Structure via PubChem · Public domain (PubChem)
hepzidine
Sign in to saveHepzidine (INN) is a tricyclic antidepressant which was never marketed. It was first described by 1966. ==Synthesis== The synthesis has been described in the chemical literature: 700px|center| 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).
Chemical data
- Formula
- C21H25NO
- Molecular weight
- 307.4 g/mol
- IUPAC name
- 1-methyl-4-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenyloxy)piperidine
- SMILES
- CN1CCC(CC1)OC2C3=CC=CC=C3CCC4=CC=CC=C24
- InChIKey
- MNIZCABHARMLFF-UHFFFAOYSA-N
- XLogP
- 4.2
- Polar surface area
- 12.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 307.194
Show 3 more facts
- chemical formula
- C₂₁H₂₅NO
- canonical SMILES
- CN1CCC(CC1)OC2C3=CC=CC=C3CCC4=CC=CC=C24
- Commons category
- Hepzidine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- See also
- References
Hepzidine (INN) is a tricyclic antidepressant which was never marketed. It was first described by 1966. ==Synthesis== The synthesis has been described in the chemical literature: 700px|center| 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== 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.
Excerpted from Wikipedia’s “hepzidine” article, available under the CC BY-SA 4.0 licence.