lysergic acid diethylamide

Summary

Summary: Semisynthetic derivative of ergot (Claviceps purpurea). It has complex effects on serotonergic systems including antagonism at some peripheral serotonin receptors, both agonist and antagonist actions at central nervous system serotonin receptors, and possibly effects on serotonin turnover. It is a potent hallucinogen, but the mechanisms of that effect are not well understood.

Top Publications

  1. Marona Lewicka D, Nichols D. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol Biochem Behav. 2007;87:453-61 pubmed
    ..The results reported here support and extend our previous conclusion that the delayed temporal effects of LSD are mediated by activation of a dopaminergic system. ..
  2. Song J, Hanniford D, Doucette C, Graham E, Poole M, Ting A, et al. Development of homogeneous high-affinity agonist binding assays for 5-HT2 receptor subtypes. Assay Drug Dev Technol. 2005;3:649-59 pubmed
    ..The high-affinity sites for the 5-HT2B receptor were labeled with [3H]lysergic acid diethylamide. Total receptor expression was determined with the 5-HT2 antagonist [3H]mesulergine for the 5-HT2B and 5-..
  3. Romano A, Quinn J, Liu R, Dave K, Schwab D, Alexander G, et al. Effect of serotonin depletion on 5-HT2A-mediated learning in the rabbit: evidence for constitutive activity of the 5-HT2A receptor in vivo. Psychopharmacology (Berl). 2006;184:173-81 pubmed
    ..would impair trace eyeblink conditioning or the enhancement of conditioning produced by the agonist lysergic acid diethylamide (LSD) and the retardation of conditioning produced by the inverse agonist MDL11,939...
  4. Benneyworth M, Smith R, Barrett R, Sanders Bush E. Complex discriminative stimulus properties of (+)lysergic acid diethylamide (LSD) in C57Bl/6J mice. Psychopharmacology (Berl). 2005;179:854-62 pubmed
    ..To establish the training procedures and characterize the stimulus properties of (+)lysergic acid diethylamide (LSD) in mice...
  5. Marona Lewicka D, Chemel B, Nichols D. Dopamine D4 receptor involvement in the discriminative stimulus effects in rats of LSD, but not the phenethylamine hallucinogen DOI. Psychopharmacology (Berl). 2009;203:265-77 pubmed publisher
    b>Lysergic acid diethylamide (LSD) differs from other types of hallucinogens in that it possesses direct dopaminergic effects. The exact nature of this component has not been elucidated...
  6. Arora R, Meltzer H. Increased serotonin2 (5-HT2) receptor binding as measured by 3H-lysergic acid diethylamide (3H-LSD) in the blood platelets of depressed patients. Life Sci. 1989;44:725-34 pubmed
    3H-Lysergic acid diethylamide (3H-LSD) binding, a putative measure of 5-HT2 receptor binding, was studied in the blood platelets of 29 depressed patients and 24 normal controls...
  7. Nichols D, Frescas S, Marona Lewicka D, Kurrasch Orbaugh D. Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J Med Chem. 2002;45:4344-9 pubmed
    ..The incorporation of isomeric dialkylazetidines into other biologically active molecules may be a useful strategy to model the active conformations of dialkylamines and dialkylamides. ..
  8. Halberstadt A, Geyer M. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology. 2011;61:364-81 pubmed publisher
    ..such as mescaline and 2,5-dimethoxy-4-methylamphetamine (DOM), and indoleamines such as (+)-lysergic acid diethylamide (LSD) and psilocybin...
  9. Nichols C, Garcia E, Sanders Bush E. Dynamic changes in prefrontal cortex gene expression following lysergic acid diethylamide administration. Brain Res Mol Brain Res. 2003;111:182-8 pubmed
    b>Lysergic acid diethylamide (LSD) is a psychoactive drug that transiently alters human perception, behavior, and mood at extremely low doses...

