Hydrastine
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| Clinical data | |
|---|---|
| ATC code |
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| Pharmacokinetic data | |
| Metabolism | Hepatic |
| Excretion | Renal |
| Identifiers | |
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JSmol) | |
| Melting point | 132 °C (270 °F) |
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Hydrastine is an
haemostatic drug[2] during the 1910s. It is present in Hydrastis canadensis (thus the name) and other plants of the family Ranunculaceae
.
Total synthesis
The first attempt for the
Sir Robert Robinson and co-workers[3] in 1931. Following studies[4][5] where the synthesis of the key lactonic amide intermediate (structure 4 in figure) was the most troublesome, the major breakthrough was achieved in 1981 when J. R. Falck and co-workers[6] reported a four-step total synthesis of hydrastine from simple starting materials. The key step in the Falck synthesis was using a Passerini reaction
to construct the lactonic amide intermediate 4.
Starting from a simple phenylbromide variant 1, alkylation reaction with lithium methylisocyanide gives the
POCl3 and then a catalyzed hydrogenation using PtO2 as the catalyst. Finally, hydrastine was synthesized by installing the N-methyl group via reductive amination reaction with formaldehyde
.
See also
- Bicuculline (very similar in structure)
References
- ^ Perrins JD (July 1862). "On Hydrastine, an Alkaloid Occurring in Hydrastis Canadensis". Pharmaceutical Journal: A Weekly Record of Pharmacy and Allied Sciences. J. Churchill: 547–.
{{cite journal}}: CS1 maint: date and year (link) - ^ Römpp CD, Georg Thieme Verlag, 2006
- ISSN 0368-1769.
- S2CID 4198366.
- ISSN 0368-1769.
- ISSN 0040-4039.
External links
- Chisholm, Hugh, ed. (1911). . Encyclopædia Britannica. Vol. 14 (11th ed.). Cambridge University Press. p. 34.