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(8β)-N-(Hexan-2-yl)-6-methyl-9,10-didehydroergoline-8-carboxamide
5321
Variant: N skeleton isomers all
Analogues: 31 14 4 49

IUPAC: (8β)-N-(Hexan-2-yl)-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C22H29N3O Molecular weight: 351.48516 g/mol InChI Key: XPLDMBFWNMAYJN-ANGYQSCVSA-N

InChI=1S/C22H29N3O/c1-4-5-7-14(2)24-22(26)16-10-18-17-8-6-9-19-21(17)15(12-23-19)11-20(18)25(3)13-16/h6,8-10,12,14,16,20,23H,4-5,7,11,13H2,1-3H3,(H,24,26)/t14?,16-,20-/m1/s1

PubChem CID: 10405716; ChemSpider: 23240253

See also TiHKAL: #26 LSD        

Nichols, DE; Monte, A; Huang, X; Marona-Lewicka, D. Stereoselective pharmacological effects of lysergic acid amides possessing chirality in the amide substituent. Behav. Brain Sci., 15 Dec 1995, 73 (1–2), 117–119. 267 kB. doi:10.1016/0166-4328(96)00080-0

Monte, AP; Marona-Lewicka, D; Kanthasamy, A; Sanders-Bush, E; Nichols, DE. Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes. J. Med. Chem., 1 Jan 1995, 38 (6), 958–966. 1156 kB. doi:10.1021/jm00006a015

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.

31 N analogues:
5026
Analogue 1: Substituting Diethyl for Hexan-2-yl at N

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

See also PiHKAL: #5 ALEPH-4
#6 ALEPH-6
#7 ALEPH-7
#9 ASB
#21 3C-BZ
#25 3C-E
#28 2C-G-3
#30 2C-G-5
#31 2C-G-N
#41 2C-T-4
#43 2C-T-7
#52 DESOXY
#58 DMMDA
#62 DOB
#66 DOET
#67 DOI
#68 DOM
#69 Ψ-DOM
#79 F-2
#80 F-22
#81 FLEA
#97 4-MA
#100 MDA
#101 MDAL
#108 MDIP
#111 MDMEO
#118 MDPR
#125 META-DOT
#132 MMDA
#134 MMDA-3a
#156 4-TM
#160 TMA-4
#161 TMA-5
#170 5-TOET
See also TiHKAL: #1 AL-LAD
#2 DBT
#6 DMT
#9 DPT
#12 ETH-LAD
#16 4-HO-DET
#17 4-HO-DIPT
#18 4-HO-DMT
#19 5-HO-DMT
#28 4,5-MDO-DIPT
#37 5-MeO-DIPT
#48 α-MT
#51 PRO-LAD
#53 T
#57 DALT

See also Transcripts: 2.214, 2.247, 2.249, 2.256, 2.267, 2.269, 2.288, 2.317, 2.323.2, 3.330, 3.336, 3.344, 3.366, 3.376, 3.387, 3.398, 3.399, 3.405, 4.469, 4.508, 5.600, 5.601, 5.622, 5.623, 5.624, 5.632, 5.657, 5.658, 5.659, 5.660, 5.662

See also Pharmacology notes II: app. 2, Abuse week
p. 214, LSD: A recalibration
p. 247, LSD: Window exploitation studies
p. 249, LSD: Window exploitation studies
p. 256, LSD: Window exploitation studies
p. 267, LSD: Window exploitation studies
p. 269, LSD: Calibration
p. 288, LSD: Primer studies
p. 317, LSD: Primer studies

Fenderson5555. Total synthesis of lysergic acid. 25 Jun 2011. 4413 kB.

Fenderson5555. Total synthesis of lysergic acid via Pd-catalysed domino cyclizations. 4 Dec 2011. 6394 kB.

Fenderson5555. A more modern lysergic acid synthesis. 28 Jun 2011. 3348 kB.

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

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

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

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

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

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. doi:10.1520/JFS11642J

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

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

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

Chemel, BR. Exploring the molecular determinants of binding selectivity and efficacy for D1 dopamine receptor agonists. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 May 2010. 1919 kB.

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

Gomes, MM; Dörr, 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. doi:10.1007/s11419-011-0131-4

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. doi:10.1520/JFS13514J

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.

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. 1213 kB. doi:10.1016/j.neuropharm.2014.03.013

Schindler, EAD. Behavioral and biochemical distinctions in the pharmacology of two common hallucinogens. Ph. D. Thesis, Drexel University, Philadelphia, PA, USA, 1 Apr 2010. 5870 kB.

Ang, RLL. Molecular basis of the action of hallucinogens. Ph. D. Thesis, New York University, New York, NY, USA, 2010. 2402 kB.

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

Regina, MJ. Biochemical changes associated with serotonergic hallucinogens. Ph. D. Thesis, State University of New York, Buffalo, NY, USA, 1 Jun 2005. 3431 kB.

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. doi:10.1016/0014-2999(87)90121-X

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. doi:10.1016/j.jep.2013.04.044

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

Shulgin, AT. LSD and pregnancy. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 28 Jan 2004.

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

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

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

Meyers-Riggs, B. Non-LSD ergoloids. countyourculture: rational exploration of the underground, 1 Dec 2011.

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

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

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

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

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

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

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.

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Shulgin, AT. Morning glory seeds. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 17 Oct 2002.

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

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

Shulgin, AT. Profiles of psychedelic drugs. 9. LSD. J. Psychedelic Drugs, 1 Jan 1980, 12 (2), 173–174. 1025 kB. doi:10.1080/02791072.1980.10471571

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.

