ETH-LAD

ETH-LAD Summary

IUPAC Name: N,N,6-Triethyl-9,10-didehydroergoline-8β-carboxamide

Molecular Weight: 337.459

Formula: C21H27N3O

InChI: 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

InChI Key: MYNOUXJLOHVSMQ-DNVCBOLYSA-N

SMILES: CCN(C(=O)[[email protected]]1CN(CC)[[email protected]]2C(=C1)c1cccc3c1c(C2)c[nH]3)CC

Links:

Similar Compounds:

5-MEO-DALT
2-ME-DMT
DIPT
MIPT
MPT
MET
DPT
4-ACO-DMT
4-ACO-MET
4-ACO-DET
4-HO-MIPT
4-HO-MET
4-ACO-DPT
4-ACO-MIPT
4-HO-DET
4-HO-MCPT
4-HO-EPT
4-HO-MPT
4-HO-MALT
4-MEO-MIPT
EPT
METHALLYLESCALINE
1P-LSD
MIPLA
1B-LSD
1P-ETH-LAD
1CP-LSD
ALD-52

References:

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, Lisbon, 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., 17 Oct 2018, 9 (10), 2331–2343. 1.1 MB. https://doi.org/10.1021/acschemneuro.8b00043

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, ; pp 74–91. 51 kB.

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

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

Wagmann, L; Richter, LHJ; Kehl, T; Wack, F; Bergstrand, MP; Brandt, SD; Stratford, A; Maurer, HH; Meyer, MR. In vitro metabolic fate of nine LSD-based new psychoactive substances and their analytical detectability in different urinary screening procedures. Anal. Bioanal. Chem., 7 Jan 2019, n/a. 3.8 MB. https://doi.org/10.1007/s00216-018-1558-9 #16  MS

Heim, R. Synthesis and pharmacology of potent 5-HT_2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. 3.9 MB. #22 In German. MS,NMR,IR

McCorvy, JD. Mapping the binding site of the 5-HT_2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics. Ph. D. Thesis, Purdue University, 1 Jan 2012. 3.9 MB. #Eth-LAD