LSD
Chemistry
- 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
- Albert Hofmann — first synthesis, 1938
- Albert Hofmann — discovered its activity, 1943
Discovered by accidental absorption, then confirmed deliberately on 19 April 1943.
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