12-Hydroxy-LSD
Pharmaceutical compound From Wikipedia, the free encyclopedia
12-Hydroxy-LSD is a drug of the ergoline and lysergamide families and a derivative of lysergic acid diethylamide (LSD).[1][2][3][4] In terms of chemical structure, 12-hydroxy-LSD is to LSD as bufotenin (5-HO-DMT) is to dimethyltryptamine (DMT), with 12-hydroxy-LSD notably containing bufotenin within its rigidified structure.[5] 12-Hydroxy-LSD produces psychedelic-like effects in animals,[6] whereas reports on its activities in humans are very limited and have been conflicting.[1][4][2][7][3]
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| Other names | 12-Hydroxylysergic acid diethylamide; 12-OH-LSD; 12-HO-LSD; "5-OH-LSD"; "5-HO-LSD"; "5-Hydroxy-LSD"; 9,10-Didehydro-N,N-diethyl-6-methyl-12-hydroxyergoline-8β-carboxamide |
| Drug class | Serotonin receptor modulator |
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| Formula | C20H25N3O2 |
| Molar mass | 339.439 g·mol−1 |
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Pharmacology
Summarize
Perspective
12-Hydroxy-LSD is known to be pharmacologically active in animal studies.[1] The drug's effects in rabbits include antiserotonergic activity (25% of that of LSD) and hyperthermia (dose ratio relative to LD50 of 1:44 for 12-hydroxy-LSD and 1:725 for LSD).[1] In addition, like LSD, it is highly potent in terms of lethality, with a median lethal dose (LD50) of 0.3 mg/kg i.v. in rabbits (relative to 0.1 mg/kg for LSD).[1][2] 12-Hydroxy-LSD also produces LSD-like electroencephalogram (EEG) changes in rabbits.[8]
According to Robert C. Pfaff and David E. Nichols and colleagues, 12-hydroxy-LSD substitutes for LSD in rodent drug discrimination tests.[6] Hence, it appears to show psychedelic-like effects in animals.[6] However, 12-hydroxy-LSD was described as having unremarkable properties in this assay and only having about 20% of the potency of LSD.[6] It was reported in the 1960s that 12-hydroxy-LSD does not produce hallucinogenic effects in humans.[1][4][2][7] On the other hand however, Michael Valentine Smith claimed in his 1981 book Psychedelic Chemistry that 12-hydroxy-LSD has "about the same activity as LSD".[3]
Presumably 12-hydroxy-LSD acts as an agonist of serotonin and dopamine receptors, as with LSD and other related lysergamides, but its pharmacology has not been studied with modern techniques.[1][2]
Chemistry
Synthesis
The chemical synthesis of 12-hydroxy-LSD is described as being very difficult.[6]
Analogues
An analogue of 12-hydroxy-LSD is 12-methoxy-LSD, which would be structurally akin to 5-MeO-DMT.[1][2][3] As with 12-hydroxy-LSD, it has been reported that 12-methoxy-LSD is inactive as a psychedelic in humans.[1]
History
12-Hydroxy-LSD was first described in the scientific literature by 1962.[9][10][11][1] Subsequently, it was further described in the 1970s and 1980s.[2][7][8][3][4] David E. Nichols and colleagues reported that 12-hydroxy-LSD produces psychedelic-like effects in animals in 1994.[6] It was initially thought that 12-hydroxy-LSD might be a metabolite of LSD,[9][12] but this proved not to be the case.[11][13][14]
See also
- 12-Methoxy-LSD
- 2-Bromo-LSD
- Bufotenin (5-HO-DMT)
References
External links
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