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

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

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

5309
Analogue 2: Removing Hexan-2-yl at N

LA-111
LSA
LAA
Ergine
d-Lysergamide

IUPAC: (8β)-6-Methyl-9,10-didehydroergoline-8-carboxamide

Formula: C16H17N3O Molecular weight: 267.32568 g/mol InChI Key: GENAHGKEFJLNJB-QMTHXVAHSA-N

InChI=1S/C16H17N3O/c1-19-8-10(16(17)20)5-12-11-3-2-4-13-15(11)9(7-18-13)6-14(12)19/h2-5,7,10,14,18H,6,8H2,1H3,(H2,17,20)/t10-,14-/m1/s1

PubChem CID: 3016; ChemSpider: 390611; Drugs Forum: LSA; Erowid: LSA; Wikipedia: Ergine

See also TiHKAL: #26 LSD        

Kremer, C; Paulke, A; Wunder, C; Toennes, SW. Variable adverse effects in subjects are ingestion of equal doses of Argyreia nervosa seeds. Forensic Sci. Int., 10 Jan 2012, 214 (1–3), e6–e8. 220 kB. doi:10.1016/j.forsciint.2011.06.025

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. doi:10.1016/j.jep.2013.04.044

5310
Analogue 3: Substituting Methyl for Hexan-2-yl at N

N-Methyllysergamide

IUPAC: (8β)-N,6-Dimethyl-9,10-didehydroergoline-8-carboxamide

Formula: C17H19N3O Molecular weight: 281.35226 g/mol InChI Key: NINBUXQQTOVMAB-IAQYHMDHSA-N

InChI=1S/C17H19N3O/c1-18-17(21)11-6-13-12-4-3-5-14-16(12)10(8-19-14)7-15(13)20(2)9-11/h3-6,8,11,15,19H,7,9H2,1-2H3,(H,18,21)/t11-,15-/m1/s1

PubChem CID: 56841679; ChemSpider: 21161369

See also TiHKAL: #26 LSD        
5311
Analogue 4: Substituting Ethyl for Hexan-2-yl at N

LAE-32
N-Ethyllysergamide

IUPAC: (8β)-N-Ethyl-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C18H21N3O Molecular weight: 295.37884 g/mol InChI Key: VEBWTGYUIBTVNR-MLGOLLRUSA-N

InChI=1S/C18H21N3O/c1-3-19-18(22)12-7-14-13-5-4-6-15-17(13)11(9-20-15)8-16(14)21(2)10-12/h4-7,9,12,16,20H,3,8,10H2,1-2H3,(H,19,22)/t12-,16-/m1/s1

PubChem CID: 12304966; ChemSpider: 19975296; Wikipedia: LAE-32

See also TiHKAL: #26 LSD        

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

5312
Analogue 5: Substituting Propyl for Hexan-2-yl at N

N-Propyllysergamide

IUPAC: (8β)-6-Methyl-N-propyl-9,10-didehydroergoline-8-carboxamide

Formula: C19H23N3O Molecular weight: 309.40542 g/mol InChI Key: VHECNRXVHIGFCO-CXAGYDPISA-N

InChI=1S/C19H23N3O/c1-3-7-20-19(23)13-8-15-14-5-4-6-16-18(14)12(10-21-16)9-17(15)22(2)11-13/h4-6,8,10,13,17,21H,3,7,9,11H2,1-2H3,(H,20,23)/t13-,17-/m1/s1

See also TiHKAL: #26 LSD        
5313
Analogue 6: Substituting 1-Hydroxypropan-2-yl for Hexan-2-yl at N

Ergonovine
Ergometrine
N-(1-Hydroxypropan-2-yl)lysergamide

IUPAC: (8β)-N-(1-Hydroxypropan-2-yl)-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C19H23N3O2 Molecular weight: 325.40482 g/mol InChI Key: WVVSZNPYNCNODU-STQVRIHGSA-N

InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11?,13-,17-/m1/s1

PubChem CID: 443884; ChemSpider: 390049; Wikipedia: Ergometrine

See also TiHKAL: #26 LSD        

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. doi:10.1016/j.jep.2013.04.044

5314
Analogue 7: Substituting Butyl for Hexan-2-yl at N

N-Butyllysergamide

IUPAC: (8β)-N-Butyl-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C20H25N3O Molecular weight: 323.432 g/mol InChI Key: PZRGRDXQFPWKCS-RDTXWAMCSA-N

InChI=1S/C20H25N3O/c1-3-4-8-21-20(24)14-9-16-15-6-5-7-17-19(15)13(11-22-17)10-18(16)23(2)12-14/h5-7,9,11,14,18,22H,3-4,8,10,12H2,1-2H3,(H,21,24)/t14-,18-/m1/s1

PubChem CID: 3039392; ChemSpider: 2302861

See also TiHKAL: #26 LSD        
5315
Analogue 8: Substituting sec-Butyl for Hexan-2-yl at N

LSB
LAMPA
2-Butyllysergamide
Lysergic acid methylpropylamide
N-Butan-2-yllysergamide

IUPAC: (8β)-N-(Butan-2-yl)-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C20H25N3O Molecular weight: 323.432 g/mol InChI Key: NYFSQPDQLFFBRA-OLTOQGTGSA-N

InChI=1S/C20H25N3O/c1-4-12(2)22-20(24)14-8-16-15-6-5-7-17-19(15)13(10-21-17)9-18(16)23(3)11-14/h5-8,10,12,14,18,21H,4,9,11H2,1-3H3,(H,22,24)/t12?,14-,18-/m1/s1

ChemSpider: 23241709; Wikipedia: Lysergic acid 2-butyl amide

See also TiHKAL: #26 LSD        

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

Nichols, DE; Monte, A; Huang, X; Marona-Lewicka, D. Stereoselective pharmacological effects of lysergic acid amides possessing chirality in the amide substituent. Behav. Brain Sci., 15 Dec 1995, 73 (1–2), 117–119. 267 kB. doi:10.1016/0166-4328(96)00080-0

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

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: rational exploration of the underground, 1 Dec 2011.

