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
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
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL214 |
0.003 µM [Ki] | ||
Target ID: CHEMBL224 |
0.004 µM [Ki] | ||
Target ID: CHEMBL225 |
0.015 µM [Ki] | ||
Target ID: CHEMBL3371 |
6.31 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/ |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive [IC50 0.9296 uM] | ||||
inconclusive [IC50 23.1093 uM] | ||||
inconclusive [IC50 82.8488 uM] | ||||
inconclusive [IC50 82.8488 uM] | ||||
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
PERSISTENCE OF LYSERGIC ACID DIETHYLAMIDE IN THE PLASMA OF HUMAN SUBJECTS. | 1964 Sep-Oct |
|
[Pharmacokinetic and toxicokinetic parameters of some drugs of abuse]. | 2001 |
|
Evaluation of ODS-AQ stationary phase for use in capillary electrochromatography. | 2001 Apr |
|
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 |
|
A case study of space-time distortion during a total lunar eclipse following street use of LSD. | 2001 Jul-Sep |
|
Association of a 5-HT(5A) receptor polymorphism, Pro15Ser, to schizophrenia. | 2001 Mar |
|
[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 |
|
RNA-editing of the 5-HT(2C) receptor alters agonist-receptor-effector coupling specificity. | 2001 Sep |
|
Hallucinogens and Drosophila: linking serotonin receptor activation to behavior. | 2002 |
|
Lysergic acid diethylamide-induced Fos expression in rat brain: role of serotonin-2A receptors. | 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 |
|
Exposure opportunity as a mechanism linking youth marijuana use to hallucinogen use. | 2002 Apr 1 |
|
The hallucinogen d-lysergic acid diethylamide (d-LSD) induces the immediate-early gene c-Fos in rat forebrain. | 2002 Dec 27 |
|
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 |
|
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 |
|
Higher expression of serotonin 5-HT(2A) receptors in the postmortem brains of teenage suicide victims. | 2002 Mar |
|
NHS settles claim of patients treated with LSD. | 2002 Mar 2 |
|
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 |
|
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 |
|
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 |
|
Prevalence and risk factors for LSD use among young women. | 2003 Apr |
|
D-cycloserine-Naloxone interactions in opioid-dependent humans under a novel-response naloxone discrimination procedure. | 2003 Aug |
|
Discriminative stimulus properties of 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane [(+/-)DOI] in C57BL/6J mice. | 2003 Feb |
|
[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 |
|
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 |
|
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 |
|
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8819525
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
Edited
Fri Dec 15 18:07:54 GMT 2023
by
admin
on
Fri Dec 15 18:07:54 GMT 2023
|
Record UNII |
79LNZ35K7M
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
24656-41-5
Created by
admin on Fri Dec 15 18:07:54 GMT 2023 , Edited by admin on Fri Dec 15 18:07:54 GMT 2023
|
PRIMARY | |||
|
6441445
Created by
admin on Fri Dec 15 18:07:54 GMT 2023 , Edited by admin on Fri Dec 15 18:07:54 GMT 2023
|
PRIMARY | |||
|
79LNZ35K7M
Created by
admin on Fri Dec 15 18:07:54 GMT 2023 , Edited by admin on Fri Dec 15 18:07:54 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE | |||
|
PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |