35779-43-2

Usage

Uses

Used in Pharmaceutical Industry:
6-NORLYSERGIC ACID DIETHYLAMIDE is used as a research chemical for the development of new treatments for mental health conditions such as depression and anxiety. Its psychoactive effects are milder than those of LSD, making it a potential candidate for therapeutic applications.
Used in Neuroscientific Research:
6-NORLYSERGIC ACID DIETHYLAMIDE is used as a research tool in neuroscientific studies to investigate the role of the 5-HT2A receptor in various mental health conditions and to understand the mechanisms of action of psychedelic substances.
Used in Controlled Substances Regulation:
6-NORLYSERGIC ACID DIETHYLAMIDE is used as a reference substance in the regulation and control of psychoactive substances in many countries, due to its classification as a controlled substance.

InChI:InChI=1/C19H23N3O/c1-3-22(4-2)19(23)13-8-15-14-6-5-7-16-18(14)12(10-20-16)9-17(15)21-11-13/h5-8,10,13,17,20-21H,3-4,9,11H2,1-2H3/t13-,17-/m1/s1

Upstream product

• 35779-41-0 9,10-didehydro-N,N-diethyl-6-cyanoergoline-8β-carboxamide 
• 50-37-3 lysergide 

Downstream Products

• 65527-61-9 N-AllylnorLSD 
• 65527-62-0 N⁶-Ethyl-norlysergic acid diethylamide 
• 65527-63-1 N-PropylnorLSD 
• 96930-88-0 (6aR,9R)-7-Phenethyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid diethylamide 
• 50-37-3 lysergide 
• 1198111-11-3 C₂₆H₂₇N₃O₃ 

Relevant academic research and scientific papers

Synthetic LSD metabolite for preparing haptens used in an LSD metabolite immunoassay

A general method for the synthesis of OH-LSD and its analogs has been successfully developed. This method is convenient and efficient and allows preparation of a series of OH-LSD analogs with linkers attached at various (C-8, N-6 or N-1) positions.

Reagents for lysergic acid diethylamide immunoassay

The present invention provides hapten derivatives that are useful for the preparation of antigens, antibodies and reagents having superior performance characteristics for use in immunoassays for the detection of LSD and nor-LSD. In the present invention the LSD nucleus is derivatized out of the indole nitrogen to form an aminoalkyl derivative. Derivatives have also been synthesized out of the piperidine nitrogen of the LSD nucleus. The resulting haptens can then be further modified at these functionalized positions for linking to appropriate antigenic or labelling groups to provide reagents for LSD immunoassays having excellent sensitivity and selectivity for both LSD and nor-LSD.

Stereochemical and NMR Reassignment of 6-Norlysergic Acid Diethylamide and 6-Nor-6-allyllysergic Acid Diethylamide

Conditions are described for the preparation of a salt of 8β-norlysergic acid diethylamide (8β-nor-LSD) 1 as a single epimer from cyanamide 3, whereas earlier preparations gave mixtures of 1 with the 8α epimer 4 in variable proportions: the earlier NMR assignment of 1 is amended and the N(6) alkylation of 1 and 4 with allyl bromide is discussed.

Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives

A convenient method for the synthesis of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives was developed. A series of these compounds was synthesized and tested for substitution in the two-lever drug discrimination assay, in rats trained to discriminate injections of d-LSD tartrate (185.5 nmol/kg, ip) from saline. A dose-response curve for each of the compounds in the series was generated. Structure-activity relationships were developed, based on comparison of the estimated ED50 values from these curves. Of the compounds that substituted for LSD, the N(6)-ethyl and -allyl were approximately 2-3 times more potent than LSD itself. The N(6)-propyl was equipotent to LSD, while the isopropyl derivative was half as active. The n-butyl compound was 1 order of magnitude less potent than LSD, suggesting a similarity to the SAR of certain serotonin and dopamine agonists. By contrast, no generalization occurred to norlysergic acid N,N-diethylamide and the N(6)-2-phenethyl derivative.