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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

Molecular Formula C21H25NO4
Molecular Weight 355.4275
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
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
DL-Tetrahydropalmatine may act through inhibition of amygdaloid release of dopamine to inhibit an epileptic attack in rats.
2001 Jul 20
The hypothermic effects of dl-tetrahydropalmatine in rats.
2001 Nov 23
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
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
Chiral high-performance liquid chromatographic separation of the enantiomers of tetrahydropalmatine and tetrahydroberberine, isolated from Corydalis yanhusuo.
2006 Feb
Determination of DL-tetrahydropalmatine in Corydalis yanhusuo by L-tetrahydropalmatine imprinted monolithic column coupling with reversed-phase high performance liquid chromatography.
2006 Jun 9
[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
[Effects of rotundine injection on nitric oxide synthase in tissues of different organs after ischemia/reperfusion of brain in rats].
2007 Jun
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
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
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
Levo-tetrahydropalmatine attenuates oxycodone-induced conditioned place preference in rats.
2009 Jan 14
[Comparison of microwave-assisted and conventional extraction of Corydalis yanhusuo].
2009 Jul
[Pharmacokinetics of three alkaloids in Huanglianjiedu decoction in rat serum by LC-MS-MS].
2009 May
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
[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
Preparative separation of isoquinoline alkaloids from Stephania yunnanensis by pH-zone-refining counter-current chromatography.
2010 Jul 1
Protective effects of tetrahydropalmatine against gamma-radiation induced damage to human endothelial cells.
2010 Jul 3
Simultaneous HPLC determination of three bioactive alkaloids in the Asian medicinal plant Stephania rotunda.
2010 Jun
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
Study on the stereoselective excretion of tetrahydropalmatine enantiomers in rats and identification of in vivo metabolites by liquid chromatography-tandem mass spectrometry.
2010 Mar
Correlation between synergistic action of Radix Angelica dahurica extracts on analgesic effects of Corydalis alkaloid and plasma concentration of dl-THP.
2010 May 4
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
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.
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:52:54 UTC 2023
Edited
by admin
on Thu Jul 06 02:52:54 UTC 2023
Record UNII
3X69CO5I79
Record Status Validated (UNII)
Record Version
  • Download
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