Aphylline

CAS Registry Number: 577-37-7

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinolizidine Alkaloids

Biological sources: Anabasis aphylla

C₁₅H₂₄N₂O: 248.1889

Mp: 52–53°C (Et₂O), 231°C (dec. picrolonate), 213°C (methiodide) [1]

Solubility: very sol. H₂O, EtOH; spar. sol. Et₂O [1]

[α]_D +10° (MeOH)

IR: 3000–2800, 1660 [2]

MS m/z: 248(M⁺, 35), 247(33), 220(43), 191(19), 137(46), 136(100), 98(31), 97(40), 96(35), 84(32), 41(47) [3]

¹ H NMR: 1.49(Ha-8), 1.85(2H, H-7, He-8), 2.04(H-9), 2.17(Ha-2), 2.45(He-17), 2.50 (He-15), 2.80 (Ha-15), 2.82(H-11), 2.99(Ha-17), 3.14(H-6), 4.56(He-2) [4]

¹³ C NMR: [4]

Table 1

C-2	45.0	C-7	33.8	C-12	26.3
3	28.8	8	27.8	13	20.1
4	23.7	9	43.2	14	23.7
5	30.2	10	172.9	15	54.9
6	59.7	11	59.7	17	49.7

¹³ C NMR: [5]

Table 2

C-2	41.1 t	C-7	32.0 d	C-12	22.6 t
3	24.3 t	8	23.3 t	13	24.9 t
4	23.7 t	9	42.8 d	14	19.2 t
5	28.3 t	10	172.2 s	15	54.4 t
6	59.1 d	11	59.3 d	17	53.1 t

ORD: [6]

Pharm./Biol.: Local anesthetic action not...