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Record Information
Version2.0
Creation Date2009-08-12 19:36:03 UTC
Update Date2014-12-24 20:26:10 UTC
Accession NumberT3D3582
Identification
Common NameLysergic Acid Diethylamide
ClassSmall Molecule
DescriptionLysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family. It was first synthesized by Albert Hofmann in 1938 from ergot, a grain fungus that typically grows on rye. LSD is non-addictive and non-toxic. It is well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, a sense of time distortion, ego death and spiritual experiences, as well as for its key role in 1960s counterculture. It is used mainly by psychonauts as an entheogen, recreational drug and as an agent in psychedelic therapy. (9). Debate continues over the nature and causes of chronic flashbacks. Explanations in terms of LSD physically remaining in the body for months or years after consumption have been discounted by experimental evidence. Some say Hallucinogen persisting perception disorder (HPPD) is a manifestation of post-traumatic stress disorder, not related to the direct action of LSD on brain chemistry, and varies according to the susceptibility of the individual to the disorder. Many emotionally intense experiences can lead to flashbacks when a person is reminded acutely of the original experience. However, not all published case reports of chronic flashbacks appear to describe an anxious hyper-vigilant state reminiscent of post-traumatic stress disorder.
Compound Type
  • Amide
  • Amine
  • Drug
  • Hallucinogen
  • Hypnotic and Sedative
  • Organic Compound
  • Serotonin Antagonist
  • Serotonin Receptor Agonist
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(+)-LSD
(+)-lysergic acid diethylamide
9,10-Didehydro-N,N-diethyl-6-methylergoline-8b-carboxamide
D-LSD
D-LSD-25
D-lysergic acid dethylamide
D-lysergic acid diethylamide
D-lysergic acid n,n-diethylamide
Delysid
Dextrolysergic acid diethylamide
Diethylamid kyseliny lysergove
LSD
LSD-25
Lysergamid
Lysergamide
Lysergate diethylamide
Lysergaure diethylamid
Lysergic acid amide
Lysergic acid diethylamide
Lysergic acid diethylamide-25
Lysergide
Lysergidum
n,n-diethyl-(+)-lysergamide
N,N-Diethyl-6-methyl-9,10-didehydroergoline-8-carboxamide
N,n-diethyl-d-lysergamide
N,n-diethyllysergamide
Chemical FormulaC20H25N3O
Average Molecular Mass323.432 g/mol
Monoisotopic Mass323.200 g/mol
CAS Registry Number50-37-3
IUPAC Name(4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
Traditional Namelysergic acid diethylamide
SMILES[H][C@@]1(CN(C)[C@]2([H])CC3=CNC4=CC=CC(=C34)C2=C1)C(=O)N(CC)CC
InChI IdentifierInChI=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
InChI KeyInChIKey=VAYOSLLFUXYJDT-RDTXWAMCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lysergic acids and derivatives. These are alkaloids with a structure based on the lysergic acid skeleton.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassErgoline and derivatives
Sub ClassLysergic acids and derivatives
Direct ParentLysergic acids and derivatives
Alternative Parents
Substituents
  • Lysergic acid or derivatives
  • Indoloquinoline
  • Benzoquinoline
  • Pyrroloquinoline
  • Quinoline-3-carboxamide
  • Quinoline
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Isoindole or derivatives
  • Aralkylamine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxamide group
  • Amino acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point82.5°C
Boiling PointNot Available
Solubility2.70e-01 mg/mL
LogP2.95
Predicted Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
logP3.3ALOGPS
logP2.28ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)17.02ChemAxon
pKa (Strongest Basic)7.98ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area39.34 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.73 m³·mol⁻¹ChemAxon
Polarizability37.54 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-2974000000-f1e2685ff289086cda8eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0039000000-0c8c5c6f20ba70601559JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-1192000000-d79836ee7c6c1c7188f9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006y-1930000000-f3842b756b9de7728012JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0019000000-8b183da29a0819eb03e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-4269000000-1ed7d38484edc8814edaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9160000000-591093e8af2970f7d331JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00di-1894000000-61a7a87f966b104602ecJSpectraViewer | MoNA
Toxicity Profile
Route of ExposureRapidly absorbed. Oral (usually on a substrate such as absorbent blotter paper, a sugar cube, or gelatin) (9); Intramuscular or intravenous injection (9)
