Tetrahydropalmatine
Title: Tetrahydropalmatine
CAS Registry Number: 10097-84-4
CAS Name: 5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo[a,g]quinolizine
Additional Names: 2,3,9,10-tetramethoxyberbine; 2,3,9,10-tetramethoxydibenzo[a,g]quinolizidine; hyndarin
Molecular Formula: C21H25NO4
Molecular Weight: 355.43
Percent Composition: C 70.96%, H 7.09%, N 3.94%, O 18.01%
Literature References: Synthesis of dl-form: Haworth et al., J. Chem. Soc. 1927, 548; Bradsher, Dutta, J. Org. Chem. 26, 2231 (1961); T. Kametani, M. Ihara, J. Chem. Soc. C 1967, 530; G. D. Pandey, K. P.Tiwari, Indian J. Chem. 18B, 545 (1979); Z. Kiparissides et al., Can. J. Chem. 58, 2770 (1980); N. S. Narasimhan et al., Tetrahedron Lett. 22, 2797 (1981). Biosynthesis: D. S. Bhakuni et al., Tetrahedron 36, 2491 (1980). See also Palmatine. Both optically active forms are found in plants.
 
Derivative Type: l-Form
Additional Names: Caseanine; gindarine; rotundine
Properties: Crystals from dil methanol, mp 147°. [a]D20 -291° (c = 0.8 in 95% alcohol). Also a hydrate, mp 115° (effervescence).
Melting point: mp 147°; mp 115° (effervescence)
Optical Rotation: [a]D20 -291° (c = 0.8 in 95% alcohol)
 
Derivative Type: Hydrochloride
Molecular Formula: C21H25NO4.HCl
Molecular Weight: 391.89
Percent Composition: C 64.36%, H 6.69%, N 3.57%, O 16.33%, Cl 9.05%
Properties: Crystals.
 
Derivative Type: d-Form
Properties: Crystals from methanol, mp 141-142° (evac tube). [a]D14 +292° (c = 0.8 in 95% alcohol).
Melting point: mp 141-142° (evac tube)
Optical Rotation: [a]D14 +292° (c = 0.8 in 95% alcohol)
 
Derivative Type: Hydrochloride
Properties: Crystals, mp 266°.
Melting point: mp 266°
 
Derivative Type: dl-Form
Properties: Crystals from methanol upon addition of water. mp 148-149°.
Melting point: mp 148-149°
 
Derivative Type: Hydrochloride
Properties: Needles from methanol, mp 215-216°.
Melting point: mp 215-216°

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