LSM-775

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]

LSM-775

Clinical data
Other names	LSM775; 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	DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act Illegal in France[1]
Identifiers
IUPAC name [(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]-morpholin-4-ylmethanone
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]}

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

See also

• Substituted lysergamide
• Lysergic acid pyrrolidide (LPD-824)
• Lysergic acid piperidide (LSD-Pip)
• Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ)