Stereoselective pharmacological effects of lysergic acid amides possessing chirality in the amide substituent.
D E Nichols, A Monte, X Huang, Danuta Marona‐lewicka
Behavioural Brain Research 1996 DOI: 10.1016/0166-4328(96)00080-0 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Peer reviewed |
|---|---|
| Population | Rats trained to discriminate LSD from saline (in vivo assays); receptor binding assays |
| Interventions | Lysergic acid amides prepared from chiral 2-aminoalkanes LSD |
| Key points | Amides with R-configuration alkyl groups showed stereoselective binding preference at both 5-HT2A and 5-HT1A receptors, and were most potent in rats trained to discriminate LSD from saline. The 5-HT2A receptor tolerated long alkyl groups less well than the 5-HT1A subtype. |
Abstract
Studies of the affinities for serotonin 5-HT2A and 5-HT1A receptor subtypes of lysergic acid amides prepared from chiral 2-aminoalkanes showed a stereoselective preference at both receptor types for the amides with alkyl groups containing the R configuration. The 5-HT2A receptor was less tolerant of long alkyl groups than was the 5-HT1A subtype. In vivo assays in rats trained to discriminate LSD from saline also showed that amides with alkyl groups having the R configuration were most potent.
Citations in the library
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- Return of the lysergamides. Part I: Analytical and behavioural characterization of 1‐propionyl‐d‐lysergic acid diethylamide (1P‐LSD) Drug Testing and Analysis October 12, 2015
- Structural pharmacology and therapeutic potential of 5-methoxytryptamines. Nature June 1, 2024
- Return of the lysergamides. Part II: Analytical and behavioural characterization of N6-allyl-6-norlysergic acid diethylamide (AL-LAD) and (2’S,4’S)-lysergic acid 2,4-dimethylazetidide (LSZ) Drug Testing and Analysis June 6, 2016
and 2 more in the library
Cites 3
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- Stereoselective LSD-like activity in d-lysergic acid amides of R- and S-2-aminobutane Journal of Medicinal Chemistry 1992
- LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors. Psychopharmacology April 1995