12-Methoxy-LSD

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12-Methoxy-LSD
Clinical data
Other names12-MeO-LSD; "5-MeO-LSD"; "5-Methoxy-LSD"; 9,10-Didehydro-N,N-diethyl-6-methyl-12-methoxyergoline-8β-carboxamide
Drug classSerotonin receptor modulator
Identifiers
  • (6aR,9R)-N,N-diethyl-1-methoxy-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
ChemSpider
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC21H27N3O2
Molar mass353.466 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=C3C(=C(C=C4)OC)C2=C1)C
  • InChI=1S/C21H27N3O2/c1-5-24(6-2)21(25)14-9-15-17(23(3)12-14)10-13-11-22-16-7-8-18(26-4)20(15)19(13)16/h7-9,11,14,17,22H,5-6,10,12H2,1-4H3/t14-,17-/m1/s1
  • Key:AYFDTTGGASATFS-RHSMWYFYSA-N

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 conformationally constrained 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]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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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 LD50Tooltip median lethal dose 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.Tooltip intravenous administration 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]

Chemistry

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Synthesis

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The chemical synthesis of 12-substituted lysergamides is described as being very difficult.[7]

Analogues

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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]

History

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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

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References

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