LA-Pip

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Compound related to LSD

title: "LA-Pip" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["5-ht2a-agonists", "carboxamides", "lysergamides", "1-piperidinyl-compounds", "serotonin-receptor-agonists"] description: "Compound related to LSD" topic_path: "general/5-ht2a-agonists" source: "https://en.wikipedia.org/wiki/LA-Pip" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Compound related to LSD ::

| verifiedrevid = 451555059 | image = LSD-Pip.svg | image_class = skin-invert-image | width = 175px | image2 = LA-Pip 3D.png | image_class2 = bg-transparent | width2 = 200px

| tradename = | routes_of_administration = | class = Serotonin receptor modulator

| CAS_number_Ref = | CAS_number = 50485-23-9 | UNII_Ref = | UNII = CKN3AJ58H9 | PubChem = 308707 | ChemSpiderID = 35303396 | DrugBank_Ref = | synonyms = LSD-Pip; N-Piperidinyllysergamide; N-Piperidine lysergamide; LA-Pip; LSDPip; LAPip; 6-Methyl-8β-(piperidin-1-ylcarbonyl)-9,10-didehydroergoline

| IUPAC_name = [(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]-piperidin-1-ylmethanone | C=21 | H=25 | N=3 | O=1 | SMILES = CN1CC@@HC(=O)N5CCCCC5 | StdInChI = 1S/C21H25N3O/c1-23-13-15(21(25)24-8-3-2-4-9-24)10-17-16-6-5-7-18-20(16)14(12-22-18)11-19(17)23/h5-7,10,12,15,19,22H,2-4,8-9,11,13H2,1H3/t15-,19-/m1/s1 | StdInChIKey = URDULHYODQAQTM-DNVCBOLYSA-N

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 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 indicate 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. The drug is not a controlled substance in Canada as of 2025.

References

References

  1. (30 October 2007). "Toward a molecular understanding of hallucinogen action".
  2. (2007). "Towards a biophysical understanding of hallucinogen action". Purdue University.
  3. (2018). "Chemistry and Structure-Activity Relationships of Psychedelics".
  4. (2012). "Structure–activity relationships of serotonin 5-HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling.
  5. (January 1958). "Comparative Study on the Serotonin Antagonism of Amide Derivatives of Lysergic Acid and of Ergot Alkaloids". The Journal of Pharmacology and Experimental Therapeutics.
  6. (1 December 1983). "QSAR studies on hallucinogens". Chemical Reviews.
  7. (2001). "LSD and Its Lysergamide Cousins". [[Heffter Research Institute]].
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  9. (1991). "Biochemistry and Physiology of Substance Abuse". CRC Press.
  10. (May 1989). "Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens". Purdue University.
  11. (1955). "Amide der stereoisomeren Lysergsäuren und Dihydro-lysergsäuren. 38. Mitteilung über Mutterkornalkaloide". Helvetica Chimica Acta.
  12. (1958). "Chemical Concepts of Psychosis: Proceedings of the Symposium on Chemical Concepts of Psychosis held at the Second International Congress of Psychiatry in Zurich, Switzerland, September 1 to 7, 1957". McDowell, Obolensky.
  13. (June 1959). "Psychotomimetic drugs; chemical and pharmacological aspects". Acta Physiologica et Pharmacologica Neerlandica.
  14. "Amide-like derivatives of lysergic and isolysergic acids".
  15. "Lysergic acid amides".
  16. (October 2020). "Analytical profile of N-ethyl-N-cyclopropyl lysergamide (ECPLA), an isomer of lysergic acid 2,4-dimethylazetidide (LSZ)". Drug Testing and Analysis.
  17. "Controlled Drugs and Substances Act".

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5-ht2a-agonistscarboxamideslysergamides1-piperidinyl-compoundsserotonin-receptor-agonists