LSD
LSD-25
METH-LAD
Acid
N,N-Diethyllysergamide
Lysergide
d-Lysergic acid diethylamide
d-Lysergamide, N,N-diethyl
N,N-Diethyl-d-lysergamide
9,10-Didehydro-N,N-diethyl-6-methylergoline-8β-carboxamide
IUPAC: (8β)-N,N-Diethyl-6-methyl-9,10-didehydroergoline-8-carboxamide
Formula: C20H25N3O Molecular weight: 323.432 g/mol InChI Key: VAYOSLLFUXYJDT-RDTXWAMCSA-N
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
PubChem CID: 5761; ChemSpider: 5558; Drugs Forum: LSD; Erowid: LSD; Wikipedia: Lysergic acid diethylamide
Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B
Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133
Gorodetzky, CW; Isbell, H. A comparison of 2,3-dihydro-lysergic acid diethylamide with LSD-25. Psychopharmacology, 1 May 1964, 6 (3), 229–233. 317 kB. doi:10.1007/BF00404013
Watts, VJ; Mailman, RB; Lawler, CP; Neve, KA; Nichols, DE. LSD and structural analogs: Pharmacological evaluation at D1 dopamine receptors. Psychopharmacology, 1 Jan 1995, 118 (4), 401–409. 1367 kB. doi:10.1007/BF02245940
Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3077 kB. doi:10.1007/BF02818560
Marona-Lewicka, D; Kurrasch-Orbaugh, DM; Selken, JR; Cumbay, MG; Lisnicchia, JG; Nichols, DE. Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioural effects overlap its other properties in rats. Psychopharmacology, 1 Oct 2002, 164 (1), 93–107. 293 kB. doi:10.1007/s00213-002-1141-z
Huang, X; Marona-Lewicka, D; Pfaff, RC; Nichols, DE. Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives. Pharmacol. Biochem. Behav., 1 Jan 1994, 47 (3), 667–673. 650 kB. doi:10.1016/0091-3057(94)90172-4
Lieberman, JA; Mailman, RB; Duncan, G; Sikich, L; Chakos, M; Nichols, DE; Kraus, JE. Serotonergic basis of antipsychotic drug effects in schizophrenia. Biol. Psychiat., 1 Dec 1998, 44 (11), 1099–1117. 154 kB. doi:10.1016/S0006-3223(98)00187-5
Nichols, DE. Structural correlation between apomorphine and LSD: Involvement of dopamine as well as serotonin in the actions of hallucinogens. J. Theor. Biol., 1 Jun 1976, 59 (1), 167–177. 614 kB. doi:10.1016/S0022-5193(76)80030-6
Moreno, JL; Holloway, T; Albizu, L; Sealfon, SC; González-Maeso, J. Metabotropic glutamate mGlu2 receptor is necessary for the pharmacological and behavioral effects induced by hallucinogenic 5-HT2A receptor agonists. Neurosci. Lett., 15 Apr 2011, 493 (3), 76–79. 196 kB. doi:10.1016/j.neulet.2011.01.046
Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017
Marona-Lewicka, D; Nichols, CD; Nichols, DE. An animal model of schizophrenia based on chronic LSD administration: Old idea, new results. Neuropharmacology, 1 Sep 2011, 61 (3), 503–512. 803 kB. doi:10.1016/j.neuropharm.2011.02.006
Schindler, EAD; Dave, KD; Smolock, EM; Aloyo, VJ; Harvey, JA. Serotonergic and dopaminergic distinctions in the behavioral pharmacology of (±)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Pharmacol. Biochem. Behav., 1 Mar 2012, 101 (1), 69–76. 722 kB. doi:10.1016/j.pbb.2011.12.002
Oberlender, R; Pfaff, RC; Johnson, MP; Huang, X; Nichols, DE. Stereoselective LSD-like activity in d-lysergic acid amides of R- and S-2-aminobutane. J. Med. Chem., 1 Jan 1992, 35 (2), 203–211. 1143 kB. doi:10.1021/jm00080a001
Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014
Hoffman, AJ; Nichols, DE. Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives. J. Med. Chem., 1 Jan 1985, 28 (9), 1252–1255. 583 kB. doi:10.1021/jm00147a022
Ginzel, KH; Mayer-Gross, W. Prevention of psychological effects of d-lysergic acid diethylamide (LSD 25) by its 2-brom derivative (BOL 148). Nature, 28 Jul 1956, 178 (4526), 210. 129 kB. doi:10.1038/178210a0
Green, AR. Gaddum and LSD: the birth and growth of experimental and clinical neuropharmacology research on 5-HT in the UK. Br. J. Pharmacol., 1 Aug 2008, 1554 (8), 1583–1599. 418 kB. doi:10.1038/bjp.2008.207
Vollenweider, FX; Kometer, M. The neurobiology of psychedelic drugs: implications for the treatment of mood disorders. Nat. Rev. Neurosci., 1 Sep 2010, 11 (9), 642–651. 588 kB. doi:10.1038/nrn2884
Passie, T; Halpern, JH; Stichtenoth, DO; Emrich, HM; Hintzen, A. The pharmacology of lysergic acid diethylamide: A review. CNS Neurosci. Ther., 1 Jan 2008, 14 (4), 295–314. 690 kB. doi:10.1111/j.1755-5949.2008.00059.x
Urban, JD; Clarke, WP; Zastrow, M; Nichols, DE; Kobilka, B; Weinstein, H; Javitch, JA; Roth, BL; Christopoulos, A; Sexton, PM; Miller, KJ; . Functional selectivity and classical concepts of quantitative pharmacology. J. Pharmacol. Exp. Ther., 1 Jan 2007, 320 (1), 1–13. 506 kB. doi:10.1124/jpet.106.104463
Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. doi:10.1124/mol.107.039255
Abramson, HA. Lysergic acid diethylamide (LSD-25) XXXI. Comparison by questionnaire of psychotomimetic activity of congeners on normal subjects and drug addicts. Br. J. Psychiatry, 1 Jul 1960, 106 (444), 1120–1123. 425 kB. doi:10.1192/bjp.106.444.1120
Ray, TS. Psychedelics and the human receptorome. PLoS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019
Pfaff, RC; Huang, X; Marona-Lewicka, D; Oberlender, R; Nichols, DE. Lysergamides revisited. In Hallucinogens: An update. NIDA Research Monograph 146; Lin, GC; Glennon, RA, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1994; pp 52–73. 181 kB.
Anderson, GM; Braun, G; Braun, U; Nichols, DE; Shulgin, AT. Absolute configuration and psychotomimetic activity. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 8–15. 457 kB.
Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.
Shulgin, AT. Profiles of psychedelic drugs. 9. LSD. J. Psychedelic Drugs, 1 Jan 1980, 12 (2), 173–174. 1025 kB.
Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.
Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.
Meyers-Riggs, B. Non-LSD ergoloids. countyourculture: rational exploration of the underground, 1 Dec 2011.
Shulgin, AT. LSD and pregnancy. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 28 Jan 2004.
Shulgin, AT. Morning glory seeds. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 17 Oct 2002.
Fenderson5555. A more modern lysergic acid synthesis. 28 Jun 2011.
Fenderson5555. Total synthesis of lysergic acid via Pd-catalysed domino cyclizations. 4 Dec 2011.
Fenderson5555. Total synthesis of lysergic acid. 25 Jun 2011.
