LA-Pip

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]

LA-Pip

Clinical data
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
Identifiers
IUPAC name [(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]-piperidin-1-ylmethanone
CAS Number	50485-23-9 Y
PubChem CID	308707
ChemSpider	35303396
UNII	CKN3AJ58H9
CompTox Dashboard (EPA)	DTXSID20308999
Chemical and physical data
Formula	C21H25N3O
Molar mass	335.451 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1C[C@@H](C=C2[C@H]1Cc3c[nH]c4c3c2ccc4)C(=O)N5CCCCC5
InChI 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)

The drug has fairly similar affinity and efficacy as a serotonin 5-HT_2A 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-HT_1A and 5-HT_2C 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

• Substituted lysergamide
• Lysergic acid pyrrolidide (LPD-824)
• Lysergic acid morpholide (LSM-775)
• Lysergic acid 2-butyl amide (LSB)
• Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ)
• 25B-NAcPip