Mechanism of ToxicityLSD preferentially inhibits serotonergic cell firing by acting as an agonist at the 5-HT1A receptors in the raphe nuclei, locus coeruleus, and cortex. It also acts as a partial agonist on the postsynaptic 5-HT1A site and has high affinity for the other 5-HT1 subtypes 5-HT1B, 5-HT1D, and 5-HT1E. LSD's hallucinogenic effects are caused by its ability to act as a partial agonist at the 5-HT2A receptor, especially on neocortical pyramidal cells. Activation of 5-HT2A also leads to increased cortical glutamate levels. Effects of LSD on 5-HT2C, 5-HT5A, 5-HT6, and 5-HT7 receptors have also been described, but their significance remains uncertain. In addition, LSD shows agonistic and antagonistic behavior at the central dopamine D1 and D2-receptors. (9, 8)
MetabolismLSD's effects normally last from 6 - 12 hours depending on dosage, tolerance, body weight and age. Its half-life in humans is 175 min. It is metabolized in the liver by NADH-dependent microsomal enzymes and its metabolites may be quantified in the urine. The major metabolite is 2-oxy-3-hydroxy-LSD. Other metabolites include 2-oxy-LSD, LAE, nor-LSD, di-hydroxy-LSD, 13- and 14-hydroxy-LSD as glucoronides, lysergic acid ethyl-2-hydroxyethylamide (LEO), and trioxylated LSD. (9, 8)
Toxicity ValuesEstimates for the lethal dosage (LD50) of LSD range from 200 ug/kg to more than 1 mg/kg of human body mass, though most sources report that there are no known human cases of such an overdose.
Lethal DoseLSD has not been known to cause death on its own. (7)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesLysergic acid diethylamide, is one of the most widely known psychedelic drugs. It has been used mainly as an entheogen, a tool to supplement various practices for transcendence, including meditation, psychonautics, art projects, and (formerly legal) psychedelic therapy, and as a recreational drug. Formally, LSD is classified as a hallucinogen of the psychedelic type. (9)
Minimum Risk LevelNot Available
Health EffectsChronic effects of LSD toxicity include flashbacks, psychosis, and exacerbation of latent mental disorders, particularly schizophrenia. Overdosage can result in “bad trips” that are characterized by intense anxiety, combativeness, confusion, and panic attacks. LSD is not considered to be addictive, and withdrawal syndrome are absent. Because of its relatively high therapeutic index, no deaths have been directly attributed to LSD use alone. (7, 9)
SymptomsLSD reliably causes pupil dilation, reduced appetite, and wakefulness. Other physical reactions to LSD are highly variable and nonspecific, and some of these reactions may be secondary to the psychological effects of LSD. The following symptoms have been reported: numbness, weakness, nausea, hypothermia or hyperthermia, elevated blood sugar, goose bumps, increase in heart rate, jaw clenching, perspiration, saliva production, mucus production, sleeplessness, hyperreflexia, and tremors. LSD also causes expansion and an altered experience of senses, emotions, memories, time, and awareness. These psychological effects (colloquially called a "trip") vary greatly from person to person. Visual effects may include morphing objects, illusion of movement of static surfaces, after image-like trails of moving objects, the appearance of moving colored geometric patterns, an intensification of colors and brightness, new textures on objects, blurred vision, and shape suggestibility. The auditory effects of LSD may include echo-like distortions of sounds, changes in ability to discern concurrent auditory stimuli, and a general intensification of the experience of music. Higher doses often cause intense and fundamental distortions of sensory perception such as synaesthesia, the experience of additional spatial or temporal dimensions, and temporary dissociation. (9)
TreatmentAdverse effects of psychotropics are often treated with fast-acting benzodiazepines like diazepam or triazolam that have calming and antianxiety effects but do not directly affect the specific actions of psychotropics. Theoretically, specific 5-HT2A receptor antagonists, which most commonly means atypical antipsychotics (quetiapine, olanzapine, risperidone, etc.) or other 5-HT2A antagonist such as trazodone or mirtazapine, would be direct antidotes, although some anecdotal reports claim otherwise. (1, 9)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB04829
HMDB IDNot Available
PubChem Compound ID5761
ChEMBL IDCHEMBL263881
ChemSpider ID5558
KEGG IDC07542
UniProt IDNot Available
OMIM ID
ChEBI ID6605
BioCyc IDNot Available
CTD IDNot Available
Stitch IDLysergic Acid Diethylamide
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkLysergic_acid_diethylamide
References
Synthesis Reference

Jean-Luc Henri Sigier Emmanuel, “Device for maintaining the inner surface of gun barrels and method for producing same.” U.S. Patent US5657570, issued September, 1918.

