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14-Methoxy-LSD
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14-Methoxy-LSD 2D.svg skin-invert-image 175px None 14-Methoxylysergic acid diethylamide; 14-OMe-LSD; 14-MeO-LSD; N,N-Diethyl-14-methoxy-6-methyl-9,10-didehydroergoline-8β-carboxamide N,N-diethyl-2-methoxy-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide 21 27 3 2 O=C([C@@]1C=C2C3C=CC(OC)=C4C=3C(=CN4[H])C[C@@]2([H])N(C)C1)N(CC)CC 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 RLYRADCNGTXJDX-QGZVFWFLSA-N
14-Methoxy-LSD is a lysergamide related to lysergic acid diethylamide (LSD). Siddik ZH, Barnes RD, Dring LG, Smith RL, Williams RT 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 October 1979 117811 10.1016/0006-2952(79)90618-x 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. It is the derivative of LSD with a methoxy group at the 14 position and is the O-methyl ether of 14-hydroxy-LSD. Unlike 13-hydroxy-LSD and 13-methoxy-LSD and other related compounds like 12-hydroxy-LSD and 12-methoxy-LSD, 14-hydroxy-LSD and 14-methoxy-LSD did not produce LSD-like electroencephalogram (EEG) changes in rabbits. 14-Methoxy-LSD was first described in the scientific literature by 1979.
See also
Substituted lysergamide
14-Hydroxy-LSD
14-Methyl-LSD
13-Methoxy-LSD
12-Methoxy-LSD
LA-MeO
7-MeO-DMT
References
Category:Diethylamides
Category:Lysergamides
Category:Methoxy compounds