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.[H][C@@]12CC3=CNC4=C3C(=CC=C4)C1=C[C@H](CN2C)C(=O)N(CC)CC
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 | C4H6O6 |
Molecular Weight | 150.0868 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
---|---|---|
Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors. | 2000 Feb |
|
LSD-induced Hallucinogen Persisting Perception Disorder treated with clonazepam: two case reports. | 2001 |
|
[Pharmacokinetic and toxicokinetic parameters of some drugs of abuse]. | 2001 |
|
A 5-HT(7) receptor-mediated depolarization in the anterodorsal thalamus. I. Pharmacological characterization. | 2001 Apr |
|
Serotonergic function in major depression and effect of sertraline and paroxetine treatment. | 2001 Mar |
|
EEG coherence in post-LSD visual hallucinations. | 2001 Oct 1 |
|
LSD-induced Hallucinogen Persisting Perception Disorder with depressive features treated with reboxetine: case report. | 2002 |
|
LSD therapy in Dutch psychiatry: changing socio-political settings and medical sets. | 2002 Apr |
|
False-positive lysergic acid diethylamide immunoassay screen associated with fentanyl medication. | 2002 Jan |
|
An analysis of the utility of differential outcome procedures in drug discrimination research. | 2002 Jul |
|
A single dose of lysergic acid diethylamide influences gene expression patterns within the mammalian brain. | 2002 May |
|
Poisoning in children 5: rare and dangerous poisons. | 2002 Nov |
|
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 |
|
[Hawaiian baby woodrose: (Psycho-) Pharmacological effects of the seeds of Argyreia nervosa. A case-orientated demonstration]. | 2002 Sep |
|
A common oscillator for perceptual rivalries? | 2003 |
|
Discovering risperidone: the LSD model of psychopathology. | 2003 Apr |
|
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 |
|
Dynamic changes in prefrontal cortex gene expression following lysergic acid diethylamide administration. | 2003 Mar 17 |
|
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 |
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 15:09:44 GMT 2023
by
admin
on
Fri Dec 15 15:09:44 GMT 2023
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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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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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