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Structure via PubChem · Public domain (PubChem)
alfetamine
Sign in to saveAlfetamine, or α-allyl-phenethylamine, is a chemical compound of the phenethylamine family. It was briefly investigated as a possible antidepressant in the early 1970s. Its activity profile was said to be very similar to imipramine and amitriptyline, two tricyclic antidepressants. It has now been largely superseded by the newer compounds in this class, and only rarely found in scientific literature. The "alpha" in its name refers to its prodrug form, alfetamine. In addition to being an antidepressant, alfetamine is also a neuroprotective agent that acts as a weak dopamine antagonist and a high
In the Vinony graph
Vinony's link graph records 1,490 inbound references to alfetamine, and connects out to N-methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine, 2C-G and (RS)-4-hydroxyamphetamine.
It sits within the topics Abandoned drugs, Alkene derivatives and Allyl compounds.
Vinony links it to 4 Wikipedia language editions.
Chemical data
- Formula
- C11H15N
- Molecular weight
- 161.24 g/mol
- IUPAC name
- 1-phenylpent-4-en-2-amine
- SMILES
- C=CCC(CC1=CC=CC=C1)N
- InChIKey
- WQKXQJYCZMWOSD-UHFFFAOYSA-N
- XLogP
- 2.5
- Polar surface area
- 26 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 161.12
Show 3 more facts
- chemical formula
- C₁₁H₁₅N
- canonical SMILES
- C=CCC(CC1=CC=CC=C1)N
- Commons category
- Alfetamine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Alfetamine, or α-allyl-phenethylamine, is a chemical compound of the phenethylamine family. It was briefly investigated as a possible antidepressant in the early 1970s. Its activity profile was said to be very similar to imipramine and amitriptyline, two tricyclic antidepressants. It has now been largely superseded by the newer compounds in this class, and only rarely found in scientific literature. The "alpha" in its name refers to its prodrug form, alfetamine. In addition to being an antidepressant, alfetamine is also a neuroprotective agent that acts as a weak dopamine antagonist and a high affinity κ-opioid receptor agonist.
Alfetamine was synthesized by Kenji Tsukada and colleagues at Shinshu University and Dow Chemical Company in the 1960s and early 1970s.
Excerpted from Wikipedia’s “alfetamine” article, available under the CC BY-SA 4.0 licence.