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Lysergic acid diethylamide
Identification
- Name
- Lysergic acid diethylamide
- Accession Number
- DB04829
- Description
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 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.
- Type
- Small Molecule
- Groups
- Illicit, Investigational, Withdrawn
- Structure
Structure for Lysergic acid diethylamide (DB04829)
- Weight
- Average: 323.432
Monoisotopic: 323.199762437 - Chemical Formula
- C20H25N3O
- Synonyms
- (+)-LSD
- D-lysergic acid diethylamide
- Diethylamid kyseliny lysergove
- LSD
- LSD 25
- Lysergic acid diethylamide
- Lysergide
- Lysergidum
- Lysergsäurediäthylamid
- Lysergsäurediethylamid
- N,N-diethyl-(+)-lysergamide
- N,N-diethyl-D-lysergamide
- N,N-diethyllysergamide
Pharmacology
- Indication
- Not Available
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
Target Actions Organism U5-hydroxytryptamine receptor 1A Not Available Humans U5-hydroxytryptamine receptor 2B agonistHumans U5-hydroxytryptamine receptor 6 Not Available Humans - Absorption
Rapidly absorbed.
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
Hepatic.
- Route of elimination
- Not Available
- Half-life
3 hours
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Estimates for the lethal dosage (LD50) of LSD range from 200 µg/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.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbametapir The serum concentration of Lysergic acid diethylamide can be increased when it is combined with Abametapir. Abatacept The metabolism of Lysergic acid diethylamide can be increased when combined with Abatacept. Abiraterone The metabolism of Lysergic acid diethylamide can be decreased when combined with Abiraterone. Acebutolol Acebutolol may increase the vasoconstricting activities of Lysergic acid diethylamide. Aceclofenac The risk or severity of hypertension can be increased when Lysergic acid diethylamide is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Lysergic acid diethylamide is combined with Acemetacin. Acenocoumarol The risk or severity of adverse effects can be increased when Lysergic acid diethylamide is combined with Acenocoumarol. Acetaminophen The metabolism of Lysergic acid diethylamide can be decreased when combined with Acetaminophen. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Lysergic acid diethylamide. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Lysergic acid diethylamide. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- International/Other Brands
- Delysid (Sandoz Laboratories)
Categories
- Drug Categories
- Agents that produce hypertension
- Alkaloids
- Antidepressive Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Ergolines
- Ergot Alkaloids and Derivatives
- Hallucinogens
- Heterocyclic Compounds, Fused-Ring
- Lysergic Acid
- Neurotransmitter Agents
- Psychotropic Drugs
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT2 Receptor Agonists
- Serotonin Agents
- Serotonin Receptor Agonists
- Serotonin Receptor Antagonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Ergoline and derivatives
- Sub Class
- Lysergic acids and derivatives
- Direct Parent
- Lysergic acids and derivatives
- Alternative Parents
- Indoloquinolines / Benzoquinolines / Quinoline-3-carboxamides / Pyrroloquinolines / 3-alkylindoles / Isoindoles and derivatives / Aralkylamines / Benzenoids / Heteroaromatic compounds / Pyrroles show 8 more
- Substituents
- 3-alkylindole / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzoquinoline / Carbonyl group / Carboxamide group show 22 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organic heterotetracyclic compound, monocarboxylic acid amide, ergoline alkaloid (CHEBI:6605) / Indole alkaloids (C07542)
Chemical Identifiers
- UNII
- 8NA5SWF92O
- CAS number
- 50-37-3
- InChI Key
- VAYOSLLFUXYJDT-RDTXWAMCSA-N
- InChI
- 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
- 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
- SMILES
- [H][[email protected]@]12CC3=CNC4=CC=CC(=C34)C1=C[[email protected]](CN2C)C(=O)N(CC)CC
References
- Synthesis Reference
- US5657570
- General References
- 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. [PubMed:13497365]
