Structure via PubChem · Public domain (PubChem)
oxaprotiline
Sign in to saveOxaprotiline (developmental code name C 49-802 BDA), also known as hydroxymaprotiline, is a norepinephrine reuptake inhibitor belonging to the tetracyclic antidepressant (TeCA) family and is related to maprotiline. Though investigated as an antidepressant, it was never marketed.
Chemical data
- Formula
- C20H23NO
- Molecular weight
- 293.4 g/mol
- IUPAC name
- 1-(methylamino)-3-(1-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)propan-2-ol
- SMILES
- CNCC(CC12CCC(C3=CC=CC=C31)C4=CC=CC=C24)O
- InChIKey
- FDXQKWSTUZCCTM-UHFFFAOYSA-N
- XLogP
- 3.6
- Polar surface area
- 32.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
150 papers- Oxaprotiline in the treatment of endogenous depressed inpatients an early clinical trial.Pharmacopsychiatry · 1985
- Second-generation antidepressants.The Psychiatric clinics of North America · 1984
- Oxaprotiline: induction of central noradrenergic subsensitivity of its (+)-enantiomer.Life sciences · 1982
- The metabolic fate of 14C-oxaprotiline X HCl in man. III. Stereospecific disposition.Biopharmaceutics & drug disposition · 1984
- Pharmacological effects of oxaprotiline enantiomers on the central serotonin system.Polish journal of pharmacology and pharmacy · 1989
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 293.178
Show 4 more facts
- chemical formula
- C₂₀H₂₃NO
- canonical SMILES
- CNCC(CC12CCC(C3=CC=CC=C31)C4=CC=CC=C24)O
- subject has role
- antidepressant
- Commons category
- Oxaprotiline
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Pharmacology
- Chemistry
- See also
- References
Oxaprotiline (developmental code name C 49-802 BDA), also known as hydroxymaprotiline, is a norepinephrine reuptake inhibitor belonging to the tetracyclic antidepressant (TeCA) family and is related to maprotiline. Though investigated as an antidepressant, it was never marketed.
==Pharmacology== Dextroprotiline acts as a potent norepinephrine reuptake inhibitor and H1 receptor antagonist, as well as a very weak α1-adrenergic receptor antagonist. It has negligible affinity for the serotonin transporter, dopamine transporter, α2-adrenergic receptor, and muscarinic acetylcholine receptors. Whether it has any antagonistic effects on the 5-HT2, 5-HT7, or D2 receptors like its relative maprotiline is unclear.
Excerpted from Wikipedia’s “oxaprotiline” article, available under the CC BY-SA 4.0 licence.