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(CC)C([C@H]1CN(CCCl)[C@@]2(CC3=CNC4=CC=CC(C2=C1)=C34)[H])=O
  • 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).[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]

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-HT2A receptor that could help facilitate study of serotonin 5-HT2A 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 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-HT2A receptor as LSD.[3]

See also

References

  1. ^ a b c d e f g h Morris H (8 February 2021). "Ultra LSD". Hamilton's Pharmacopeia. Season 3. Episode 6. Vice Media. Event occurs at 19:41–22:17. Viceland. [Morris:] Once one of the only chemists licensed to produce LSD, Nichols is now retired but continues to synthesize psychedelics at UNC-Chapel Hill. His illustrious career spanning the synthesis of hundreds of novel compounds is now winding down, with one final creation—a nitrogen mustard derivative of nor-LSD he calls CE-LAD. [Morris:] Is there any compound you've wanted to synthesize but you just couldn't figure out a way to do it? [Nichols:] Well for a long time it was this one. [Morris:] Nichols's psychedelic nitrogen mustard would form an electrophilic aziridinium ion that he hopes would alkylate a mutant 5-HT2A receptor forming an irreversible bond that could facilitate study of the drug-receptor complex.
  2. ^ a b c d e f Bauer BE (9 February 2021). "Pharmacopeia Season Finale Recap". Psychedelic Science Review. Retrieved 10 April 2025. Morris also visited David Nichols at his lab at UNC-Chapel Hill, where he learned about his current research focus dubbed CELAD (Nichols also made the LSD that Roth used in his crystal structure work). The CELAD acronym stands for ChloroEthyl-Lysergic Acid Diethylamide and is described as a "nitrogen mustard derivative of nor-LSD." The chemical structure of CELAD. Image courtesy of Hamilton Morris. [...] In his quintessential Pharmacopeia manner, Morris relates how Nichols plans to apply CELAD to his psychedelic research. "Nichols' psychedelic nitrogen mustard would form an electrophilic aziridinium ion that he hopes would alkylate a mutant 5-HT2A receptor forming an irreversible bond that could facilitate study of the drug-receptor complex."
  3. ^ WO 2022/008627, Grill M, "Improved Method for the Production of Lysergic Acid Diethylamide (LSD) and Novel Derivatives thereof.", published 13 January 2022, assigned to Compass Pathfinder Limited 

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