
Molecular cloning and characterization of tetrahydroprotoberberine cis-N-methyltransferase, an enzyme involved in alkaloid biosynthesis in opium poppy.
2007 May 18
[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
Comparative studies on pharmacokinetic fates of tetrahydropalmatine enantiomers in different chemical environments in rats.
2008 Feb
Medication of l-tetrahydropalmatine significantly ameliorates opiate craving and increases the abstinence rate in heroin users: a pilot study.
2008 Jul
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
[Pharmacokinetic studies of tetrahydropalmatine and dehydrocorydaline in rat after oral administration of yanhusuo extraction by LC-MS/MS method].
2008 Nov
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
[Chemical constituents from Corydalis yanhusuo].
2009 Aug
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
[Comparison of microwave-assisted and conventional extraction of Corydalis yanhusuo].
2009 Jul
[Influence of combination of extractum Angelicae Dahuricae Siccum and total alkaloids of Rhizoma Corydalis on pharmacokinetics of tetrahydropalmatine in rats].
2009 Jun
[Evaluation of different combinations of components of Chinese formulation shuangshentongguan by using AUC values].
2009 Sep
Tinospora cordifolia (Willd.) Hook. f. and Thoms. (Guduchi) - validation of the Ayurvedic pharmacology through experimental and clinical studies.
2010 Apr
Shotgun approach based comparative proteomic analysis of levo-tetrahydropalmatine-induced apoptosis in hepatocytes.
2010 Apr 15
Levo-tetrahydropalmatine attenuates cocaine self-administration under a progressive-ratio schedule and cocaine discrimination in rats.
2010 Dec
Preparative separation of isoquinoline alkaloids from Stephania yunnanensis by pH-zone-refining counter-current chromatography.
2010 Jul 1
[In vitro O-demethylation of rotundine by recombinant human CYP isoenzymes].
2010 Mar
Screening of antinociceptive components in Corydalis yanhusuo W.T. Wang by comprehensive two-dimensional liquid chromatography/tandem mass spectrometry.
2010 Mar
Study on the stereoselective excretion of tetrahydropalmatine enantiomers in rats and identification of in vivo metabolites by liquid chromatography-tandem mass spectrometry.
2010 Mar
Chemical fingerprint analysis of Phellodendri Amurensis Cortex by ultra performance LC/Q-TOF-MS methods combined with chemometrics.
2010 Nov
Tetrahydropalmatine inhibits pro-inflammatory mediators in lipopolysaccharide-stimulated THP-1 cells.
2010 Oct
Levo-tetrahydropalmatine retards the growth of ectopic endometrial implants and alleviates generalized hyperalgesia in experimentally induced endometriosis in rats.
2011 Jan
Organic cation transporter 1 mediates the uptake of monocrotaline and plays an important role in its hepatotoxicity.
2013 Sep 15
Involvement of organic cation transporter 1 and CYP3A4 in retrorsine-induced toxicity.
2014 Aug 1
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
TETRAHYDROPALMATINE
WHO-DD  
Common 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
(-)-CORYDALIS B
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 Thu Jul 06 02:52:54 UTC 2023 , Edited by admin on Thu Jul 06 02:52:54 UTC 2023
PRIMARY
SMS_ID
100000127779
Created by admin on Thu Jul 06 02:52:54 UTC 2023 , Edited by admin on Thu Jul 06 02:52:54 UTC 2023
PRIMARY
MERCK INDEX
M10630
Created by admin on Thu Jul 06 02:52:54 UTC 2023 , Edited by admin on Thu Jul 06 02:52:54 UTC 2023
PRIMARY Merck Index
EVMPD
SUB33902
Created by admin on Thu Jul 06 02:52:54 UTC 2023 , Edited by admin on Thu Jul 06 02:52:54 UTC 2023
PRIMARY
WIKIPEDIA
TETRAHYDROPALMATINE
Created by admin on Thu Jul 06 02:52:54 UTC 2023 , Edited by admin on Thu Jul 06 02:52:54 UTC 2023
PRIMARY
CHEBI
16563
Created by admin on Thu Jul 06 02:52:54 UTC 2023 , Edited by admin on Thu Jul 06 02:52:54 UTC 2023
PRIMARY
DRUG BANK
DB12093
Created by admin on Thu Jul 06 02:52:54 UTC 2023 , Edited by admin on Thu Jul 06 02:52:54 UTC 2023
PRIMARY
PUBCHEM
72301
Created by admin on Thu Jul 06 02:52:54 UTC 2023 , Edited by admin on Thu Jul 06 02:52:54 UTC 2023
PRIMARY
EPA CompTox
DTXSID701020650
Created by admin on Thu Jul 06 02:52:54 UTC 2023 , Edited by admin on Thu Jul 06 02:52:54 UTC 2023
PRIMARY
MESH
C014215
Created by admin on Thu Jul 06 02:52:54 UTC 2023 , Edited by admin on Thu Jul 06 02:52:54 UTC 2023
PRIMARY
FDA UNII
3X69CO5I79
Created by admin on Thu Jul 06 02:52:54 UTC 2023 , Edited by admin on Thu Jul 06 02:52:54 UTC 2023
PRIMARY