Hepzidine
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| Formula | C21H25NO |
| Molar mass | 307.437 g·mol−1 |
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Hepzidine (INN) is a tricyclic antidepressant which was never marketed.[1] It was first described by 1966.[1]
Synthesis
[edit]The synthesis has been described in the chemical literature:[2]
The reduction of dibenzosuberone (1) gives dibenzosuberol [1210-34-0] (2). This alcohol forms ethers exceedingly easily, probably via the carbonium ion. Treatment with N-methyl-4-piperidinol [106-52-5] (3) in the presence of acid gives hepzidine (4).
See also
[edit]- Diphenylpyraline is selfsame but is based on a benzhydrol aromatic pharmacophore.
- Dibenzosuberol is also used in the synthesis of Deptramine (DPH analog) as well as Oxitriptyline & Deptropine.
References
[edit]- 1 2 Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 624. ISBN 978-1-4757-2085-3. Retrieved 20 October 2024.
- ↑ van der Stelt C, Funcke AB, Tersteege HM, Nauta WT (October 1966). "The effect of alkyl substitution in drugs. XVI. Basic ethers of 10,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-ol and some related compounds". Arzneimittel-Forschung. 16 (10): 1342–5. PMID 6014925.