LSM-775

Last updated
LSM-775
LSM-775.svg
Clinical data
Other namesLSM-775, N-Morpholinyllysergamide, Lysergic acid morpholide
Routes of
administration
Oral
Legal status
Legal status
Pharmacokinetic data
Metabolism hepatic
Excretion renal
Identifiers
  • (8β)-6-Methyl-8-(morpholin-4-ylcarbonyl)-9,10-didehydroergoline
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C20H23N3O2
Molar mass 337.423 g·mol−1
3D model (JSmol)
  • O=C(N1CCOCC1)[C@@H]5C=C4c2cccc3c2c(c[nH]3)C[C@H]4N(C)C5
  • InChI=1S/C20H23N3O2/c1-22-12-14(20(24)23-5-7-25-8-6-23)9-16-15-3-2-4-17-19(15)13(11-21-17)10-18(16)22/h2-4,9,11,14,18,21H,5-8,10,12H2,1H3/t14-,18-/m1/s1 Yes check.svgY
  • Key:OTQWCDNEJVKXKG-RDTXWAMCSA-N Yes check.svgY
   (verify)

N-Morpholinyllysergamide (LSM-775) is a derivative of ergine. [2] 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. [3] [ dubious ]

See also

Related Research Articles

<span class="mw-page-title-main">LSD</span> Hallucinogenic drug

Lysergic acid diethylamide, commonly known as LSD, and known colloquially as acid or lucy is a potent psychedelic drug. Effects typically include intensified thoughts, emotions, and sensory perception. At sufficiently high dosages LSD manifests primarily mental, visual, and 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 psychedelic with the greatest scientific and cultural significance. LSD is synthesized as a solid compound, typically in the form of a powder or a crystalline material. This solid LSD is then dissolved in a liquid solvent, such as ethanol or distilled water, to create a solution. The liquid serves as a carrier for the LSD, allowing for accurate dosage and administration onto small pieces of blotter paper called tabs. LSD is typically either swallowed or held under the tongue. In pure form, LSD is clear or white in color, has no smell, and is crystalline. It breaks down with exposure to ultraviolet light.

<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, 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.

<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 a 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.

<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">PARGY-LAD</span> Chemical compound

PARGY-LAD is an analogue of LSD. It is described by Alexander Shulgin in the book TiHKAL. PARGY-LAD is a hallucinogenic drug similar to LSD, but is considerably less potent than LSD with a dose of 160 micrograms producing only mild effects, and 500 micrograms required for full activity.

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

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.

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

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.

<span class="mw-page-title-main">Lysergic acid 2-butyl amide</span> Chemical compound

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).

<span class="mw-page-title-main">LSD-Pip</span> Compound related to LSD

LSD-Pip is a compound from the ergoline family, related to LSD but with the N,N-diethyl substitution replaced by a piperidine group. It is more potent than the corresponding pyrrolidine and morpholine analogues, but is still several times less potent than LSD as a 5-HT2A agonist. Early studies suggested this compound to be inactive as a psychedelic in humans, though this does not seem to have been confirmed by any more recent work.

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

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.

<span class="mw-page-title-main">1P-ETH-LAD</span> Chemical compound

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.

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

ECPLA (N-ethyl-N-cyclopropyllysergamide) is an analog of lysergic acid diethylamide (LSD) developed by Synex Synthetics. In studies in mice, it was found to have approximately 40% the potency of LSD.

<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, 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.

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

1cP-AL-LAD is an analog of lysergic acid diethylamide (LSD) which has psychedelic effects and is thought to act as a prodrug for AL-LAD. It has been sold as a designer drug, first identified in France in June 2021.

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

FLUORETH-LAD is a lysergamide derivative. It was first proposed by Alexander and Ann Shulgin in their book TiHKAL, but was never synthesised by Shulgin. Synthesis and activity data for the compound were first reported in a 2022 patent by Matthias Grill, in which pharmacological testing showed it to have similar affinity to LSD at some targets such as the 5-HT1A and 5-HT2A serotonin receptors, but much lower affinity at other targets such as 5-HT2C and at dopamine receptors, giving it comparatively greater selectivity compared to LSD.Currently new lysergamide derivates are in the development phase at MiHKAL GmbH in Switzerland.

References

  1. "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants" [Order of May 20, 2021 amending the order of February 22, 1990 setting the list of substances classified as narcotics]. www.legifrance.gouv.fr (in French). 20 May 2021.
  2. Gogerty JH, Dille JM (July 1957). "Pharmacology of d-lysergic acid morpholide (LSM)". The Journal of Pharmacology and Experimental Therapeutics. 120 (3): 340–8. PMID   13476356.
  3. Shulgin A, Shulgin A. "TiHKAL #26, LSD-25". Erowid.