Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H25N3O.C4H6O6 |
| Molecular Weight | 473.5188 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]([C@@H](O)C(O)=O)C(O)=O.CCN(CC)C(=O)[C@H]1CN(C)[C@@H]2CC3=CNC4=C3C(=CC=C4)C2=C1
InChI
InChIKey=HQMPRARIZOUKRO-AJLBZGGQSA-N
InChI=1S/C20H25N3O.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t14-,18-;1-,2-/m11/s1
| Molecular Formula | C20H25N3O |
| Molecular Weight | 323.432 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | C4H6O6 |
| Molecular Weight | 150.0868 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Lysergide (LSD) is a semi-synthetic hallucinogen and is one of the most potent drugs known. Recreational use became popular between the 1960s to 1980s, but is now less common. LSD was first synthesized by Albert Hoffman while working for Sandoz Laboratories in Basel in 1938. Some years later, during a re-evaluation of the compound, he accidentally ingested a small amount and described the first ‘trip’. During the 1950s and 1960s, Sandoz evaluated the drug for therapeutic purposes and marketed it under the name Delysid®. It was used for research into the chemical origins of mental illness. Recreational use started in the 1960s and is associated with the ‘psychedelic period’. LSD possesses a complex pharmacological profile that includes direct activation of
serotonin, dopamine and norepinephrine receptors. In addition, one of its chief sites of
action is that of compound-specific (“allosteric”) alterations in secondary messengers
associated with 5HT2A and 5HT2C receptor activation and changes in gene expression.
The hallucinogenic effects of LSD are likely due to agonism at 5HT2A and 5HT2C
receptors. LSD is also an agonist at the majority of known
serotonin receptors, including 5HT1A, 5HT1B, 5HT1D, 5HT5A, 5HT6 and 5HT7 receptors. During the 1960s, LSD was investigated for a variety of psychiatric indications, including the following: as an aid in treatment of schizophrenia; as a means of creating a "model psychosis"; as a direct antidepressant; and as an adjunct to psychotherapy. LSD is listed in Schedule I of the United Nations 1971 Convention on Psychotropic Substances.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL214 |
0.003 µM [Ki] | ||
Target ID: CHEMBL224 |
0.004 µM [Ki] | ||
Target ID: CHEMBL225 |
0.015 µM [Ki] | ||
Target ID: CHEMBL3371 |
6.31 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/ |
200 μg single, oral dose: 200 μg route of administration: Oral experiment type: SINGLE co-administered: |
LYSERGIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/ |
100 μg single, oral dose: 100 μg route of administration: Oral experiment type: SINGLE co-administered: |
LYSERGIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
20.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/ |
200 μg single, oral dose: 200 μg route of administration: Oral experiment type: SINGLE co-administered: |
LYSERGIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
8.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/ |
100 μg single, oral dose: 100 μg route of administration: Oral experiment type: SINGLE co-administered: |
LYSERGIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/ |
200 μg single, oral dose: 200 μg route of administration: Oral experiment type: SINGLE co-administered: |
LYSERGIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/ |
100 μg single, oral dose: 100 μg route of administration: Oral experiment type: SINGLE co-administered: |
LYSERGIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| inconclusive [IC50 0.9296 uM] | ||||
| inconclusive [IC50 23.1093 uM] | ||||
| inconclusive [IC50 82.8488 uM] | ||||
| inconclusive [IC50 82.8488 uM] | ||||
| no |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Serotonergic/glutamatergic interactions: the effects of mGlu2/3 receptor ligands in rats trained with LSD and PCP as discriminative stimuli. | 2004-03 |
|
| Pharmacological characterization of a serotonin receptor (5-HT7) stimulating cAMP production in human corneal epithelial cells. | 2003-11 |
|
| Serotonin receptors in platelets of bipolar and schizoaffective patients: effect of lithium treatment. | 2003-11 |
|
| Biochemical outcome of blocking the ergot alkaloid pathway of a grass endophyte. | 2003-10-22 |
|
| Role of the serotonin 5-HT(2A) receptor in learning. | 2003-10-15 |
|
| Transcriptome fingerprints distinguish hallucinogenic and nonhallucinogenic 5-hydroxytryptamine 2A receptor agonist effects in mouse somatosensory cortex. | 2003-10-01 |
|
| LC-MS analysis of 2-oxo-3-hydroxy LSD from urine using a Speedisk positive-pressure processor with Cerex PolyChrom CLIN II columns. | 2003-10 |
|
| D-cycloserine-Naloxone interactions in opioid-dependent humans under a novel-response naloxone discrimination procedure. | 2003-08 |
|
| Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands. | 2003-07-31 |
|
| Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM. | 2003-07 |
|
| The development and application of a gas chromatography-mass spectrometric (GC-MS) assay to determine the presence of 2-oxo-3-hydroxy-LSD in urine. | 2003-06-25 |
|
| Blue light (clearlight) for acne vulgaris. | 2003-06-23 |
|
| Effects of autoshaping procedures on 3H-8-OH-DPAT-labeled 5-HT1a binding and 125I-LSD-labeled 5-HT2a binding in rat brain. | 2003-06-13 |
|
| Case report: an ingestion of Hawaiian Baby Woodrose seeds associated with acute psychosis. | 2003-06 |
