Amides of lysergic acid are collectively known as lysergamides, and include a number of compounds with potent agonist and/or antagonist activity at various serotonin and dopamine receptors.
ALD-52, also known as 1-acetyl-LSD, has chemical structural features similar to lysergic acid diethylamide (LSD), a known psychedelic drug. Similarly, ALD-52 has been reported to produce psychoactive effects, but its pharmacological effects on humans are poorly understood. Given its psychoactive properties, it has been reported to be consumed as a recreational drug, and the purported first confirmed detection of the substance on the illicit market occurred in April 2016.
Methylergometrine, also known as methylergonovine and sold under the brand name Methergine, is a medication of the ergoline and lysergamide groups which is used as an oxytocic in obstetrics and in the treatment of migraine. It reportedly produces psychedelic effects similar to those of lysergic acid diethylamide (LSD) at high doses.
Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.
AL-LAD, also known as 6-allyl-6-nor-LSD, is a psychedelic drug and an analog of lysergic acid diethylamide (LSD). It is described by Alexander Shulgin in the book TiHKAL. It is synthesized starting from nor-LSD as a precursor, using allyl bromide as a reactant.
ETH-LAD, 6-ethyl-6-nor-lysergic acid diethylamide is an analogue of LSD. Its human psychopharmacology was first described by Alexander Shulgin in the book TiHKAL. ETH-LAD is a psychedelic drug similar to LSD, and is slightly more potent than LSD itself, with an active dose reported at between 20 and 150 micrograms. ETH-LAD has subtly different effects to LSD, described as less demanding.
PRO-LAD is an analogue of LSD. It is described by Alexander Shulgin in the book TiHKAL. PRO-LAD is a psychedelic drug similar to LSD, and is around as potent as LSD itself with an active dose reported at between 100 and 200 micrograms.
N-Morpholinyllysergamide (LSM-775) is a derivative of ergine. It is less potent than LSD but is reported to have some LSD-like effects at doses ranging from 75 to 700 micrograms and a shorter duration. There are fewer signs of cardiovascular stimulation and peripheral toxicity with LSM-775 compared to LSD.
Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ) is an analog of LSD developed by the team led by David E. Nichols at Purdue University. It was developed as a rigid analog of LSD with the diethylamide group constrained into an azetidine ring in order to map the binding site at the 5-HT2A receptor. There are three possible stereoisomers around the azetidine ring, with the (S,S)-(+) isomer being the most active, slightly more potent than LSD itself in drug discrimination tests using trained rats.
Methylisopropyllysergamide is an analogue of LSD that was originally discovered by Albert Hofmann at Sandoz during the original structure-activity research into LSD. It has subsequently been investigated in more detail by the team led by David E. Nichols at Purdue University. Methylisopropyllysergamide is a structural isomer of LSD, with the alkyl groups on the amide nitrogen having been subjected to a methylene shuffle. MIPLA and its ethylisopropyl homologue are the only simple N,N-dialkyl lysergamides that approach the potency of LSD itself, being around 1/3-1/2 the potency of LSD, while all other dialkyl analogues tested are only around 1/10 as potent as LSD, although some N-monoalkyl lysergamides such as the sec-butyl and t-butyl derivatives were also found to show an activity profile and potency comparable to LSD, and the mono-isopropyl derivative is only slightly weaker than MIPLA. Apart from its lower potency, the hallucinogenic effects of methylisopropyllysergamide are similar to those of LSD itself, and the main use for this drug has been in studies of the binding site at the 5-HT2A receptor through which LSD exerts most of its pharmacological effects.
Lysergic acid 2-butyl amide (2-Butyllysergamide, LSB) is an analogue of LSD originally developed by Richard Pioch at Eli Lilly in the 1950s, but mostly publicised through research conducted by the team led by David E. Nichols at Purdue University. It is a structural isomer of LSD, with the two ethyl groups on the amide nitrogen having been replaced by a single sec-butyl group, joined at the 2-position. It is one of the few lysergamide derivatives to exceed the potency of LSD in animal drug discrimination assays, with the (R) isomer having an ED50 of 33nmol/kg for producing drug-appropriate responding, vs 48nmol/kg for LSD itself. The corresponding (R)-2-pentyl analogue has higher binding affinity for the 5-HT1A and 5-HT2A receptors, but is less potent in producing drug-appropriate responding, suggesting that the butyl compound has a higher efficacy at the receptor target. The drug discrimination assay for LSD in rats involves both 5-HT1A and 5-HT2A mediated components, and while lysergic acid 2-butyl amide is more potent than LSD as a 5-HT1A agonist, it is slightly less potent as a 5-HT2A agonist, and so would probably be slightly less potent than LSD as a hallucinogen in humans. The main use for this drug has been in studies of the binding site at the 5-HT2A receptor through which LSD exerts most of its pharmacological effects, with the stereoselective activity of these unsymmetric monoalkyl lysergamides foreshadowing the subsequent development of compounds such as lysergic acid 2,4-dimethylazetidide (LSZ).
Ehrlich's reagent or Ehrlich reagent is a reagent containing p-dimethylaminobenzaldehyde (DMAB) and thus can act as an indicator to presumptively identify indoles and urobilinogen. Several Ehrlich tests use the reagent in a medical test; some are drug tests and others contribute to diagnosis of various diseases or adverse drug reactions. It is named after Nobel Prize winner Paul Ehrlich who used it to distinguish typhoid from simple diarrhoea.
1P-LSD is a psychedelic drug of the lysergamide class that is a derivative and functional analogue of LSD and a homologue of ALD-52. It originated in 2015 when it appeared a designer drug sold online. It modifies the LSD molecule by adding a propionyl group to the nitrogen molecule of LSD's indole group.
1P-ETH-LAD is an analog of LSD. 1P-ETH-LAD is a psychedelic drug similar to LSD. Research has shown formation of ETH-LAD from 1P-ETH-LAD incubated in human serum, suggesting that it functions as a prodrug. It is part of the lysergamide chemical class. Like ETH-LAD, this drug has been reported to be significantly more potent than LSD itself, and is reported to largely mimic ETH-LAD's psychedelic effects.
1cP-LSD is an acylated derivative of lysergic acid diethylamide (LSD), which has been sold as a designer drug. In tests on mice it was found to be an active psychedelic with similar potency to 1P-LSD.
1B-LSD is an acylated derivative of lysergic acid diethylamide (LSD), which has been sold as a designer drug. In tests on mice it was found to be an active psychedelic, though with only around 1/7 the potency of LSD itself.
LAMPA is a structural analogue of lysergic acid diethylamide (LSD) that has been studied as a potential treatment for alcoholism. In animal studies, LAMPA was found to be nearly equipotent to ECPLA and MIPLA for inducing a head-twitch response. LAMPA appears to be significantly less potent than LSD in humans, producing little to no noticeable effects at doses of 100 µg.
1D-LSD is a psychotropic substance and a research chemical that has potential psychedelic effects. It is believed to be a prodrug for LSD and has replaced 1V-LSD in Germany after 1V-LSD became covered by the German NpSG law in 2022. It is also available as tartrate.
1P-AL-LAD is a derivative of lysergic acid diethylamide (LSD) which has psychedelic effects and has been sold as a designer drug. It is believed to act as a prodrug for AL-LAD and produces a head-twitch response in animal studies.
1T-LSD is an acylated derivative of lysergic acid diethylamide (LSD), which has been sold as a designer drug. It was first identified in Japan in 2023 on blotter paper misrepresented as containing 1D-LSD, but which on analysis was determined to contain 1T-LSD instead.
