CE-LAD

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).^[1][2] It was developed by psychedelic chemist David E. Nichols at UNC-Chapel Hill (formerly Purdue University) for potential use in scientific research.^[1][2]

CE-LAD

Clinical data
Other names	6-(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 class	Possible alkylating or irreversible serotonin 5-HT2A receptor ligand
Identifiers
IUPAC name (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
Formula	C21H25ClN3O
Molar mass	370.90 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCN(C([C@H]1CN([C@]2([H])CC3=CN([H])C4=CC=CC(C2=C1)=C34)CCCl)=O)CC
InChI 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

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.^[1][2] Nichols developed CE-LAD in hopes that it would be an alkylating irreversible ligand of a mutant serotonin 5-HT_2A receptor that could help facilitate study of serotonin 5-HT_2A protein–ligand complexes.^[1][2]

CE-LAD was said by journalist Hamilton Morris to have been one of Nichols's final creations prior to his full retirement.^[1] It was described by Morris in 2021 in the final episode of his TV show Hamilton's Pharmacopeia.^[1][2] Nichols related that the compound had previously proved to be synthetically inaccessible for many years.^[1] 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.^[1][2]

In 2022, a closely related drug, FLUORETH-LAD (FE-LAD), was synthesized and found to have similarly high affinity for the serotonin 5-HT_2A receptor as LSD.^[3]

See also

• Substituted lysergamide
• FLUORETH-LAD
• FP-LAD
• LA-3Cl-SB