MSDST3D3582.pdf
General References
  1. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
  2. GREINER T, BURCH NR, EDELBERG R: Psychopathology and psychophysiology of minimal LSD-25 dosage; a preliminary dosage-response spectrum. AMA Arch Neurol Psychiatry. 1958 Feb;79(2):208-10. [13497365 ]
  3. AGHAJANIAN GK, BING OH: PERSISTENCE OF LYSERGIC ACID DIETHYLAMIDE IN THE PLASMA OF HUMAN SUBJECTS. Clin Pharmacol Ther. 1964 Sep-Oct;5:611-4. [14209776 ]
  4. Nichols DE: Hallucinogens. Pharmacol Ther. 2004 Feb;101(2):131-81. [14761703 ]
  5. Papac DI, Foltz RL: Measurement of lysergic acid diethylamide (LSD) in human plasma by gas chromatography/negative ion chemical ionization mass spectrometry. J Anal Toxicol. 1990 May-Jun;14(3):189-90. [2374410 ]
  6. Jacobs BL, Heym J, Rasmussen K: Raphe neurons: firing rate correlates with size of drug response. Eur J Pharmacol. 1983 Jun 3;90(2-3):275-8. [6873185 ]
  7. Schiff PL: Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. [17149427 ]
  8. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A: The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi: 10.1111/j.1755-5949.2008.00059.x. [19040555 ]
  9. Wikipedia. Lysergic acid diethylamide. Last Updated 21 April 2010. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling inhibits adenylate cyclase activity and activates a phosphatidylinositol-calcium second messenger system that regulates the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of 5-hydroxytryptamine release and in the regulation of dopamine and 5-hydroxytryptamine metabolism. Plays a role in the regulation of dopamine and 5-hydroxytryptamine levels in the brain, and thereby affects neural activity, mood and behavior. Plays a role in the response to anxiogenic stimuli.
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular Weight:
46106.335 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.0011 uMNot AvailableBindingDB 21342
References
  1. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A: The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi: 10.1111/j.1755-5949.2008.00059.x. [19040555 ]
  2. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM: Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J Med Chem. 2002 Sep 12;45(19):4344-9. [12213075 ]
  3. Chambers JJ, Parrish JC, Jensen NH, Kurrasch-Orbaugh DM, Marona-Lewicka D, Nichols DE: Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands. J Med Chem. 2003 Jul 31;46(16):3526-35. [12877591 ]
General Function:
Virus receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction.(Microbial infection) Acts as a receptor for human JC polyomavirus/JCPyV.
