Palmatine
Title: Palmatine
CAS Registry Number: 3486-67-7
CAS Name: 5,6-Dihydro-2,3,9,10-tetramethoxydibenzo[a,g]quinolizinium
Additional Names: 7,8,13,13a-tetradehydro-2,3,9,10-tetramethoxyberbinium; calystigine
Molecular Formula: [C21H22NO4]+
Literature References: Obtained only in form of its salts. First isolated from Calumba root (Jateorhiza palmata (DC.) Miers, Menispermaceae). Now found in many other genera. Palmatine and tetrahydropalmatine, q.v. are probably the most widely distributed Berberis alkaloids. Extraction procedure: Feist, Dschu, Arch. Pharm. 263, 301 (1925). Structure: Feist, Sandstede, ibid. 256, 2, 5 (1918); Späth, Lang, Ber. 54, 3064, 3068 (1921); Späth, Böhm, Ber. 55, 2988 (1922); Späth, Meinhard, Ber. 75, 400 (1942). Synthesis: Späth, Quientensky, Ber. 58, 2267 (1925); R. D. Haworth et al., J. Chem. Soc. 1927, 548; Z. Kiparissides et al., Can. J. Chem. 58, 2770 (1980). Identity with calystigine, alkaloid of the Chinese drug Chi-Kuo-Lan: Huang, Chen, C.A. 52, 15827i (1958).
Properties: Palmatine forms addn products with acetone and chloroform, as does berberine.
 
Derivative Type: Iodide
Molecular Formula: (C21H22NO4)I
Molecular Weight: 479.31
Percent Composition: C 52.62%, H 4.63%, N 2.92%, O 13.35%, I 26.48%
Properties: Yellow needles from water, dec 239°; also a dihydrate. Sparingly sol in hot water and alc.
 
Derivative Type: Nitrate
Molecular Formula: (C21H22NO4)NO3
Molecular Weight: 414.41
Percent Composition: C 60.86%, H 5.35%, N 6.76%, O 27.03%
Properties: Sesqui- or dihydrate, yellow needles, dec 239°. Freely sol in most solvents.
 
Derivative Type: Chloride trihydrate
Molecular Formula: (C21H22NO4)Cl.3H2O
Molecular Weight: 441.90
Percent Composition: C 57.08%, H 6.39%, N 3.17%, O 25.34%, Cl 8.02%
Properties: Yellowish-green needles from water. Freely sol in hot water and alc.
 
Derivative Type: Sulfate pentahydrate
Molecular Formula: (C21H22NO4)2SO4.5H2O
Molecular Weight: 890.95
Percent Composition: C 56.62%, H 6.11%, N 3.14%, O 30.53%, S 3.60%
Properties: Yellow needles, mp 250°. Very sol in alc, sol in water.
Melting point: mp 250°

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