More Information

Publications62

  1. Cussac D, Boutet Robinet E, Ailhaud M, Newman Tancredi A, Martel J, Danty N, et al. Agonist-directed trafficking of signalling at serotonin 5-HT2A, 5-HT2B and 5-HT2C-VSV receptors mediated Gq/11 activation and calcium mobilisation in CHO cells. Eur J Pharmacol. 2008;594:32-8 pubmed publisher
    ..At the h5-HT2A receptor, d-lysergic acid diethylamide (LSD) and the antiparkinsonian agents lisuride, bromocriptine and pergolide exhibit a higher potency for ..
  2. Halpern J, Pope H. Hallucinogen persisting perception disorder: what do we know after 50 years?. Drug Alcohol Depend. 2003;69:109-19 pubmed
    ..Although it may be difficult to collect large samples of HPPD cases, further studies are critically needed to augment the meager data presently available regarding the prevalence, etiology, and treatment of HPPD. ..
  3. Spencer A. Permissive group therapy with lysergic acid diethylamide. Br J Psychiatry. 1963;109:37-45 pubmed
  4. Gresch P, Strickland L, Sanders Bush E. Lysergic acid diethylamide-induced Fos expression in rat brain: role of serotonin-2A receptors. Neuroscience. 2002;114:707-13 pubmed
    b>Lysergic acid diethylamide (LSD) produces altered mood and hallucinations in humans and binds with high affinity to serotonin-2A (5-HT(2A)) receptors...
  5. Nichols C, Sanders Bush E. A single dose of lysergic acid diethylamide influences gene expression patterns within the mammalian brain. Neuropsychopharmacology. 2002;26:634-42 pubmed
    Hallucinogenic drugs such as lysergic acid diethylamide (LSD) have profound effects on humans including hallucinations and detachment from reality...
  6. Nichols C, Sanders Bush E. Molecular genetic responses to lysergic acid diethylamide include transcriptional activation of MAP kinase phosphatase-1, C/EBP-beta and ILAD-1, a novel gene with homology to arrestins. J Neurochem. 2004;90:576-84 pubmed
    We recently demonstrated that the potent hallucinogenic drug lysergic acid diethylamide (LSD) dynamically influences the expression of a small collection of genes within the mammalian prefrontal cortex...
  7. Seeman P, Guan H, Hirbec H. Dopamine D2High receptors stimulated by phencyclidines, lysergic acid diethylamide, salvinorin A, and modafinil. Synapse. 2009;63:698-704 pubmed publisher
    ..when compared with 80 nM for dopamine, 89 nM for salvinorin A (48 nM for D2Long), 105 nM for lysergic acid diethylamide (LSD), 120 nM for R-modafinil, 710 nM for dizocilpine, 1030 nM for ketamine, and >10,000 nM for S-..
  8. Marona Lewicka D, Kurrasch Orbaugh D, Selken J, Cumbay M, Lisnicchia J, Nichols D. Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioral effects overlap its other properties in rats. Psychopharmacology (Berl). 2002;164:93-107 pubmed
    ..The lack of full substitution of lisuride for lysergic acid diethylamide (LSD) in drug discrimination experiments and induction of a pronounced 5-HT syndrome by this compound at ..
  9. Krebs T, Johansen P. Lysergic acid diethylamide (LSD) for alcoholism: meta-analysis of randomized controlled trials. J Psychopharmacol. 2012;26:994-1002 pubmed publisher
    Assessments of lysergic acid diethylamide (LSD) in the treatment of alcoholism have not been based on quantitative meta-analysis...
  10. Bunzow J, Sonders M, Arttamangkul S, Harrison L, Zhang G, Quigley D, et al. Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor. Mol Pharmacol. 2001;60:1181-8 pubmed
  11. Ouagazzal A, Grottick A, Moreau J, Higgins G. Effect of LSD on prepulse inhibition and spontaneous behavior in the rat. A pharmacological analysis and comparison between two rat strains. Neuropsychopharmacology. 2001;25:565-75 pubmed
    ..These findings provide empirical evidence to support the view that the hallucinogenic effects of LSD are mediated by a direct agonist effect at 5-HT(2A) receptors. ..
