LSD-Pip

LSD-Pip is a compound from the ergoline family, related to LSD but with the N,N-diethyl substitution replaced by a piperidine group. It is more potent than the corresponding pyrrolidine and morpholine analogues (LPD-824 and LSM-775 respectively), but is still several times less potent than LSD as a 5-HT2A agonist.[1] Early studies suggested this compound to be inactive as a psychedelic in humans,[2] though this does not seem to have been confirmed by any more recent work.

LSD-Pip
Identifiers
IUPAC name
  • (8β)-6-methyl-8-(piperidin-1-ylcarbonyl)-9,10-didehydroergoline
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H25N3O
Molar mass335.451 g·mol−1
3D model (JSmol)
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)

See also

References
  1. Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.
  2. Cerletti A, Doepfner W (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. 122 (1): 124–36. PMID 13502837.
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