5316
Analogue 9: Substituting 1-Hydroxybutan-2-yl for Hexan-2-yl at N

Methergine
Methylergonovine
Methylergometrine
N-(1-Hydroxybutan-2-yl)lysergamide

IUPAC: (8β)-N-(1-Hydroxybutan-2-yl)-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C20H25N3O2 Molecular weight: 339.4314 g/mol InChI Key: UNBRKDKAWYKMIV-VZGYSGOJSA-N

InChI=1S/C20H25N3O2/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/t13-,14?,18-/m1/s1

PubChem CID: 8226; ChemSpider: 102713; Wikipedia: Methylergometrine

See also TiHKAL: #26 LSD        
5317
Analogue 10: Substituting Pentyl for Hexan-2-yl at N

N-Pentyllysergamide

IUPAC: (8β)-6-Methyl-N-pentyl-9,10-didehydroergoline-8-carboxamide

Formula: C21H27N3O Molecular weight: 337.45858 g/mol InChI Key: ZWLCMQVCVMIVGG-DNVCBOLYSA-N

InChI=1S/C21H27N3O/c1-3-4-5-9-22-21(25)15-10-17-16-7-6-8-18-20(16)14(12-23-18)11-19(17)24(2)13-15/h6-8,10,12,15,19,23H,3-5,9,11,13H2,1-2H3,(H,22,25)/t15-,19-/m1/s1

PubChem CID: 15815935

See also TiHKAL: #26 LSD        
5318
Analogue 11: Substituting Pentan-2-yl for Hexan-2-yl at N

N-Pentan-2-yllysergamide

IUPAC: (8β)-6-Methyl-N-(pentan-2-yl)-9,10-didehydroergoline-8-carboxamide

Formula: C21H27N3O Molecular weight: 337.45858 g/mol InChI Key: JGLCNUHMSLNTLJ-NWLOPNIYSA-N

InChI=1S/C21H27N3O/c1-4-6-13(2)23-21(25)15-9-17-16-7-5-8-18-20(16)14(11-22-18)10-19(17)24(3)12-15/h5,7-9,11,13,15,19,22H,4,6,10,12H2,1-3H3,(H,23,25)/t13?,15-,19-/m1/s1

PubChem CID: 10427207; ChemSpider: 23240517

See also TiHKAL: #26 LSD        

Nichols, DE; Monte, A; Huang, X; Marona-Lewicka, D. Stereoselective pharmacological effects of lysergic acid amides possessing chirality in the amide substituent. Behav. Brain Sci., 15 Dec 1995, 73 (1–2), 117–119. 267 kB. doi:10.1016/0166-4328(96)00080-0

Monte, AP; Marona-Lewicka, D; Kanthasamy, A; Sanders-Bush, E; Nichols, DE. Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes. J. Med. Chem., 1 Jan 1995, 38 (6), 958–966. 1156 kB. doi:10.1021/jm00006a015

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.

5319
Analogue 12: Substituting Pentan-3-yl for Hexan-2-yl at N

LSP
N-Pentan-3-yllysergamide

IUPAC: (8β)-6-Methyl-N-(pentan-3-yl)-9,10-didehydroergoline-8-carboxamide

Formula: C21H27N3O Molecular weight: 337.45858 g/mol InChI Key: ZQONRMXCBQXYCK-AUUYWEPGSA-N

InChI=1S/C21H27N3O/c1-4-15(5-2)23-21(25)14-9-17-16-7-6-8-18-20(16)13(11-22-18)10-19(17)24(3)12-14/h6-9,11,14-15,19,22H,4-5,10,12H2,1-3H3,(H,23,25)/t14-,19-/m1/s1

PubChem CID: 10019984; ChemSpider: 8195557

See also TiHKAL: #26 LSD        

Monte, AP; Marona-Lewicka, D; Kanthasamy, A; Sanders-Bush, E; Nichols, DE. Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes. J. Med. Chem., 1 Jan 1995, 38 (6), 958–966. 1156 kB. doi:10.1021/jm00006a015

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: rational exploration of the underground, 1 Dec 2011.

5320
Analogue 13: Substituting Hexyl for Hexan-2-yl at N

N-Hexyllysergamide

IUPAC: (8β)-N-Hexyl-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C22H29N3O Molecular weight: 351.48516 g/mol InChI Key: KJCRMZZACWZRNL-OXQOHEQNSA-N

InChI=1S/C22H29N3O/c1-3-4-5-6-10-23-22(26)16-11-18-17-8-7-9-19-21(17)15(13-24-19)12-20(18)25(2)14-16/h7-9,11,13,16,20,24H,3-6,10,12,14H2,1-2H3,(H,23,26)/t16-,20-/m1/s1

See also TiHKAL: #26 LSD        
5322
Analogue 14: Substituting Heptyl for Hexan-2-yl at N

N-Heptyllysergamide

IUPAC: (8β)-N-Heptyl-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C23H31N3O Molecular weight: 365.51174 g/mol InChI Key: MDMVZMYXEOCIOT-DYESRHJHSA-N

InChI=1S/C23H31N3O/c1-3-4-5-6-7-11-24-23(27)17-12-19-18-9-8-10-20-22(18)16(14-25-20)13-21(19)26(2)15-17/h8-10,12,14,17,21,25H,3-7,11,13,15H2,1-2H3,(H,24,27)/t17-,21-/m1/s1

See also TiHKAL: #26 LSD        
5323
Analogue 15: Substituting Heptan-2-yl for Hexan-2-yl at N

N-Heptan-2-yllysergamide

IUPAC: (8β)-N-(Heptan-2-yl)-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C23H31N3O Molecular weight: 365.51174 g/mol InChI Key: HTJZHVCGODLWLI-NZAAYYPMSA-N

InChI=1S/C23H31N3O/c1-4-5-6-8-15(2)25-23(27)17-11-19-18-9-7-10-20-22(18)16(13-24-20)12-21(19)26(3)14-17/h7,9-11,13,15,17,21,24H,4-6,8,12,14H2,1-3H3,(H,25,27)/t15?,17-,21-/m1/s1

PubChem CID: 10361495; ChemSpider: 23240347

See also TiHKAL: #26 LSD        

Nichols, DE; Monte, A; Huang, X; Marona-Lewicka, D. Stereoselective pharmacological effects of lysergic acid amides possessing chirality in the amide substituent. Behav. Brain Sci., 15 Dec 1995, 73 (1–2), 117–119. 267 kB. doi:10.1016/0166-4328(96)00080-0

Monte, AP; Marona-Lewicka, D; Kanthasamy, A; Sanders-Bush, E; Nichols, DE. Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes. J. Med. Chem., 1 Jan 1995, 38 (6), 958–966. 1156 kB. doi:10.1021/jm00006a015

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.

