EiPLA

EiPLA
Clinical data
Other namesEiPLA; Ethylisopropyllysergamide; N-Ethyl-N-isopropyllysergamide; Lysergic acid ethylisopropylamide
Routes of
administration		Oral
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
Identifiers
IUPAC name
  • (6aR,9R)-N-ethyl-7-methyl-N-propan-2-yl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
Chemical and physical data
FormulaC21H27N3O
Molar mass337.467 g·mol−1
3D model (JSmol)
SMILES
  • CCN(C(C)C)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
InChI
  • 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
  • Key:JLPRDEGOBAGMHN-DNVCBOLYSA-N

EiPLA, also known as N-ethyl-N-isopropyllysergamide or as lysergic acid ethylisopropylamide, is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD).[1][2][3] It is an isomer of ETH-LAD.[3]

Interactions

Pharmacology

Pharmacodynamics

In drug discrimination tests in rodents, EiPLA was found to have approximately half the potency of LSD.[1][2][3]

Chemistry

Analogues

Analogues of EiPLA include MiPLA, LAMPA (MPLA), EPLA, EcPLA, and ETFELA, among others.

History

EiPLA was first described in the scientific literature by David E. Nichols and colleagues by at least 1994.[1] It appears to have emerged as a novel designer drug by 2019.[3]

See also

  • Substituted lysergamide
  • Lizard Labs

References

  1. 1 2 3 Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE (March 1994). "Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives". Pharmacology, Biochemistry, and Behavior. 47 (3): 667–673. doi:10.1016/0091-3057(94)90172-4. PMID 8208787.
  2. 1 2 Nichols DE (October 2018). "Dark Classics in Chemical Neuroscience: Lysergic Acid Diethylamide (LSD)". ACS Chemical Neuroscience. 9 (10): 2331–2343. doi:10.1021/acschemneuro.8b00043. PMID 29461039.
  3. 1 2 3 4 Brandt SD, Kavanagh PV, Westphal F, Pulver B, Schwelm HM, Stratford A, et al. (February 2024). "Analytical and behavioral characterization of N-ethyl-N-isopropyllysergamide (EIPLA), an isomer of N6 -ethylnorlysergic acid N,N-diethylamide (ETH-LAD)". Drug Testing and Analysis. 16 (2): 187–198. doi:10.1002/dta.3530. PMID 37321559.
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