Exploring ETH-LAD. To explore a different substance…

Names:
ETH-LAD
N-Ethyl-nor-LSD
6-Norlysergic acid, 6,N,N-triethylamide
6-Norlysergamide, 6,N,N-triethyl
N-(6)-Ethylnorlysergic acid, N,N-diethylamide
9,10-Didehydro-N,N,6-triethylergoline-8β-carboxamide
6,N,N-Triethyl-6-norlysergamide
IUPAC name:
(8β)-N,N,6-Triethyl-9,10-didehydroergoline-8-carboxamide
5012 · C21H27N3O · 337.459
InChI=1S/C21H27N3O/c1-4-23(5-2)21(25)15-10-17-16-8-7-9-18-20(16)14(12-22-18)11-19(17)24(6-3)13-15/h7-10,12,15,19,22H,4-6,11,13H2,1-3H3/t15-,19-/m1/s1
MYNOUXJLOHVSMQ-DNVCBOLYSA-N This stereoisomer Any stereoisomer
CCN(C(=O)[C@H]1CN(CC)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CC

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 Sep 1985, 28 (9), 1252–1255. 583 kB. https://doi.org/10.1021/jm00147a022

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

Watts, VJ; Mailman, RB; Lawler, CP; Neve, KA; Nichols, DE. LSD and structural analogs: Pharmacological evaluation at D1 dopamine receptors. Psychopharmacology, 1 Apr 1995, 118 (4), 401–409. 1.4 MB. https://doi.org/10.1007/BF02245940

Brandt, SD; Kavanagh, PV; Westphal, F; Elliott, SP; Wallach, J; Stratford, A; Nichols, DE; Halberstadt, AL. Return of the lysergamides. Part III: Analytical characterization of N6-ethyl-6-norlysergic acid diethylamide (ETH-LAD) and 1-propionyl ETH-LAD (1P-ETH-LAD). Drug Test. Analysis, 1 Oct 2017, 9 (10), 1641-1649. 1.2 MB. https://doi.org/10.1002/dta.2196

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, 1 Feb 2018, 10 (2), 310-322. 1.2 MB. https://doi.org/10.1002/dta.2222

EMCDDA. New drugs in Europe, 2016, European Monitoring Centre for Drugs and Drug Addiction, 1 May 2017. 489 kB. #43

Nichols, DE. Psychedelics. Pharmacol. Rev., 1 Apr 2016, 68 (2), 264-355. 1.9 MB. https://doi.org/10.1124/pr.115.011478 Updated with published correction to Figure 4 (the α-methyl group was missing in the original)

Nichols, DE. DARK classics in chemical neuroscience: Lysergic acid diethylamide (LSD). ACS Chem. Neurosci., 20 Feb 2018, n/a. 1.1 MB. https://doi.org/10.1021/acschemneuro.8b00043

Shulgin, AT. Basic Pharmacology and Effects. In Hallucinogens. A Forensic Drug Handbook; Laing, R; Siegel, JA, Eds., Academic Press, London, 2003; pp 67–137. 6.3 MB.

Jacob, P; Shulgin, AT. Structure-activity relationships of the classic hallucinogens and their analogs. 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 74–91. 51 kB.

Hoffman, AJ. Synthesis and pharmacological evaluation of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives. Ph. D. Thesis, Purdue University, 1 Aug 1987. 9.3 MB. #2

MLD-41
N-Pentyllysergamide
2-LSP · N-Pentan-2-yllysergamide
LSP · N-Pentan-3-yllysergamide
EPLA · N-Ethyl-N-propyllysergamide
EIPLA · N-Ethyl-N-isopropyllysergamide
N-tert-Butyllysergamide
18 October 2018 · Creative Commons BY-NC-SA ·