CH₃CH₃

LSD

Chemistry

49 atoms · Conformer computed and published by PubChem.
Formula
C20H25N3O
Molar mass
323.4 g/mol
IUPAC name
(6aR,9R)-N,N-diethyl-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
InChIKey
VAYOSLLFUXYJDT-RDTXWAMCSA-N

Chemistry from PubChem CID 5761.

Also known as

  • Lysergide
  • LYSERGIC ACID DIETHYLAMIDE
  • D-Lsd
  • N,N-Diethyllysergamide
  • 50-37-3
  • Lysergsaeurediaethylamid
  • N,N-Diethyl-D-lysergamide
  • Lysergaure diethylamid

Stereoisomers

4 distinct stereoisomers are registered for this structure.

  • d-LSD (5R,8R) this area CID 5761

    The psychoactive one. "LSD" means this isomer.

  • iso-LSD (5R,8S) CID 638252

    Inactive. LSD interconverts with it, so it appears as a synthesis and storage impurity.

  • l-LSD (5S,8S) CID 6098175

    Inactive.

  • l-iso-LSD (5S,8R) CID 56841613

    Inactive.

  • D-lysergic acid diethylamide (unspecified) mixture CID 3981

    A PubChem record with the stereochemistry left undefined rather than a distinct substance.

Stereocentres at C5 and C8 give LSD four stereoisomers, and only one of them does anything: d-LSD, the (5R,8R) form, which is what "LSD" means. iso-LSD (5R,8S) is inactive but worth knowing about, because LSD interconverts with it and it turns up as a synthesis and degradation impurity. l-LSD and l-iso-LSD are laboratory curiosities.

Attribution

  • Portrait of Albert Hofmann
    Albert Hofmann — first synthesis, 1938

    Synthesised 16 November 1938 as the 25th compound in his lysergic acid amide series (hence LSD-25), intended as a circulatory/respiratory stimulant analogous to nikethamide. No psychoactivity was noticed in animal screening and it was shelved for five years. First described in print in Stoll & Hofmann, Helv. Chim. Acta 26, 944-965 (1943).

    source

  • Portrait of Albert Hofmann
    Albert Hofmann — discovered its activity, 1943

    On 16 April 1943 he re-made LSD-25, absorbed a trace accidentally and recorded the effects; on 19 April 1943 he deliberately took 250 micrograms, which he expected to be a threshold dose. That deliberate dose, and the bicycle ride home, is the origin of 'Bicycle Day'.

    source

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