CH₃CH₃

Amphetamine

Chemistry

23 atoms · Conformer computed and published by PubChem.
Formula
C9H13N
Molar mass
135.21 g/mol
IUPAC name
1-phenylpropan-2-amine
InChIKey
KWTSXDURSIMDCE-UHFFFAOYSA-N

Chemistry from PubChem CID 3007.

Also known as

  • Amfetamine
  • 1-phenylpropan-2-amine
  • dl-Amphetamine
  • 1-Phenyl-2-aminopropane
  • Desoxynorephedrine
  • Norephedrane
  • 300-62-9
  • Elastonon

Stereoisomers

2 distinct stereoisomers are registered for this structure. This area's record is the racemate — the mixture, which is normally the form encountered.

Dextroamphetamine is roughly three to four times the CNS stimulant that levoamphetamine is; levoamphetamine has proportionally more peripheral cardiovascular action. Which one you meet depends entirely on the product: dexamfetamine preparations are the single d-enantiomer, while Adderall is a fixed mixture of both.

Attribution

  • Portrait of Lazăr Edeleanu
    Lazăr Edeleanu — first synthesis, 1887

    Published as phenylisopropylamine in 'Über einige Derivate der Phenylmethacrylsäure und der Phenylisobuttersäure', Ber. Dtsch. Chem. Ges. 20:616 (1887). Edeleanu reported no pharmacology; the stimulant effects were found only after Gordon Alles independently resynthesised it in 1929–30. He is not connected to methamphetamine (Nagai 1893, Ogata 1919).

    source

  • Gordon Alles — discovered its activity, 1929

    Alles did not invent amphetamine: Lazar Edeleanu synthesised it in 1887 and it sat unexamined for forty years. Alles re-prepared it as an ephedrine substitute and had 50 mg injected into himself on 3 June 1929, recording the nasal decongestion, palpitations and 'feeling of well being'. He patented the sulfate and hydrochloride salts (US 1,879,003, filed 2 September 1930, granted 27 September 1932) and assigned the rights to Smith, Kline & French in December 1934; SKF sold them as Benzedrine. Sources put the discovery variously at 1927, 1928 and 1929; the dated self-experiment is the firmest anchor.

    source

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