  12. Passie T, Halpern J, Stichtenoth D, Emrich H, Hintzen A. The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008;14:295-314 pubmed publisher
    b>Lysergic acid diethylamide (LSD) was synthesized in 1938 and its psychoactive effects discovered in 1943...
  13. Muschamp J, Regina M, Hull E, Winter J, Rabin R. Lysergic acid diethylamide and [-]-2,5-dimethoxy-4-methylamphetamine increase extracellular glutamate in rat prefrontal cortex. Brain Res. 2004;1023:134-40 pubmed
    ..The hallucinogen lysergic acid diethylamide (LSD; 0.1 mg/kg, i.p...
  14. Spigset O, Kristoffersson A, Mjorndal T. Platelet serotonin 5-HT2A receptor binding in patients with carcinoid tumor. Scand J Clin Lab Invest. 2004;64:3-8 pubmed
    ..3H]lysergic acid diethylamide ([3H]LSD) binding to the platelet serotonin 5-HT2A receptor was investigated in nine patients with ..
  15. Niblock M, Kinney H, Luce C, Belliveau R, Filiano J. The development of the medullary serotonergic system in the piglet. Auton Neurosci. 2004;110:65-80 pubmed
    ..Tritiated (3H)-lysergic acid diethylamide (LSD) binding to 5-HT1A-D and 5-HT2 receptors and 3H-8-hydroxy-2-[di-N-propylamine]tetralin (8-OH-DPAT) ..
  16. Sjöqvist A, Cassuto J, Jodal M, Lundgren O. Actions of serotonin antagonists on cholera-toxin-induced intestinal fluid secretion. Acta Physiol Scand. 1992;145:229-37 pubmed
    ..It was also demonstrated that zimeldine, an inhibitor of presynaptic 5-HT reuptake, diminished choleraic secretion, an effect that may be ascribed to a 5-HT tachyphylaxis caused by an accumulation of 5-HT in a synaptic cleft. ..
  17. Eckler J, Chang Fong J, Rabin R, Smith C, Teitler M, Glennon R, et al. Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM. Pharmacol Biochem Behav. 2003;75:845-52 pubmed
    ..DOM (2-DM-DOM) and 5-O-desmethyl DOM (5-DM-DOM) to substitute for the stimulus properties of (+)lysergic acid diethylamide (LSD)...
  18. Waeber C, Grailhe R, Yu X, Hen R, Moskowitz M. Putative 5-ht5 receptors: localization in the mouse CNS and lack of effect in the inhibition of dural protein extravasation. Ann N Y Acad Sci. 1998;861:85-90 pubmed
    ..These results suggest that the inhibitory effects of 5-CT are not mediated by a site with the characteristics of the putative 5-ht5 receptor. ..
  19. Sandison R. A role for psychedelics in psychiatry?. Br J Psychiatry. 2005;187:483; author reply 484-5 pubmed
  20. Singh A, Barlas C, Saeedi H, Mishra R. Effect of loxapine on peripheral dopamine-like and serotonin receptors in patients with schizophrenia. J Psychiatry Neurosci. 2003;28:39-47 pubmed
    ..Loxapine down-regulated both lymphocyte D2-like and platelet 5-HT2A receptors to the same extent, suggesting that both receptors are involved in the mechanism of action of loxapine in patients with schizophrenia. ..
  21. Lerner A, Shufman E, Kodesh A, Rudinski D, Kretzmer G, Sigal M. Risperidone-associated, benign transient visual disturbances in schizophrenic patients with a past history of LSD abuse. Isr J Psychiatry Relat Sci. 2002;39:57-60 pubmed
    ..Conclusions based on two case reports should be taken with appropriate caution. ..
