CE-LAD

CE-LAD
Clinical data
Other names6-(2-Chloroethyl)-6-nor-lysergic acid diethylamide; 6-(2-Chloroethyl)-6-nor-LSD; 6-(2-Chloroethyl)-LAD; CELAD; Cl-ETH-LAD; CHLORETH-LAD; CHLORETHLAD; 9,10-Didehydro-N,N-diethyl-6-(2-chloroethyl)-ergoline-8β-carboxamide
Drug classPossible alkylating or irreversible serotonin 5-HT2A receptor ligand
Identifiers
  • (6aR,9R)-N,N-diethyl-7-(2-chloroethyl)-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
Chemical and physical data
FormulaC21H25ClN3O
Molar mass370.90 g·mol−1
3D model (JSmol)
  • CCN(C([C@H]1CN([C@]2([H])CC3=CN([H])C4=CC=CC(C2=C1)=C34)CCCl)=O)CC
  • InChI=1S/C21H26ClN3O/c1-3-24(4-2)21(26)15-10-17-16-6-5-7-18-20(16)14(12-23-18)11-19(17)25(13-15)9-8-22/h5-7,10,12,15,19,23H,3-4,8-9,11,13H2,1-2H3/t15-,19-/m1/s1
  • Key:MRUUQMMGHGQGEK-DNVCBOLYSA-N

CE-LAD, or CHLORETH-LAD, also known as 6-(2-chloroethyl)-LAD or 6-(2-chloroethyl)-6-nor-LSD, is a compound of the lysergamide family related to the serotonergic psychedelic lysergic acid diethylamide (LSD). It was developed by psychedelic chemist David E. Nichols at UNC-Chapel Hill (formerly Purdue University) for potential use in scientific research.

The compound is an analogue of LSD and ETH-LAD (6-ethyl-6-nor-LSD) in which the 6-position N-alkyl chain has been replaced with a nitrogen mustard 2-chloroethyl group. Nichols developed CE-LAD in hopes that it would be an alkylating irreversible ligand of a mutant serotonin 5-HT2A receptor that could help facilitate study of serotonin 5-HT2A protein–ligand complexes.

CE-LAD was said by journalist Hamilton Morris to have been one of Nichols's final creations prior to his full retirement. It was described by Morris in 2021 in the final episode of his TV show Hamilton's Pharmacopeia. Nichols related that the compound had previously proved to be synthetically inaccessible for many years. Although Nichols appears to have successfully synthesized CE-LAD, the results of the work with the compound do not appear to have been published or reported.

In 2022, a closely related drug, FLUORETH-LAD (FE-LAD), was synthesized and found to have similarly high affinity for the serotonin 5-HT2A receptor as LSD.