|
| The effective treatment of acne vulgaris by a high-intensity, narrow band 405-420 nm light source. | 2003-06 |
|
| [Clinical methods in evolutional physiology]. | 2003-05-13 |
|
| Acute effects of drugs of abuse. | 2003-05-10 |
|
| Effect of the 5-HT6 receptor antagonists Ro04-6790 and Ro65-7199 on latent inhibition and prepulse inhibition in the rat: comparison to clozapine. | 2003-05 |
|
| Prevalence and risk factors for LSD use among young women. | 2003-04 |
|
| Discovering risperidone: the LSD model of psychopathology. | 2003-04 |
|
| Dynamic changes in prefrontal cortex gene expression following lysergic acid diethylamide administration. | 2003-03-17 |
|
| Hallucinogen persisting perception disorder: what do we know after 50 years? | 2003-03-01 |
|
| Enhancing action of LSD on neuronal responsiveness to serotonin in a brain structure involved in obsessive-compulsive disorder. | 2003-03 |
|
| Persisting visual hallucinations and illusions in previously drug-addicted patients. | 2003-03 |
|
| Determination of lysergic acid diethylamide (LSD) in mouse blood by capillary electrophoresis/ fluorescence spectroscopy with sweeping techniques in micellar electrokinetic chromatography. | 2003-03 |
|
| On-line identification of lysergic acid diethylamide (LSD) in tablets using a combination of a sweeping technique and micellar electrokinetic chromatography/77 K fluorescence spectroscopy. | 2003-03 |
|
| Salvinorin A: the "magic mint" hallucinogen finds a molecular target in the kappa opioid receptor. | 2003-03 |
|
| Clonazepam treatment of lysergic acid diethylamide-induced hallucinogen persisting perception disorder with anxiety features. | 2003-03 |
|
| Creation, expression, and characterization of a constitutively active mutant of the human serotonin 5-HT6 receptor. | 2003-03 |
|
| A selective and sensitive method for quantitation of lysergic acid diethylamide (LSD) in whole blood by gas chromatography-ion trap tandem mass spectrometry. | 2003-02-18 |
|
| Characterization of the discriminative stimulus properties of centrally administered (-)-DOM and LSD. | 2003-02 |
|
| Discriminative stimulus properties of 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane [(+/-)DOI] in C57BL/6J mice. | 2003-02 |
|
| Use of dynamically coated capillaries with added cyclodextrins for the analysis of opium using capillary electrophoresis. | 2003-01-10 |
|
| Effect of loxapine on peripheral dopamine-like and serotonin receptors in patients with schizophrenia. | 2003-01 |
|
| A common oscillator for perceptual rivalries? | 2003 |
|
| The hallucinogen d-lysergic acid diethylamide (d-LSD) induces the immediate-early gene c-Fos in rat forebrain. | 2002-12-27 |
|
| Chemical casualties. Centrally acting incapacitants. | 2002-12 |
|
| The serotonergic system and mysticism: could LSD and the nondrug-induced mystical experience share common neural mechanisms? | 2002-11-09 |
|
| Jekyll and Hyde revisited: paradoxes in the appreciation of drug experiences and their effects on creativity. | 2002-11-09 |
|
| Hallucinogens and redemption. | 2002-11-09 |
|
| Poisoning in children 5: rare and dangerous poisons. | 2002-11 |
|
| Comparison of EMIT II, CEDIA, and DPC RIA assays for the detection of lysergic acid diethylamide in forensic urine samples. | 2002-10 |
|
| The effects of psychotomimetics and psychomotor stimulants on two schedules promoting response switching in the rat. | 2002-10 |
|
| Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioral effects overlap its other properties in rats. | 2002-10 |
|
| Hallucinogens and Drosophila: linking serotonin receptor activation to behavior. | 2002 |
|
| Flashback and Hallucinogen Persisting Perception Disorder: clinical aspects and pharmacological treatment approach. | 2002 |
|
| LSD-induced Hallucinogen Persisting Perception Disorder with depressive features treated with reboxetine: case report. | 2002 |
|
| PERSISTENCE OF LYSERGIC ACID DIETHYLAMIDE IN THE PLASMA OF HUMAN SUBJECTS. | 1964-09-01 |
|
| Psychopathology and psychophysiology of minimal LSD-25 dosage; a preliminary dosage-response spectrum. | 1958-02 |
|
| [Chemical structure and lysergic acid derivative psychoses]. | 1956-08-09 |
Patents
Sample Use Guides
Lysergide (LSD) is active at doses from about 20 ug. Typical doses are now about 20 to 80 ug although, in the past, doses as high as 300 ug were common.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8819525
Curator's Comment: Low concentrations of both LSD (3-100 nM) and the phenethylamine hallucinogen 1-(2,5-dimethoxy-4-iodophenyl-2-aminopropane (DOI; 0.3-10 uM) on rat piriform cortical interneurons that were excited by 5-HT were studied.
Lysergide (LSD) (3-100 nM) and DOI (0.3-10 uM) excited almost every cell excited by 5-HT. The maximal excitation achieved with LSD and DOI was 39% and 55% of the effect of a near-maximal 5-HT concentration (100 uM).
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
KXF3755R6D
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| Record Status |
Validated (UNII)
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| Record Version |
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PARENT -> SALT/SOLVATE |
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PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
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