LSM-775

Chemical compound From Wikipedia, the free encyclopedia

LSM-775, also known as N-morpholinyllysergamide or as lysergic acid morpholide, is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD).^[1]^[3]

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
administrationOral^[1]

Drug classSerotonin receptor modulator; Serotonin 5-HT_2A receptor agonist; Serotonergic psychedelic; Hallucinogen

Legal status

DE: NpSG (Industrial and scientific use only)
UK: Under Psychoactive Substances Act
Illegal in France^[2]

Quick facts Clinical data, Other names ...

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^[1]
Drug class	Serotonin receptor modulator; Serotonin 5-HT_2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act Illegal in France^[2]
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
(verify)

Use and effects

LSM-775 is less potent than LSD but is reported to have some LSD-like effects at doses ranging from 75 to 1,000 μg orally and a shorter duration.^[1]^[4]^[3] It may only produce weak or threshold psychedelic effects in humans.^[4] There have been said to be fewer signs of cardiovascular stimulation and peripheral toxicity with LSM-775 compared to LSD.^[1] On the other hand, more recent reports suggest that LSM-75 produces considerable nausea and feelings of lethargy and sedation.^[4]

Interactions

Pharmacology

Pharmacodynamics

LSM-775 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]

Chemistry

Synthesis

The chemical synthesis of LSM-775 has been described.^[1]

Analogues

Analogues of LSM-775 include the cyclized lysergic acid piperidide (LA-Pip), lysergic acid azepane (LA-Azepane), lysergic acid pyrrolidide (LA-Pyr; LPD-824), lysergic acid pyrrolinide (LPN), and lysergic acid 2,4-dimethylazetidide (LA-Az, LSZ) and the non-cyclized LEO, LA-MeO, ergometrine, and methylergometrine, among others.^[1]^[5]

History

LSM-775 was first described in the scientific literature by Albert Hofmann and colleagues by 1955.^[4]^[6] It emerged as a novel designer drug in 2013.^[4]

Society and culture

Legal status

Canada

LSM-775 is not a controlled substance in Canada as of 2025.^[7]

United States

LSM-775 is not an explicitly controlled substance in the United States.^[8] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

References

[1]
Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml "LSM-775, N-Morpholinyllysergamide. There are conflicting reports; one states that 75 micrograms is an effective dose, comparable to a similar dose of LSD, and the other stated that between 350 and 700 micrograms was needed to elicit this response, and that there were fewer signs of cardiovascular stimulation and peripheral toxicity."
[2]
"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.
[3]
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.
[4]
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. Although lysergic acid morpholide (LSM-775) appeared on the NPS market in 2013, there is disagreement in the literature regarding the potency and psychoactive properties of LSM-775 in humans. [...] The preparation of LSM-775 was first described in the 1950s by Stoll and Hoffmann18 and several other routes have also been reported.19–21 There is disagreement in the literature regarding the potency and psychoactive properties of LSM-775 in humans. Goggerty and Dille reported that 75 µg LSM-775 produced approximately the same response as 50 µg LSD in two subjects, although LSM-775 had a shorter duration of action than LSD.22 In a blinded experiment conducted by Abramson, two subjects administered 150 µg LSM-775 estimated that they had received 25–35 µg LSD, whereas a third subject estimated that they had received a placebo.23 Isbell et al. found that higher doses of LSM-775 (4.5 and 9 µg/kg) produced effects roughly equivalent to a threshold dose of LSD, but with a shorter duration.24,25 One potential explanation for these discrepant findings is that LSM-775 may be capable of producing only a threshold psychedelic response. However, the methodological weaknesses in early human studies with LSM-775 make interpretation challenging. [...] LSM-775 has been distributed by online vendors as an NPS. According to reports on Internet discussion forums and websites, 1 mg LSM-775 mimics the effects produced by low doses of LSD, but also induces considerable nausea and feelings of lethargy and sedation.57 Similarly, when tested in preliminary clinical trials, LSM-775 was only capable of producing a weak psychedelic response, similar to low or threshold doses of LSD.
[5]
Nichols DE (2001). "LSD and Its Lysergamide Cousins" (PDF). The Heffter Review of Psychedelic Research. 2. Heffter Research Institute: 80–87. ISSN 1534-9640. The two ethyl groups [of LSD] were incorporated into ring structures such as the pyrrolidide, piperidide, and morpholide, shown above, but these also had reduced anti-serotonin and psychedelic effects (Cerletti and Doepfner 1958). Although the morpholide had less than one-tenth of the potency of LSD in blocking the action of serotonin, it did however have nearly 75% of the potency of LSD as a psychedelic (Gogerty and Dille 1957).
[6]
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.
[7]
"Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
[8]
Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026

LSM-775

Use and effects

Interactions

Pharmacology

Pharmacodynamics

Chemistry

Synthesis

Analogues

History

Society and culture

Legal status

Canada

United States

See also

References

External links

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