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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H25NO4
Molecular Weight 355.4283
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TETRAHYDROPALMATINE

SMILES

COc1ccc2C[C@@]3([H])c4cc(c(cc4CCN3Cc2c1OC)OC)OC

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 355.4283
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
DL-tetrahydropalmatine-produced hypotension and bradycardia in rats through the inhibition of central nervous dopaminergic mechanisms.
1995 Oct
[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
[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
[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
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
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
[Comparison of microwave-assisted and conventional extraction of Corydalis yanhusuo].
2009 Jul
[Study on the influence on Rhizoma Corydalis by different harvest time and processing methods].
2009 Jul
[Influence of combination of extractum Angelicae Dahuricae Siccum and total alkaloids of Rhizoma Corydalis on pharmacokinetics of tetrahydropalmatine in rats].
2009 Jun
[Pharmacokinetics of three alkaloids in Huanglianjiedu decoction in rat serum by LC-MS-MS].
2009 May
Purification of alkaloids from Corydalis yanhusuo W. T. Wang using preparative 2-D HPLC.
2009 May
[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
[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis].
2010 Dec
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
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
[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
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
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:34:39 UTC 2021
Edited
by admin
on Sat Jun 26 16:34:39 UTC 2021
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 [WHO-DD]
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
2,3,9,10-TETRAMETHOXYBERBINE
Systematic Name English
Code System Code Type Description
CAS
483-14-7
Created by admin on Sat Jun 26 16:34:39 UTC 2021 , Edited by admin on Sat Jun 26 16:34:39 UTC 2021
PRIMARY
MERCK INDEX
M10630
Created by admin on Sat Jun 26 16:34:39 UTC 2021 , Edited by admin on Sat Jun 26 16:34:39 UTC 2021
PRIMARY Merck Index
EVMPD
SUB33902
Created by admin on Sat Jun 26 16:34:39 UTC 2021 , Edited by admin on Sat Jun 26 16:34:39 UTC 2021
PRIMARY
WIKIPEDIA
TETRAHYDROPALMATINE
Created by admin on Sat Jun 26 16:34:39 UTC 2021 , Edited by admin on Sat Jun 26 16:34:39 UTC 2021
PRIMARY
DRUG BANK
DB12093
Created by admin on Sat Jun 26 16:34:39 UTC 2021 , Edited by admin on Sat Jun 26 16:34:39 UTC 2021
PRIMARY
PUBCHEM
72301
Created by admin on Sat Jun 26 16:34:39 UTC 2021 , Edited by admin on Sat Jun 26 16:34:39 UTC 2021
PRIMARY
MESH
C014215
Created by admin on Sat Jun 26 16:34:39 UTC 2021 , Edited by admin on Sat Jun 26 16:34:39 UTC 2021
PRIMARY
FDA UNII
3X69CO5I79
Created by admin on Sat Jun 26 16:34:39 UTC 2021 , Edited by admin on Sat Jun 26 16:34:39 UTC 2021
PRIMARY