5324
Analogue 16: Substituting Dimethyl for Hexan-2-yl at N

DAM-57
N,N-Dimethyllysergamide

IUPAC: (8β)-N,N,6-Trimethyl-9,10-didehydroergoline-8-carboxamide

Formula: C18H21N3O Molecular weight: 295.37884 g/mol InChI Key: FWHSERNVTGTIJE-MLGOLLRUSA-N

InChI=1S/C18H21N3O/c1-20(2)18(22)12-7-14-13-5-4-6-15-17(13)11(9-19-15)8-16(14)21(3)10-12/h4-7,9,12,16,19H,8,10H2,1-3H3/t12-,16-/m1/s1

PubChem CID: 199478; ChemSpider: 172668; Wikipedia: DAM-57

See also TiHKAL: #26 LSD        

Bailey, K; Grey, AA. A conformational study of lysergic acid and iso-lysergic acid dialkylamides by proton magnetic resonance spectroscopy. Can. J. Chem., 1 Dec 1972, 50 (23), 3876–3885. 342 kB. doi:10.1139/v72-611

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

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

5325
Analogue 17: Substituting Methyl and Ethyl for Hexan-2-yl at N

N-Ethyl-N-methyllysergamide

IUPAC: (8β)-N-Ethyl-N,6-dimethyl-9,10-didehydroergoline-8-carboxamide

Formula: C19H23N3O Molecular weight: 309.40542 g/mol InChI Key: BROWGWCWLHAXPI-CXAGYDPISA-N

InChI=1S/C19H23N3O/c1-4-21(2)19(23)13-8-15-14-6-5-7-16-18(14)12(10-20-16)9-17(15)22(3)11-13/h5-8,10,13,17,20H,4,9,11H2,1-3H3/t13-,17-/m1/s1

See also TiHKAL: #26 LSD        
5326
Analogue 18: Substituting Methyl and Propyl for Hexan-2-yl at N

LMP
N-Methyl-N-propyllysergamide

IUPAC: (8β)-N,6-Dimethyl-N-propyl-9,10-didehydroergoline-8-carboxamide

Formula: C20H25N3O Molecular weight: 323.432 g/mol InChI Key: CZRJGQXHVRNZRZ-RDTXWAMCSA-N

InChI=1S/C20H25N3O/c1-4-8-22(2)20(24)14-9-16-15-6-5-7-17-19(15)13(11-21-17)10-18(16)23(3)12-14/h5-7,9,11,14,18,21H,4,8,10,12H2,1-3H3/t14-,18-/m1/s1

PubChem CID: 497668

See also TiHKAL: #26 LSD        

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

5327
Analogue 19: Substituting Methyl and Isopropyl for Hexan-2-yl at N

MIPLA
LA-Me/iso
Lamide
N-Isopropyl-N-methyllysergamide

IUPAC: (8β)-N,6-Dimethyl-N-(propan-2-yl)-9,10-didehydroergoline-8-carboxamide

Formula: C20H25N3O Molecular weight: 323.432 g/mol InChI Key: ROICYBLUWUMJFF-RDTXWAMCSA-N

InChI=1S/C20H25N3O/c1-12(2)23(4)20(24)14-8-16-15-6-5-7-17-19(15)13(10-21-17)9-18(16)22(3)11-14/h5-8,10,12,14,18,21H,9,11H2,1-4H3/t14-,18-/m1/s1

Wikipedia: Methylisopropyllysergamide

See also TiHKAL: #26 LSD        

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

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

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.

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.

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.

5328
Analogue 20: Substituting Methyl and 1-Phenylpropan-2-yl for Hexan-2-yl at N

N-Methyl-N-(1-phenylpropan-2-yl)lysergamide

IUPAC: (8β)-N,6-Dimethyl-N-(1-phenylpropan-2-yl)-9,10-didehydroergoline-8-carboxamide

Formula: C26H29N3O Molecular weight: 399.52796 g/mol InChI Key: XLCLTSBDVIHWOC-GXQNRAESSA-N

InChI=1S/C26H29N3O/c1-17(12-18-8-5-4-6-9-18)29(3)26(30)20-13-22-21-10-7-11-23-25(21)19(15-27-23)14-24(22)28(2)16-20/h4-11,13,15,17,20,24,27H,12,14,16H2,1-3H3/t17?,20-,24-/m1/s1

See also TiHKAL: #26 LSD        
5330
Analogue 21: Substituting Ethyl and Propyl for Hexan-2-yl at N

N-Ethyl-N-propyllysergamide

IUPAC: (8β)-N-Ethyl-6-methyl-N-propyl-9,10-didehydroergoline-8-carboxamide

Formula: C21H27N3O Molecular weight: 337.45858 g/mol InChI Key: LRVSYILBFXYJOP-DNVCBOLYSA-N

InChI=1S/C21H27N3O/c1-4-9-24(5-2)21(25)15-10-17-16-7-6-8-18-20(16)14(12-22-18)11-19(17)23(3)13-15/h6-8,10,12,15,19,22H,4-5,9,11,13H2,1-3H3/t15-,19-/m1/s1

See also TiHKAL: #26 LSD        

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

5331
Analogue 22: Substituting Dipropyl for Hexan-2-yl at N

N,N-Dipropyllysergamide

IUPAC: (8β)-6-Methyl-N,N-dipropyl-9,10-didehydroergoline-8-carboxamide

Formula: C22H29N3O Molecular weight: 351.48516 g/mol InChI Key: QKKQYCDPPPJVQI-OXQOHEQNSA-N

InChI=1S/C22H29N3O/c1-4-9-25(10-5-2)22(26)16-11-18-17-7-6-8-19-21(17)15(13-23-19)12-20(18)24(3)14-16/h6-8,11,13,16,20,23H,4-5,9-10,12,14H2,1-3H3/t16-,20-/m1/s1

See also TiHKAL: #26 LSD        

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

5332
Analogue 23: Substituting Diisopropyl for Hexan-2-yl at N

DIPLA
N,N-Diisopropyllysergamide

IUPAC: (8β)-6-Methyl-N,N-di(propan-2-yl)-9,10-didehydroergoline-8-carboxamide

Formula: C22H29N3O Molecular weight: 351.48516 g/mol InChI Key: UGLFFFFNSMDCNO-OXQOHEQNSA-N

InChI=1S/C22H29N3O/c1-13(2)25(14(3)4)22(26)16-9-18-17-7-6-8-19-21(17)15(11-23-19)10-20(18)24(5)12-16/h6-9,11,13-14,16,20,23H,10,12H2,1-5H3/t16-,20-/m1/s1

See also TiHKAL: #26 LSD        

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

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.

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.

5333
Analogue 24: Substituting Diallyl for Hexan-2-yl at N

DAL
N,N-Diallyllysergamide

IUPAC: (8β)-6-Methyl-N,N-di(prop-2-en-1-yl)-9,10-didehydroergoline-8-carboxamide

Formula: C22H25N3O Molecular weight: 347.4534 g/mol InChI Key: VAMQYGHNZLRSSA-OXQOHEQNSA-N

InChI=1S/C22H25N3O/c1-4-9-25(10-5-2)22(26)16-11-18-17-7-6-8-19-21(17)15(13-23-19)12-20(18)24(3)14-16/h4-8,11,13,16,20,23H,1-2,9-10,12,14H2,3H3/t16-,20-/m1/s1

PubChem CID: 57481013; ChemSpider: 21106294; Wikipedia: Diallyllysergamide

See also TiHKAL: #26 LSD        
5334
Analogue 25: Substituting Dibutyl for Hexan-2-yl at N

N,N-Dibutyllysergamide

IUPAC: (8β)-N,N-Dibutyl-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C24H33N3O Molecular weight: 379.53832 g/mol InChI Key: GVTRJLOTMIDJSS-XMSQKQJNSA-N

InChI=1S/C24H33N3O/c1-4-6-11-27(12-7-5-2)24(28)18-13-20-19-9-8-10-21-23(19)17(15-25-21)14-22(20)26(3)16-18/h8-10,13,15,18,22,25H,4-7,11-12,14,16H2,1-3H3/t18-,22-/m1/s1

See also TiHKAL: #26 LSD        
5364
Analogue 26: Substituting 1-Hydroxyethyl for Hexan-2-yl at N

LSH
Lysergic acid N-(α-hydroxyethyl)amide

IUPAC: (8β)-N-(1-Hydroxyethyl)-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C18H21N3O2 Molecular weight: 311.37824 g/mol InChI Key: WYTJZJPVCDWOOI-WPJLSRQMSA-N

InChI=1S/C18H21N3O2/c1-10(22)20-18(23)12-6-14-13-4-3-5-15-17(13)11(8-19-15)7-16(14)21(2)9-12/h3-6,8,10,12,16,19,22H,7,9H2,1-2H3,(H,20,23)/t10?,12-,16-/m1/s1

PubChem CID: 134553; ChemSpider: 118592; Wikipedia: Lysergic acid hydroxyethylamide

5567
Analogue 27: Substituting Isopropyl for Hexan-2-yl at N

IPLA
N-Isopropyllysergamide

IUPAC: (8β)-6-Methyl-N-(propan-2-yl)-9,10-didehydroergoline-8-carboxamide

Formula: C19H23N3O Molecular weight: 309.40542 g/mol InChI Key: XSQDFRPRMRYUHM-CXAGYDPISA-N

InChI=1S/C19H23N3O/c1-11(2)21-19(23)13-7-15-14-5-4-6-16-18(14)12(9-20-16)8-17(15)22(3)10-13/h4-7,9,11,13,17,20H,8,10H2,1-3H3,(H,21,23)/t13-,17-/m1/s1

PubChem CID: 5282400; ChemSpider: 4445555

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

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.

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.

5569
Analogue 28: Substituting Isopropyl and Ethyl for Hexan-2-yl at N

EIPLA
N-Ethyl-N-isopropyllysergamide

IUPAC: (8β)-N-Ethyl-6-methyl-N-(propan-2-yl)-9,10-didehydroergoline-8-carboxamide

Formula: C21H27N3O Molecular weight: 337.45858 g/mol InChI Key: JLPRDEGOBAGMHN-DNVCBOLYSA-N

InChI=1S/C21H27N3O/c1-5-24(13(2)3)21(25)15-9-17-16-7-6-8-18-20(16)14(11-22-18)10-19(17)23(4)12-15/h6-9,11,13,15,19,22H,5,10,12H2,1-4H3/t15-,19-/m1/s1

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

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.

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.

5080
Analogue 29: Substituting 2,2,2-Trifluoroethyl and Ethyl for Hexan-2-yl at N

LA-CH2CF3

IUPAC: (8β)-N-Ethyl-6-methyl-N-(2,2,2-trifluoroethyl)-9,10-didehydroergoline-8-carboxamide

Formula: C20H22F3N3O Molecular weight: 377.4033896 g/mol InChI Key: VAHPXTJQSWECIC-CXAGYDPISA-N

InChI=1S/C20H22F3N3O/c1-3-26(11-20(21,22)23)19(27)13-7-15-14-5-4-6-16-18(14)12(9-24-16)8-17(15)25(2)10-13/h4-7,9,13,17,24H,3,8,10-11H2,1-2H3/t13-,17-/m1/s1

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

5083
Analogue 30: Substituting 3-Phenylbutan-2-yl for Hexan-2-yl at N

N-(3-Phenylbutan-2-yl)lysergamide

IUPAC: (8β)-6-Methyl-N-(3-phenylbutan-2-yl)-9,10-didehydroergoline-8-carboxamide

Formula: C26H29N3O Molecular weight: 399.52796 g/mol InChI Key: HBRPGJLOSRLGCI-WBIUCTKCSA-N

InChI=1S/C26H29N3O/c1-16(18-8-5-4-6-9-18)17(2)28-26(30)20-12-22-21-10-7-11-23-25(21)19(14-27-23)13-24(22)29(3)15-20/h4-12,14,16-17,20,24,27H,13,15H2,1-3H3,(H,28,30)/t16?,17?,20-,24-/m1/s1

Nichols, DE; Monte, A; Huang, X; Marona-Lewicka, D. Stereoselective pharmacological effects of lysergic acid amides possessing chirality in the amide substituent. Behav. Brain Sci., 15 Dec 1995, 73 (1–2), 117–119. 267 kB. doi:10.1016/0166-4328(96)00080-0

5081
Analogue 31: Substituting Methoxymethyl and Ethyl for Hexan-2-yl at N

LA-MeO

IUPAC: (8β)-N-Ethyl-N-(methoxymethyl)-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C20H25N3O2 Molecular weight: 339.4314 g/mol InChI Key: QIWCKKPOQVUMQP-RDTXWAMCSA-N

InChI=1S/C20H25N3O2/c1-4-23(12-25-3)20(24)14-8-16-15-6-5-7-17-19(15)13(10-21-17)9-18(16)22(2)11-14/h5-8,10,14,18,21H,4,9,11-12H2,1-3H3/t14-,18-/m1/s1

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

14 skeleton analogues:
5335
Analogue 1: With Lysergic acid-cyclic-amine skeleton

LPD-824
LA-Pyr
N-Pyrrolidyllysergamide

IUPAC: [(8β)-6-Methyl-9,10-didehydroergolin-8-yl)](pyrrolidin-1-yl)methanone

Formula: C20H23N3O Molecular weight: 321.41612 g/mol InChI Key: SETDYMMXQQXCRP-RDTXWAMCSA-N

InChI=1S/C20H23N3O/c1-22-12-14(20(24)23-7-2-3-8-23)9-16-15-5-4-6-17-19(15)13(11-21-17)10-18(16)22/h4-6,9,11,14,18,21H,2-3,7-8,10,12H2,1H3/t14-,18-/m1/s1

PubChem CID: 200628; ChemSpider: 173678; Wikipedia: LPD-824

See also TiHKAL: #26 LSD        

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

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

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

5336
Analogue 2: With Lysergic acid-cyclic-amine skeleton

N-(2,5-Dihydro-1H-pyrrolyl)lysergamide

IUPAC: 2,5-Dihydro-1H-pyrrol-1-yl[(8β)-6-methyl-9,10-didehydroergolin-8-yl]methanone

Formula: C20H21N3O Molecular weight: 319.40024 g/mol InChI Key: HCABJTFBYLKAMQ-RDTXWAMCSA-N

InChI=1S/C20H21N3O/c1-22-12-14(20(24)23-7-2-3-8-23)9-16-15-5-4-6-17-19(15)13(11-21-17)10-18(16)22/h2-6,9,11,14,18,21H,7-8,10,12H2,1H3/t14-,18-/m1/s1

See also TiHKAL: #26 LSD        
5337
Analogue 3: With Lysergic acid-cyclic-amine skeleton

LSD-Pip
LA-Pip
N-Piperidinyllysergamide

IUPAC: [(8β)-6-Methyl-9,10-didehydroergolin-8-yl](piperidin-1-yl)methanone

Formula: C21H25N3O Molecular weight: 335.4427 g/mol InChI Key: URDULHYODQAQTM-DNVCBOLYSA-N

InChI=1S/C21H25N3O/c1-23-13-15(21(25)24-8-3-2-4-9-24)10-17-16-6-5-7-18-20(16)14(12-22-18)11-19(17)23/h5-7,10,12,15,19,22H,2-4,8-9,11,13H2,1H3/t15-,19-/m1/s1

See also TiHKAL: #26 LSD        

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.

5338
Analogue 4: With Lysergic acid-cyclic-amine skeleton

LSM-775
LA-Morph
N-Morpholinyllysergamide

IUPAC: [(8β)-6-Methyl-9,10-didehydroergolin-8-yl](morpholin-4-yl)methanone

Formula: C20H23N3O2 Molecular weight: 337.41552 g/mol InChI Key: OTQWCDNEJVKXKG-RDTXWAMCSA-N

InChI=1S/C20H23N3O2/c1-22-12-14(20(24)23-5-7-25-8-6-23)9-16-15-3-2-4-17-19(15)13(11-21-17)10-18(16)22/h2-4,9,11,14,18,21H,5-8,10,12H2,1H3/t14-,18-/m1/s1

PubChem CID: 199507; ChemSpider: 172695; Wikipedia: LSM-775

See also TiHKAL: #26 LSD        

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

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

5363
Analogue 5: With Lysergic acid-cyclic-amine skeleton

LA-SS-Az
LSZ
Lysergic acid 2,4-dimethylazetidide

IUPAC: [(2R,4R)-2,4-Dimethylazetidin-1-yl][(8β)-6-methyl-9,10-didehydroergolin-8-yl]methanone

