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| Other names | 14-Hydroxylysergic acid diethylamide; 14-OH-LSD; 14-HO-LSD; N,N-Diethyl-14-hydroxy-6-methyl-9,10-didehydroergoline-8β-carboxamide |
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| Chemical and physical data | |
| Formula | C20H25N3O2 |
| Molar mass | 339.439 g·mol−1 |
| 3D model (JSmol) | |
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14-Hydroxy-LSD is a lysergamide and a metabolite of the psychedelic drug lysergic acid diethylamide (LSD). [1] [2] [3] [4] [5] [6] It is formed via aromatic hydroxylation at position 14 of the lysergic acid moiety and is subsequently excreted as a glucuronide conjugate. [1] [2] [3] [6]
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14-Hydroxy-LSD is a major metabolite of LSD in rats and guinea pigs, where it is excreted predominantly as a glucuronide in bile and urine. [1] [2] [7] [5] [8] [9] [10] In contrast, it appears only as a minor metabolite in rhesus monkeys and humans. [1] [2] [7] [5] [8] [9] Studies using human liver microsomes and urine samples have confirmed its presence in humans, but in low concentrations that are often below quantification limits. [7] [3] [6]
The specific enzymes involved in the formation of hydroxylated LSD metabolites like 14-hydroxy-LSD remain unidentified. [5] As of 2016, David E. Nichols noted that the pharmacology of hydroxylated LSD metabolites, including 14-hydroxy-LSD, had not been studied. [11] Notably, 14-hydroxy-LSD does not induce LSD-like changes in the EEG of rabbits, in contrast to LSD and 13-hydroxy-LSD. [10]
14-Hydroxy-LSD was first reported in the scientific literature by at least 1975. [1] [12] [13] [14]