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Identification
NameLysergic Acid Diethylamide
Accession NumberDB04829
Typesmall molecule
Groupsillicit, withdrawn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
SynonymLanguageCode
(+)-LSDNot AvailableNot Available
(+)-lysergic acid diethylamideNot AvailableNot Available
9,10-Didehydro-N,N-diethyl-6-methylergoline-8b-carboxamideNot AvailableNot Available
D-LSDNot AvailableNot Available
D-LSD-25Not AvailableNot Available
D-lysergic acid dethylamideNot AvailableNot Available
D-lysergic acid diethylamideNot AvailableNot Available
D-lysergic acid n,n-diethylamideNot AvailableNot Available
Dextrolysergic acid diethylamideNot AvailableNot Available
Diethylamid kyseliny lysergoveCzechNot Available
LSDNot AvailableNot Available
LSD-25Not AvailableNot Available
LysergamidNot AvailableNot Available
LysergamideNot AvailableNot Available
Lysergaure diethylamidNot AvailableNot Available
Lysergic acid amideNot AvailableNot Available
Lysergic acid diethylamide-25Not AvailableNot Available
LysergideNot AvailableINN
LysergidumLatinINN
n,n-diethyl-(+)-lysergamideNot AvailableNot Available
N,N-Diethyl-6-methyl-9,10-didehydroergoline-8-carboxamideNot AvailableNot Available
N,n-diethyl-d-lysergamideNot AvailableNot Available
N,n-diethyllysergamideNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
DelysidSandoz Laboratories
Brand mixturesNot Available
Categories
CAS number50-37-3
WeightAverage: 323.432
Monoisotopic: 323.199762437
Chemical FormulaC20H25N3O
InChI KeyInChIKey=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[7.6.1.0^{2,7}.0^{12,16}]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
Mass Specshow(10.1 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassQuinolines and Derivatives
SubclassIndoloquinolines
Direct parentIndoloquinolines
Alternative parentsBenzoquinolines; Quinoline Carboxamides; Pyrroloquinolines; N-substituted Nicotinamides; Indoles; Isoindoles and Derivatives; Tetrahydropyridines; Benzene and Substituted Derivatives; Pyrroles; Tertiary Carboxylic Acid Amides; Tertiary Amines; Polyamines; Carboxylic Acids; Enolates; Ergoline Derivatives
Substituentsbenzoquinoline; quinoline-3-carboxamide; pyrroloquinoline; n-substituted nicotinamide; isoindole or derivative; indole; indole or derivative; tetrahydropyridine; benzene; pyrrole; tertiary carboxylic acid amide; carboxamide group; tertiary amine; carboxylic acid derivative; polyamine; carboxylic acid; enolate; amine; organonitrogen compound
Classification descriptionThis compound belongs to the indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionRapidly absorbed.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half life3 hours
ClearanceNot Available
ToxicityEstimates 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.8509
CYP450 2D6 substrate Inhibitor 0.6612
CYP450 2C19 substrate Non-inhibitor 0.8438
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point82.5 °CPhysProp
logP2.95HANSCH,C ET AL. (1995)
pKa7.8SANGSTER (1994)
Predicted Properties
PropertyValueSource
water solubility2.70e-01 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 area39.34ChemAxon
rotatable bond count3ChemAxon
refractivity98.73ChemAxon
polarizability37.54ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot 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 Reference
  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
  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
  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
  4. Nichols DE: Hallucinogens. Pharmacol Ther. 2004 Feb;101(2):131-81. Pubmed
  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
  6. 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
External Links
ResourceLink
KEGG CompoundC07542
PubChem Compound5761
PubChem Substance46506397
ChemSpider5558
BindingDB21342
IUPHAR219
Guide to Pharmacology219
Drug Product Database683094
WikipediaLysergic_acid_diethylamide
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. 5-hydroxytryptamine receptor 1A

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 1A P08908 Details

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

Comments
Drug created on September 11, 2007 14:49 / Updated on September 16, 2013 17:25