Lysergic acid methyl ester

Last updated
Lysergic acid methyl ester
Lysergic acid methyl ester.svg
Names
Preferred IUPAC name
Methyl (6aR,9R)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid
Other names
Methyl lysergate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.022.696 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C17H18N2O2/c1-19-9-11(17(20)21-2)6-13-12-4-3-5-14-16(12)10(8-18-14)7-15(13)19/h3-6,8,11,15,18H,7,9H2,1-2H3/t11-,15-/m1/s1 Yes check.svgY
    Key: RNHDWLRHUJZABX-IAQYHMDHSA-N Yes check.svgY
  • InChI=1/C17H18N2O2/c1-19-9-11(17(20)21-2)6-13-12-4-3-5-14-16(12)10(8-18-14)7-15(13)19/h3-6,8,11,15,18H,7,9H2,1-2H3/t11-,15-/m1/s1
    Key: RNHDWLRHUJZABX-IAQYHMDHBA
  • O=C(OC)[C@@H]3/C=C2/c4cccc1c4c(c[nH]1)C[C@H]2N(C3)C
Properties
C17H18N2O2
Molar mass 282.343 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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=Lysergic acid methyl ester is an analogue of lysergic acid diethylamide (LSD). It is a member of the tryptamine family and is extremely uncommon. [1] It acts on the 5-HT receptors in the brain, as do most tryptamines. [2]

Related Research Articles

<span class="mw-page-title-main">Lysergic acid diethylamide</span> Hallucinogenic drug

Lysergic acid diethylamide (LSD), also known colloquially as acid, is a potent psychedelic drug. Effects typically include intensified thoughts, emotions, and sensory perception. At sufficiently high dosages LSD manifests primarily mental, visual, as well as auditory, hallucinations. Dilated pupils, increased blood pressure, and increased body temperature are typical. Effects typically begin within half an hour and can last for up to 20 hours. LSD is also capable of causing mystical experiences and ego dissolution. It is used mainly as a recreational drug or for spiritual reasons. LSD is both the prototypical psychedelic and one of the "classical" psychedelics, being the psychedelics with the greatest scientific and cultural significance. LSD is typically either swallowed or held under the tongue. It is most often sold on blotter paper and less commonly as tablets, in a watery solution or in gelatin squares.

<span class="mw-page-title-main">Psychedelic drug</span> Hallucinogenic class of psychoactive drug

Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness. This causes specific psychological, visual, and auditory changes, and often a substantially altered state of consciousness. Psychedelic states are often compared to meditative, psychodynamic or transcendental types of alterations of mind. The "classical" psychedelics, the psychedelics with the largest scientific and cultural influence, are mescaline, LSD, psilocybin, and DMT.

<span class="mw-page-title-main">Lysergamides</span> Class of chemical compounds

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.

<span class="mw-page-title-main">ALD-52</span> Chemical compound

ALD-52, also known as 1-acetyl-LSD, is a chemical analogue of lysergic acid diethylamide (LSD). It was originally discovered by Albert Hofmann in 1957 but was not widely studied until the rise in popularity of psychedelics in the 1960s.

<span class="mw-page-title-main">Lysergic acid hydroxyethylamide</span> Chemical compound

D-Lysergic acid α-hydroxyethylamide, also known as D-lysergic acid methyl carbinolamide, is an alkaloid of the ergoline family, believed to be present in small amounts in various species in the Convolvulaceae, as well as some species of fungi.

<span class="mw-page-title-main">AL-LAD</span> Chemical compound (psychedelic drug)

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.

<span class="mw-page-title-main">ETH-LAD</span> Chemical compound

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.

<span class="mw-page-title-main">PRO-LAD</span> Chemical compound

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.

<span class="mw-page-title-main">N1-Methyl-lysergic acid diethylamide</span>

N1-Methyl-lysergic acid diethylamide (MLD-41) is a derivative of LSD that has about one-third the psychoactive effects. It has been studied in cross-tolerance of LSD.

