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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GroupsIllicit, Withdrawn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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
DelysidSandoz Laboratories
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number50-37-3
WeightAverage: 323.432
Monoisotopic: 323.199762437
Chemical FormulaC20H25N3O
InChI KeyVAYOSLLFUXYJDT-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
Taxonomy
DescriptionThis 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.
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
  • Quinoline-3-carboxamide
  • Pyrroloquinoline
  • Quinoline
  • Isoindole or derivatives
  • Indole or derivatives
  • Indole
  • Aralkylamine
  • Tetrahydropyridine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
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 substrateNon-inhibitor0.8509
CYP450 2D6 substrateInhibitor0.6612
CYP450 2C19 substrateNon-inhibitor0.8438
CYP450 3A4 substrateNon-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
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 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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (10.1 KB)
SpectraMS
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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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

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