1-Dimethylaminomethyl-LSD

vanc 6 1-Dimethylaminomethyl-LSD.svg skin-invert-image 150px 1-Dimethylaminomethyl-LSD 3D.png bg-transparent 225px None 1-Dimethylaminomethyl-N,N-diethyllysergamide; 1-[(Dimethylamino)methyl]-N,N-diethyl-6-methyl-9,10-didehydroergoline-8β-carboxamide (6aR,9R)-4-[(dimethylamino)methyl]-N,N-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide 23 32 4 1 CCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)cn3CN(C)C)CC 1S/C23H32N4O/c1-6-26(7-2)23(28)17-11-19-18-9-8-10-20-22(18)16(12-21(19)25(5)13-17)14-27(20)15-24(3)4/h8-11,14,17,21H,6-7,12-13,15H2,1-5H3/t17-,21-/m1/s1 NSFZERINUKJKQV-DYESRHJHSA-N 1-Dimethylaminomethyl-LSD is a lysergamide derivative related to the psychedelic drug lysergic acid diethylamide (LSD). https://erowid.org/library/books_online/tihkal/tihkal26.shtml "1-Hydroxymethyl-LSD, 1-dimethylaminomethyl-LSD and 2-iodo-LSD. These three additional compounds are shown here because they were described in a synthetic flurry that followed the discovery the activity of LSD. But at the moment I know neither their internal Sandoz codes nor if they had ever been explored in man. This is a kind of frustrating catch-all entry, in that the long index will send you here, and once here you realize that nothing is known. Well, at least the compounds are known, and perhaps there is something in the Sandoz vaults that might be interesting. I do not have access to them." Sankar DV LSD - A Total Study Westbury, N.Y. 130–131, 133 1975 72-95447 978-0-9600290-3-7 PJD Publications https://www.samorini.it/doc1/alt_aut/sz/sankar-lsd-a-total-study.pdf The hydrogen atom in position 1 of LSD was substituted by the following radicals: acetyl, methyl, hydroxymethyl and dimethylaminomethyl (24,25). [...] 1-Dimethylaminomethyl-d-lysergic acid diethylamide was formed by Mannich-reaction, when a solution of LSD (free base) in glacial acetic acid was added with diethylamine followed by formaldehyde. [...] 1-Dimethylaminomethyl-LSD is resistant to hydrolysis in diluted alkaline or acid solutions at room temperature, but is hydrolyzed when these solutions are heated. [...] TABLE III: Derivatives of LSD with Substitution at Position 1 [...] 1-dimethylaminomethyl-d-lysergic acid diethylamide [...] Hofmann A Psychotomimetic drugs; chemical and pharmacological aspects Acta Physiologica et Pharmacologica Neerlandica 8 240–258 June 1959 13852489 Table II summarizes the substitutions which have been made in the ring system of LSD (TROXLER and HOFMANN, 1957). [...] TABLE II: Substitutions in the ring system: [...] R1 = CH2N(CH3)2. R2 = H. Dimethylaminomethyl-LSD Rutschmann J, Stadler PA Berde B, Schild HO Chemical Background Ergot Alkaloids and Related Compounds 49 29–85 1978 10.1007/978-3-642-66775-6_2 Handbook of Experimental Pharmacology (HEP) Springer Berlin Heidelberg Berlin, Heidelberg 978-3-642-66777-0 https://books.google.com/books?id=2JXzCAAAQBAJ Reaction of formaldehyde with lysergic acid esters or amides easily yielded the corresponding I-hydroxymethyl derivatives of general formula (36c). It was, therefore, no surprise that a reaction of the Mannich type with formaldehyde and dimethylamine led to I-dimethylaminomethyl lysergic acid derivatives, (36d). Michael addition of acrylonitrile gave rise to I-cyanoethyl derivatives, formula (36e). All these compounds proved to be moderately stable against acids and bases. (TROXLER and HOFMANN, 1957b). [...] F. Subject Index: [...] Names: 1-Dimethylaminomethyl-Iysergic acid derivatives (general formula). Fig.: 13. Nr.: (36d). Troxler F, Hofmann A Substitutionen am Ringsystem der Lysergsäure I. Substitutionen am Indol-Stickstoff. 43. Mitteilung über Mutterkornalkaloide Helvetica Chimica Acta 40 6 1706–1720 1957 10.1002/hlca.19570400619 Substitutions on the Ring System of Lysergic Acid. I. Substitutions in the Indole Nitrogen. (43. Communication on Ergot Alkaloids) 0018-019X 1957HChAc..40.1706T https://bibliography.maps.org/resources/download/15476 https://web.archive.org/web/20250711074909/https://bibliography.maps.org/resources/download/15476 11 July 2025 It was synthesized and described by Albert Hofmann and Franz Troxler at Sandoz in 1957. According to Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved), 1-dimethylaminomethyl-LSD has been limitedly described, and it is unknown whether it was ever tested in humans. The 2-dimethylaminomethyl-LSD positional isomer has also been described, and was found to have 18.5% of the antiserotonergic activity of LSD in vitro. Cerletti A, Doepfner W Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids The Journal of Pharmacology and Experimental Therapeutics 122 1 124–136 January 1958 13502837 10.1016/S0022-3565(25)11933-2 https://bibliography.maps.org/resources/download/19096 TABLE 2: Antiserotonin potency of ring-substituted derivatives of LSD: [...] Substitution: [...] Name: 2-dimethylaminomethyl-LSD. Relative activity ± s.e.* (LSD = 100): 18.5 ± 1.8. https://web.archive.org/web/20250325115812/https://bibliography.maps.org/resources/download/19096 25 March 2025 See also Substituted lysergamide OML-632 (1-hydroxymethyl-LSD) MLD-41 (1-methyl-LSD) ALD-52 (1-acetyl-LSD) References External links 1-Dimethylaminomethyl-LSD - Isomer Design LSD-25 (Discusses 1-Dimethylaminomethyl-LSD) - TiHKAL - Erowid LSD-25 (Discusses 1-Dimethylaminomethyl-LSD) - TiHKAL - Isomer Design Category:Diethylamides Category:Dimethylamino compounds Category:Methyl compounds Category:Lysergamides