| Identification | Back Directory | [Name]
[S-(R*,R*)]-6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)phthalide | [CAS]
521-40-4 | [Synonyms]
narcotoline
Desmethylnarcotine
Noscapine Impurity 6(Narcotoline)
S-(R*,R*)]-6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)phthalide
[S-(R*,R*)]-6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)phthalide
(3S)-3-[(5R)-4-hydroxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-3H-2-benzofuran-1-one
(3S)-3-[(5R)-4-hydroxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-3H-isobenzofuran-1-one
(3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]isobenzofuran-1(3H)-one
1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (3S)- | [EINECS(EC#)]
208-313-6 | [Molecular Formula]
C21H21NO7 | [MOL File]
521-40-4.mol | [Molecular Weight]
399.39 |
| Chemical Properties | Back Directory | [Melting point ]
202° | [alpha ]
D20 -189° (0.1 g in 25 ml chloroform, 20 cm tube); D20 +5.8° (0.065 g in 5 ml 0.1N HCl in 20 cm tube) | [storage temp. ]
-20°C Freezer, Under inert atmosphere | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [color ]
Pale Yellow to Light Yellow |
| Hazard Information | Back Directory | [Description]
Wrede has obtained this alkaloid from the seed capsules of Papaver somniferum.
It crystallizes from aqueous MeOH in colourless rectangular rods and has [0:]5° -
189° (CHCI3) and + 5.8° (c 0.1 NiHCI). One phenolic hydroxyl group is present
in the molecule and the base forms the O-acetate, m.p. 208-9°C, giving a hydro_x0002_chloride as the monohydrate, m.p. 230-3°C (dry); [0:]5° + 94.8° (H 20). The
acid tartrate forms colourless needles which, decompose at 190-205°C and the
picrolonate has m.p. 202-3°C. On treatment with CH2N2, the alkaloid gives
Narcotine (q.v.). | [Uses]
Desmethylnarcotine is an impurity of Narcotoline an opiate alkaloid and a structure analogue of Nascapine (N882000), an antitussive agent. Noscapine (N882000) metabolite. | [Definition]
ChEBI: Narcotoline is a member of isoquinolines. | [References]
Wrede., r;hem. Zentr., I, 2611 (1937)
Wrede., ibid, II, 863 (1938) |
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