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14-Methoxy-LSD

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Pharmaceutical compound
14-Methoxy-LSD
Clinical data
Other names14-Methoxylysergic acid diethylamide; 14-OMe-LSD; 14-MeO-LSD;N,N-Diethyl-14-methoxy-6-methyl-9,10-didehydroergoline-8β-carboxamide
ATC code
  • None
Identifiers
  • N,N-diethyl-2-methoxy-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
Chemical and physical data
FormulaC21H27N3O2
Molar mass353.466 g·mol−1
3D model (JSmol)
  • O=C([C@@]1C=C2C3C=CC(OC)=C4C=3C(=CN4[H])C[C@@]2([H])N(C)C1)N(CC)CC
  • InChI=1S/C21H26N3O2/c1-5-24(6-2)21(25)14-9-16-15-7-8-18(26-4)20-19(15)13(11-22-20)10-17(16)23(3)12-14/h7-9,11,17,22H,5-6,10,12H2,1-4H3/t17-/m1/s1
  • Key:RLYRADCNGTXJDX-QGZVFWFLSA-N

14-Methoxy-LSD is alysergamide related tolysergic acid diethylamide (LSD).[1] It is thederivative of LSD with amethoxy group at the 14 position and is theO-methylether of14-hydroxy-LSD.[1] Unlike13-hydroxy-LSD and13-methoxy-LSD and other related compounds like12-hydroxy-LSD and12-methoxy-LSD, 14-hydroxy-LSD and 14-methoxy-LSD did not produce LSD-likeelectroencephalogram (EEG) changes in rabbits.[1] 14-Methoxy-LSD was first described in thescientific literature by 1979.[1]

See also

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References

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  1. ^abcdSiddik ZH, Barnes RD, Dring LG, Smith RL, Williams RT (October 1979). "The fate of lysergic acid DI[14C]ethylamide ([14C]LSD) in the rat, guinea pig and rhesus monkey and of [14C]iso-LSD in rat".Biochemical Pharmacology.28 (20):3093–3101.doi:10.1016/0006-2952(79)90618-x.PMID 117811.EEG studies. Synthetic and biosynthetic metabolites of LSD were injected intravenously into conscious restrained male chinchilla rabbits. With LSD itself, de-ethyl-LSD, 12-hydroxy-LSD, 12-methoxy-LSD, 13-hydroxy-LSD, 13-methoxy-LSD and 13-hydroxy-LSD glucuronide, a persistent alerting EEG trace was seen as indicated by an increase in frequency and decrease in amplitude of the waveform. No changes were observed after administration of lysergic acid, di-LSD-disulphide [10], nor-LSD, 14-hydroxy-LSD-glucuronide, 14-methoxy-LSD, lumi-LSD or the metabolic 2-oxo-LSD. [...] Preliminary studies have indicated that some of the metabolites of LSD, as well as the drug itself. produce an activation of the EEG of the conscious rabbit suggesting they may have central activity. These findings will be published elsewhere.
Ergolines
(incl.lysergines)
Clavines
(6,8-dimethylergolines)
Lysergamides
(lysergic acid amides)
Ergopeptines
(peptide ergolines)
Partial ergolines
Related compounds
Natural sources
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