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
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
DL-tetrahydropalmatine-produced hypotension and bradycardia in rats through the inhibition of central nervous dopaminergic mechanisms.
1995 Oct
[Stereoselective pharmacokinetics of tetrahydropalmatine in rats].
2005 Aug
[Studies on the alkaloids from herb of Corydalis adunca].
2005 Nov
Asymmetric synthesis of tetrahydropalmatine via tandem 1,2-addition/cyclization.
2005 Nov 11
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
Chiral high-performance liquid chromatographic separation of the enantiomers of tetrahydropalmatine and tetrahydroberberine, isolated from Corydalis yanhusuo.
2006 Feb
Evaluation of Cytotoxic Effects of Dichloromethane Extract of Guduchi (Tinospora cordifolia Miers ex Hook F & THOMS) on Cultured HeLa Cells.
2006 Jun
Determination of DL-tetrahydropalmatine in Corydalis yanhusuo by L-tetrahydropalmatine imprinted monolithic column coupling with reversed-phase high performance liquid chromatography.
2006 Jun 9
[Protective effect of dl-tetrahydropalmatine on liver injury induced by carbon tetrachloride in mice].
2006 Mar
[Effects of different types and standard of processing vinegaron inherent constituents in rhizoma of Corydalis yanhusuo].
2006 Mar
Large-scale separation of alkaloids from Corydalis decumbens by pH-zone-refining counter-current chromatography.
2006 May 19
[Comparison of pharmacokinetics of tetrahydropalmatine monomer and extractive of corydalis and corydalis processed with vinegar].
2007 Dec
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
[Effects of rotundine injection on nitric oxide synthase in tissues of different organs after ischemia/reperfusion of brain in rats].
2007 Jun
[Difference absorption of l-tetrahydropalmatine and dl-tetrahydropalmatine in intestine of rats].
2007 May
Molecular cloning and characterization of tetrahydroprotoberberine cis-N-methyltransferase, an enzyme involved in alkaloid biosynthesis in opium poppy.
2007 May 18
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
Medication of l-tetrahydropalmatine significantly ameliorates opiate craving and increases the abstinence rate in heroin users: a pilot study.
2008 Jul
[Studies on active ingredients in Corydalis, broken cell wall corydalis and its processed products].
2008 Jun
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
One-step purification of palmatine and its derivative dl-tetrahydropalmatine from Enantia chlorantha using high-performance displacement chromatography.
2008 Oct 24
Isoquinoline alkaloids isolated from Corydalis yanhusuo and their binding affinities at the dopamine D1 receptor.
2008 Sep 25
Cytotoxic activity of alkaloids isolated from Stephania rotunda [corrected].
2009 Apr
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
Tinospora cordifolia (Willd.) Hook. f. and Thoms. (Guduchi) - validation of the Ayurvedic pharmacology through experimental and clinical studies.
2010 Apr
Levo-tetrahydropalmatine attenuates cocaine self-administration under a progressive-ratio schedule and cocaine discrimination in rats.
2010 Dec
[Comparison of pharmacokinetics about ermiao capsules and ermiao pellet].
2010 Feb
[Effects of four components of Rhizoma Corydalis on anoxia and peroxidation injuries in neonatal cardiomyocytes].
2010 Jan
Protective effects of tetrahydropalmatine against gamma-radiation induced damage to human endothelial cells.
2010 Jul 3
Affinity capillary electrophoresis coupling with partial filling technique and field-amplified sample injection for enantioseparation and determination of DL-tetrahydropalmatine.
2010 Jun
Combined comparative and chemical proteomics on the mechanisms of levo-tetrahydropalmatine-induced antinociception in the formalin test.
2010 Jun 4
[In vitro O-demethylation of rotundine by recombinant human CYP isoenzymes].
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
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  
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
(-)-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 Sat Dec 16 19:59:23 GMT 2023 , Edited by admin on Sat Dec 16 19:59:23 GMT 2023
PRIMARY
SMS_ID
100000127779
Created by admin on Sat Dec 16 19:59:23 GMT 2023 , Edited by admin on Sat Dec 16 19:59:23 GMT 2023
PRIMARY
MERCK INDEX
m10630
Created by admin on Sat Dec 16 19:59:23 GMT 2023 , Edited by admin on Sat Dec 16 19:59:23 GMT 2023
PRIMARY Merck Index
EVMPD
SUB33902
Created by admin on Sat Dec 16 19:59:23 GMT 2023 , Edited by admin on Sat Dec 16 19:59:23 GMT 2023
PRIMARY
WIKIPEDIA
TETRAHYDROPALMATINE
Created by admin on Sat Dec 16 19:59:23 GMT 2023 , Edited by admin on Sat Dec 16 19:59:23 GMT 2023
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CHEBI
16563
Created by admin on Sat Dec 16 19:59:23 GMT 2023 , Edited by admin on Sat Dec 16 19:59:23 GMT 2023
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DRUG BANK
DB12093
Created by admin on Sat Dec 16 19:59:23 GMT 2023 , Edited by admin on Sat Dec 16 19:59:23 GMT 2023
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PUBCHEM
72301
Created by admin on Sat Dec 16 19:59:23 GMT 2023 , Edited by admin on Sat Dec 16 19:59:23 GMT 2023
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EPA CompTox
DTXSID701020650
Created by admin on Sat Dec 16 19:59:23 GMT 2023 , Edited by admin on Sat Dec 16 19:59:23 GMT 2023
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MESH
C014215
Created by admin on Sat Dec 16 19:59:23 GMT 2023 , Edited by admin on Sat Dec 16 19:59:23 GMT 2023
PRIMARY
FDA UNII
3X69CO5I79
Created by admin on Sat Dec 16 19:59:23 GMT 2023 , Edited by admin on Sat Dec 16 19:59:23 GMT 2023
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