U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 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-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

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
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
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
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
Effects of long-term lithium treatment on monoaminergic functions in major depression.
2001 Dec 15
Solid phase synthesis of sulphonamides: novel ligands of 5-HT6 receptors.
2001 Jul
A case study of space-time distortion during a total lunar eclipse following street use of LSD.
2001 Jul-Sep
[Interferon alpha-associated agranulocytosis during clozapine treatment. Case report and status of current knowledge].
2001 Nov
Is the U.S. experiencing an incipient epidemic of hallucinogen use?
2001 Oct
Effect of LSD on prepulse inhibition and spontaneous behavior in the rat. A pharmacological analysis and comparison between two rat strains.
2001 Oct
Effects of Stealth adulterant on immunoassay testing for drugs of abuse.
2001 Sep
Influence of postmenopausal hormone replacement therapy on platelet serotonin uptake site and serotonin 2A receptor binding.
2001 Sep
LSD-induced Hallucinogen Persisting Perception Disorder with depressive features treated with reboxetine: case report.
2002
Exposure opportunity as a mechanism linking youth marijuana use to hallucinogen use.
2002 Apr 1
Chemical casualties. Centrally acting incapacitants.
2002 Dec
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
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
NHS settles claim of patients treated with LSD.
2002 Mar 2
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
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
Prevalence and risk factors for LSD use among young women.
2003 Apr
Discovering risperidone: the LSD model of psychopathology.
2003 Apr
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
[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
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
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
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
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 Dec 15 15:09:44 GMT 2023
Edited
by admin
on Fri Dec 15 15:09:44 GMT 2023
Record UNII
KXF3755R6D
Record Status Validated (UNII)
Record Version
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Name Type Language
LYSERGIDE TARTRATE
Common Name English
LYSERGIC ACID DIETHYLAMIDE BITARTRATE
Common Name English
Lysergic Acid Diethylamide Tartrate
Common Name English
ERGOLINE-8-CARBOXAMIDE, 9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYL-, (8.BETA.)-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1)
Systematic Name English
ERGOLINE-8-CARBOXAMIDE, 9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYL-, (8.BETA.)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (1:1)
Systematic Name English
LSD BITARTRATE
Common Name English
Code System Code Type Description
FDA UNII
KXF3755R6D
Created by admin on Fri Dec 15 15:09:45 GMT 2023 , Edited by admin on Fri Dec 15 15:09:45 GMT 2023
PRIMARY
CAS
113-41-7
Created by admin on Fri Dec 15 15:09:45 GMT 2023 , Edited by admin on Fri Dec 15 15:09:45 GMT 2023
PRIMARY
PUBCHEM
161116
Created by admin on Fri Dec 15 15:09:45 GMT 2023 , Edited by admin on Fri Dec 15 15:09:45 GMT 2023
PRIMARY
EVMPD
SUB184889
Created by admin on Fri Dec 15 15:09:45 GMT 2023 , Edited by admin on Fri Dec 15 15:09:45 GMT 2023
PRIMARY
SMS_ID
100000170666
Created by admin on Fri Dec 15 15:09:45 GMT 2023 , Edited by admin on Fri Dec 15 15:09:45 GMT 2023
PRIMARY
INCB IDS CODE
PL 002
Created by admin on Fri Dec 15 15:09:45 GMT 2023 , Edited by admin on Fri Dec 15 15:09:45 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY