Haplamine

CAS Registry Number: 52617-31-9

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinoline Alkaloids

Biological sources: Haplophyllum acutifolium, H. perforatum

C₁₅H₁₅NO₃: 257.1051

Mp: 201–202°C (dec., EtOH), 232°C (dihydro), 95°C (O–Me) [1]

Solubility: very sol. CHCl₃; sol. Et₂O, EtOH; insol. H₂O, acids [1]

UV: 220, 243, 323 sh, 340, 359, 377 (4.45, 4.44, 3.64, 3.70, 4.02, 3.98) [1]

IR: 3155, 1660, 1630, 1600, 1505, 1490, 1470, 1425, 1354, 1330, 1280, 1238, 1220, 1130, 1048, 860, 835 [1]

MS m/z: 257(M⁺, 47), 242(100) [1]

¹ H NMR(CCl₄): 1.50(6H, s, 2 × CH₃), 3.80(3H, s, OCH₃), 5.43, 6.72(each 1H, J = 10, CH = CH), 7.01(1H, dd, J = 8.5, 3, H-7), 7.05(1H, br s, H-5), 7.36(1H, d, J = 8.5, H-8) [1]

Pharm./Biol.: LD₅₀ 1020 mg/kg (i/p, mice). Sedative and estrogenic action [2, 3]