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12-Methoxy-LSD
Pharmaceutical compound From Wikipedia, the free encyclopedia
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12-Methoxy-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-methoxy-LSD is to LSD as 5-MeO-DMT is to dimethyltryptamine (DMT), with 12-methoxy-LSD notably containing 5-MeO-DMT within its rigidified structure.[5] Both 12-methoxy-LSD and its analogue 12-hydroxy-LSD have been described as non-hallucinogenic in humans.[1][2][3][6] However, in other more recent reports, 12-hydroxy-LSD produced psychedelic-like effects in rodents[7] and was said to have similar activity as LSD in humans.[8]
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Pharmacology
It has been reported that 12-methoxy-LSD does not produce hallucinogenic effects in humans.[1][2][3][6] However, it is nonetheless pharmacologically active in animal studies.[1] The drug's effects in rabbits include antiserotonergic activity (20% of that of LSD) and hyperthermia (dose ratio relative to LD50 of 1:17 for 12-methoxy-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 0.1 mg/kg i.v. in rabbits (relative to 0.1 mg/kg for LSD).[1][3][4] 12-Methoxy-LSD also produces LSD-like electroencephalogram (EEG) changes in rabbits.[9]
Presumably 12-methoxy-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][3]
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Chemistry
Synthesis
The chemical synthesis of 12-substituted lysergamides is described as being very difficult.[7]
Analogues
An analogue of 12-methoxy-LSD is 12-hydroxy-LSD, which would be structurally akin to bufotenin (5-HO-DMT).[1][3][8] As with 12-methoxy-LSD, it has been reported that 12-hydroxy-LSD is inactive as a psychedelic in humans.[1] Contrary to this report however, Michael Valentine Smith claimed in his 1981 book Psychedelic Chemistry that 12-hydroxy-LSD has "about the same activity as LSD".[8] In addition, 12-hydroxy-LSD has been found to substitute for LSD in rodent drug discrimination tests with about 20% of its potency.[7]
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History
12-Methoxy-LSD was first described in the scientific literature by 1967.[1] Subsequently, it was further described in the 1970s and 1980s.[3][4][6][9][8][2]
See also
References
External links
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