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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
HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products.
1992 May 29
Formation of protoberberine-type alkaloids by the tubers of somatic embryo-derived plants of Corydalis yanhusuo.
2001 Dec
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
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
[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
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
[Difference absorption of l-tetrahydropalmatine and dl-tetrahydropalmatine in intestine of rats].
2007 May
[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
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
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
Levo-tetrahydropalmatine attenuates oxycodone-induced conditioned place preference in rats.
2009 Jan 14
[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
[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
Simultaneous HPLC determination of three bioactive alkaloids in the Asian medicinal plant Stephania rotunda.
2010 Jun
Stereoselective protein binding of tetrahydropalmatine enantiomers in human plasma, HSA, and AGP, but not in rat plasma.
2010 Jun
Screening of antinociceptive components in Corydalis yanhusuo W.T. Wang by comprehensive two-dimensional 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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 19:59:23 GMT 2023
Edited
by admin
on Sat Dec 16 19:59:23 GMT 2023
Record UNII
3X69CO5I79
Record Status Validated (UNII)
Record Version
  • Download
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY