Alfetamine

Chemical compound
  • none
Identifiers
  • 1-phenylpent-4-en-2-amine
CAS Number
  • 4255-23-6 ☒N
PubChem CID
  • 20254
ChemSpider
  • 19080 checkY
UNII
  • Q3V87119BP
ChEMBL
  • ChEMBL2110598 ☒N
Chemical and physical dataFormulaC11H15NMolar mass161.248 g·mol−13D model (JSmol)
  • Interactive image
  • NC(Cc1ccccc1)C\C=C
InChI
  • InChI=1S/C11H15N/c1-2-6-11(12)9-10-7-4-3-5-8-10/h2-5,7-8,11H,1,6,9,12H2 checkY
  • Key:WQKXQJYCZMWOSD-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Alfetamine, or alpha-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was said to be very similar to imipramine and amitriptyline, two tricyclic antidepressants.[1] It has now been largely superseded by the newer compounds in this class, and only rarely found in scientific literature.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.[medical citation needed]

Alfetamine was synthesized by Kenji Tsukada and colleagues at Shinshu University and Dow Chemical Company in the 1960s and early 1970s.

References

  1. ^ Hitchens JT, Orzechowski R, Goldstein S, Shemano I (March 1972). "Pharmacologic evaluation of aletamine (alpha-allylphenethylamine hydrochloride) as an antidepressant". Toxicology and Applied Pharmacology. 21 (3): 302–14. doi:10.1016/0041-008X(72)90150-0. PMID 5063697.
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Stimulants
AdamantanesAdenosine antagonistsAlkylaminesAmpakinesArylcyclohexylaminesBenzazepinesCathinonesCholinergicsConvulsantsEugeroicsOxazolinesPhenethylamines
PhenylmorpholinesPiperazinesPiperidinesPyrrolidinesRacetamsTropanesTryptaminesOthers
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DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
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Phenethylamines


Stimulants: Phenylethanolamine

Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
Phenylalkylpyrrolidines
Catecholamines
(and close relatives)
Miscellaneous