Tetrahydropalmatine

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Tetrahydropalmatine
Tetrahydropalmatine.png
Systematic (IUPAC) name
(13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
Identifiers
CAS Number 10097-84-4 N
PubChem CID: 72301
ChemSpider 65252 YesY
ChEBI CHEBI:16563 YesY
ChEMBL CHEMBL487182 YesY
Chemical data
Formula C21H25NO4
Molecular mass 355.428 g/mol
  • 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 YesY
  • Key:AEQDJSLRWYMAQI-KRWDZBQOSA-N YesY
 NYesY (what is this?)  (verify)

Tetrahydropalmatine (THP) is an alkaloid found in several different plant species, mainly in the Corydalis genus (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.

Effects

Tetrahydropalmatine has been demonstrated to possess analgesic effects and may be beneficial in the treatment of heart disease and liver damage.[4][5] It is a blocker of voltage-activated L-type calcium channel active potassium channels.[citation needed] It is a potent muscle relaxant.[citation needed] It has also shown potential in the treatment of drug addiction to both cocaine and opiates, and preliminary human studies have shown promising results.[6][7][8]

Animal experiments have shown that the sedative effect of THP results from blocking dopaminergic neurons in the brain. Dopamine is an important neurotransmitter in the central nervous system where it occurs in several important signaling systems that regulate muscular activity and attention, as well as feelings of joy, enthusiasm, and creativity. Therefore, THP causes no feelings of euphoria, and has been seen as an alternative to addictive drugs for people suffering from anxiety and pain, and as a possibility for relief for people not helped by existing drugs.[citation needed]

Cases of poisoning

Several cases of poisoning related to THP have been reported.[9] These cases involved negative effects on respiration, cardiac activity, and the nervous system. In addition, chronic hepatitis has been reported, caused by THP production in East Asia under conditions that were insufficiently sterile. Fatalities started to be reported in 1999 in cases where THP had been used in combination with other drugs having analgesic and anti-anxiety effects. All 1999 deaths could be tied to a single THP-based supplement, sold under the name "Jin Bu Huan Anodyne Tablets". This product was therefore blacklisted by US and European health authorities. In some other countries, such as Singapore, THP is treated as a controlled substance, and license is required to sell it.[citation needed]

See also

References

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