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bifemelane
Sign in to saveBifemelane (INN), sold under the brand names Alnert and Celeport, is an antidepressant and cerebral activator that was widely used in the treatment of cerebral infarction patients with depressive symptoms in Japan, and in the treatment of dementia as well. It also appears to be useful in the treatment of glaucoma. It has been discontinued in Japan since 1998, when it was removed from the market reportedly for lack of effectiveness.
Chemical data
- Formula
- C18H23NO
- Molecular weight
- 269.4 g/mol
- IUPAC name
- 4-(2-benzylphenoxy)-N-methylbutan-1-amine
- SMILES
- CNCCCCOC1=CC=CC=C1CC2=CC=CC=C2
- InChIKey
- QSQQPMHPCBLLGX-UHFFFAOYSA-N
- XLogP
- 4.1
- Polar surface area
- 21.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- major depressive disorder
via ChEMBL · EBI
Research
122 papers- Bifemelane enhances high K(+)-evoked release of glutamate from mossy fiber synaptosomes of guinea-pig hippocampus.European journal of pharmacology · 1992
- Bifemelane protects cultured cortical neurons against N-methyl-D-aspartate receptor-mediated glutamate cytotoxicity.Japanese journal of pharmacology · 1998
- Bifemelane hydrochloride protects against cytotoxicity of hydrogen peroxide on cultured rat neuroblastoma cell line.Neurochemical research · 1999
- Specific binding sites for bifemelane in the hippocampus of the guinea pig, relevant to its pharmacological actions.Neuropharmacology · 1991
- Bifemelane hydrochloride reduces plasma beta-endorphin-like immunoreactivity levels in rats.Experimental and clinical endocrinology · 1990
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 269.178
Show 4 more facts
- chemical formula
- C₁₈H₂₃NO
- canonical SMILES
- CNCCCCOC1=CC=CC=C1CC2=CC=CC=C2
- subject has role
- nootropic
- Commons category
- Bifemelane
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Bifemelane (INN), sold under the brand names Alnert and Celeport, is an antidepressant and cerebral activator that was widely used in the treatment of cerebral infarction patients with depressive symptoms in Japan, and in the treatment of dementia as well. It also appears to be useful in the treatment of glaucoma. It has been discontinued in Japan since 1998, when it was removed from the market reportedly for lack of effectiveness.
Bifemelane acts as a monoamine oxidase inhibitor (MAOI) of both isoenzymes, with competitive reversible inhibition of MAO-A (Ki = 4.20 μM), making it a reversible inhibitor of monoamine oxidase A (RIMA) and non-competitive irreversible inhibition of MAO-B (Ki = 46.0 μM), and also acts (weakly) as a norepinephrine reuptake inhibitor (NRI). The drug has nootropic, neuroprotective, and antidepressant-like effects in animal models, and appears to enhance the cholinergic system in the brain.
Excerpted from Wikipedia’s “bifemelane” article, available under the CC BY-SA 4.0 licence.