- AGHAJANIAN GK, BING OH: PERSISTENCE OF LYSERGIC ACID DIETHYLAMIDE IN THE PLASMA OF HUMAN SUBJECTS. Clin Pharmacol Ther. 1964 Sep-Oct;5:611-4. [PubMed:14209776]
- 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. [PubMed:2374410]
- Nichols DE: Hallucinogens. Pharmacol Ther. 2004 Feb;101(2):131-81. [PubMed:14761703]
- 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. [PubMed:6873185]
- External Links
- KEGG Compound
- C07542
- PubChem Compound
- 5761
- PubChem Substance
- 46506397
- ChemSpider
- 5558
- BindingDB
- 21342
- ChEBI
- 6605
- ChEMBL
- CHEMBL263881
- ZINC
- ZINC000096903803
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- 7LD
- Wikipedia
- Lysergic_acid_diethylamide
- PDB Entries
- 5tvn
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Anxiety 1 2 Recruiting Treatment Anxiety Disorders / Patients 1 2 Recruiting Treatment Cluster Headache 1 2 Recruiting Treatment Major Depressive Disorder (MDD) 1 1 Completed Other Healthy Volunteers 1 1 Not Yet Recruiting Basic Science Healthy Volunteers 1 0 Completed Basic Science Healthy Volunteers 4 0 Recruiting Basic Science Healthy Volunteers 1 Not Available Completed Basic Science Healthy Volunteers 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 82.5 °C PhysProp logP 2.95 HANSCH,C ET AL. (1995) pKa 7.8 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.27 mg/mL ALOGPS logP 3.3 ALOGPS logP 2.28 ChemAxon logS -3.1 ALOGPS pKa (Strongest Acidic) 17.02 ChemAxon pKa (Strongest Basic) 7.98 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 39.34 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 98.73 m3·mol-1 ChemAxon Polarizability 37.54 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9775 Caco-2 permeable - 0.5938 P-glycoprotein substrate Substrate 0.7616 P-glycoprotein inhibitor I Inhibitor 0.8066 P-glycoprotein inhibitor II Inhibitor 0.7347 Renal organic cation transporter Inhibitor 0.5699 CYP450 2C9 substrate Non-substrate 0.8544 CYP450 2D6 substrate Non-substrate 0.6804 CYP450 3A4 substrate Substrate 0.7593 CYP450 1A2 substrate Non-inhibitor 0.5399 CYP450 2C9 inhibitor Non-inhibitor 0.8509 CYP450 2D6 inhibitor Inhibitor 0.6612 CYP450 2C19 inhibitor Non-inhibitor 0.8438 CYP450 3A4 inhibitor Non-inhibitor 0.6198 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.629 Ames test AMES toxic 0.634 Carcinogenicity Non-carcinogens 0.9157 Biodegradation Not ready biodegradable 0.9564 Rat acute toxicity 3.1459 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8864 hERG inhibition (predictor II) Inhibitor 0.5
Spectra
- Mass Spec (NIST)
- Download (10.1 KB)
- Spectra
Spectrum Spectrum Type Splash Key GC-MS Spectrum - EI-B GC-MS splash10-00di-2974000000-f1e2685ff289086cda8e Mass Spectrum (Electron Ionization) MS splash10-00di-1894000000-61a7a87f966b104602ec Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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...
- Gene Name
- HTR1A
- Uniprot ID
- P08908
- Uniprot Name
- 5-hydroxytryptamine receptor 1A
- Molecular Weight
- 46106.335 Da
References
- AGHAJANIAN GK, BING OH: PERSISTENCE OF LYSERGIC ACID DIETHYLAMIDE IN THE PLASMA OF HUMAN SUBJECTS. Clin Pharmacol Ther. 1964 Sep-Oct;5:611-4. [PubMed:14209776]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- 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...
- Gene Name
- HTR2B
- Uniprot ID
- P41595
- Uniprot Name
- 5-hydroxytryptamine receptor 2B
- Molecular Weight
- 54297.41 Da
References
- 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. [PubMed:14659797]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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 ...
- Gene Name
- HTR6
- Uniprot ID
- P50406
- Uniprot Name
- 5-hydroxytryptamine receptor 6
- Molecular Weight
- 46953.625 Da
References
- 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. [PubMed:21866910]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Yu AM: Indolealkylamines: biotransformations and potential drug-drug interactions. AAPS J. 2008 Jun;10(2):242-53. doi: 10.1208/s12248-008-9028-5. Epub 2008 May 3. [PubMed:18454322]
Drug created on September 11, 2007 14:49 / Updated on June 30, 2020 20:40
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