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular Weight:
52602.58 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.0026 uMNot AvailableBindingDB 21342
Inhibitory0.0027 uMNot AvailableBindingDB 21342
Inhibitory0.0031 uMNot AvailableBindingDB 21342
Inhibitory0.0035 uMNot AvailableBindingDB 21342
Inhibitory0.004 uMNot AvailableBindingDB 21342
Inhibitory0.0052 uMNot AvailableBindingDB 21342
References
  1. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A: The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi: 10.1111/j.1755-5949.2008.00059.x. [19040555 ]
  2. Nichols DE, Frescas SP, Chemel BR, Rehder KS, Zhong D, Lewin AH: High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): a high-affinity 5-HT2A receptor-selective agonist radioligand. Bioorg Med Chem. 2008 Jun 1;16(11):6116-23. doi: 10.1016/j.bmc.2008.04.050. Epub 2008 Apr 25. [18468904 ]
  3. Egan C, Grinde E, Dupre A, Roth BL, Hake M, Teitler M, Herrick-Davis K: Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors. Synapse. 2000 Feb;35(2):144-50. [10611640 ]
General Function:
Serotonin receptor activity
Specific Function:
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase. It has a high affinity for tricyclic psychotropic drugs (By similarity). Controls pyramidal neurons migration during corticogenesis, through the regulation of CDK5 activity (By similarity). Is an activator of TOR signaling (PubMed:23027611).
Gene Name:
HTR6
Uniprot ID:
P50406
Molecular Weight:
46953.625 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.0069 uMNot AvailableBindingDB 21342
References
  1. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A: The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi: 10.1111/j.1755-5949.2008.00059.x. [19040555 ]
  2. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM: Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J Med Chem. 2002 Sep 12;45(19):4344-9. [12213075 ]
  3. van Loevezijn A, Venhorst J, Iwema Bakker WI, de Korte CG, de Looff W, Verhoog S, van Wees JW, van Hoeve M, van de Woestijne RP, van der Neut MA, Borst AJ, van Dongen MJ, de Bruin NM, Keizer HG, Kruse CG: N'-(arylsulfonyl)pyrazoline-1-carboxamidines as novel, neutral 5-hydroxytryptamine 6 receptor (5-HT(6)R) antagonists with unique structural features. J Med Chem. 2011 Oct 27;54(20):7030-54. doi: 10.1021/jm200466r. Epub 2011 Sep 26. [21866910 ]
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity. Regulates the release of 5-hydroxytryptamine in the brain, and thereby affects neural activity. May also play a role in regulating the release of other neurotransmitters. May play a role in vasoconstriction.
Gene Name:
HTR1D
Uniprot ID:
P28221
Molecular Weight:
41906.38 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.0039 uMNot AvailableBindingDB 21342
References
  1. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A: The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi: 10.1111/j.1755-5949.2008.00059.x. [19040555 ]
  2. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM: Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J Med Chem. 2002 Sep 12;45(19):4344-9. [12213075 ]
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various alkaloids and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity.
Gene Name:
HTR1E
Uniprot ID:
P28566
Molecular Weight:
41681.57 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.093 uMNot AvailableBindingDB 21342
References
  1. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A: The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi: 10.1111/j.1755-5949.2008.00059.x. [19040555 ]
  2. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM: Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J Med Chem. 2002 Sep 12;45(19):4344-9. [12213075 ]
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of dopamine and 5-hydroxytryptamine release, 5-hydroxytryptamine uptake and in the regulation of extracellular dopamine and 5-hydroxytryptamine levels, and thereby affects neural activity. May play a role in the perception of pain. Plays a role in the regulation of behavior, including impulsive behavior. Required for normal proliferation of embryonic cardiac myocytes and normal heart development. Protects cardiomyocytes against apoptosis. Plays a role in the adaptation of pulmonary arteries to chronic hypoxia. Plays a role in vasoconstriction. Required for normal osteoblast function and proliferation, and for maintaining normal bone density. Required for normal proliferation of the interstitial cells of Cajal in the intestine.
Gene Name:
HTR2B
Uniprot ID:
P41595
Molecular Weight:
54297.41 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.03 uMNot AvailableBindingDB 21342
References
  1. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM: Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J Med Chem. 2002 Sep 12;45(19):4344-9. [12213075 ]
  2. Blanpain C, Le Poul E, Parma J, Knoop C, Detheux M, Parmentier M, Vassart G, Abramowicz MJ: Serotonin 5-HT(2B) receptor loss of function mutation in a patient with fenfluramine-associated primary pulmonary hypertension. Cardiovasc Res. 2003 Dec 1;60(3):518-28. [14659797 ]
General Function:
Serotonin receptor activity
Specific Function:
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins.
