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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25N3O
Molecular Weight 323.4328
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LYSERGIDE

SMILES

CCN(CC)C(=O)[C@]1([H])C=C2c3cccc4c3c(C[C@@]2([H])N(C)C1)c[nH]4

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

HIDE SMILES / InChI

Molecular Formula C20H25N3O
Molecular Weight 323.4328
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
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

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 Jun 25 20:33:14 UTC 2021
Edited
by admin
on Fri Jun 25 20:33:14 UTC 2021
Record UNII
8NA5SWF92O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LYSERGIDE
HSDB   INN   MI   WHO-DD  
INN  
Official Name English
9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYL-ERGOLINE-8B-CARBOXAMIDE
Common Name English
LSD-25
Common Name English
(8.BETA.)-9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYLERGOLINE-8-CARBOXAMIDE
Systematic Name English
ERGOLINE-8-CARBOXAMIDE, 9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYL-, (5.BETA., 8.BETA.)-
Common Name English
N,N-DIETHYLLYSERGAMIDE
Common Name English
LYSERGIDE [WHO-DD]
Common Name English
LYSERGIDE [INN]
Common Name English
LYSERGIDE [MI]
Common Name English
LYSERGIDE [HSDB]
Common Name English
LYSERGIC ACID DIETHYLAMIDE
Common Name English
LSD
Code English
LYSERGIC ACID DIETHYLAMIDE TARTRATE CI
USP-RS  
Common Name English
(+)-LYSERGIDE [INCB:GREEN LIST]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66885
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
CFR 21 CFR 862.3580
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
NCI_THESAURUS C47794
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
DEA NO. 7315
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
Code System Code Type Description
DRUG CENTRAL
1621
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
HSDB
3920
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
CAS
50-37-3
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
INN
729
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
MERCK INDEX
M6965
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
LYSERGIC ACID DIETHYLAMIDE
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
INCB IDS CODE
PL 002
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
EPA CompTox
50-37-3
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
ChEMBL
CHEMBL263881
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-033-2
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
EVMPD
SUB08628MIG
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
DRUG BANK
DB04829
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
NCI_THESAURUS
C76104
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
FDA UNII
8NA5SWF92O
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
PUBCHEM
5761
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
MESH
D008238
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
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SALT/SOLVATE -> PARENT
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METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
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ACTIVE MOIETY