Lysergic Acid Diethylamide

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Illicit, Investigational, Withdrawn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][[email protected]@]12CC3=CNC4=CC=CC(=C34)C1=C[[email protected]](CN2C)C(=O)N(CC)CC

Pharmacology

Indication
Not Available
Structured Indications
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
DrugInteractionDrug group
AcetaminophenThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Acetaminophen.Approved
AcetazolamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Acetazolamide.Approved, Vet Approved
AldesleukinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Aldesleukin.Approved
AlprazolamThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Alprazolam.Approved, Illicit, Investigational
AmbroxolThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ambroxol.Approved, Investigational
AmlodipineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Amlodipine.Approved
AmprenavirThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Amprenavir.Approved
AnastrozoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Anastrozole.Approved, Investigational
AntipyrineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Antipyrine.Approved
Arsenic trioxideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Arsenic trioxide.Approved, Investigational
AstemizoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Astemizole.Approved, Withdrawn
AtazanavirThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Atazanavir.Approved, Investigational
AtomoxetineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Atomoxetine.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Atorvastatin.Approved
AzelastineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Azelastine.Approved
AzithromycinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Azithromycin.Approved
BetamethasoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Betamethasone.Approved, Vet Approved
BicalutamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Bicalutamide.Approved
BifonazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Bifonazole.Approved, Investigational
BoceprevirThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Boceprevir.Approved, Withdrawn
BortezomibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Bortezomib.Approved, Investigational
Brentuximab vedotinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Brentuximab vedotin.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Bromocriptine.Approved, Investigational
BuprenorphineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
CabergolineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Cabergoline.Approved
CaffeineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Caffeine.Approved
CapsaicinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Capsaicin.Approved
CaspofunginThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Caspofungin.Approved
CeritinibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ceritinib.Approved
CerivastatinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Cerivastatin.Withdrawn
ChloramphenicolThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Chloramphenicol.Approved, Vet Approved
ChlorzoxazoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Chlorzoxazone.Approved
CilostazolThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Cilostazol.Approved
CiprofloxacinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ciprofloxacin.Approved, Investigational
CisaprideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Cisapride.Approved, Investigational, Withdrawn
ClarithromycinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Clarithromycin.Approved
ClemastineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Clemastine.Approved
ClindamycinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Clindamycin.Approved, Vet Approved
ClofazimineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Clofazimine.Approved, Investigational
ClomifeneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Clomifene.Approved, Investigational
ClotiazepamThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Clotiazepam.Approved, Illicit
ClotrimazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Clozapine.Approved
CobicistatThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Cobicistat.Approved
CocaineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Cocaine.Approved, Illicit
ColchicineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Colchicine.Approved
ConivaptanThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Conivaptan.Approved, Investigational
Cortisone acetateThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Cortisone acetate.Approved
CrizotinibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Crizotinib.Approved
CyclophosphamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Cyclosporine.Approved, Investigational, Vet Approved
DalfopristinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Dalfopristin.Approved
DanazolThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Danazol.Approved
DarunavirThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Darunavir.Approved
DasatinibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Dasatinib.Approved, Investigational
DaunorubicinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Daunorubicin.Approved
DelavirdineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Delavirdine.Approved
DesipramineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Desipramine.Approved
DexamethasoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextropropoxypheneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Dextropropoxyphene.Approved, Illicit, Investigational, Withdrawn
DiazepamThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Diazepam.Approved, Illicit, Vet Approved
DiethylstilbestrolThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Diethylstilbestrol.Approved, Investigational
DihydroergotamineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Dihydroergotamine.Approved
Dimethyl sulfoxideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Dimethyl sulfoxide.Approved, Vet Approved
DocetaxelThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Docetaxel.Approved, Investigational
DoxorubicinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Doxorubicin.Approved, Investigational
DoxycyclineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Dronedarone.Approved
EconazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Econazole.Approved
EfavirenzThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Efavirenz.Approved, Investigational
ElbasvirThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Elbasvir.Approved
EnasidenibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Enasidenib.Approved
EpinephrineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Epinephrine.Approved, Vet Approved
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ergoloid mesylate.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ergonovine.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ergotamine.Approved
ErythromycinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Erythromycin.Approved, Vet Approved
EthanolThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ethanol.Approved
EtoposideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Etoposide.Approved
EtoricoxibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Etoricoxib.Approved, Investigational
EzetimibeThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ezetimibe.Approved
FelodipineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Felodipine.Approved, Investigational
FentanylThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FluoxetineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Fluoxetine.Approved, Vet Approved
Fluticasone propionateThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Fluticasone propionate.Approved
FluvastatinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Fluvastatin.Approved
FluvoxamineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Fosamprenavir.Approved
FosaprepitantThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Fosaprepitant.Approved
GemfibrozilThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Gemfibrozil.Approved
GlyburideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Glyburide.Approved
Glycerol PhenylbutyrateThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Glycerol Phenylbutyrate.Approved
HaloperidolThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Haloperidol.Approved
HistamineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Histamine.Approved, Investigational
HydralazineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Hydralazine.Approved
HydrocortisoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Hydrocortisone.Approved, Vet Approved
IdelalisibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Idelalisib.Approved
IfosfamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ifosfamide.Approved
IloperidoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Iloperidone.Approved
ImatinibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Imatinib.Approved
IndinavirThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Indinavir.Approved
indisulamThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with indisulam.Investigational
IrbesartanThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Irbesartan.Approved, Investigational
IrinotecanThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Irinotecan.Approved, Investigational
IsavuconazoniumThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Isavuconazonium.Approved, Investigational
IsoniazidThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Isoniazid.Approved
IsradipineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Isradipine.Approved
ItraconazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Itraconazole.Approved, Investigational
IvacaftorThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ivacaftor.Approved
JosamycinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Josamycin.Approved, Investigational
KetazolamThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ketazolam.Approved
KetoconazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ketoconazole.Approved, Investigational
LansoprazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Lansoprazole.Approved, Investigational
LapatinibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Lapatinib.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Lercanidipine.Approved, Investigational
LevofloxacinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Levofloxacin.Approved, Investigational
LevosalbutamolThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Levosalbutamol.Approved
LidocaineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Lidocaine.Approved, Vet Approved
LinagliptinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Linagliptin.Approved
LomitapideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Lomitapide.Approved
LomustineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Lomustine.Approved
LopinavirThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Lopinavir.Approved
LoratadineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Loratadine.Approved
LosartanThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Losartan.Approved
LovastatinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Lovastatin.Approved, Investigational
LuliconazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Luliconazole.Approved
LurasidoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Lurasidone.Approved
ManidipineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Manidipine.Approved, Investigational
MefloquineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Mefloquine.Approved
MequitazineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Mequitazine.Approved
MethadoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Methadone.Approved
MethazolamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Methazolamide.Approved
MethimazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Methimazole.Approved
MethylergometrineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Methylergometrine.Approved
MethylprednisoloneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Methylprednisolone.Approved, Vet Approved
MetronidazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Metronidazole.Approved
MetyraponeThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Metyrapone.Approved
MibefradilThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Mibefradil.Investigational, Withdrawn
MiconazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Miconazole.Approved, Investigational, Vet Approved
MidazolamThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Midazolam.Approved, Illicit
MifepristoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Mifepristone.Approved, Investigational
MirtazapineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Mirtazapine.Approved
MitoxantroneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Mitoxantrone.Approved, Investigational
ModafinilThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Modafinil.Approved, Investigational
NelfinavirThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Nelfinavir.Approved
NetupitantThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Netupitant.Approved
NevirapineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Nevirapine.Approved
NicardipineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Nicardipine.Approved
NicotinamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Nicotinamide.Approved
NifedipineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Nifedipine.Approved
NilotinibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Nilotinib.Approved, Investigational
NilvadipineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Nilvadipine.Approved, Investigational
NisoldipineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Nitrendipine.Approved, Investigational
Nitric OxideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Nitric Oxide.Approved
NorfloxacinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Norfloxacin.Approved
NoscapineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Noscapine.Investigational
OlanzapineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Olanzapine.Approved, Investigational
OlaparibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Olaparib.Approved
OmeprazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Omeprazole.Approved, Investigational, Vet Approved
OxybutyninThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Oxybutynin.Approved, Investigational
OxymetholoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Oxymetholone.Approved, Illicit
PaclitaxelThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Paclitaxel.Approved, Vet Approved
PalbociclibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Palbociclib.Approved
ParamethasoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Paramethasone.Approved
PazopanibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Pazopanib.Approved
PergolideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Pergolide.Approved, Investigational, Vet Approved, Withdrawn
PhenelzineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Phenelzine.Approved
PilocarpineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Pilocarpine.Approved
PimozideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Pimozide.Approved
PosaconazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Pravastatin.Approved
PrednisoloneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Prednisolone.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Prednisone.Approved, Vet Approved
PrimaquineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Primaquine.Approved
ProgesteroneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Progesterone.Approved, Vet Approved
PropofolThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Propofol.Approved, Investigational, Vet Approved
QuinidineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Quinidine.Approved
QuinineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Quinine.Approved
QuinupristinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Quinupristin.Approved
RabeprazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Rabeprazole.Approved, Investigational
RaloxifeneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Raloxifene.Approved, Investigational
RanitidineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ranitidine.Approved
RanolazineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ranolazine.Approved, Investigational
RegorafenibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Regorafenib.Approved
RepaglinideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Repaglinide.Approved, Investigational
ResveratrolThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Resveratrol.Approved, Experimental, Investigational
RilpivirineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Rilpivirine.Approved
RisperidoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Risperidone.Approved, Investigational
RitonavirThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ritonavir.Approved, Investigational
RivastigmineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Rivastigmine.Approved, Investigational
RolitetracyclineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Rolitetracycline.Approved
RosuvastatinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Rosuvastatin.Approved
RoxithromycinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Roxithromycin.Approved, Investigational, Withdrawn
RucaparibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Rucaparib.Approved, Investigational
RutinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Rutin.Experimental, Investigational
SalbutamolThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Salbutamol.Approved, Vet Approved
SaquinavirThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Saquinavir.Approved, Investigational
SarilumabThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Sarilumab.Approved
SertralineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Sertraline.Approved
SildenafilThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Sildenafil.Approved, Investigational
SimeprevirThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Simeprevir.Approved
SimvastatinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Simvastatin.Approved
SirolimusThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Sirolimus.Approved, Investigational
SitaxentanThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Sitaxentan.Approved, Investigational, Withdrawn
SorafenibThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Sorafenib.Approved, Investigational
StiripentolThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Stiripentol.Approved
SulfamethoxazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Sulfamethoxazole.Approved
SulfanilamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Sulfanilamide.Approved
SulfinpyrazoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Sulfinpyrazone.Approved
SulfisoxazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Sulfisoxazole.Approved, Vet Approved
TacrolimusThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Tacrolimus.Approved, Investigational
TadalafilThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Tadalafil.Approved, Investigational
TamoxifenThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Tamoxifen.Approved
TelaprevirThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Telaprevir.Approved, Withdrawn
TelithromycinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Telithromycin.Approved
TemsirolimusThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Temsirolimus.Approved
TeniposideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Teniposide.Approved
TerfenadineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Terfenadine.Withdrawn
TesmilifeneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Tesmilifene.Investigational
TestosteroneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Testosterone.Approved, Investigational
TetracyclineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Tetracycline.Approved, Vet Approved
ThiopentalThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Thiopental.Approved, Vet Approved
TicagrelorThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ticagrelor.Approved
TiclopidineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ticlopidine.Approved
TioconazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Tioconazole.Approved
TipranavirThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Tipranavir.Approved, Investigational
TofisopamThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Tofisopam.Approved
TopiroxostatThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Topiroxostat.Approved, Investigational
TopotecanThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Topotecan.Approved, Investigational
TramadolThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Tramadol.Approved, Investigational
TranylcypromineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Tranylcypromine.Approved
TroglitazoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Troglitazone.Investigational, Withdrawn
TroleandomycinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Troleandomycin.Approved
Valproic AcidThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Valproic Acid.Approved, Investigational
VenlafaxineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Venlafaxine.Approved
VinblastineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Vinblastine.Approved
VincristineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Vincristine.Approved, Investigational
VinorelbineThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Vinorelbine.Approved, Investigational
VoriconazoleThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Voriconazole.Approved, Investigational
ZafirlukastThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Zafirlukast.Approved, Investigational
ZiprasidoneThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ziprasidone.Approved
ZucapsaicinThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Zucapsaicin.Approved
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
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]

Drug created on September 11, 2007 14:49 / Updated on December 01, 2017 15:33