TETRAHYDROPALMATINE HYDROCHLORIDE, (±)-

Details

Stereochemistry	RACEMIC
Molecular Formula	C21H25NO4.ClH
Molecular Weight	391.888
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of TETRAHYDROPALMATINE HYDROCHLORIDE, (±)-

Structure Search

SMILES

Cl.COC1=C(OC)C=C2C3CC4=C(CN3CCC2=C1)C(OC)=C(OC)C=C4

InChI

InChIKey=MGSZZQQRTPWMEI-UHFFFAOYSA-N

InChI=1S/C21H25NO4.ClH/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;1H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16722379 | https://www.ncbi.nlm.nih.gov/pubmed/21889526 | https://www.ncbi.nlm.nih.gov/pubmed/12921909 | https://www.ncbi.nlm.nih.gov/pubmed/11438389 | https://www.ncbi.nlm.nih.gov/pubmed/8886500

DL-Tetrahydropalmatine (dl-THP), an active component isolated from Corydalis species (a Chinese herbal medicine). dl-THP has inhibitory effects on liver injury induced by carbon tetrachloride in mice. The drug demonstrated anxiolytic and anti-nociceptive effects in animal models. dl-THP may act through inhibition of amygdaloid dopamine release to inhibit an epileptic attack – it is a very effective anti-epileptogenic and anticonvulsant agent. dl-THP has been found to have antihypertensive effects. It acts through the 5-HT2 and/or D2-receptor antagonism in the hypothalamus to induce hypotension and bradycardia in rats.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D2 receptor 297 Target ID: CHEMBL339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8577817 \| https://www.ncbi.nlm.nih.gov/pubmed/8886500	Antagonist 2778
Serotonin 2 (5-HT2) receptor 87 Target ID: CHEMBL2093870 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8886500 \| https://www.ncbi.nlm.nih.gov/pubmed/8569056 \| https://www.ncbi.nlm.nih.gov/pubmed/11711213	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Acute liver injury 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16722379	Preventing	Preclinical	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21889526 https://www.ncbi.nlm.nih.gov/pubmed/20855279 https://www.ncbi.nlm.nih.gov/pubmed/20307640	Primary	Preclinical	Unknown Approved Use Unknown
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12921909 https://www.ncbi.nlm.nih.gov/pubmed/16491459	Primary	Preclinical	Unknown Approved Use Unknown
Epilepsy 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11852175 https://www.ncbi.nlm.nih.gov/pubmed/11438389	Primary	Preclinical	Unknown Approved Use Unknown
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8886500 https://www.ncbi.nlm.nih.gov/pubmed/8577817 https://www.ncbi.nlm.nih.gov/pubmed/8569056 https://www.ncbi.nlm.nih.gov/pubmed/10364840	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[On the pharmacology of rotundine].	1961 May-Jun	13778302
Pharmacological study of tetrahydropalmatine and its analogs. A new type of central depressants.	1962 Oct 1	13955299
SOME PHARMACOLOGICAL PROPERTIES OF CORYDALIS B (TETRAHYDROPALMATINE) AND ITS RELATED COMPOUNDS.	1964 Apr	14168947
[STUDIES ON THE PHARMACOLOGICAL ACTIONS OF CORYDALIS. XII. THE EFFECTS OF OPTICAL ISOMERS OF TETRAHYDROPALMATINE (THP) ON THE CENTRAL NERVOUS SYSTEM].	1964 Mar	14184587
[RESEARCH ON THE COMPARATIVE PHARMACOLOGY OF PALMATINE AND DL-TETRAHYDROPALMATINE].	1965 Mar	14316670
A novel synthesis of tetrahydropalmatine.	1969 May 10	5781510
[Difference absorption of l-tetrahydropalmatine and dl-tetrahydropalmatine in intestine of rats].	2007 May	17703779
Antinociceptive effects of intragastric DL-tetrahydropalmatine on visceral and somatic persistent nociception and pain hypersensitivity in rats.	2011 Nov	21889526

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 20, 40 mg/kg daily for 9 days

Route of Administration: Intraperitoneal

In Vitro Use Guide

In an isolated perfused rat heart model, dl-tetrahydropalmatine (THP) at the concentration of 100 uM was found to have a negative effect (-45%) on left ventricular pressure and this effect was produced concentration-dependently from concentrations lower than 50 uM. In isolated cardiomyocytes, radioactive calcium influx was also inhibited significantly by THP at the concentration of 100 uM and this effect was also in a concentration-dependent manner (-39%).

Name

Type

Language

TETRAHYDROPALMATINE HYDROCHLORIDE, (±)-

Common Name

English

(±)-TETRAHYDROPALMATINE HYDROCHLORIDE

Common Name

English

TETRAHYDROPALMATINE DL-FORM HYDROCHLORIDE [MI]

Common Name

English

TETRAHYDROPALMATINE HCL [INCI]

Common Name

English

TETRAHYDROPALMATINE HCL

Official Name

English

DL-TETRAHYDROPALMATINE HYDROCHLORIDE

Common Name

English

NSC-209411

Code

English

BERBINE, 2,3,9,10-TETRAMETHOXY-, HYDROCHLORIDE, (±)-

Systematic Name

English

6H-DIBENZO(A,G)QUINOLIZINE, 5,8,13,13A-TETRAHYDRO-2,3,9,10-TETRAMETHOXY-, HYDROCHLORIDE (1:1)

Systematic Name

English

NSC-132057

Code

English

Code System Code Type Description

CAS

6024-85-7