  22. Lurie I, Hays P, Parker K. Capillary electrophoresis analysis of a wide variety of seized drugs using the same capillary with dynamic coatings. Electrophoresis. 2004;25:1580-91 pubmed
    ..of exhibits analyzed using diode array UV detection include phenethylamines, cocaine, oxycodone, heroin, lysergic acid diethylamide (LSD), opium, hallucinogenic mushrooms, and gamma-hydroxybutyrate-gamma-butyrolactone (GHB-GBL)...
  23. Novak S. Second thoughts on psychedelic drugs. Endeavour. 1998;22:21-3 pubmed
    ..Proponents of psychedelics point to the widespread medical experimentation with mescaline and lysergic acid diethylamide-125 (LSD) in the 1950s as proof of their safety and efficacy...
  24. Mashour G. Altered states: LSD and the Anesthesia Laboratory of Henry Knowles Beecher. Bull Anesth Hist. 2005;23:11-4 pubmed
  25. Mashour G. From LSD to the IRB: Henry Beecher's psychedelic research and the foundation of clinical ethics. Int Anesthesiol Clin. 2007;45:105-11 pubmed
  26. Moreno J, Holloway T, Umali A, Rayannavar V, Sealfon S, Gonzalez Maeso J. Persistent effects of chronic clozapine on the cellular and behavioral responses to LSD in mice. Psychopharmacology (Berl). 2013;225:217-26 pubmed publisher
    ..the cellular and behavioral responses induced by the hallucinogenic serotonin 5-HT(2A) receptor agonist lysergic acid diethylamide (LSD) as a mouse model of psychosis. Mice were treated chronically (21 days) with 25 mg/kg/day clozapine...
  27. Kaplan R. Humphry Fortescue Osmond (1917-2004), a radical and conventional psychiatrist: The transcendent years. J Med Biogr. 2016;24:115-24 pubmed publisher
  28. Leng A, Ouagazzal A, Feldon J, Higgins G. Effect of the 5-HT6 receptor antagonists Ro04-6790 and Ro65-7199 on latent inhibition and prepulse inhibition in the rat: comparison to clozapine. Pharmacol Biochem Behav. 2003;75:281-8 pubmed
    ..Since each of these tests bear some predictive validity for the detection of antipsychotic drugs, the present studies do not support a therapeutic potential of 5-HT6 receptor antagonists in this regard. ..
  29. Winter J, Petti D. The effects of 8-hydroxy-2-(di-n-propylamino)tetralin and other serotonergic agonists on performance in a radial maze: a possible role for 5-HT1A receptors in memory. Pharmacol Biochem Behav. 1987;27:625-8 pubmed
    ..The effects of pretreatment with (+)-Lysergic acid diethylamide (+)-tartrate (LSD), m-trifluoromethylphenylpiperazine (TFMPP), 5-methoxy-N,N-dimethyltryptamine oxalate (..
  30. Berg T, Jørgenrud B, Strand D. Determination of buprenorphine, fentanyl and LSD in whole blood by UPLC-MS-MS. J Anal Toxicol. 2013;37:159-65 pubmed publisher
    ..method has been developed and validated for the quantification of buprenorphine, fentanyl and lysergic acid diethylamide (LSD) in whole blood...
  31. Burnley B, George S. The development and application of a gas chromatography-mass spectrometric (GC-MS) assay to determine the presence of 2-oxo-3-hydroxy-LSD in urine. J Anal Toxicol. 2003;27:249-52 pubmed
    ..enable the Laboratory to determine the presence and concentration of the 2-oxo-3-hydroxy metabolite of lysergic acid diethylamide (OH-LSD) in urine. The limit of detection was 0.5 ng/mL, with a limit of quantitation established as 1...
  32. Strajhar P, Schmid Y, Liakoni E, Dolder P, Rentsch K, Kratschmar D, et al. Acute Effects of Lysergic Acid Diethylamide on Circulating Steroid Levels in Healthy Subjects. J Neuroendocrinol. 2016;28:12374 pubmed publisher
    b>Lysergic acid diethylamide (LSD) is a serotonin 5-hydroxytryptamine-2A (5-HT2A ) receptor agonist that is used recreationally worldwide...
  33. Horn C, Klette K, Stout P. LC-MS analysis of 2-oxo-3-hydroxy LSD from urine using a Speedisk positive-pressure processor with Cerex PolyChrom CLIN II columns. J Anal Toxicol. 2003;27:459-63 pubmed
    A rapid and sensitive solid-phase extraction method for the lysergic acid diethylamide (LSD) metabolite 2-oxo-3-hydroxy-LSD (O-H-LSD) was developed for use in a forensic laboratory...
  34. Walker E, Kohut S, Hass R, Brown E, Prabandham A, Lefever T. Selective and nonselective serotonin antagonists block the aversive stimulus properties of MK212 and m-chlorophenylpiperazine (mCPP) in mice. Neuropharmacology. 2005;49:1210-9 pubmed
    ..Taken together, these data indicate that the serotonin agonists MK212 and mCPP produce conditioned taste aversion and that these effects are mediated predominantly through 5-HT(2C) receptors. ..
  35. Chapin E, Andrade R. A 5-HT(7) receptor-mediated depolarization in the anterodorsal thalamus. I. Pharmacological characterization. J Pharmacol Exp Ther. 2001;297:395-402 pubmed
    ..These results identify the receptor mediating the serotonin-induced membrane depolarization in the ADn as the 5-HT7 subtype. ..
  36. Fang C, Liu J, Lin C. Optimization of the separation of lysergic acid diethylamide in urine by a sweeping technique using micellar electrokinetic chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2002;775:37-47 pubmed
    The separation and on-line concentrations of lysergic acid diethylamide (LSD), iso-lysergic acid diethylamide (iso-LSD) and lysergic acid N,N-methylpropylamide (LAMPA) in human urine were investigated by capillary electrophoresis-..
  37. Harvey J, Quinn J, Liu R, Aloyo V, Romano A. Selective remodeling of rabbit frontal cortex: relationship between 5-HT2A receptor density and associative learning. Psychopharmacology (Berl). 2004;172:435-42 pubmed
    ..More generally, these results suggest an approach for functional remodeling of brain regions in the adult animal. ..
  38. Skopp G, Pötsch L, Mattern R, Aderjan R. Short-term stability of lysergic acid diethylamide (LSD), N-desmethyl-LSD, and 2-oxo-3-hydroxy-LSD in urine, assessed by liquid chromatography-tandem mass spectrometry. Clin Chem. 2002;48:1615-8 pubmed
  39. Ramo D, Grov C, Delucchi K, Kelly B, Parsons J. Typology of club drug use among young adults recruited using time-space sampling. Drug Alcohol Depend. 2010;107:119-27 pubmed publisher
    ..MDMA), ketamine, gamma-hydroxybutyrate (GHB), cocaine, methamphetamine, and D-lysergic acid diethylamide (LSD)) within the prior 3 months...
  40. Schechter M. 'Candyflipping': synergistic discriminative effect of LSD and MDMA. Eur J Pharmacol. 1998;341:131-4 pubmed
    The co-administration of D-lysergic acid diethylamide (LSD; 'Acid') and 3,4-methylenedioxymethamphetamine (MDMA; 'Ecstasy'; 'XTC'), has reached a prevalence that has allowed for the street terminology 'candyflipping' to describe the ..
  41. CUTNER M. Analytic work with LSD 25. Psychiatr Q. 1959;33:715-57 pubmed
  42. Arvanian V, Manuzon H, Davenport M, Bushell G, Mendell L, Robinson J. Combined treatment with neurotrophin-3 and LSD facilitates behavioral recovery from double-hemisection spinal injury in neonatal rats. J Neurotrauma. 2006;23:66-74 pubmed
    ..Rearing frequency reached sham control levels by P40. Our results suggest this combination treatment may be a promising new strategy for facilitating recovery from moderate spinal cord injury. ..
