Ergoline is a chemical compound whose structural skeleton is contained in a variety of alkaloids, referred to as ergoline derivatives or ergoline alkaloids. Ergoline alkaloids, one being ergine, were initially characterized in ergot. Some of these are implicated in the condition ergotism, which can take a convulsive form or a gangrenous form. Even so, many ergoline alkaloids have been found to be clinically useful. Annual world production of ergot alkaloids has been estimated at 5,000–8,000 kg of all ergopeptines and 10,000–15,000 kg of lysergic acid, used primarily in the manufacture of semi-synthetic derivatives.
Lysergic acid, also known as D-lysergic acid and (+)-lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and found in the seeds of Turbina corymbosa (ololiuhqui), Argyreia nervosa, and Ipomoea tricolor.
Amides of lysergic acid are collectively known as lysergamides or ergoamides, and include a number of compounds with potent agonist and/or antagonist activity at various serotonin and dopamine receptors. Lysergamides contain an embedded tryptamine structure, and as a result can produce similar, often psychedelic, effects to those of the true tryptamines.
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.
D-Lysergic acid α-hydroxyethylamide, also known as D-lysergic acid methyl carbinolamide, is a Lysergamide and alkaloid of the Ergoline family, it is present in higher concentrations in the parasitic fungi species "Claviceps", mainly the Claviceps paspali, also in Claviceps Purpurea. This fungi grows in various species in the Convolvulaceae family like the Ipomoea violacea, the Rivea corymbosa (Ololiuhqui), and the Argyreia nervosa. Heavenly Blue Morning Glory and Hawaiian Baby Woodrose especially contain high amounts of LSH, with content varying between species and by how fresh the seeds are. LSH is a psychoactive Ergoline and has effects similar to LSD due to similarity in the structure and is the main psychoactive compound found in Claviceps Paspali and in (fresh) Heavenly Blue Morning Glory Seeds. LSH is unstable and breaks down into LSA quickly, so old seeds often only contains LSA and iso-LSA. When the seeds are fresh, they contain significantly higher amounts of LSH.
Lysergol is an alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi, and in the morning glory family of plants (Convolvulaceae), including the hallucinogenic seeds of Rivea corymbosa (ololiuhqui), Argyreia nervosa and Ipomoea violacea. Lysergol is not a controlled substance in the USA. Its possession and sale is also legal under the U.S. Federal Analog Act because it does not have a known pharmacological action or a precursor relationship to LSD, which is a controlled substance. However, lysergol is an intermediate in the manufacture of some ergoloid medicines.
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.
N-Morpholinyllysergamide, also known as lysergic acid morpholide, is a derivative of ergine (lysergamide). It is less potent than lysergic acid diethylamide (LSD) but is reported to have some LSD-like effects at doses ranging from 75 to 700 micrograms and a shorter duration. LSM-775 may only produce weak or threshold psychedelic effects in humans.
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 EIPLA 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).
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 was first synthesized as a legal-LSD alternative by Lizard Labs, a Netherlands based research chemical laboratory. It modifies the LSD molecule by adding a propionyl group to the nitrogen atom 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. It was first synthesized as a legal-LSD alternative by Lizard Labs, a Netherlands based research chemical laboratory. 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.
1V-LSD, sometimes nicknamed Valerie, is a psychotropic substance and a research chemical with psychedelic effects. 1V-LSD is an artificial derivative of natural lysergic acid, which occurs in ergot alkaloids, as well as being an analogue of LSD. 1V-LSD has been sold online until an amendment to the German NpSG was enforced in 2022 which controls 1P-LSD and now 1cP-LSD, 1V-LSD and several other lysergamides.
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 and liquid.
1DD-LSD is an acylated derivative of lysergic acid diethylamide (LSD). In animal studies it produces a weak head-twitch response but with 27x lower potency than LSD itself. It is being researched as a potential slow-onset, long lasting prodrug for LSD which is expected to have reduced psychoactive effects.
