LSM-775

N-Morpholinyllysergamide (developmental code name LSM-775), also known 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]

LSM-775

Clinical data
Other names	LSM-775, N-Morpholinyllysergamide, Lysergic acid morpholide
Routes of administration	Oral
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act Illegal in France[1]
Pharmacokinetic data
Metabolism	hepatic
Excretion	renal
Identifiers
IUPAC name (8β)-6-Methyl-8-(morpholin-4-ylcarbonyl)-9,10-didehydroergoline
CAS Number	4314-63-0 Y
PubChem CID	199507
ChemSpider	172695 Y
UNII	168Y0PXM7S
CompTox Dashboard (EPA)	DTXSID50195718
Chemical and physical data
Formula	C20H23N3O2
Molar mass	337.423 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(N1CCOCC1)[C@@H]5C=C4c2cccc3c2c(c[nH]3)C[C@H]4N(C)C5
InChI 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 Y Key:OTQWCDNEJVKXKG-RDTXWAMCSA-N Y
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The drug is a potent full agonist of the serotonin 5-HT_1A receptor and a potent partial agonist of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C 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-HT_1A receptor antagonist WAY-100635.^[4] These findings indicate that serotonin 5-HT_1A 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]}

See also

• 1cP-LSD
• 1B-LSD
• 1P-ETH-LAD
• 1P-LSD
• 1V-LSD
• ALD-52
• AL-LAD
• ETH-LAD
• Lysergic acid 2,4-dimethylazetidide (LSZ)
• Lysergic acid diethylamide (LSD)
• O-Acetylpsilocin (4-AcO-DMT)
• PRO-LAD

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. PMID 13476356.
3. Shulgin A, Shulgin A. "TiHKAL #26, LSD-25". Erowid.
4. Brandt SD, Kavanagh PV, Twamley B, Westphal F, Elliott SP, Wallach J, Stratford A, Klein LM, McCorvy JD, Nichols DE, Halberstadt AL (February 2018). "Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM-775)". Drug Test Anal. 10 (2): 310–322. doi:10.1002/dta.2222. PMC 6230476. PMID 28585392.