1-Dimethylaminomethyl-LSD

1-Dimethylaminomethyl-LSD is a lysergamide derivative related to the psychedelic drug lysergic acid diethylamide (LSD).^[1]^[2]^[3]^[4]^[5] It was synthesized and described by Albert Hofmann and Franz Troxler at Sandoz in 1957.^[1]^[3]^[4]^[5] 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.^[1] 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.^[6]

Other names1-Dimethylaminomethyl-N,N-diethyllysergamide; 1-[(Dimethylamino)methyl]-N,N-diethyl-6-methyl-9,10-didehydroergoline-8β-carboxamide

ATC code

None

FormulaC₂₃H₃₂N₄O

Molar mass380.536 g·mol⁻¹

Quick facts Clinical data, Other names ...

1-Dimethylaminomethyl-LSD
Clinical data


Other names	1-Dimethylaminomethyl-N,N-diethyllysergamide; 1-[(Dimethylamino)methyl]-N,N-diethyl-6-methyl-9,10-didehydroergoline-8β-carboxamide
ATC code	None
Identifiers
IUPAC name (6aR,9R)-4-[(dimethylamino)methyl]-N,N-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
Chemical and physical data
Formula	C₂₃H₃₂N₄O
Molar mass	380.536 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)cn3CN(C)C)CC
InChI InChI=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 Key:NSFZERINUKJKQV-DYESRHJHSA-N

References

[1]
Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. 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."
[2]
Sankar DV (1975). LSD - A Total Study (PDF). Westbury, N.Y.: PJD Publications. pp. 130–131, 133. ISBN 978-0-9600290-3-7. LCCN 72-95447. 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 [...]
[3]
Hofmann A (June 1959). "Psychotomimetic drugs; chemical and pharmacological aspects". Acta Physiologica et Pharmacologica Neerlandica. 8: 240–258. PMID 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
[4]
Rutschmann J, Stadler PA (1978). "Chemical Background". In Berde B, Schild HO (eds.). Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology (HEP). Vol. 49. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 29–85. doi:10.1007/978-3-642-66775-6_2. ISBN 978-3-642-66777-0. 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).
[5]
Troxler F, Hofmann A (1957). "Substitutionen am Ringsystem der Lysergsäure I. Substitutionen am Indol-Stickstoff. 43. Mitteilung über Mutterkornalkaloide" [Substitutions on the Ring System of Lysergic Acid. I. Substitutions in the Indole Nitrogen. (43. Communication on Ergot Alkaloids)]. Helvetica Chimica Acta. 40 (6): 1706–1720. Bibcode:1957HChAc..40.1706T. doi:10.1002/hlca.19570400619. ISSN 0018-019X. Archived from the original on 11 July 2025.
[6]
Cerletti A, Doepfner W (January 1958). "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. doi:10.1016/S0022-3565(25)11933-2. PMID 13502837. Archived from the original on 25 March 2025. 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.

1-Dimethylaminomethyl-LSD

See also

References

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