Identification

Name
Lysergic Acid Diethylamide
Accession Number
DB04829
Type
Small Molecule
Groups
Illicit, Investigational, Withdrawn
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.

Structure
Thumb
Synonyms
  • (+)-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
  • Dextrolysergic acid diethylamide
  • Diethylamid kyseliny lysergove
  • LSD
  • LSD-25
  • Lysergamid
  • Lysergamide
  • Lysergaure diethylamid
  • Lysergic acid amide
  • 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
International/Other Brands
Delysid (Sandoz Laboratories)
Categories
UNII
8NA5SWF92O
CAS number
50-37-3
Weight
Average: 323.432
Monoisotopic: 323.199762437
Chemical Formula
C20H25N3O
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][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N(CC)CC

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U5-hydroxytryptamine receptor 1ANot AvailableHuman
U5-hydroxytryptamine receptor 2B
agonist
Human
U5-hydroxytryptamine receptor 6Not AvailableHuman
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
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
DrugInteraction
(R)-warfarinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Lysergic Acid Diethylamide.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Lysergic Acid Diethylamide is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when 3,4-Methylenedioxyamphetamine is combined with Lysergic Acid Diethylamide.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Lysergic Acid Diethylamide.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineLysergic Acid Diethylamide may increase the hypertensive activities of 4-Methoxyamphetamine.
4-MethoxyamphetamineLysergic Acid Diethylamide may increase the hypertensive and vasoconstricting activities of 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Lysergic Acid Diethylamide is combined with 5-methoxy-N,N-dimethyltryptamine.
Food Interactions
Not Available

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.

US5657570
General References
  1. 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]
  2. 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]
  3. 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]
  4. Nichols DE: Hallucinogens. Pharmacol Ther. 2004 Feb;101(2):131-81. [PubMed:14761703]
  5. 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
50241702
ChEBI
6605
ChEMBL
CHEMBL263881
IUPHAR
219
Guide to Pharmacology
GtP Drug Page
HET
7LD
Wikipedia
Lysergic_acid_diethylamide
PDB Entries
5tvn

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingBasic ScienceHealthy Volunteers1
0CompletedBasic ScienceHealthy Volunteers2
0Not Yet RecruitingBasic ScienceHealthy Volunteers1
0RecruitingBasic ScienceHealthy Volunteers1
2CompletedTreatmentFeeling Anxious1
2RecruitingTreatmentAnxiety Disorders / Patients1
Not AvailableCompletedBasic ScienceHealthy Volunteers1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)82.5 °CPhysProp
logP2.95HANSCH,C ET AL. (1995)
pKa7.8SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.27 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.73 m3·mol-1ChemAxon
Polarizability37.54 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9775
Caco-2 permeable-0.5938
P-glycoprotein substrateSubstrate0.7616
P-glycoprotein inhibitor IInhibitor0.8066
P-glycoprotein inhibitor IIInhibitor0.7347
Renal organic cation transporterInhibitor0.5699
CYP450 2C9 substrateNon-substrate0.8544
CYP450 2D6 substrateNon-substrate0.6804
CYP450 3A4 substrateSubstrate0.7593
CYP450 1A2 substrateNon-inhibitor0.5399
CYP450 2C9 inhibitorNon-inhibitor0.8509
CYP450 2D6 inhibitorInhibitor0.6612
CYP450 2C19 inhibitorNon-inhibitor0.8438
CYP450 3A4 inhibitorNon-inhibitor0.6198
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.629
Ames testAMES toxic0.634
CarcinogenicityNon-carcinogens0.9157
BiodegradationNot ready biodegradable0.9564
Rat acute toxicity3.1459 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8864
hERG inhibition (predictor II)Inhibitor0.5
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.1 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-00di-2974000000-f1e2685ff289086cda8e
Mass Spectrum (Electron Ionization)MSsplash10-00di-1894000000-61a7a87f966b104602ec
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Lysergic acid or derivatives / Indoloquinoline / Benzoquinoline / Pyrroloquinoline / Quinoline-3-carboxamide / Quinoline / 3-alkylindole / Indole / Indole or derivatives / Isoindole or derivatives
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heterotetracyclic compound, monocarboxylic acid amide, ergoline alkaloid (CHEBI:6605) / Indole alkaloids (C07542)

Targets

Kind
Protein
Organism
Human
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
  1. 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
Human
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
  1. 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
Human
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
  1. 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
Human
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
Human
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
  1. 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 October 10, 2018 21:54