CE-LAD

Pharmaceutical compound From Wikipedia, the free encyclopedia

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]

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
FormulaC21H25ClN3O
Molar mass370.90 g·mol−1
Quick facts Clinical data, Other names ...
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
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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

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