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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
Structure of LYSERGIDE D-TARTRATE

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

HIDE SMILES / InChI

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.

Originator

Curator's Comment: Lysergide (LSD) was first synthesised by Albert Hoffman while working for Sandoz Laboratories in Basel in 1938.

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.1 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
20.3 ng × h/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.5 h
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
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

OverviewOther

Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
[Chemical structure and lysergic acid derivative psychoses].
1956 Aug 9
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
LSD-induced Hallucinogen Persisting Perception Disorder treated with clonazepam: two case reports.
2001
Human 5-HT(5) receptors: the 5-HT(5A) receptor is functional but the 5-HT(5B) receptor was lost during mammalian evolution.
2001 Apr 27
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
Selective and divergent regulation of cortical 5-HT(2A) receptors in rabbit.
2001 Dec
Solid phase synthesis of sulphonamides: novel ligands of 5-HT6 receptors.
2001 Jul
Improvement of hallucinogen persisting perception disorder by treatment with a combination of fluoxetine and olanzapine: case report.
2001 Jun
Serotonergic function in major depression and effect of sertraline and paroxetine treatment.
2001 Mar
Is the U.S. experiencing an incipient epidemic of hallucinogen use?
2001 Oct
Hallucinogens and Drosophila: linking serotonin receptor activation to behavior.
2002
[Current drugs. New clinical problems].
2002
Risperidone-associated, benign transient visual disturbances in schizophrenic patients with a past history of LSD abuse.
2002
LSD therapy in Dutch psychiatry: changing socio-political settings and medical sets.
2002 Apr
Immunoassay screening of lysergic acid diethylamide (LSD) and its confirmation by HPLC and fluorescence detection following LSD ImmunElute extraction.
2002 Apr
Drugs of abuse monitoring in blood for control of driving under the influence of drugs.
2002 Apr
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
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
LC-mS analysis of human urine specimens for 2-oxo-3-hydroxy LSD: method validation for potential interferants and stability study of 2-oxo-3-hydroxy LSD under various storage conditions.
2002 May-Jun
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
Substituted hexahydrobenzodipyrans as 5-HT2A/2C receptor probes.
2002 Oct
Short-term stability of lysergic acid diethylamide (LSD), N-desmethyl-LSD, and 2-oxo-3-hydroxy-LSD in urine, assessed by liquid chromatography-tandem mass spectrometry.
2002 Sep
Differential activation of Gq/11 and Gi(3) proteins at 5-hydroxytryptamine(2C) receptors revealed by antibody capture assays: influence of receptor reserve and relationship to agonist-directed trafficking.
2002 Sep
Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD).
2002 Sep 12
A common oscillator for perceptual rivalries?
2003
Discovering risperidone: the LSD model of psychopathology.
2003 Apr
Use of dynamically coated capillaries with added cyclodextrins for the analysis of opium using capillary electrophoresis.
2003 Jan 10
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
Case report: an ingestion of Hawaiian Baby Woodrose seeds associated with acute psychosis.
2003 Jun
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
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
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
Transcriptome fingerprints distinguish hallucinogenic and nonhallucinogenic 5-hydroxytryptamine 2A receptor agonist effects in mouse somatosensory cortex.
2003 Oct 1
Patents

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
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 Fri Dec 15 15:08:28 GMT 2023
Edited
by admin
on Fri Dec 15 15:08:28 GMT 2023
Record UNII
7WNP51KA7M
Record Status Validated (UNII)
Record Version
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Name Type Language
LYSERGIDE D-TARTRATE
Common Name English
ERGOLINE-8-CARBOXAMIDE, 9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYL-, (8.BETA.)-, (S-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1)
Systematic Name English
LYSERGIC ACID DIETHYLAMIDE D-TARTRATE
Common Name English
D-LYSERGIC ACID DIETHYLAMIDE D-TARTRATE
Common Name English
LSD D-(-)-TARTRATE
Common Name English
ERGOLINE-8-CARBOXAMIDE, 9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYL-, (8.BETA.)-, (2S,3S)-2,3-DIHYDROXYBUTANEDIOATE (1:1)
Systematic Name English
ERGOLINE-8.BETA.-CARBOXAMIDE, 9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYL-, (-)-TARTRATE (1:1)
Common Name English
Code System Code Type Description
CAS
32426-57-6
Created by admin on Fri Dec 15 15:08:28 GMT 2023 , Edited by admin on Fri Dec 15 15:08:28 GMT 2023
PRIMARY
FDA UNII
7WNP51KA7M
Created by admin on Fri Dec 15 15:08:28 GMT 2023 , Edited by admin on Fri Dec 15 15:08:28 GMT 2023
PRIMARY
PUBCHEM
208570
Created by admin on Fri Dec 15 15:08:28 GMT 2023 , Edited by admin on Fri Dec 15 15:08:28 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY