Exploring LSD. To explore a different substance…

Names:
LSD · METH-LAD · LSD-25 · EA-1729 · Lysergide · Acid · N,N-Diethyllysergamide · d-Lysergic acid diethylamide · N,N-Diethyl-d-lysergamide · 9,10-Didehydro-N,N-diethyl-6-methylergoline-8β-carboxamide · d-Lysergamide, N,N-diethyl
IUPAC name:
(8β)-N,N-Diethyl-6-methyl-9,10-didehydroergoline-8-carboxamide
ID: 5026 · Formula: C20H25N3O · Molecular weight: 323.432
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

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. http://dx.doi.org/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. http://dx.doi.org/10.1002/cmdc.200800133

Brandt, SD; Kavanagh, PV; Twamley, B; Westphal, F; Elliott, SP; Wallach, J; Stratford, A; Klein, LM; McCorvy, JD; Nichols, DE; Halberstadt, AL. Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM-775). Drug Test. Analysis, 27 Jul 2017, n/a-n/a. 1.2 MB. http://dx.doi.org/10.1002/dta.2222

Passie, T; Benzenhöfer, U. MDA, MDMA and other mescaline-like substances in the US military’s search for a truth drug (1940s to 1960s). Drug Test. Analysis, 31 Aug 2017, n/a-n/a. 840 kB. http://dx.doi.org/10.1002/dta.2292

Nichols, DE. Structure-activity relationships of serotonin 5-HT2A agonists. WIREs Membr. Transp. Signal, 1 Sep 2012, 1 (5), 559-579. 573 kB. http://dx.doi.org/10.1002/wmts.42

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. http://dx.doi.org/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. 1.4 MB. http://dx.doi.org/10.1007/BF02245940

Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3.1 MB. http://dx.doi.org/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. http://dx.doi.org/10.1007/s00213-002-1141-z

Gomes, MM; Dõrr, FA; Catalani, LH; Campa, A. Oxidation of lysergic acid diethylamide (LSD) by peroxidises: a new metabolic pathway. Forensic Toxicol., 1 Jul 2012, 30 (2), 87–97. 632 kB. http://dx.doi.org/10.1007/s11419-011-0131-4

McKenna, DJ; Saavedra, JM. Autoradiography of LSD and 2,5-dimethoxyphenylisopropylamine psychotomimetics demonstrates regional, specific cross-displacement in the rat brain. Eur. J. Pharmacol., 13 Oct 1987, 142 (2), 313–315. 263 kB. http://dx.doi.org/10.1016/0014-2999(87)90121-X

Glennon, RA; Titeler, M; McKenney, JD. Evidence for 5-HT2 involvement in the mechanism of action of hallucinogenic agents. Life Sci., 17 Dec 1984, 35 (25), 2505–2511. 332 kB. http://dx.doi.org/10.1016/0024-3205(84)90436-3

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. http://dx.doi.org/10.1016/0091-3057(94)90172-4

Wacker, D; Wang, S; McCorvy, JD; Betz, RM; Venkatakrishnan, AJ; Levit, A; Lansu, K; Schools, ZL; Che, T; Nichols, DE; Shoichet, BK; Dror, RO; Roth, BL. Crystal Structure of an LSD-Bound Human Serotonin Receptor. Cell, 26 Jan 2017, 168 (3), 377–389.e12. 5.4 MB. http://dx.doi.org/10.1016/j.cell.2016.12.033 Open access DOI

Chen, Q; Tesmer, JJ. A Receptor on Acid. Cell, 26 Jan 2017, 168 (3), 339–341. 588 kB. http://dx.doi.org/10.1016/j.cell.2017.01.012

Paulke, A; Kremer, C; Wunder, C; Achenbach, J; Djahanschiri, B; Elias, A; Schwed, JS; Hübner, H; Gmeiner, P; Proschak, E; Toennes, SW; Stark, H. Argyreia nervosa (Burm. f.): Receptor profiling of lysergic acid amide and other potential psychedelic LSD-like compounds by computational and binding assay approaches. J. Ethnopharmacol., 9 Jul 2013, 148 (2), 492–497. 555 kB. http://dx.doi.org/10.1016/j.jep.2013.04.044

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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1016/j.neuropharm.2011.02.006

Martin, DA; Marona-Lewicka, D; Nichols, DE; Nichols, CD. Chronic LSD alters gene expression profiles in the mPFC relevant to schizophrenia. Neuropharmacology, 1 Aug 2014, 83, 1–8. 1.2 MB. http://dx.doi.org/10.1016/j.neuropharm.2014.03.013