  43. Simpson D, Braithwaite R, Jarvie D, Stewart M, Walker S, Watson I, et al. Screening for drugs of abuse (II): Cannabinoids, lysergic acid diethylamide, buprenorphine, methadone, barbiturates, benzodiazepines and other drugs. Ann Clin Biochem. 1997;34 ( Pt 5):460-510 pubmed
    ..It will also be essential to ensure that computer libraries contain spectra for all substances likely to be encountered in drugs of abuse screening. ..
  44. Palenicek T, Hlinak Z, Bubenikova Valesova V, Novak T, Horacek J. Sex differences in the effects of N,N-diethyllysergamide (LSD) on behavioural activity and prepulse inhibition. Prog Neuropsychopharmacol Biol Psychiatry. 2010;34:588-96 pubmed publisher
    ..On the contrary although LSD disrupted PPI in males and MD female rats, EP females were protected from this disruptive effect. Thus, EP females seem to have a lower sensitivity to LSD behavioural actions. ..
  45. Riordan M, Rylance G, Berry K. Poisoning in children 5: rare and dangerous poisons. Arch Dis Child. 2002;87:407-10 pubmed
  46. Grailhe R, Waeber C, Dulawa S, Hornung J, Zhuang X, Brunner D, et al. Increased exploratory activity and altered response to LSD in mice lacking the 5-HT(5A) receptor. Neuron. 1999;22:581-91 pubmed
    ..These results suggest that 5-HT5A receptors modulate the activity of neural circuits involved specifically in exploratory behavior and suggest that some of the psychotropic effects of LSD may be mediated by 5-HT5A receptors. ..
  47. Sessa B. Is it time to revisit the role of psychedelic drugs in enhancing human creativity?. J Psychopharmacol. 2008;22:821-7 pubmed publisher
    ..Nevertheless, with today's current renaissance in psychedelic drug research and the growing interest in cognitive enhancing drugs, now may be the time to re-visit these studies with contemporary research methods. ..
  48. Ryan A, Eklund P. A framework for semantic interoperability in healthcare: a service oriented architecture based on health informatics standards. Stud Health Technol Inform. 2008;136:759-64 pubmed
  49. Dyck E. Flashback: psychiatric experimentation with LSD in historical perspective. Can J Psychiatry. 2005;50:381-8 pubmed
    In the popular mind, d-lysergic acid diethylamide (LSD) research in psychiatry has long been associated with the CIA-funded experiments conducted by Ewen Cameron at the Allen Memorial Institute in Montreal, Quebec...
  50. de Rios M, Grob C, Baker J. Hallucinogens and redemption. J Psychoactive Drugs. 2002;34:239-48 pubmed
    ..Research by two of the authors with the Uñaio do Vegetal (UDV) Church in Brazil is examined in terms of the model...
  51. Gatch M, Kozlenkov A, Huang R, Yang W, Nguyen J, Gonzalez Maeso J, et al. The HIV antiretroviral drug efavirenz has LSD-like properties. Neuropsychopharmacology. 2013;38:2373-84 pubmed publisher
  52. Nichols C, Ronesi J, Pratt W, Sanders Bush E. Hallucinogens and Drosophila: linking serotonin receptor activation to behavior. Neuroscience. 2002;115:979-84 pubmed
    ..The present studies define the behavioral and molecular effects of the powerful hallucinogen lysergic acid diethylamide in Drosophila...
  53. Flodrops H, Houdon L, Harvet G, Enaud L, Renouil M. [Voluntary intoxication by D-lysergic acid amide (LSA) in a 15-year-old teenager via Internet: new fact of society]. Arch Pediatr. 2006;13:1158-9 pubmed