ETH-LAD

Summary

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,[2] with an active dose reported at between 20 and 150 micrograms. ETH-LAD has subtly different effects to LSD, described as less demanding. The true tryptamine counterpart of ETH-LAD is MET, a simplified version of this structure.

ETH-LAD
Clinical data
Other namesETH-LAD, 6-ethyl-6-nor-Lysergic acid diethylamide
Routes of
administration
Oral
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • Illegal in France[1]
Pharmacokinetic data
MetabolismHepatic
ExcretionRenal
Identifiers
  • (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 checkY
PubChem CID
  • 44457783
ChemSpider
  • 21106300 checkY
UNII
  • 21Z2736X9Q
ChEMBL
  • ChEMBL22694 checkY
CompTox Dashboard (EPA)
  • DTXSID90215823 Edit this at Wikidata
Chemical and physical data
FormulaC21H27N3O
Molar mass337.467 g·mol−1
3D model (JSmol)
  • Interactive image
  • CCN(C([C@@H]1C=C2C3=CC=CC4=C3C(C[C@H]2N(CC)C1)=CN4)=O)CC
  • 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 checkY
  • Key:MYNOUXJLOHVSMQ-DNVCBOLYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Legality edit

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.[3] The UK Home office accepted this advice and announced a ban of the substance to be enacted on 6 January 2015.[4]

ETH-LAD is illegal in Switzerland as of December 2015.[5]

See also edit

References edit

  1. ^ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.
  2. ^ Hoffman AJ, Nichols DE (September 1985). "Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives". Journal of Medicinal Chemistry. 28 (9): 1252–5. doi:10.1021/jm00147a022. PMID 4032428.
  3. ^ Advisory Council on the Misuse of Drugs (ACMD) (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Retrieved 10 June 2014.
  4. ^ "The Misuse of Drugs Act 1971 (Amendment) (No. 2) Order 2014".
  5. ^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien". Der Bundesrat.

Further reading edit

  • Hoffman AJ, Nichols DE (September 1985). "Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives". Journal of Medicinal Chemistry. 28 (9): 1252–5. doi:10.1021/jm00147a022. PMID 4032428.
  • Watts VJ, Lawler CP, Fox DR, Neve KA, Nichols DE, Mailman RB (April 1995). "LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors". Psychopharmacology. 118 (4): 401–9. doi:10.1007/BF02245940. PMID 7568626. S2CID 21484356.
  • Niwaguchi T, Nakahara Y, Ishii H (May 1976). "[Studies on lysergic acid diethylamide and related compounds. IV. Syntheses of various amide derivatives of norlysergic acid and related compounds]". Yakugaku Zasshi. 96 (5): 673–8. doi:10.1248/yakushi1947.96.5_673. PMID 987200.
  • Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994). "Lysergamides Revisited" (PDF). NIDA Research Monograph 146: Hallucinogens: An Update. United States Department of Health and Human Services. p. 52. Archived from the original (PDF) on 2015-07-23.
  • Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Stratford A, et al. (October 2017). "6 -ethyl-6-norlysergic acid diethylamide (ETH-LAD) and 1-propionyl ETH-LAD (1P-ETH-LAD)". Drug Testing and Analysis. 9 (10): 1641–1649. doi:10.1002/dta.2196. PMC 6230477. PMID 28342178.

External links edit

  • ETH-LAD entry in TIHKAL
  • ETH-LAD entry in Isomerdesign