Tetrahydropalmatine

Tetrahydropalmatine
Identifiers
  • (13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.241.370 Edit this at Wikidata
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 checkY
  • Key:AEQDJSLRWYMAQI-KRWDZBQOSA-N checkY
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Tetrahydropalmatine (THP) is an isoquinoline alkaloid found in several different plant species, mainly in the genus Corydalis (Yan Hu Suo),[1][2] but also in other plants such as Stephania rotunda.[3] These plants have traditional uses in Chinese herbal medicine. The pharmaceutical industry has synthetically produced the more potent enantiomer Levo-tetrahydropalmatine (Levo-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 1.2–1.5% and he named this compound rotundine. 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.[4]

  1. ^ Sutin EL, Jacobowitz DM (1991). "Neurochemicals in the dorsal pontine tegmentum". Neurobiology of the Locus Coeruleus. Progress in Brain Research. Vol. 88. pp. 3–14. doi:10.1016/S0079-6123(08)63796-6. ISBN 9780444813947. PMID 1726029.
  2. ^ Ma ZJ, Li XD, Gu XZ, Cheng LP, Mao SJ (March 2006). "[Effects of different types and standard of processing vinegaron inherent constituents in rhizoma of Corydalis yanhusuo]". Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica. 31 (6): 465–7. PMID 16722373.
  3. ^ Andersson C, Bergarp E, Hedman G (January 1992). "[Sick-listed but active]". Läkartidningen. 89 (5): 281–3. PMID 1738250.
  4. ^ Do TL (2004). Những cây thuốc và vị thuốc Việt Nam. Hà Nội: Nhà xuất bản Y học. p. 780.