LA-Pip
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| Other names | LSD-Pip; N-Piperidinyllysergamide; N-Piperidine lysergamide; LA-Pip; LSDPip; LAPip; 6-Methyl-8β-(piperidin-1-ylcarbonyl)-9,10-didehydroergoline |
| Drug class | Serotonin receptor modulator |
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| Formula | C21H25N3O |
| Molar mass | 335.451 g·mol−1 |
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Lysergic acid piperidide (LA-Pip or LSD-Pip), also known as N-piperidinyllysergamide, is a serotonin receptor modulator of the lysergamide family related to lysergic acid diethylamide (LSD). It is the analogue of LSD in which the N,N-diethyl substitution has been replaced with an N-piperidide ring.
The drug has fairly similar affinity and efficacy as a serotonin 5-HT2A receptor agonist compared to LSD, though is variably less potent in terms of EC50 depending on the assay. It also has high affinity for the serotonin 5-HT1A and 5-HT2C receptors. LA-Pip has about 8.5% of the antiserotonergic activity of LSD (relative to 2.0% for LSM-775 and 4.7% for LPD-824) in the isolated rat uterus in vitro.
LA-Pip has been said to be non-hallucinogenic or much less psychedelic than LSD in humans. However, this does not appear to have actually been stated anywhere in the originally cited source. Other sources imply that LA-Pip has not been assessed in humans. Correspondingly, the dose range and potency of LA-Pip as a psychedelic relative to LSD have not been reported.
LA-Pip was first described in the scientific literature by Albert Hofmann and colleagues by 1955. There were additional publications on the compound in the later 1950s. It has not been encountered as a designer drug as of 2020.