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ETH-LAD

Clinical data
Synonyms	ETH-LAD, 6-ethyl-6-nor-Lysergic acid diethylamide
Routes of administration	Oral
Legal status
Legal status	UK: Class A
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
IUPAC name (6aR,9R)-N,N-diethyl-7-ethyl-4,6,6a,7,8,9- hexahydroindolo-[4,3-fg]quinoline-9-carboxamide
CAS Number	65527-62-0 Y
PubChem CID	44457783
ChemSpider	21106300 Y
UNII	21Z2736X9Q
ChEMBL	CHEMBL22694 Y
Chemical and physical data
Formula	C21H27N3O
Molar mass	337.47 g/mol
3D model (JSmol)	Interactive image
SMILES CCN(C([C@@H]1C=C2C3=CC=CC4=C3C(C[C@H]2N(CC)C1)=CN4)=O)CC
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 Y Key:MYNOUXJLOHVSMQ-DNVCBOLYSA-N Y
NY (what is this?)  (verify)

ETH-LAD, 6-ethyl-6-nor-lysergic acid diethylamide is an analogue of LSD. Its human psychopharmacology was first described by Alexander Shulgin in the book TiHKAL. ETH-LAD is a psychedelic drug similar to LSD, and is slightly more potent than LSD itself,^[1] with an active dose reported at between 20 and 150 micrograms. ETH-LAD has subtly different effects to LSD, described as less demanding.

Legality

On June 10, 2014 the UK Advisory Council on the Misuse of Drugs (ACMD) recommended that ETH-LAD be specifically named in the UK Misuse of Drugs Act as a class A drug despite not identifying it as ever having been sold or any harm associated with its use.^[2] The UK Home office accepted this advice and announced a ban of the substance to be enacted on 6 January 2015 as part of The Misuse of Drugs Act 1971 (Amendment) (No. 2) Order 2014.

ETH-LAD is illegal in Switzerland as of December 2015.^[3]

Literature

• Andrew J. Hoffman, David E. Nichols: Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives. In: Journal of Medicinal Chemistry. 28, 1985, p. 1252–1255, doi:10.1021/jm00147a022.


• V. J. Watts, R. B. Mailman, C. P. Lawler, K. A. Neve, D. E. Nichols: LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors. In: Psychopharmacology. 118, 1995, p. 401–409, doi:10.1007/BF02245940.


• T. Niwaguchi, Y. Nakahara, H. Ishii: Studies on lysergic acid diethylamide and related compounds. IV. Syntheses of various amide derivatives of norlysergic acid and related compounds. In: Yakugaku Zasshi. Vol. 96, No. 5, May 1976, p. 673–678, .mw-parser-output cite.citationfont-style:inherit.mw-parser-output qquotes:"""""""'""'".mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em
  PMID 987200.


• Robert C. Pfaff, Xuemei Huang, Danuta Marona-Lewicka, Robert Oberlender and David E. Nichols: Lysergamides Revisited. In: NIDA Research Monograph 146: Hallucinogens: An Update. p. 52, 1994, United States Department of Health and Human Services.


• Simon D. Brandt, Pierce V. Kavanagh et 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). In: Drug Testing and Analysis. 2017, doi:10.1002/dta.2196.

See also

• 1P-ETH-LAD


• LSD


• AL-LAD


• PRO-LAD

References

External links

• ETH-LAD entry in TIHKAL


• ETH-LAD entry in Isomerdesign

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