6994. Palmatine

Nomenclature

CAS number: 3486-67-7
5,6-Dihydro-2,3,9,10-tetramethoxydibenzo[a,g]quinolizinium; 7,8,13,13a-tetradehydro-2,3,9,10-tetramethoxyberbinium; calystigine.
[C21H22NO4]+.

Description and 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); Sp"ath, Lang, Ber. 54, 3064, 3068 (1921); Sp"ath, B"ohm, Ber. 55, 2988 (1922); Sp"ath, Meinhard, Ber. 75, 400 (1942). Synthesis: Sp"ath, 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).

Chemical structure

Properties

Palmatine forms addn products with acetone and chloroform, as does berberine.

Derivative

Iodide.
(C21H22NO4)I; mol wt 479.31.
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

Nitrate.
(C21H22NO4)NO3; mol wt 414.41.
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

Chloride trihydrate.
(C21H22NO4)Cl.3H2O; mol wt 441.90.
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

Sulfate pentahydrate.
(C21H22NO4)2SO4.5H2O; mol wt 890.95.
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.