Compound: Lysergide
SMILES: O=C(N(CC)CC)[C@@H]1C=C2c3c4c([nH]cc4C[C@H]2N(C1)C)ccc3
InChIKey: VAYOSLLFUXYJDT-RDTXWAMCSA-N
Synonyms: Lysergide, LYSERGIC ACID DIETHYLAMIDE, D-Lsd, N,N-Diethyllysergamide, 50-37-3, Lysergsaeurediaethylamid, N,N-Diethyl-D-lysergamide, Lysergaure diethylamid, LSD-25, LSD 25, Lisergide, Lysergidum, N,N-Diethyl-(+)-Lysergamide, (+)-Lysergic acid diethylamide, Dextrolysergic Acid diethylamide, lisergida, 8NA5SWF92O, (+)-Lysergide, Diethylamid kyseliny lysergove, DTXSID1023231, CHEBI:6605, DTXCID003231, Ergoline-8-carboxamide, 9,10-didehydro-N,N-diethyl-6-methyl-, (8beta)-, (8R)-9,10-didehydro-N,N-diethyl-6-methylergoline-8-carboxamide, (6aR,9R)-N,N-diethyl-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide, (4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide, (4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo(7.6.1.0^(2,7).0^(12,16))hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide, (6aR,9R)-N,N-diethyl-7-methyl-6,6a,8,9-tetrahydro-4H-indolo(4,3-fg)quinoline-9-carboxamide, RefChem:5968, Acid Diethylamide, Lysergic, Diethylamide, Lysergic Acid, (4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo(7.6.1.02,7.012,16)hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide, 200-033-2, D-Lysergic acid diethylamide, Delysid, Lysergamid, LSD, LSD (alkaloid), Lysergic acid diethylamide-25, Lysergsauerediaethylamid, Lysergamide, N,N-diethyl-, HSDB 3920, (+)-LSD, Lysergsaeurediethylamid, [3H]-LSD, CHEMBL263881, Cubes, Pearly gates, Heavenly Blue, Royal blue, Acid [Street Name], Cubes [Street Name], NCGC00168265-01, NCGC00168265-02, Royal Blue [Street Name], Lysergidum [INN-Latin], Pearly gates [Street Name], Wedding bells [Street Name], Heavenly Blue [Street Name], Lisergide [DCIT], Clearlight, Ubergluben, Barrels, Bartman, Cupcakes, Greenies, Lisergido, Microdots, Spoonies, Sunshine, Trippers, Yellows, Beast, CHEMBL463207, Chief, Domes, Fifty, Flats, Owsley, Scapes, Wedges, Chocolate Chips, Orange Mushroom, Orange Sunshine, Purple Microdot, Gelatin Chips, Mellow Yellow, Orange Wedges, Bart Simpson, Blotter Acid, Contact Lens, (8alpha)-N,N-Diethyl-6-Methyl-9,10-Didehydroergoline-8-Carboxamide, Purple Haze, White Light, Window Pane, Blue Cheer, Brown Dots, Cherry Top, Lisergido [INN-Spanish], Mean Green, Paper Acid, Sugar Lump, Blue Acid, Blue Mist, Blue Star, Strawberry Fields, The Hawk, CAS-50-37-3, California Sunshine, LSD (d-Lysergic acid N,N-diethylamide), Lysergide [INN:BAN:DCF], Diethylamid kyseliny lysergove [Czech], Big F, (+)-Lysergide (1.0 mg/mL in Acetonitrile), (+)-Lysergide (100 microg/mL in Methanol), EINECS 200-033-2, UNII-8NA5SWF92O, BRN 0094179, Hawk, Haze, Lids, Lucy in the Sky with Diamonds, Instant Zen, DEA No. 7315, Lysergide (LSD), Wedding Bells Acid, 7LD, [N-methyl-3H]LSD, LYSERGIDE [INN], LYSERGIDE [MI], LSD,l-, LYSERGIDE [HSDB], 9,10-Didehydro-N,N-diethyl-6-methyl-ergoline-8-beta-carboxamide, Ergoline-8beta-carboxamide, 9,10-didehydro-N,N-diethyl-6-methyl-, GTPL17, Indolo[4,3-fg]quinoline, ergoline-8-carboxamide deriv., LYSERGIDE [WHO-DD], 4-25-00-00939 (Beilstein Handbook Reference), SCHEMBL113755, NIOSH/KE4200000, SCHEMBL29349465, BDBM21342, LSD,(+), 9,10-Didehydro-N,N-diethyl-6-methylergoline-8b-carboxamide, Lysergic acid diethylamide, l-isomer, Tox21_112872, Tox21_113508, BDBM50241702, Ergoline-8-beta-carboxamide, 9,10-didehydro-N,N-diethyl-6-methyl-, Ergoline-8-carboxamide, 9,10-didehydro-N,N-diethyl-6-methyl-, (8b)-, PDSP1_001431, PDSP1_001540, PDSP2_001415, PDSP2_001524, Lysergic acid diethylamide tartrate ci, DB04829, US20240166618, Compound LSD, (+)-LYSERGIDE (INCB:GREEN LIST), LSD (Lysergic Acid Diethylamide;Lysergide), KE42000000, NS00000052, C07542, Q23118, LSD (Lysergic Acid Diethylamide) 0.025 mg/ml in Acetonitrile, LSD (Lysergic Acid Diethylamide) 1.0 mg/ml in Acetonitrile, N,N-Diethyl-6-methyl-9,10-didehydroergoline-8beta-carboxamide, (8beta)-N,N-diethyl-6-methyl-9,10-didehydroergoline-8-carboxamide, 9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYL-ERGOLINE-8B-CARBOXAMIDE, LSD (d-Lysergic acid N,N-diethylamide), 0.1mg/ml in Acetonitrile, LSD (d-Lysergic acid N,N-diethylamide), 1mg/ml in Acetonitrile, Ergoline-8-beta-carboxamide, 9,10-didehydro-N,N-diethyl-6-methyl-, (-)-, Ergoline-8b-carboxamide, 9,10-didehydro-N,N-diethyl-6-methyl- (8CI), (8.BETA.)-9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYLERGOLINE-8-CARBOXAMIDE, ERGOLINE-8-CARBOXAMIDE, 9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYL-, (5.BETA., 8.BETA.)-, (6aR,9R)-N,N-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
