laurotetanine
- Product Name
- laurotetanine
- CAS No.
- 128-76-7
- Chemical Name
- laurotetanine
- Synonyms
- Litsoeine;NSC106610;NSC-106610;NSC 106610;Laurotetanin;laurotetanine;(6aS)-5,6,6a,7-Tetrahydro-1,2,10-trimethoxy-4H-dibenzo[de,g]quinolin-9-ol;[S,(+)]-5,6,6a,7-Tetrahydro-1,2,10-trimethoxy-4H-dibenzo[de,g]quinolin-9-ol;4H-Dibenzo[de,g]quinolin-9-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-, (6aS)-
- CBNumber
- CB01339347
- Molecular Formula
- C19H21NO4
- Formula Weight
- 327.37
- MOL File
- 128-76-7.mol
laurotetanine Property
- Melting point:
- 125°C
- Boiling point:
- 465.27°C (rough estimate)
- Density
- 1.2223 (rough estimate)
- refractive index
- 1.5000 (estimate)
- pka
- 9.76±0.20(Predicted)
N-Bromosuccinimide Price
- Product number
- PXT0004920
- Product name
- LAUROTETANINE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $498.81
- Updated
- 2021/12/16
laurotetanine Chemical Properties,Usage,Production
Description
The noraporphine alkaloid was first isolated by Greshoff from Litsea chrysocorna and subsequently from other species of Lauraceae including L. citrata and L. cubeba. When freshly crystallized from Me2 CO it yields colourless crystals but these become yellow in air. The alkaloid behaves as a phenolic base giving salts with mineral acids which all contain H20 of crystallization. The picrate monohydrate has m.p. 1480 C, the dibenzoyl derivative, m.p. 169-1700 C and the phenylthiocarbamide, m.p. 211-2°C. Three methoxyl groups, an imino group and a phenolic hydroxyl group are present, the latter giving the O-methyl ether which is an amorphous powder but yields a crystalline hydrochloride, m.p. 245°C; an oxalate, m.p. 233°C and the thiocarbamide, m.p. 154-5°C. The Nmethyl derivative (q.v.) is found naturally in Peurnus boldus and the O,Ndimethyl derivative is glaucine. The structure has been determined from chemical degradation and synthesis.
Uses
Laurotetanine ((+)-Laurotetanine) is an potent and orally active isoquinoline alkaloid and could be extracted from the roots of Litsea cubeba (Lour.) Pers. Laurotetanine exerts an anti-asthmatic effect by inhibition of IgE, histamine, and inflammatory reactions via down-regulating MUC5AC and NF-κB signaling pathways[1].
Definition
ChEBI: Litsoeine is an isoquinoline alkaloid.
in vivo
Laurotetanine ((+)-Laurotetanine; 20-60 mg/kg; p.o.; daily, for 21 d; Sprague Dawley (SD) rats) has anti-asthmatic effect in rats by down-regulating MUC5AC and NF-κB signaling pathways[1].
| Animal Model: | Sprague Dawley (SD) rats (180-220g) [1] |
| Dosage: | 20, 40, and 60 mg/kg |
| Administration: | Oral administration; daily, for 21 days |
| Result: | Reduced inflammatory cells, including eosinophils, neutrophils, lymphocytes, and macrophages. Decreased inflammatory cytokines viz IL-4, IL-6, IL-13 and increased IFN-γ. Reduced serum IgE and histamine. Decreased MUC5AC expression and increased NF-κB and IκB expression in lung tissues. |
References
Greshoff., Ber., 23,3537 (1890)
Filippo., Arch. Pharm., 236, 601 (1898)
Gorter., Bull. Jard. bot. Buitenzorg., 3, 180 (1921)
Barger, Silberschmidt.,J. Chem. Soc., 2919 (1928)
Barger et al., Ber., 66, 450 (1933)
Ruegger., Helv. Chim. Acta, 42,754 (1959)
Kikkawa.,J. Pharm. Soc., Japan, 79,83,425 (1959)
laurotetanine Preparation Products And Raw materials
Raw materials
Preparation Products
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