Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H25N3O |
Molecular Weight | 323.432 |
Optical Activity | ( + ) |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC3=CNC4=C3C(=CC=C4)C1=C[C@H](CN2C)C(=O)N(CC)CC
InChI
InChIKey=VAYOSLLFUXYJDT-RDTXWAMCSA-N
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
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 |
---|---|---|
[Chemical structure and lysergic acid derivative psychoses]. | 1956 Aug 9 |
|
Psychopathology and psychophysiology of minimal LSD-25 dosage; a preliminary dosage-response spectrum. | 1958 Feb |
|
PERSISTENCE OF LYSERGIC ACID DIETHYLAMIDE IN THE PLASMA OF HUMAN SUBJECTS. | 1964 Sep-Oct |
|
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 |
|
Chemical casualties. Centrally acting incapacitants. | 2002 Dec |
|
The hallucinogen d-lysergic acid diethylamide (d-LSD) induces the immediate-early gene c-Fos in rat forebrain. | 2002 Dec 27 |
|
The serotonergic system and mysticism: could LSD and the nondrug-induced mystical experience share common neural mechanisms? | 2002 Jul-Sep |
|
Jekyll and Hyde revisited: paradoxes in the appreciation of drug experiences and their effects on creativity. | 2002 Jul-Sep |
|
Hallucinogens and redemption. | 2002 Jul-Sep |
|
Poisoning in children 5: rare and dangerous poisons. | 2002 Nov |
|
Comparison of EMIT II, CEDIA, and DPC RIA assays for the detection of lysergic acid diethylamide in forensic urine samples. | 2002 Oct |
|
The effects of psychotomimetics and psychomotor stimulants on two schedules promoting response switching in the rat. | 2002 Oct |
|
Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioral effects overlap its other properties in rats. | 2002 Oct |
|
A common oscillator for perceptual rivalries? | 2003 |
|
Prevalence and risk factors for LSD use among young women. | 2003 Apr |
|
Discovering risperidone: the LSD model of psychopathology. | 2003 Apr |
|
D-cycloserine-Naloxone interactions in opioid-dependent humans under a novel-response naloxone discrimination procedure. | 2003 Aug |
|
Characterization of the discriminative stimulus properties of centrally administered (-)-DOM and LSD. | 2003 Feb |
|
Discriminative stimulus properties of 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane [(+/-)DOI] in C57BL/6J mice. | 2003 Feb |
|
Effect of loxapine on peripheral dopamine-like and serotonin receptors in patients with schizophrenia. | 2003 Jan |
|
Use of dynamically coated capillaries with added cyclodextrins for the analysis of opium using capillary electrophoresis. | 2003 Jan 10 |
|
[Clinical methods in evolutional physiology]. | 2003 Jan-Feb |
|
A selective and sensitive method for quantitation of lysergic acid diethylamide (LSD) in whole blood by gas chromatography-ion trap tandem mass spectrometry. | 2003 Jan-Feb |
|
Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM. | 2003 Jul |
|
Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands. | 2003 Jul 31 |
|
Case report: an ingestion of Hawaiian Baby Woodrose seeds associated with acute psychosis. | 2003 Jun |
|
The effective treatment of acne vulgaris by a high-intensity, narrow band 405-420 nm light source. | 2003 Jun |
|
Effects of autoshaping procedures on 3H-8-OH-DPAT-labeled 5-HT1a binding and 125I-LSD-labeled 5-HT2a binding in rat brain. | 2003 Jun 13 |
|
Blue light (clearlight) for acne vulgaris. | 2003 Jun 23 |
|
Enhancing action of LSD on neuronal responsiveness to serotonin in a brain structure involved in obsessive-compulsive disorder. | 2003 Mar |
|
Persisting visual hallucinations and illusions in previously drug-addicted patients. | 2003 Mar |
|
Determination of lysergic acid diethylamide (LSD) in mouse blood by capillary electrophoresis/ fluorescence spectroscopy with sweeping techniques in micellar electrokinetic chromatography. | 2003 Mar |
|
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 Mar |
|
Salvinorin A: the "magic mint" hallucinogen finds a molecular target in the kappa opioid receptor. | 2003 Mar |
|
Clonazepam treatment of lysergic acid diethylamide-induced hallucinogen persisting perception disorder with anxiety features. | 2003 Mar |
|
Creation, expression, and characterization of a constitutively active mutant of the human serotonin 5-HT6 receptor. | 2003 Mar |
|
Hallucinogen persisting perception disorder: what do we know after 50 years? | 2003 Mar 1 |
|
Dynamic changes in prefrontal cortex gene expression following lysergic acid diethylamide administration. | 2003 Mar 17 |
|
Acute effects of drugs of abuse. | 2003 Mar-Apr |
|
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 May |
|
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 May-Jun |
|
Pharmacological characterization of a serotonin receptor (5-HT7) stimulating cAMP production in human corneal epithelial cells. | 2003 Nov |
|
Serotonin receptors in platelets of bipolar and schizoaffective patients: effect of lithium treatment. | 2003 Nov |
|
LC-MS analysis of 2-oxo-3-hydroxy LSD from urine using a Speedisk positive-pressure processor with Cerex PolyChrom CLIN II columns. | 2003 Oct |
|
Transcriptome fingerprints distinguish hallucinogenic and nonhallucinogenic 5-hydroxytryptamine 2A receptor agonist effects in mouse somatosensory cortex. | 2003 Oct 1 |
|
Biochemical outcome of blocking the ergot alkaloid pathway of a grass endophyte. | 2003 Oct 22 |
|
Role of the serotonin 5-HT(2A) receptor in learning. | 2003 Sep-Oct |
|
Serotonergic/glutamatergic interactions: the effects of mGlu2/3 receptor ligands in rats trained with LSD and PCP as discriminative stimuli. | 2004 Mar |
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).
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C66885
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CFR |
21 CFR 862.3580
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NCI_THESAURUS |
C47794
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WIKIPEDIA |
TiHKAL
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DEA NO. |
7315
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1621
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3920
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50-37-3
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m6965
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6605
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LYSERGIC ACID DIETHYLAMIDE
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PL 002
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DTXSID1023231
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CHEMBL263881
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200-033-2
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SUB08628MIG
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DB04829
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C76104
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8NA5SWF92O
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5761
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D008238
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100000081735
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
PRODRUG (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)