Structure via PubChem · Public domain (PubChem)
prenylamine
Sign in to saveAlso known as B-436, N-(1-Methyl-2-phenylethyl)-3,3-diphenyl-1-propanamine, N-(3,3-Diphenylpropyl)-alpha-methylphenethylamine, N-(3'-Phenyl-2-propyl)-1,1-diphenyl-3-propyloamine, 1-Phenyl-2-(1',1'-diphenylpropyl-3'-amino)propane, DL-prenylamine, N-(1-Methyl-2-phenylethyl)-gamma-phenylbenzenepropanamine, N-(3,3-Diphenylpropyl)-alpha-methylphenaethylamin
Prenylamine (Segontin) is a calcium channel blocker of the amphetamine chemical class that was used as a vasodilator in the treatment of angina pectoris. It produces amphetamine as a metabolite.
Chemical data
- Formula
- C24H27N
- Molecular weight
- 329.5 g/mol
- IUPAC name
- 3,3-diphenyl-N-(1-phenylpropan-2-yl)propan-1-amine
- SMILES
- CC(CC1=CC=CC=C1)NCCC(C2=CC=CC=C2)C3=CC=CC=C3
- InChIKey
- IFFPICMESYHZPQ-UHFFFAOYSA-N
- XLogP
- 6
- Polar surface area
- 12 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- Indications
- cardiovascular disease
via ChEMBL · EBI
Research
746 papers- Basic mechanisms underlying prenylamine-induced 'torsade de pointes': differences between prenylamine and fendiline due to basic actions of the isomers.Current medical research and opinion · 1988
- The role of prenylamine in the prevention of adriamycin-induced cardiotoxicity. A review of experimental and clinical findings.The Journal of international medical research · 1988
- Acute prenylamine poisoning.Archiv fur Toxikologie · 1974
- Analytical developments of p-hydroxy prenylamine reference material for dope control research: Characterization and purity assessment.Drug testing and analysis · 2022
- Local anesthetic properties of prenylamine.Anesthesiology · 2001
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 329.21435
- Has use
- medication
Show 4 more facts
- chemical formula
- C₂₄H₂₇N
- canonical SMILES
- CC(CC1=CC=CC=C1)NCCC(C2=CC=CC=C2)C3=CC=CC=C3
- defined daily dose
- 0.12
- subject has role
- calcium channel blocker
Sources (3)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- History
- Mechanism of action
- References
Prenylamine (Segontin) is a calcium channel blocker of the amphetamine chemical class that was used as a vasodilator in the treatment of angina pectoris. It produces amphetamine as a metabolite.
==History == Prenylamine was introduced in the 1960s by German manufacturer Albert-Roussel pharma gmbh, which was acquired by Hoechst AG in 1974 and which in turn became part of Sanofi Aventis in 2005.
Excerpted from Wikipedia’s “prenylamine” article, available under the CC BY-SA 4.0 licence.