Formula: C21H25N3O Molecular weight: 335.4427 g/mol InChI Key: DUKNIHFTDAXJON-CTQRGLTFSA-N

InChI=1S/C21H25N3O/c1-12-7-13(2)24(12)21(25)15-8-17-16-5-4-6-18-20(16)14(10-22-18)9-19(17)23(3)11-15/h4-6,8,10,12-13,15,19,22H,7,9,11H2,1-3H3/t12-,13-,15+,19+/m0/s1

PubChem CID: 10472143; Wikipedia: Lysergic acid 2,4-dimethylazetidide

Nichols, DE; Frescas, SP; Marona-Lewicka, D; Kurrasch-Orbaugh, DM. 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., 1 Jan 2002, 45 (19), 4344–4349. 268 kB. doi:10.1021/jm020153s

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

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

5077
Analogue 6: With Lysergic acid-cyclic-amine skeleton

LA-Cispyr
(8β)-8-{[(2R,5S)-2,5-Dimethylpyrrolidin-1-yl]carbonyl}-6-methyl-9,10-didehydroergoline

IUPAC: [(2R,5S)-2,5-Dimethylpyrrolidin-1-yl][(8β)-6-methyl-9,10-didehydroergolin-8-yl]methanone

Formula: C22H27N3O Molecular weight: 349.46928 g/mol InChI Key: BOEUPXAGFWCCGL-FKEXNYPISA-N

InChI=1S/C22H27N3O/c1-13-7-8-14(2)25(13)22(26)16-9-18-17-5-4-6-19-21(17)15(11-23-19)10-20(18)24(3)12-16/h4-6,9,11,13-14,16,20,23H,7-8,10,12H2,1-3H3/t13-,14+,16-,20-/m1/s1

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

5078
Analogue 7: With Lysergic acid-cyclic-amine skeleton

LA-RR-Az
Lysergic acid 2,4-dimethylazetidide
(8β)-8-{[(2R,4R)-2,4-Dimethylazetidin-1-yl]carbonyl}-6-methyl-9,10-didehydroergoline

IUPAC: [(2R,4R)-2,4-Dimethylazetidin-1-yl][(8β-6-methyl-9,10-didehydroergolin-8-yl]methanone

Formula: C21H25N3O Molecular weight: 335.4427 g/mol InChI Key: DUKNIHFTDAXJON-DZDCQFRTSA-N

InChI=1S/C21H25N3O/c1-12-7-13(2)24(12)21(25)15-8-17-16-5-4-6-18-20(16)14(10-22-18)9-19(17)23(3)11-15/h4-6,8,10,12-13,15,19,22H,7,9,11H2,1-3H3/t12-,13-,15-,19-/m1/s1

Wikipedia: Lysergic acid 2,4-dimethylazetidide

Nichols, DE; Frescas, SP; Marona-Lewicka, D; Kurrasch-Orbaugh, DM. 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., 1 Jan 2002, 45 (19), 4344–4349. 268 kB. doi:10.1021/jm020153s

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

5079
Analogue 8: With Lysergic acid-cyclic-amine skeleton

LA-RS-Az
Lysergic acid 2,4-dimethylazetidide
(2R,4S) N-(2,4-Dimethylazetidin-1-yl)lysergamide

IUPAC: [(2R,4S)-2,4-Dimethylazetidin-1-yl][(8β)-6-methyl-9,10-didehydroergolin-8-yl]methanone

Formula: C21H25N3O Molecular weight: 335.4427 g/mol InChI Key: DUKNIHFTDAXJON-FCIKYMEBSA-N

InChI=1S/C21H25N3O/c1-12-7-13(2)24(12)21(25)15-8-17-16-5-4-6-18-20(16)14(10-22-18)9-19(17)23(3)11-15/h4-6,8,10,12-13,15,19,22H,7,9,11H2,1-3H3/t12-,13+,15-,19-/m1/s1

Wikipedia: Lysergic acid 2,4-dimethylazetidide

Nichols, DE; Frescas, SP; Marona-Lewicka, D; Kurrasch-Orbaugh, DM. 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., 1 Jan 2002, 45 (19), 4344–4349. 268 kB. doi:10.1021/jm020153s

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

5084
Analogue 9: With Lysergic acid-cyclic-amine skeleton

N-(2,3-Dimethylaziridin-1-yl)lysergamide

IUPAC: (2,3-Dimethylaziridin-1-yl)[(8β)-6-methyl-9,10-didehydroergolin-8-yl]methanone

Formula: C20H23N3O Molecular weight: 321.41612 g/mol InChI Key: JWVUYYPVOKOFGC-BVAZEHJSSA-N

InChI=1S/C20H23N3O/c1-11-12(2)23(11)20(24)14-7-16-15-5-4-6-17-19(15)13(9-21-17)8-18(16)22(3)10-14/h4-7,9,11-12,14,18,21H,8,10H2,1-3H3/t11?,12?,14-,18-,23?/m1/s1

ChemSpider: 24604704

5702
Analogue 10: With Ergoline skeleton

12-MeO-6-Me-Ergoline

IUPAC: 12-Methoxy-6-methylergoline

Formula: C16H20N2O Molecular weight: 256.3428 g/mol InChI Key: OYPZSOWGCXXXTG-WCQYABFASA-N

InChI=1S/C16H20N2O/c1-18-7-3-4-11-13(18)8-10-9-17-12-5-6-14(19-2)16(11)15(10)12/h5-6,9,11,13,17H,3-4,7-8H2,1-2H3/t11-,13+/m0/s1

Lee, S. The total syntheses of ring-A substituted ergolines. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 1998. 4709 kB. Note: The structure for Ergoline seems to be 6-Methylergoline.