<span class="mw-page-title-main">LAE-32</span>

D-Lysergic acid ethylamide (LAE-32) is a derivative of ergine. It is reported to have some LSD-like effects but is weaker and shorter lasting, with an active dose reported to be between 0.5 and 1.5 milligrams.

<span class="mw-page-title-main">LSM-775</span> Chemical compound

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.

<span class="mw-page-title-main">Lysergic acid 2,4-dimethylazetidide</span> Chemical compound

Lysergic acid 2,4-dimethylazetidide 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.

<span class="mw-page-title-main">Effect of psychoactive drugs on animals</span>

Psychoactive drugs, such as caffeine, amphetamine, mescaline, lysergic acid diethylamide (LSD), marijuana, chloral hydrate, theophylline, IBMX and others, can have strong effects on certain animals. It is believed that plants developed caffeine as a chemical defense against insects.

<span class="mw-page-title-main">2-Bromo-LSD</span> Chemical compound

2-Bromo-LSD, also known as BOL-148, is a derivative of lysergic acid invented by Albert Hofmann, as part of the original research from which the closely related compound LSD was also derived. 2-Bromo-LSD was found to be inactive as a psychedelic and so was comparatively little researched for many years, although its similar behavior in the body made it useful for radiolabelling studies. It was found to bind to many of the same receptors as LSD, but acting as a neutral antagonist rather than an agonist. However its generally similar behavior to LSD in some respects has shown to be very useful in one specific area, the treatment of cluster headaches. These debilitating attacks have been known for some time to be amenable to treatment with certain hallucinogenic drugs such as LSD and psilocybin, but because of the illegal status of these drugs and the kind of mental changes they induce, research into their medical use has been slow and therapeutic application limited to very specific circumstances under strict supervision. It had been thought that this specific therapeutic action against cluster headaches was limited to hallucinogenic drugs of this type, and would always present a major barrier to their clinical use. However a serendipitous discovery found that 2-bromo-LSD is also able to produce this therapeutic effect, despite lacking the other effects of LSD. This has led to a resurgence of interest and research into 2-bromo-LSD and its possible medical uses. Some isolated incidents of hallucinogenic responses have been reported, but as with other non-hallucinogenic LSD analogues such as lisuride, this appears to be a rare side effect occurring only in individuals with an as yet unexplained susceptibility to this reaction. 2-Bromo-LSD reportedly attenuates the effects of LSD in humans.

<span class="mw-page-title-main">6-Isopropyl-6-nor-lysergic acid diethylamide</span> Chemical compound

6-Isopropyl-6-nor-lysergic acid diethylamide (IP-LAD) is an analog of lysergic acid diethylamide (LSD) developed by the team of David E. Nichols. In studies on mice, it was found to be approximately 40% the potency of LSD, compared to the 60% increase in potency seen with ETH-LAD and roughly equivalent potency in AL-LAD and PRO-LAD.

<span class="mw-page-title-main">1cP-LSD</span> Chemical compound

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.

<span class="mw-page-title-main">1B-LSD</span> Chemical compound

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.

<span class="mw-page-title-main">1V-LSD</span> Chemical compound

1V-LSD or 1-valeryl-D-lysergic acid diethylamide 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.

<span class="mw-page-title-main">LAMPA</span> Chemical compound

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.

References

  1. Hwang, Kristine Anne J.; Saadabadi, Abdolreza (2022), "Lysergic Acid Diethylamide (LSD)", StatPearls, Treasure Island (FL): StatPearls Publishing, PMID   29494014, archived from the original on 2022-11-19, retrieved 2022-11-19
  2. Libânio Osório Marta, Rui Filipe (2019-08-09). "Metabolism of lysergic acid diethylamide (LSD): an update". Drug Metabolism Reviews. 51 (3): 378–387. doi:10.1080/03602532.2019.1638931. ISSN   1097-9883. PMID   31266388. Archived from the original on 2022-11-19. Retrieved 2022-11-19 via National Library of Medicine.