| Identification | Back Directory | [Name]
SCOULERIN | [CAS]
6451-73-6 | [Synonyms]
SCOULERIN
Scoreline
l-scoulerine
l-skoulerine
Alkaloid HF-1
SCOULERIN(RG)
SCOULERIN(SH)
(-)-scoulerine
2,9-DIOXY-3,10-DIMETHOXYBERBINE
3,10-Dimethoxy-13aα-berbine-2,9-diol
3,10-dimethoxy-13a-alpha-berbine-9-diol
3,10-dimethoxy-13a-alpha-berbine-2,9-diol
Alkaloid HF 1, froM HunneMannia fuMariaefolia
g)quinolizine-2,9-diol,5,8,13,13a-tetrahydro-3,10-dimethoxy-6h-dibenzo((
(S)-5,8,13,13a-Tetrahydro-3,10-diMethoxy-6H-Dibenzo[a,g]quinolizine-2,9-diol
(13aS)-5,8,13,13a-tTtrahydro-3,10-diMethoxy-6H-dibenzo[a,g]quinolizine-2,9-diol
(13aR)-5,8,13,13a-Tetrahydro-3,10-dimethoxy-6H-dibenzo[a,g]quinolizine-2,9-diol
6H-Dibenzo[a,g]quinolizine-2,9-diol, 5,8,13,13a-tetrahydro-3,10-dimethoxy-, (13aS)-
[13aR,(+)]-5,8,13,13aβ-Tetrahydro-3,10-dimethoxy-6H-dibenzo[a,g]quinolizine-2,9-diol
(13aS)-3,10-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,9-diol | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C19H21NO4 | [MDL Number]
MFCD00221721 | [MOL File]
6451-73-6.mol | [Molecular Weight]
327.37 |
| Chemical Properties | Back Directory | [Melting point ]
192°C | [Boiling point ]
503.3±50.0 °C(Predicted) | [density ]
1.37±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [form ]
A crystalline solid | [pka]
9.88±0.20(Predicted) | [color ]
Off-white to pink |
| Hazard Information | Back Directory | [Description]
This form of the alkaloid is more widespread than the d-form, occurring in Corydalis caseana, C. micrantha, C. montana, C. scouleri, C. sibirica and Papaver somniferum. It has [α]26D - 318° (c 0.41, MeOH) or - 289° (c 0.62, MeOH). It forms pale grey needles when crystallized from MeOH. The hydrochloride has m.p. 268-9°C; the picrate, m.p. 206°C (dec.) and the diethyl ether, m.p. 155°C. The oxidation products are the same as for the preceding base. | [Chemical Properties]
Off-White to Pale Pink Solid | [Uses]
(S)-Scoulerine is an alkaloid found in the opium poppy. (S)-Scoulerine acts as an antagonist at the α2-adrenoceptor, α1D-adrenoceptor and 5-HT receptor. | [Definition]
ChEBI: A berberine alkaloid isolated from Corydalis saxicola. | [References]
Manske., Can. J. Res., 14B, 347, 354 (1936)
Manske., ibid, 17B, 57 (1939)
Manske., ibid, 18B, 414 (1940)
Manske., ibid, 20B, 49 (1942)
Brochmann-Hanssen, Nielsen., Tetrahedron Lett., 2261 (1966)
Synthesis:
Kametani., Japanese Patent, 70, 37,976, 10 December 1970 |
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