Schindler, EA; 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. http://dx.doi.org/10.1016/j.pbb.2011.12.002

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. http://dx.doi.org/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. http://dx.doi.org/10.1016/S0022-5193(76)80030-6

Perez-Aguilar, JM; Shan, J; LeVine, MV; Khelashvili, G; Weinstein, H. A Functional Selectivity Mechanism at the Serotonin-2A GPCR Involves Ligand-Dependent Conformations of Intracellular Loop 2. J. Am. Chem. Soc., 12 Nov 2014, 136 (45), 16044–16054. 4.2 MB. http://dx.doi.org/10.1021/ja508394x

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. 1.1 MB. http://dx.doi.org/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. 1.1 MB. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1038/nrn2884

Sherwood, JN; Stolaroff, MJ; Harman, WW. The psychedelic experience - A new concept in psychotherapy. J. Psychoactive Drugs, 1 Apr 1968, 1 (2), 96–111. 1.8 MB. http://dx.doi.org/10.1080/02791072.1968.10524522

Meyers, FH; Rose, AJ; Smith, DE. Incidents involving the Haight-Ashbury population and some uncommonly used drugs. J. Psychedelic Drugs, 1 Apr 1968, 1 (2), 139–146. 842 kB. http://dx.doi.org/10.1080/02791072.1968.10524531

Turek, IS; Soskin, RA; Kurland, AA. Methylenedioxyamphetamine (MDA)–Subjective Effects. J. Psychedelic Drugs, 1 Jan 1974, 6 (1), 7–14. 3.9 MB. http://dx.doi.org/10.1080/02791072.1974.10471499

Shulgin, AT. Profiles of psychedelic drugs. 9. LSD. J. Psychedelic Drugs, 1 Jan 1980, 12 (2), 173–174. 1.0 MB. http://dx.doi.org/10.1080/02791072.1980.10471571

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. http://dx.doi.org/10.1111/j.1755-5949.2008.00059.x

Urban, JD; Clarke, WP; von 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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1192/bjp.106.444.1120

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. http://dx.doi.org/10.1371/journal.pone.0009019

McDonald, P; Martin, CF; Woods, DJ; Baker, PB; Gough, TA. An analytical study of illicit lysergide. J. Forensic Sci., 1 Jan 1984, 29 (1), 120–130. 493 kB. http://dx.doi.org/10.1520/JFS11642J

Veress, T. Study of the extraction of LSD from illicit blotters for HPLC determination. J. Forensic Sci., 1 Sep 1993, 38 (5), 1105–1110. 348 kB. http://dx.doi.org/10.1520/JFS13514J

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, 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, 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, 1970; pp 21–41. 8.6 MB.

Fenderson5555. Total synthesis of lysergic acid via Pd-catalysed domino cyclizations. 4 Dec 2011. 6.4 MB.

Fenderson5555. Total synthesis of lysergic acid. 25 Jun 2011. 4.4 MB.

Fenderson5555. A more modern lysergic acid synthesis. 28 Jun 2011. 3.3 MB.

Nichols, DE. LSD and its lysergamide cousins. In Heffter Review; Nichols, DE, Ed., Heffter Research Institute, Santa Fe, NM, 2001; Vol. 2, pp 80–87. 270 kB.

Meyers-Riggs, B. Non-LSD ergoloids. countyourculture, 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.

Bailey, K; Verner, D; Legault, D. Distinction of some dialkyl amides of lysergic and iso-lysergic acids from LCD. J. Assoc. Off. Anal. Chem., 1973, 56 (1), 88–99. 513 kB.

Regina, MJ. Biochemical changes associated with serotonergic hallucinogens. Ph. D. Thesis, State University of New York, Buffalo, NY, USA, 1 Jun 2005. 3.4 MB.

Reissig, CJ. The 5-HT1A receptor and hallucinogens. Ph. D. Thesis, State University of New York, Buffalo, NY, USA, 7 Sep 2006. 943 kB.

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5.5 MB.

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB.

Ang, RLL. Molecular basis of the action of hallucinogens. Ph. D. Thesis, New York University, New York, NY, USA, 2010. 2.4 MB.

Schindler, EAD. Behavioral and biochemical distinctions in the pharmacology of two common hallucinogens. Ph. D. Thesis, Drexel University, Philadelphia, PA, USA, 1 Apr 2010. 5.9 MB.

