Tetrahydropalmatine

Tetrahydropalmatine
Clinical data
Other namesrotundine, hyndanrine
Identifiers
  • (13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.241.370
Chemical and physical data
FormulaC21H25NO4
Molar mass355.434 g·mol−1
3D model (JSmol)
  • O(c1c4c(ccc1OC)C[C@H]3c2c(cc(OC)c(OC)c2)CCN3C4)C
  • 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 Y
  • Key:AEQDJSLRWYMAQI-KRWDZBQOSA-N Y
 NY (what is this?)  (verify)

Tetrahydropalmatine (THP) is an isoquinoline alkaloid found in several different plant species, mainly in the genus Corydalis (Yan Hu Suo), but also in other plants such as Stephania rotunda. These plants have traditional uses in Chinese herbal medicine. The pharmaceutical industry has synthetically produced the more potent enantiomer Levo-tetrahydropalmatine (Levo-THP; technically l-THP, often written L-THP), which has been marketed worldwide under different brand names as an alternative to anxiolytic and sedative drugs of the benzodiazepine group and analgesics such as opiates. It is also sold as a dietary supplement.

In 1940, a Vietnamese scientist Sang Dinh Bui extracted an alkaloid from the root of Stephania rotunda with the yield of 1.21.5% and he named this compound rotundin. From 1950 to 1952, two Indian scientists studied and extracted from Stephania glabra another alkaloid named hyndanrine. In 1965, the structure of rotundine and hyndarin was proved to be the same as tetrahydropalmatine.