l-LSD
| File:(-)-LSD.svg | |
| File:L-LSD 3D.png | |
| Clinical data | |
|---|---|
| Other names | (–)-LSD; (5S,8S)-LSD; levo-LSD; l-Lysergic acid diethylamide; l-Lysergide; N,N-Diethyl-6-methyl-9,10-didehydro-5α-ergoline-8α-carboxamide |
| ATC code |
|
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| E number | {{#property:P628}} |
| CompTox Dashboard (EPA) |
|
| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C20H25N3O |
| Molar mass | 323.440 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
-LSD.svg){kind=link}
l-LSD, also known as (–)-LSD or (5S,8S)-LSD, as well as l-lysergic acid diethylamide or l-lysergide, is a lysergamide and one of four possible stereoisomers of the lysergic acid diethylamide (LSD) molecule (with the psychedelic drug actually being the enantiopure d-isomer).[1][2]
The LSD molecule has two chiral centers at carbons 5 and 8 of the ergoline ring system and hence there are four possible enantiomeric stereoisomers of LSD.[2][3] l-LSD, also known as (–)-LSD or (5S,8S)-LSD, is one of four possible stereoisomers.[2][3] The other isomers are LSD (d-LSD, (+)-LSD, or (5R,8R)-LSD), iso-LSD (d-iso-LSD, (+)-iso-LSD, or (5R-8S)-LSD), and l-iso-LSD ((–)-iso-LSD or (5S,8R)-iso-LSD).[2][3] None of them are known to have significant psychoactivity in humans besides LSD.[2][3][4]
l-LSD showed only 0.06% of the antiserotonergic activity of LSD in the isolated rat uterus.[5] Hence, it was more than 1,000-fold less potent than LSD in this assay and was regarded as essentially inactive.[5] In subsequent receptor binding studies, l-LSD showed 2,000- to 10,000-fold lower affinity for serotonin receptors than LSD.[6][7]
l-LSD showed no psychedelic effects in humans at a dose of up to 10 mg orally or up to 400 times the minimum effective dose of LSD (~25 μg).[8][9][10][11][4][1] However, Albert Hofmann reported that although l-LSD produced no LSD-like effects, it caused "very slight drowsiness" at doses above 500 μg.[4]
l-LSD was first described in the scientific literature by at least the 1950s.[5][10][4]
See also
[edit | edit source]References
[edit | edit source]- ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b c d e Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b c d Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b c d Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b c Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).