Shulgin, AT. US Chemical + Biological Testing Programme 2/2: Doctors. Dr. Alexander Shulgin, LSD Expert. 5 Apr 2016. 239 kB. Also available: 2-up, landscape layout and a less opinionated reconstruction of the original transcript.

Nichols, DE. Potential psychotomimetics: Bromomethoxyamphetamines and structural congeners of lysergic acid. Ph. D. Thesis, University of Iowa, Iowa City, IA, 1 May 1973. 13.0 MB.

LA-111
N-Methyllysergamide
LAE-32 · N-Ethyllysergamide
N-Propyllysergamide
Ergonovine
N-Butyllysergamide
LSB · N-Butan-2-yllysergamide
Methergine
N-Pentyllysergamide
N-Pentan-2-yllysergamide
LSP · N-Pentan-3-yllysergamide
N-Hexyllysergamide
N-Hexan-2-yllysergamide
N-Heptyllysergamide
N-Heptan-2-yllysergamide
DAM-57 · N,N-Dimethyllysergamide
N-Ethyl-N-methyllysergamide
LAMPA · LMP
LA-Me/iso · MIPLA
5328
N-Ethyl-N-propyllysergamide
N,N-Dipropyllysergamide
DIPLA · N,N-Diisopropyllysergamide
DAL
5334
LSH
IPLA · N-Isopropyllysergamide
EIPLA · N-Ethyl-N-isopropyllysergamide
LA-CH2CF3
5083
LA-MeO
ALD-52
MLD-41
1-Hydroxymethyl-LSD
1-Dimethylaminomethyl-LSD
1P-LSD
BOL-148 · 2-Bromo-LSD
2-Iodo-LSD
AL-LAD
ETH-LAD
PRO-LAD
PARGY-LAD
BU-LAD
PHENETH-LAD
nor-LSD
FLUORETH-LAD
CYP-LAD
LA-Pyr · LPD-824
5336
LA-Pip
LA-Morph · LSM-775
l-LSD
d-iso-LSD
l-iso-LSD
LA-SS-Az
LA-Cispyr
LA-RR-Az
LA-RS-Az
LA-Aziridine
12-MeO-6-Me-Ergoline
5705
5707
2,3-Dihydro LSD
6-Me-Ergoline
Descarboxylysergic acid
N-Butyllysergamide
LSB · N-Butan-2-yllysergamide
LAMPA · LMP
LA-Me/iso · MIPLA
LA-111
N-Methyllysergamide
LAE-32 · N-Ethyllysergamide
N-Propyllysergamide
Ergonovine
N-Butyllysergamide
LSB · N-Butan-2-yllysergamide
Methergine
N-Pentyllysergamide
N-Pentan-2-yllysergamide
LSP · N-Pentan-3-yllysergamide
N-Hexyllysergamide
N-Hexan-2-yllysergamide
N-Heptyllysergamide
N-Heptan-2-yllysergamide
DAM-57 · N,N-Dimethyllysergamide
N-Ethyl-N-methyllysergamide
LAMPA · LMP
LA-Me/iso · MIPLA
5328
N-Ethyl-N-propyllysergamide
N,N-Dipropyllysergamide
DIPLA · N,N-Diisopropyllysergamide
DAL
5334
LSH
IPLA · N-Isopropyllysergamide
EIPLA · N-Ethyl-N-isopropyllysergamide
LA-CH2CF3
5083
LA-MeO
ALD-52
MLD-41
1-Hydroxymethyl-LSD
1-Dimethylaminomethyl-LSD
1P-LSD
BOL-148 · 2-Bromo-LSD
2-Iodo-LSD
AL-LAD
ETH-LAD
PRO-LAD
PARGY-LAD
BU-LAD
PHENETH-LAD
nor-LSD
FLUORETH-LAD
CYP-LAD
LA-Pyr · LPD-824
5336
LA-Pip
LA-Morph · LSM-775
l-LSD
d-iso-LSD
l-iso-LSD
LA-SS-Az
LA-Cispyr
LA-RR-Az
LA-RS-Az
LA-Aziridine
12-MeO-6-Me-Ergoline
5705
5707
2,3-Dihydro LSD
6-Me-Ergoline
Descarboxylysergic acid
N-Butyllysergamide
LSB · N-Butan-2-yllysergamide
LAMPA · LMP
LA-Me/iso · MIPLA
24 November 2017 · Creative Commons BY-NC-SA ·