5705
Analogue 11: With Benzoergoline skeleton

IUPAC: (6aR,12bR)-7-Methyl-4,6,6a,7,8,12b-hexahydroindolo[4,3-ab]phenanthridin-2-ol

Formula: C19H18N2O Molecular weight: 290.35902 g/mol InChI Key: IGWGEZHNSGQPLV-IEBWSBKVSA-N

InChI=1S/C19H18N2O/c1-21-10-11-4-2-3-5-14(11)19-15-7-13(22)8-16-18(15)12(9-20-16)6-17(19)21/h2-5,7-9,17,19-20,22H,6,10H2,1H3/t17-,19-/m1/s1

Lee, S. The total syntheses of ring-A substituted ergolines. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 1998. 4709 kB. Note: The structure for Ergoline seems to be 6-Methylergoline.

5707
Analogue 12: With 9,10-Didehydroergoline skeleton

IUPAC: 6-Methyl-9,10-didehydroergolin-13-ol

Formula: C15H16N2O Molecular weight: 240.30034 g/mol InChI Key: OPOQIXLNKCRDLT-CQSZACIVSA-N

InChI=1S/C15H16N2O/c1-17-4-2-3-11-12-6-10(18)7-13-15(12)9(8-16-13)5-14(11)17/h3,6-8,14,16,18H,2,4-5H2,1H3/t14-/m1/s1

Lee, S. The total syntheses of ring-A substituted ergolines. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 1998. 4709 kB. Note: The structure for Ergoline seems to be 6-Methylergoline.

5747
Analogue 13: With Ergoline skeleton

6-Me-Ergoline

IUPAC: 6-Methylergoline

Formula: C15H18N2 Molecular weight: 226.31682 g/mol InChI Key: NNDATQSUZGLGQT-SBXXRYSUSA-N

InChI=1S/C15H18N2/c1-17-7-3-5-11-12-4-2-6-13-15(12)10(9-16-13)8-14(11)17/h2,4,6,9,11,14,16H,3,5,7-8H2,1H3/t11?,14-/m1/s1

ChemSpider: 23190046

1286
Analogue 14: With 9,10-Didehydroergoline skeleton

Descarboxylysergic acid
Descarboxylysergic acid

IUPAC: 6-Methyl-9,10-didehydroergoline

Formula: C15H16N2 Molecular weight: 224.30094 g/mol InChI Key: AHFZNJIKXMBLTJ-CQSZACIVSA-N

InChI=1S/C15H16N2/c1-17-7-3-5-11-12-4-2-6-13-15(12)10(9-16-13)8-14(11)17/h2,4-6,9,14,16H,3,7-8H2,1H3/t14-/m1/s1

Bach, NJ; Hall, DA; Kornfeld, EC. Descarboxylysergic acid (9,10-didehydro-6-methylergoline). J. Med. Chem., 1 Mar 1974, 17 (3), 312–314. 430 kB. doi:10.1021/jm00249a011

Four isomers:
5051
Isomer 1

PRO-LAD
6-Propyl-nor-LSD
N,N-Diethyl-6-propyl-6-norlysergamide
6-Norlysergamide, N,N-diethyl-6-propyl
N,N-Diethylnorlysergamide, 6-propyl
6-Propylnorlysergamide, N,N-diethyl
9,10-Didehydro-6-propyl-N,N-diethylergoline-8β-carboxamide

IUPAC: (8β)-N,N-Diethyl-6-propyl-9,10-didehydroergoline-8-carboxamide

Formula: C22H29N3O Molecular weight: 351.48516 g/mol InChI Key: HZKYLVLOBYNKKM-OXQOHEQNSA-N

InChI=1S/C22H29N3O/c1-4-10-25-14-16(22(26)24(5-2)6-3)11-18-17-8-7-9-19-21(17)15(13-23-19)12-20(18)25/h7-9,11,13,16,20,23H,4-6,10,12,14H2,1-3H3/t16-,20-/m1/s1

PubChem CID: 44457803; ChemSpider: 21106361; Wikipedia: PRO-LAD

See also TiHKAL: #12 ETH-LAD #26 LSD      

See also Transcripts: 5.652

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

5320
Isomer 2

N-Hexyllysergamide

IUPAC: (8β)-N-Hexyl-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C22H29N3O Molecular weight: 351.48516 g/mol InChI Key: KJCRMZZACWZRNL-OXQOHEQNSA-N

InChI=1S/C22H29N3O/c1-3-4-5-6-10-23-22(26)16-11-18-17-8-7-9-19-21(17)15(13-24-19)12-20(18)25(2)14-16/h7-9,11,13,16,20,24H,3-6,10,12,14H2,1-2H3,(H,23,26)/t16-,20-/m1/s1

See also TiHKAL: #26 LSD        
5331
Isomer 3

N,N-Dipropyllysergamide

IUPAC: (8β)-6-Methyl-N,N-dipropyl-9,10-didehydroergoline-8-carboxamide

Formula: C22H29N3O Molecular weight: 351.48516 g/mol InChI Key: QKKQYCDPPPJVQI-OXQOHEQNSA-N

InChI=1S/C22H29N3O/c1-4-9-25(10-5-2)22(26)16-11-18-17-7-6-8-19-21(17)15(13-23-19)12-20(18)24(3)14-16/h6-8,11,13,16,20,23H,4-5,9-10,12,14H2,1-3H3/t16-,20-/m1/s1

See also TiHKAL: #26 LSD        

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

5332
Isomer 4

DIPLA
N,N-Diisopropyllysergamide

IUPAC: (8β)-6-Methyl-N,N-di(propan-2-yl)-9,10-didehydroergoline-8-carboxamide

Formula: C22H29N3O Molecular weight: 351.48516 g/mol InChI Key: UGLFFFFNSMDCNO-OXQOHEQNSA-N

InChI=1S/C22H29N3O/c1-13(2)25(14(3)4)22(26)16-9-18-17-7-6-8-19-21(17)15(11-23-19)10-20(18)24(5)12-16/h6-9,11,13-14,16,20,23H,10,12H2,1-5H3/t16-,20-/m1/s1

See also TiHKAL: #26 LSD        

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

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.

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.

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