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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25N3O
Molecular Weight 323.432
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LYSERGIDE

SMILES

CCN(CC)C(=O)[C@H]1CN(C)[C@@H]2CC3=CNC4=C3C(=CC=C4)C2=C1

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
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
Is the U.S. experiencing an incipient epidemic of hallucinogen use?
2001 Oct
RNA-editing of the 5-HT(2C) receptor alters agonist-receptor-effector coupling specificity.
2001 Sep
Effects of Stealth adulterant on immunoassay testing for drugs of abuse.
2001 Sep
Lysergic acid diethylamide-induced Fos expression in rat brain: role of serotonin-2A receptors.
2002
Exposure opportunity as a mechanism linking youth marijuana use to hallucinogen use.
2002 Apr 1
An analysis of the utility of differential outcome procedures in drug discrimination research.
2002 Jul
[Hawaiian baby woodrose: (Psycho-) Pharmacological effects of the seeds of Argyreia nervosa. A case-orientated demonstration].
2002 Sep
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
[Clinical methods in evolutional physiology].
2003 Jan-Feb
Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM.
2003 Jul
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
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
Role of the serotonin 5-HT(2A) receptor in learning.
2003 Sep-Oct
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).
Name Type Language
LSD
Preferred Name English
LYSERGIDE
HSDB   INN   MI   WHO-DD  
INN  
Official Name English
(+)-LYSERGIC ACID DIETHYLAMIDE
Common Name English
9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYL-ERGOLINE-8B-CARBOXAMIDE
Common Name English
LSD-25
Common Name English
DEXTROLYSERGIC ACID DIETHYLAMIDE
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 [INN]
Common Name English
LYSERGIDE [MI]
Common Name English
LYSERGIDE [HSDB]
Common Name English
LYSERGIC ACID DIETHYLAMIDE
Common Name English
Lysergide [WHO-DD]
Common Name English
(6aR,9R)-N,N-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
Systematic Name English
(+)-LYSERGIDE (INCB:GREEN LIST)
Common Name English
D-LSD
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66885
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
CFR 21 CFR 862.3580
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
NCI_THESAURUS C47794
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
WIKIPEDIA TiHKAL
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
DEA NO. 7315
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
Code System Code Type Description
DRUG CENTRAL
1621
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
HSDB
3920
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
CAS
50-37-3
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
INN
729
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
MERCK INDEX
m6965
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY Merck Index
CHEBI
6605
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
WIKIPEDIA
LYSERGIC ACID DIETHYLAMIDE
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
INCB IDS CODE
PL 002
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
EPA CompTox
DTXSID1023231
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
ChEMBL
CHEMBL263881
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-033-2
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
EVMPD
SUB08628MIG
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
DRUG BANK
DB04829
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
NCI_THESAURUS
C76104
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
FDA UNII
8NA5SWF92O
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
PUBCHEM
5761
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
MESH
D008238
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY
SMS_ID
100000081735
Created by admin on Wed Apr 02 07:44:38 GMT 2025 , Edited by admin on Wed Apr 02 07:44:38 GMT 2025
PRIMARY