LSM-775

Last updated

LSM-775
LSM-775.svg
Clinical data
Other namesLSM775; LSM; SLM; N-Morpholinyllysergamide; Lysergic acid morpholide; LA-Morph; LA-Morpholide; Morpholine lysergamide; 6-Methyl-8β-(morpholin-4-ylcarbonyl)-9,10-didehydroergoline
Routes of
administration 		Oral
Drug class Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
Identifiers
  • [(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]-morpholin-4-ylmethanone
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)

LSM-775, also known as N-morpholinyllysergamide or as lysergic acid morpholide, is a derivative of ergine (lysergamide). [2] 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. [3] LSM-775 may only produce weak or threshold psychedelic effects in humans. [4]

Contents

The drug is a potent full agonist of the serotonin 5-HT1A receptor and a potent partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. [4] It does not produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. [4] However, LSM-775 can robustly increase head twitches if it is coadministered with the serotonin 5-HT1A receptor antagonist WAY-100635. [4] These findings indicate that serotonin 5-HT1A receptor activation suppresses the psychedelic-like effects of LSM-775. [4]

There are claimed to be fewer signs of cardiovascular stimulation and peripheral toxicity with LSM-775 compared to LSD. [3] [ dubious – discuss ]

LSM-775 was first described in the scientific literature by Albert Hofmann and colleagues by 1955. [5]

See also

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): 340–348. doi:10.1016/S0022-3565(25)23282-7. PMID   13476356.
  3. 1 2 Shulgin A, Shulgin A. "TiHKAL #26, LSD-25". Erowid.
  4. 1 2 3 4 5 Brandt SD, Kavanagh PV, Twamley B, Westphal F, Elliott SP, Wallach J, et al. (February 2018). "Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM-775)". Drug Testing and Analysis. 10 (2): 310–322. doi:10.1002/dta.2222. PMC   6230476 . PMID   28585392.
  5. ↑ Hofmann A, Stoll A (1955). "Amide der stereoisomeren Lysergsäuren und Dihydro-lysergsäuren. 38. Mitteilung über Mutterkornalkaloide" [Amides of stereoisomeric lysergic and dihydrolysergic acids. 38. Ergot alkaloids]. Helvetica Chimica Acta. 38 (2): 421–433. Bibcode:1955HChAc..38..421S. doi:10.1002/hlca.19550380207. ISSN   0018-019X . Retrieved 5 June 2025.
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