Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H25N3O.C4H4O4 |
Molecular Weight | 439.5042 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C/C(O)=O.[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N(CC)CC
InChI
InChIKey=PBZHMSZIBQNTPH-ZYXUSYCASA-N
InChI=1S/C20H25N3O.C4H4O4/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;5-3(6)1-2-4(7)8/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,18-;/m1./s1
Molecular Formula | C4H4O4 |
Molecular Weight | 116.0722 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
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 |
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 |
---|---|---|
Evaluation of ODS-AQ stationary phase for use in capillary electrochromatography. | 2001 Apr |
|
5-HT1A and 5-HT2 receptors differentially regulate the excitability of 5-HT-containing neurones of the guinea pig dorsal raphe nucleus in vitro. | 2001 Apr 27 |
|
Determination of LSD and its metabolites in human biological fluids by high-performance liquid chromatography with electrospray tandem mass spectrometry. | 2001 Dec 5 |
|
Hallucinogens and Drosophila: linking serotonin receptor activation to behavior. | 2002 |
|
Risperidone-associated, benign transient visual disturbances in schizophrenic patients with a past history of LSD abuse. | 2002 |
|
Exposure opportunity as a mechanism linking youth marijuana use to hallucinogen use. | 2002 Apr 1 |
|
Identification of a dopamine receptor from Caenorhabditis elegans. | 2002 Feb 8 |
|
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 |
|
A common oscillator for perceptual rivalries? | 2003 |
|
Prevalence and risk factors for LSD use among young women. | 2003 Apr |
|
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 |
|
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 |
|
Acute effects of drugs of abuse. | 2003 Mar-Apr |
|
Pharmacological characterization of a serotonin receptor (5-HT7) stimulating cAMP production in human corneal epithelial cells. | 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 |
|
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).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:07:54 GMT 2023
by
admin
on
Fri Dec 15 18:07:54 GMT 2023
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Record UNII |
79LNZ35K7M
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Record Status |
Validated (UNII)
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Record Version |
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |