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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
124.0 nM [Ki]
388.0 nM [Ki]
1.4 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
42.8 ng/mL
30 mg 2 times / day multiple, oral
TETRAHYDROPALMATINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
396.1 ng × h/mL
30 mg 2 times / day multiple, oral
TETRAHYDROPALMATINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
13.3 h
30 mg 2 times / day multiple, oral
TETRAHYDROPALMATINE plasma
Homo sapiens

Doses

Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
30 mg twice daily (7 total doses)
Route of Administration: Oral
In Vitro Use Guide
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
Record UNII
3X69CO5I79
Record Status Validated (UNII)
Record Version