(+) - β - Hydrastine

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Isoquinoline Alkaloids

Biological sources: Corydalis caucasica, C. pseudoadunca, C. stricta

C₂₁H₂₁NO₆: 383.1369

Mp: 131–132°C (MeOH) [1], 206°C (methiodide [MeOH])

[α]_D+63° [1]

UV: 298 [2]

IR: 1760 [2]

MS m/z: 190 [2]

¹ H NMR: 2.57(3H, s, NCH₃), 3.92, 4.08(each 3H, s, 2 × OCH₃), 3.99, 5.49(each 1H, d, J = 4), 5.92(2H, s, CH₂O₂), 6.39, 6.58(each 1H, s, p–H–Ar), 6.52, 7.08(each 1H, d, J = 8, o–H–Ar) [3]

¹³ C NMR: [4]

Table 1

C-1	66.0	C-8	107.3	C-5′	147.5
3	49.0	8a	130.0	6′	119.4
4	26.7	9	82.7	10	167.0
4a	124.5	1′	140.4	NCH3	44.7
5	108.1	2′	117.3	6,7-OCH2O	100.5
6	146.3	3′	118.5	4′-OCH3	56.7
7	145.4	4′	152.6	5′-OCH3	62.0

Abs. conf.: 1S, 9R [5]

Pharm./Biol.: LD₅₀0.97, 0.102 mg/kg (s/c, i/v, mice); 1.45(s/c, rats). Active antinarcotic agent. Its activity far exceed those of the known drugs Bemetrid, Korozal, Ervinin, and d-Bicuculline. The (hydrochloride), under the name Izokorin, is recommended for clinical trials as...