Gene Name:
HTR5A
Uniprot ID:
P47898
Molecular Weight:
40254.69 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.009 uMNot AvailableBindingDB 21342
References
  1. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A: The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi: 10.1111/j.1755-5949.2008.00059.x. [19040555 ]
  2. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM: Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J Med Chem. 2002 Sep 12;45(19):4344-9. [12213075 ]
General Function:
Serotonin receptor activity
Specific Function:
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase.
Gene Name:
HTR7
Uniprot ID:
P34969
Molecular Weight:
53554.43 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.0066 uMNot AvailableBindingDB 21342
References
  1. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A: The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi: 10.1111/j.1755-5949.2008.00059.x. [19040555 ]
  2. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM: Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J Med Chem. 2002 Sep 12;45(19):4344-9. [12213075 ]
General Function:
G-protein coupled amine receptor activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name:
DRD5
Uniprot ID:
P21918
Molecular Weight:
52950.5 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.34 uMNot AvailableBindingDB 21342
References
  1. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A: The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi: 10.1111/j.1755-5949.2008.00059.x. [19040555 ]
  2. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM: Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J Med Chem. 2002 Sep 12;45(19):4344-9. [12213075 ]
General Function:
Potassium channel regulator activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular Weight:
50618.91 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.12 uMNot AvailableBindingDB 21342
References
  1. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A: The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi: 10.1111/j.1755-5949.2008.00059.x. [19040555 ]
  2. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM: Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J Med Chem. 2002 Sep 12;45(19):4344-9. [12213075 ]
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances, such as lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity. Arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Regulates the release of 5-hydroxytryptamine, dopamine and acetylcholine in the brain, and thereby affects neural activity, nociceptive processing, pain perception, mood and behavior. Besides, plays a role in vasoconstriction of cerebral arteries.
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular Weight:
43567.535 Da
References
  1. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A: The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi: 10.1111/j.1755-5949.2008.00059.x. [19040555 ]
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelacortin neurons and the release of CRH that then regulates the release of corticosterone. Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress. Plays a role in insulin sensitivity and glucose homeostasis.
Gene Name:
HTR2C
Uniprot ID:
P28335
Molecular Weight:
51820.705 Da
References
  1. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A: The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi: 10.1111/j.1755-5949.2008.00059.x. [19040555 ]
General Function:
Receptor signaling protein activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular Weight:
51322.1 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.14 uMNot AvailableBindingDB 21342
References
  1. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM: Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J Med Chem. 2002 Sep 12;45(19):4344-9. [12213075 ]
General Function:
G-protein coupled amine receptor activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name:
DRD1
Uniprot ID:
P21728
Molecular Weight:
49292.765 Da
References
  1. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A: The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi: 10.1111/j.1755-5949.2008.00059.x. [19040555 ]
General Function:
G-protein coupled amine receptor activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name:
DRD3
Uniprot ID:
P35462
Molecular Weight:
44224.335 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.027 uMNot AvailableBindingDB 21342
References
  1. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM: Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J Med Chem. 2002 Sep 12;45(19):4344-9. [12213075 ]
General Function:
Sh3 domain binding
Specific Function:
Dopamine receptor responsible for neuronal signaling in the mesolimbic system of the brain, an area of the brain that regulates emotion and complex behavior. Its activity is mediated by G proteins which inhibit adenylyl cyclase. Modulates the circadian rhythm of contrast sensitivity by regulating the rhythmic expression of NPAS2 in the retinal ganglion cells (By similarity).
Gene Name:
DRD4
Uniprot ID:
P21917
Molecular Weight:
48359.86 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.056 uMNot AvailableBindingDB 21342
References
  1. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM: Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J Med Chem. 2002 Sep 12;45(19):4344-9. [12213075 ]
General Function:
Histamine receptor activity
Specific Function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular Weight:
55783.61 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory1.54 uMNot AvailableBindingDB 21342
References
  1. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM: Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J Med Chem. 2002 Sep 12;45(19):4344-9. [12213075 ]