 | |
 | |
| Clinical data | |
|---|---|
| Other names | 1-Dimethylaminomethyl-N,N-diethyllysergamide; 1-[(Dimethylamino)methyl]-N,N-diethyl-6-methyl-9,10-didehydroergoline-8β-carboxamide |
| ATC code |
|
| Identifiers | |
| |
| Chemical and physical data | |
| Formula | C23H32N4O |
| Molar mass | 380.536 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
1-Dimethylaminomethyl-LSD is alysergamidederivative related to thepsychedelic druglysergic acid diethylamide (LSD).[1][2][3][4][5] It wassynthesized and described byAlbert Hofmann and Franz Troxler atSandoz in 1957.[1][3][4][5] According toAlexander Shulgin in his 1997 bookTiHKAL (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-LSDpositional isomer has also been described, and was found to have 18.5% of theantiserotonergic activity of LSDin vitro.[6]
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 [...]
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
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).
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.
 | Thishallucinogen-related article is astub. You can help Wikipedia byadding missing information. |