Compound: tetrahydropalmatine
SMILES: O(c1c(OC)ccc2c1CN3CCc4c([C@@H]3C2)cc(OC)c(c4)OC)C
InChIKey: AEQDJSLRWYMAQI-KRWDZBQOSA-N
Synonyms: tetrahydropalmatine, 483-14-7, (-)-Tetrahydropalmatine, Gindarine, Hyndarine, Caseanine, (-)-Corydalis B, (-)-rotundine, Tetrahydropalmatine, l-, Tetrahydropalmatine, (-)-, (13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline, 3X69CO5I79, CHEBI:16563, 5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo(a,g)quinolizine, tetrahydropalmitine, (13aS)-2,3,9,10-tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline, DTXSID20864207, (13aS)-2,3,9,10-tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquino(3,2-a)isoquinoline, (13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino(2,1-b)isoquinoline, Tetrahydropalmatine l-, RefChem:897187, DTXCID10812752, l-Tetrahydropalmatine, (S)-Tetrahydropalmatine, 10097-84-4, MFCD03265591, levo-tetrahydropalmatine, (S)-2,3,9,10-Tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline, (S)-(-)-tetrahydropalmatine, 2,3,9,10-tetramethoxy-13aalpha-berbine, Hyndarin, (-)-Corydalis, Tetrahydropalmatine, dl-, NSC36363, Berbine, 2,3,9,10-tetramethoxy-, (-)-S-Tetrahydropalmatine, UNII-3X69CO5I79, Rotundin hydrate, Rotundine?, 2,3,9,10-tetramethoxyberbine, (12bS)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene, 13a-alpha-Berbine, 2,3,9,10-tetramethoxy-, O,O-Dimethyl-N-demethyl-cyclanoline, (-)-2,3,9,10-Tetramethoxyberbine, (-)-Tetrahydropalmatine;L-Tetrahydropalmatine, L-THP, Tetrahydropalmatine l-form, (S)-5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo(a,g)quinolizine, 6H-Dibenzo(a,g)quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (S)-, L-Tetrahydropalmatine hydrate, SCHEMBL230850, CHEMBL487182, orb1300586, orb1302346, SCHEMBL29363068, SCHEMBL29585919, SCHEMBL29716023, (13aS)-2,3,9,10-Tetramethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine, DTXSID701020650, GLXC-07964, HMS3656M19, HMS3884J17, HY-N0096, TETRAHYDROPALMATINE [WHO-DD], BDBM50424077, s2437, AKOS000277105, AC-8007, CCG-268100, CS-8092, DB12093, EBC-470070, FR27764, FR70825, TETRAHYDROPALMATINE L-FORM [MI], NCGC00346591-01, NCGC00346591-02, 219697-24-2, AC-16039, AS-17459, AS-82762, DA-67292, SY108222, (-)-Tetrahydropalmatine, >=98% (HPLC), NS00071603, SW219613-1, T3311, C02890, Q7706555, BRD-K35719256-001-02-6, (13aS)-2,3,9,10-Tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline, (13aS)-5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo[a, g]quinolizine, (S)-2,3,9,10-tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline, 2,3,9,10-Tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]is oquinoline hydrate, 2-(2,3-Dimethoxy-benzyl)-1-ethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline, 5,8,13,13a(S)-Tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo[a,g]quinolizine, 5,8,13,13A-TETRAHYDRO-(S)-2,3,9,10-TETRAMETHOXY-6H-DIBENZO(A,G)QUINOLIZINE, 6H-dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (13aS)-, InChI=1/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/s
Theoretical properties:
molecular_formula: C21H25NO4
molecular_weight: 355.4 g/mol
exact_mass: 355.17835828 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 4
heavy_atom_count: 26
topological_polar_surface_area: 40.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Tetrahydropalmatine is a berberine alkaloid obtained by formal addition of two molecules of hydrogen to the pyridine ring of palmatine. It has a role as a non-narcotic analgesic, an adrenergic agent and a dopaminergic antagonist. It is an an (S)-7,8,13,14-tetrahydroprotoberberine, a berberine alkaloid and an organic heterotetracyclic compound. It is functionally related to a palmatine.
chebi: A berberine alkaloid obtained by formal addition of two molecules of hydrogen to the pyridine ring of palmatine.
chembl: TETRAHYDROPALMATINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: 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 1.2–1.5% 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.