Tetrahydropalmatine
From DrugPedia: A Wikipedia for Drug discovery
| Tetrahydropalmatine
| |
| Systematic (IUPAC) name | |
| (13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline | |
| Identifiers | |
| CAS number | ? |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C21H25NO4 |
| Mol. mass | 355.4275 |
| SMILES | & |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
Contents |
[edit] Description
Tetrahydropalmatine (THP) is an alkaloid found in several different plant species, mainly in the Corydalis family, 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), 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.
[edit] Effects
Tetrahydropalmatine has been demonstrated to possess analgesic effects and may be beneficial in the treatment of heart disease and liver damage. It has also shown useful effects in the treatment of drug addiction to both cocaine and opiates, and preliminary human studies have shown promising results.
Animal experiments have shown that the sedative effect of THP results from blocking dopaminergic neurons in the brain. Dopamine is one of the most important neurotransmitters in the central nervous system where it occurs in several important 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.
[edit] Cases of poisoning
However, several cases of poisoning related to THP have also been reported. 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.
[edit] General Properties
*Molecular Weight
355.4275
*Molecular Formula
C21H25NO4
*IUPAC NAME
(13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
*Canonical Smiles
COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC
*Isomeric Smiles
COC1=C(C2=C(C[C@H]3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC
*XLogP
2.4
*Topological Polar Surface Area
40.2
