Chemistry:LSM-775

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;
Pharmacokinetic data
Metabolism	hepatic
Excretion	renal
Identifiers
	IUPAC name (8β)-6-Methyl-8-(morpholin-4-ylcarbonyl)-9,10-didehydroergoline;
CAS Number	4314-63-0 ;
PubChem CID	199507;
ChemSpider	172695 ;
UNII	168Y0PXM7S;
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 ; Key:OTQWCDNEJVKXKG-RDTXWAMCSA-N ;
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Short description: Chemical compound

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 – discuss]}

References

↑ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". 20 May 2021. https://www.legifrance.gouv.fr/jorf/id/JORFTEXT000043523554.
↑ "Pharmacology of d-lysergic acid morpholide (LSM)". The Journal of Pharmacology and Experimental Therapeutics 120 (3): 340–8. July 1957. PMID 13476356. http://jpet.aspetjournals.org/content/120/3/340.abstract.
↑ "TiHKAL #26, LSD-25". Erowid. https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml.

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[1] "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". 20 May 2021. https://www.legifrance.gouv.fr/jorf/id/JORFTEXT000043523554.

[2] "Pharmacology of d-lysergic acid morpholide (LSM)". The Journal of Pharmacology and Experimental Therapeutics 120 (3): 340–8. July 1957. PMID 13476356. http://jpet.aspetjournals.org/content/120/3/340.abstract.

[TiHKAL-3] "TiHKAL #26, LSD-25". Erowid. https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml.

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v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) Dihydroergosine Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergotamine Ergotoxine Ergovaline Lisuride LSD LSH Lysergic Acid Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Lysergic Acid Methyl Ester Lysergol Mesulergine Metergoline Methergine (Methylergometrine, Methylergonovine, Methylergobasine) Methysergide Pergolide Syntometrine
Psychedelic lysergamides	1B-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD DAL DAM-57 ECPLA Ergonovine ETFELA ETH-LAD IP-LAD LAMPA LAE-32 LSD LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Methylergonovine MIPLA MLD-41 PARGY-LAD PRO-LAD
clavines	agroclavine elymoclavine lysergol festuclavine fumigaclavine A fumigaclavine B fumigaclavine C
Other ergolines	Ergoline
Natural sources	Achnatherum robustum (Sleepy Grass) Claviceps spp. (Ergot) Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)

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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
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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