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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25N3O.C4H4O4
Molecular Weight 439.5042
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of LYSERGIDE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N(CC)CC

InChI

InChIKey=PBZHMSZIBQNTPH-ZYXUSYCASA-N
InChI=1S/C20H25N3O.C4H4O4/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;5-3(6)1-2-4(7)8/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,18-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
PERSISTENCE OF LYSERGIC ACID DIETHYLAMIDE IN THE PLASMA OF HUMAN SUBJECTS.
1964 Sep-Oct
LSD-induced Hallucinogen Persisting Perception Disorder treated with clonazepam: two case reports.
2001
5-HT1A and 5-HT2 receptors differentially regulate the excitability of 5-HT-containing neurones of the guinea pig dorsal raphe nucleus in vitro.
2001 Apr 27
Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor.
2001 Dec
RNA editing of the human serotonin 5-HT2C receptor. alterations in suicide and implications for serotonergic pharmacotherapy.
2001 May
[Interferon alpha-associated agranulocytosis during clozapine treatment. Case report and status of current knowledge].
2001 Nov
EEG coherence in post-LSD visual hallucinations.
2001 Oct 1
Effects of Stealth adulterant on immunoassay testing for drugs of abuse.
2001 Sep
LSD-induced Hallucinogen Persisting Perception Disorder with depressive features treated with reboxetine: case report.
2002
Risperidone-associated, benign transient visual disturbances in schizophrenic patients with a past history of LSD abuse.
2002
Drugs of abuse monitoring in blood for control of driving under the influence of drugs.
2002 Apr
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
Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioral effects overlap its other properties in rats.
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
Discriminative stimulus properties of 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane [(+/-)DOI] in C57BL/6J mice.
2003 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
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
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
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 18:07:54 UTC 2023
Edited
by admin
on Fri Dec 15 18:07:54 UTC 2023
Record UNII
79LNZ35K7M
Record Status Validated (UNII)
Record Version
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Name Type Language
LYSERGIDE MALEATE
Common Name English
LYSERGIC ACID DIETHYLAMIDE MALEATE
Common Name English
LSD MALEATE
Common Name English
ERGOLINE-8-CARBOXAMIDE, 9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYL-, (8.BETA.)-, (2Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
Code System Code Type Description
CAS
24656-41-5
Created by admin on Fri Dec 15 18:07:54 UTC 2023 , Edited by admin on Fri Dec 15 18:07:54 UTC 2023
PRIMARY
PUBCHEM
6441445
Created by admin on Fri Dec 15 18:07:54 UTC 2023 , Edited by admin on Fri Dec 15 18:07:54 UTC 2023
PRIMARY
FDA UNII
79LNZ35K7M
Created by admin on Fri Dec 15 18:07:54 UTC 2023 , Edited by admin on Fri Dec 15 18:07:54 UTC 2023
PRIMARY
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ACTIVE MOIETY