Theoretical properties:
molecular_formula: C20H25N3O
molecular_weight: 323.4 g/mol
exact_mass: 323.199762429 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 3
heavy_atom_count: 24
topological_polar_surface_area: 39.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Pointed prisms from benzene
color: Pointed prisms from benzene
odor: Odorless
melting_point: 176 to 185 °F (NTP, 1992)
solubility: Water soluble
Descriptions:
{"pubchem": "Lysergic acid diethylamide is an ergoline alkaloid arising from formal condensation of lysergic acid with diethylamine. It has a role as a hallucinogen, a serotonergic agonist and a dopamine agonist. It is a monocarboxylic acid amide, an organic heterotetracyclic compound and an ergoline alkaloid. It is functionally related to a lysergamide.", "chebi": "An ergoline alkaloid arising from formal condensation of lysergic acid with diethylamine.", "chembl": "LYSERGIDE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.", "wikipedia": "Lysergic acid diethylamide, commonly known as LSD (from German Lysergs\u00e4urediethylamid) and by the nicknames acid and lucy, is a semisynthetic hallucinogenic drug derived from ergot, known for its powerful psychological effects and serotonergic activity.\nLSD taken orally has an onset of action of 0.4 to 1.0 hours and a duration of 7 to 12 hours. In recreational settings it is commonly administered via tabs of blotter paper. LSD is extremely potent, with noticeable effects at doses as low as 20 micrograms and is sometimes taken in even smaller amounts for microdosing. Despite widespread use, no fatal human overdoses have been documented. LSD is mainly used recreationally or for spiritual purposes. LSD can cause mystical experiences. LSD exerts its effects primarily through high-affinity binding to several serotonin receptors, especially the serotonin 5-HT2A receptor, and to a lesser extent dopamine and adrenergic receptors. Neuroimaging studies indicate that LSD reduces the efficacy of thalmo-cortical information filtering, decreases oscillatory power within the default mode network, and flattens hierarchical organization of large-brain activity. At higher doses, it can induce visual and auditory hallucinations, ego dissolution, and anxiety. LSD use can cause adverse psychological effects such as paranoia and delusions and may lead to persistent visual disturbances known as hallucinogen persisting perception disorder (HPPD).\nSwiss chemist Albert Hofmann first synthesized LSD in 1938 and discovered its powerful psychedelic effects in 1943 after accidental ingestion. It became widely studied in the 1950s and 1960s. The drug was initially explored for psychiatric use due to its structural similarity to serotonin and safety profile. It was used experimentally in psychiatry for treating alcoholism and schizophrenia. By the mid-1960s, LSD became central to the youth counterculture in places like San Francisco and London, influencing art, music, and social movements through events like Acid Tests and figures such as Owsley Stanley and Michael Hollingshead. Its psychedelic effects inspired distinct visual art styles, music innovations, and caused a lasting cultural impact. However, its association with the counterculture movement of the 1960s led to its classification as a Schedule I drug in the United States in 1970. It was also listed as a Schedule I controlled substance by the United Nations in 1971 and remains without approved medical uses.\nDespite its legal restrictions, LSD remains influential in scientific and cultural contexts. Research on LSD declined due to cultural controversies by the 1960s, but has resurged since 2009. In 2024, the United States Food and Drug Administration designated LSD (code name MM120 or DT120) as a breakthrough therapy for generalized anxiety disorder. As of 2017, about 10% of people in the United States had used LSD at some point, with 0.7% having used it in the past year. Usage rates have risen, with a 56.4% increase in adult use in the United States from 2015 to 2018."}