LA-Pip

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LA-Pip
File:LSD-Pip.svg
File:LA-Pip 3D.png
Clinical data
Other namesLSD-Pip; N-Piperidinyllysergamide; N-Piperidine lysergamide; LA-Pip; LSDPip; LAPip; 6-Methyl-8β-(piperidin-1-ylcarbonyl)-9,10-didehydroergoline
Drug classSerotonin receptor modulator
Identifiers
  • [(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]-piperidin-1-ylmethanone
CAS Number
PubChem CID
ChemSpider
UNII
E number{{#property:P628}}
CompTox Dashboard (EPA)
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
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Chemical and physical data
FormulaC21H25N3O
Molar mass335.451 g·mol−1
3D model (JSmol)
  • CN1C[C@@H](C=C2[C@H]1Cc3c[nH]c4c3c2ccc4)C(=O)N5CCCCC5
  • InChI=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
  • Key:URDULHYODQAQTM-DNVCBOLYSA-N
  (verify)

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).[1][2][3] It is the analogue of LSD in which the N,N-diethyl substitution has been replaced with an N-piperidide ring.[2][3][4]

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 EC50Tooltip half-maximal effective concentration depending on the assay.[2][1][3][4] It also has high affinity for the serotonin 5-HT1A and 5-HT2C receptors.[1][3][4] 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.[5][6][7]

LA-Pip has been said to be non-hallucinogenic or much less psychedelic than LSD in humans.[1][8][9] However, this does not appear to have actually been stated anywhere in the originally cited source.[6] Other sources indicate that LA-Pip has not been assessed in humans.[10][5] Correspondingly, the dose range and potency of LA-Pip as a psychedelic relative to LSD have not been reported.[5][7]

LA-Pip was first described in the scientific literature by Albert Hofmann and colleagues by 1955.[11][6][12][13] There were additional publications on the compound in the later 1950s.[14][15][16] It has not been encountered as a designer drug as of 2020.[14]

See also

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References

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  14. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  15. ^ GB 785173, Smith G, "Amide-like derivatives of lysergic and isolysergic acids", published Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Burroughs Wellcome and Co 
  16. ^ US 2997470, Pioch RP, "Lysergic acid amides", issued Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Eli Lilly and Company 
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