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-JDQBHMBOSA-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-/m10/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 |
---|---|---|
Acute injection of drugs with low addictive potential (delta(9)-tetrahydrocannabinol, 3,4-methylenedioxymethamphetamine, lysergic acid diamide) causes a much higher c-fos expression in limbic brain areas than highly addicting drugs (cocaine and morphine). | 1999 Aug 25 |
|
Reconstitution of human 5-hydroxytryptamine5A receptor--G protein coupling in E. coli and Sf9 cell membranes with membranes from Sf9 cells expressing mammalian G proteins. | 2001 |
|
[Pharmacokinetic and toxicokinetic parameters of some drugs of abuse]. | 2001 |
|
Determination of LSD in urine with high-performance liquid chromatography--mass spectrometry. | 2001 Aug |
|
Binding of [3H]paroxetine to serotonin uptake sites and of [3H]lysergic acid diethylamide to 5-HT2A receptors in platelets from women with premenstrual dysphoric disorder during gonadotropin releasing hormone treatment. | 2001 Aug |
|
Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor. | 2001 Dec |
|
Determination of LSD and its metabolites in human biological fluids by high-performance liquid chromatography with electrospray tandem mass spectrometry. | 2001 Dec 5 |
|
Solid phase synthesis of sulphonamides: novel ligands of 5-HT6 receptors. | 2001 Jul |
|
Lysergic acid diethylamide. | 2001 Jul-Aug |
|
Serotonergic function in major depression and effect of sertraline and paroxetine treatment. | 2001 Mar |
|
EEG coherence in post-LSD visual hallucinations. | 2001 Oct 1 |
|
RNA-editing of the 5-HT(2C) receptor alters agonist-receptor-effector coupling specificity. | 2001 Sep |
|
Flashback and Hallucinogen Persisting Perception Disorder: clinical aspects and pharmacological treatment approach. | 2002 |
|
Immunoassay screening of lysergic acid diethylamide (LSD) and its confirmation by HPLC and fluorescence detection following LSD ImmunElute extraction. | 2002 Apr |
|
The serotonergic system and mysticism: could LSD and the nondrug-induced mystical experience share common neural mechanisms? | 2002 Jul-Sep |
|
Higher expression of serotonin 5-HT(2A) receptors in the postmortem brains of teenage suicide victims. | 2002 Mar |
|
NHS settles claim of patients treated with LSD. | 2002 Mar 2 |
|
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 |
|
Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioral effects overlap its other properties in rats. | 2002 Oct |
|
Discriminative stimulus properties of 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane [(+/-)DOI] in C57BL/6J mice. | 2003 Feb |
|
[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 |
|
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 |
|
Salvinorin A: the "magic mint" hallucinogen finds a molecular target in the kappa opioid receptor. | 2003 Mar |
|
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 |
|
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 |
|
Role of the serotonin 5-HT(2A) receptor in learning. | 2003 Sep-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
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admin
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Edited
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Record UNII |
7WNP51KA7M
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Record Status |
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Record Version |
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208570
Created by
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |