1.0 2009-08-12 19:36:03 UTC 2026-05-14 18:10:45 UTC T3D3582 Lysergic Acid Diethylamide SmallMolecule Lysergic Acid Diethylamide belongs to the lysergic acids and derivatives, a subclass of ergoline and derivatives within the organic compounds. It has the chemical formula C20H25N3O and an average molecular weight of 323.43 g/mol. This exogenous compound exists as a solid at room temperature. It functions as a hallucinogen, a serotonergic agonist, and a dopamine agonist. The compound acts as a partial agonist at the 5-HT2A receptor, particularly on neocortical pyramidal cells, which causes its hallucinogenic effects and increases cortical glutamate levels. It preferentially inhibits serotonergic cell firing by acting as an agonist at 5-HT1A receptors in the cortex, locus coeruleus, and raphe nuclei, where it also acts as a partial agonist on the postsynaptic site. It possesses high affinity for 5-HT1B, 5-HT1D, and 5-HT1E subtypes. While effects on 5-HT2C, 5-HT5A, 5-HT6, and 5-HT7 receptors have been described, their significance is uncertain. Additionally, it exhibits agonistic and antagonistic behavior at central dopamine D1 and D2 receptors. Other protein targets include the Beta-1 adrenergic receptor, D(3), D(4), and the Histamine H1 receptor. Lysergic acid diethylamide is recorded in 48 sources, including antibiotics, coins, key rings, and various food processing, household cleaning, and construction materials. Exposure occurs via oral and inhalation routes, with the latter supported by literature (PMC12390419). It is used as a treatment for schizophrenia (PMC12390419), though it is associated with nausea, drowsiness, weakness, and dizziness (PMC12390419). Synthetic Toxin Organic Compound Amine Amide Drug Hypnotic and Sedative Serotonin Antagonist Hallucinogen Synthetic Compound Serotonin Receptor Agonist Human Neurotoxin (+)-LSD (+)-lysergic acid diethylamide 9,10-Didehydro-N,N-diethyl-6-methylergoline-8b-carboxamide COFFEE CONCENTRATE, PURE COFFEE EXTRACT, SOLID D-LSD D-LSD-25 D-lysergic acid dethylamide D-lysergic acid diethylamide D-lysergic acid n,n-diethylamide Delysid Dextrolysergic acid diethylamide Diethylamid kyseliny lysergove LSD LSD-25 Lysergamid Lysergamide Lysergate diethylamide Lysergaure diethylamid Lysergic acid amide Lysergic acid diethylamide Lysergic acid diethylamide-25 Lysergide Lysergidum n,n-diethyl-(+)-lysergamide N,N-Diethyl-6-methyl-9,10-didehydroergoline-8-carboxamide N,n-diethyl-d-lysergamide N,n-diethyllysergamide C20H25N3O 323.432 323.199762437 (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 lysergic acid diethylamide 50-37-3 [H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N(CC)CC InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1 VAYOSLLFUXYJDT-RDTXWAMCSA-N Organic compounds Alkaloids and derivatives Ergoline and derivatives Lysergic acids and derivatives Lysergic acids and derivatives 3-alkylindoles Amino acids and derivatives Aralkylamines Azacyclic compounds Benzenoids Benzoquinolines Carbonyl compounds Heteroaromatic compounds Hydrocarbon derivatives Indoloquinolines Isoindoles and derivatives Organic oxides Organopnictogen compounds Pyrroles Pyrroloquinolines Quinoline-3-carboxamides Tertiary carboxylic acid amides Trialkylamines 3-alkylindole Amine Amino acid or derivatives Aralkylamine Aromatic heteropolycyclic compound Azacycle Benzenoid Benzoquinoline Carbonyl group Carboxamide group Carboxylic acid derivative Heteroaromatic compound Hydrocarbon derivative Indole Indole or derivatives Indoloquinoline Isoindole or derivatives Lysergic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Pyrrole Pyrroloquinoline Quinoline Quinoline-3-carboxamide Tertiary aliphatic amine Tertiary amine Tertiary carboxylic acid amide Aromatic heteropolycyclic compounds Indole alkaloids ergoline alkaloid monocarboxylic acid amide organic heterotetracyclic compound Detected and Not Quantified Exogenous Membrane Solid White powder. melting_point 82.5°C solubility 2.70e-01 mg/mL logp 2.95 logp 3.30 ALOGPS logs -3.08 ALOGPS solubility 2.70e-01 g/l ALOGPS logp 2.28 ChemAxon pka_strongest_acidic 17.02 ChemAxon pka_strongest_basic 7.98 ChemAxon iupac (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 ChemAxon average_mass 323.432 ChemAxon mono_mass 323.199762437 ChemAxon smiles [H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N(CC)CC ChemAxon formula C20H25N3O ChemAxon inchi InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1 ChemAxon inchikey VAYOSLLFUXYJDT-RDTXWAMCSA-N ChemAxon polar_surface_area 39.34 ChemAxon refractivity 98.73 ChemAxon polarizability 37.54 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Rapidly absorbed. Oral (usually on a substrate such as absorbent blotter paper, a sugar cube, or gelatin) (L1925); Intramuscular or intravenous injection (L1925) LSD preferentially inhibits serotonergic cell firing by acting as an agonist at the 5-HT1A receptors in the raphe nuclei, locus coeruleus, and cortex. It also acts as a partial agonist on the postsynaptic 5-HT1A site and has high affinity for the other 5-HT1 subtypes 5-HT1B, 5-HT1D, and 5-HT1E. LSD's hallucinogenic effects are caused by its ability to act as a partial agonist at the 5-HT2A receptor, especially on neocortical pyramidal cells. Activation of 5-HT2A also leads to increased cortical glutamate levels. Effects of LSD on 5-HT2C, 5-HT5A, 5-HT6, and 5-HT7 receptors have also been described, but their significance remains uncertain. In addition, LSD shows agonistic and antagonistic behavior at the central dopamine D1 and D2-receptors. (L1925, A2918) Estimates for the lethal dosage (LD50) of LSD range from 200 ug/kg to more than 1 mg/kg of human body mass, though most sources report that there are no known human cases of such an overdose. LSD's effects normally last from 6 - 12 hours depending on dosage, tolerance, body weight and age. Its half-life in humans is 175 min. It is metabolized in the liver by NADH-dependent microsomal enzymes and its metabolites may be quantified in the urine. The major metabolite is 2-oxy-3-hydroxy-LSD. Other metabolites include 2-oxy-LSD, LAE, nor-LSD, di-hydroxy-LSD, 13- and 14-hydroxy-LSD as glucoronides, lysergic acid ethyl-2-hydroxyethylamide (LEO), and trioxylated LSD. (L1925, A2918) Estimates for the lethal dosage (LD50) of LSD range from 200 ug/kg to more than 1 mg/kg of human body mass, though most sources report that there are no known human cases of such an overdose. LSD has not been known to cause death on its own. (A2915) No indication of carcinogenicity to humans (not listed by IARC). Lysergic acid diethylamide, is one of the most widely known psychedelic drugs. It has been used mainly as an entheogen, a tool to supplement various practices for transcendence, including meditation, psychonautics, art projects, and (formerly legal) psychedelic therapy, and as a recreational drug. Formally, LSD is classified as a hallucinogen of the psychedelic type. (L1925) #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7226a1b040> LSD reliably causes pupil dilation, reduced appetite, and wakefulness. Other physical reactions to LSD are highly variable and nonspecific, and some of these reactions may be secondary to the psychological effects of LSD. The following symptoms have been reported: numbness, weakness, nausea, hypothermia or hyperthermia, elevated blood sugar, goose bumps, increase in heart rate, jaw clenching, perspiration, saliva production, mucus production, sleeplessness, hyperreflexia, and tremors. LSD also causes expansion and an altered experience of senses, emotions, memories, time, and awareness. These psychological effects (colloquially called a "trip") vary greatly from person to person. Visual effects may include morphing objects, illusion of movement of static surfaces, after image-like trails of moving objects, the appearance of moving colored geometric patterns, an intensification of colors and brightness, new textures on objects, blurred vision, and shape suggestibility. The auditory effects of LSD may include echo-like distortions of sounds, changes in ability to discern concurrent auditory stimuli, and a general intensification of the experience of music. Higher doses often cause intense and fundamental distortions of sensory perception such as synaesthesia, the experience of additional spatial or temporal dimensions, and temporary dissociation. (L1925) Adverse effects of psychotropics are often treated with fast-acting benzodiazepines like diazepam or triazolam that have calming and antianxiety effects but do not directly affect the specific actions of psychotropics. Theoretically, specific 5-HT2A receptor antagonists, which most commonly means atypical antipsychotics (quetiapine, olanzapine, risperidone, etc.) or other 5-HT2A antagonist such as trazodone or mirtazapine, would be direct antidotes, although some anecdotal reports claim otherwise. (A308, L1925) DB04829 5761 CHEMBL263881 5558 C07542 6605 Lysergic Acid Diethylamide Lysergic_acid_diethylamide 18048412 13497365 14209776 14761703 2374410 6873185 17149427 19040555 Wikipedia. Lysergic acid diethylamide. Last Updated 21 April 2010.: http://en.wikipedia.org/wiki/LSD BE0000291 LSD preferentially inhibits serotonergic cell firing by acting as an agonist at the 5-HT1A receptors in the raphe nuclei, locus coeruleus, and cortex. It also acts as a partial agonist on the postsynaptic 5-HT1A site. (A2918) Inhibitory 0.0011 uM BindingDB 21342 BE0000451 LSD's hallucinogenic effects are caused by its ability to act as a partial agonist at the 5-HT2A receptor, especially on neocortical pyramidal cells. Activation of 5-HT2A also leads to increased cortical glutamate levels. (A2918) Inhibitory 0.0026 uM BindingDB 21342 Inhibitory 0.0027 uM BindingDB 21342 Inhibitory 0.0031 uM BindingDB 21342 Inhibitory 0.0035 uM BindingDB 21342 Inhibitory 0.004 uM BindingDB 21342 Inhibitory 0.0052 uM BindingDB 21342 BE0000945 Effects of LSD on 5-HT2C, 5-HT5A, 5-HT6, and 5-HT7 receptors have been described, but their significance remains uncertain. (A2918) Inhibitory 0.0069 uM BindingDB 21342 BE0000659 LSD preferentially inhibits serotonergic cell firing by acting as an agonist at the 5-HT1A receptors in the raphe nuclei, locus coeruleus, and cortex. It also acts as a partial agonist on the postsynaptic 5-HT1A site and has high affinity for the other 5-HT1 subtypes 5-HT1B, 5-HT1D, and 5-HT1E. (A2918) Inhibitory 0.0039 uM BindingDB 21342 BE0000476 LSD preferentially inhibits serotonergic cell firing by acting as an agonist at the 5-HT1A receptors in the raphe nuclei, locus coeruleus, and cortex. It also acts as a partial agonist on the postsynaptic 5-HT1A site and has high affinity for the other 5-HT1 subtypes 5-HT1B, 5-HT1D, and 5-HT1E. (A2918) Inhibitory 0.093 uM BindingDB 21342 BE0000393 Inhibitory 0.03 uM BindingDB 21342 BE0004688 Effects of LSD on 5-HT2C, 5-HT5A, 5-HT6, and 5-HT7 receptors have been described, but their significance remains uncertain. (A2918) Inhibitory 0.009 uM BindingDB 21342 BE0000650 Effects of LSD on 5-HT2C, 5-HT5A, 5-HT6, and 5-HT7 receptors have been described, but their significance remains uncertain. (A2918) Inhibitory 0.0066 uM BindingDB 21342 BE0000145 LSD shows agonistic and antagonistic behavior at the central dopamine D1 and D2-receptors. (A2918) Inhibitory 0.34 uM BindingDB 21342 BE0000756 LSD shows agonistic and antagonistic behavior at the central dopamine D1 and D2-receptors. (A2918) Inhibitory 0.12 uM BindingDB 21342 BE0000797 LSD preferentially inhibits serotonergic cell firing by acting as an agonist at the 5-HT1A receptors in the raphe nuclei, locus coeruleus, and cortex. It also acts as a partial agonist on the postsynaptic 5-HT1A site and has high affinity for the other 5-HT1 subtypes 5-HT1B, 5-HT1D, and 5-HT1E. (A2918) BE0000533 Effects of LSD on 5-HT2C, 5-HT5A, 5-HT6, and 5-HT7 receptors have been described, but their significance remains uncertain. (A2918) BE0000172 Inhibitory 0.14 uM BindingDB 21342 BE0000020 LSD shows agonistic and antagonistic behavior at the central dopamine D1 and D2-receptors. (A2918) BE0000581 Inhibitory 0.027 uM BindingDB 21342 BE0000389 Inhibitory 0.056 uM BindingDB 21342 BE0000442 Inhibitory 1.54 uM BindingDB 21342