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PHENETH-LAD

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(Redirected fromPHENETHY-LAD)

Pharmaceutical compound
PHENETH-LAD
Clinical data
Other namesPHENETHLAD; PHENETHY-LAD; PHENETHYLAD; 6-(β-Phenethyl)-6-nor-LSD;N-Phenethyl-nor-LSD;N,N-Diethyl-6-phenethyl-6-norlysergamide;N,N-Diethyl-6-(2-phenylethyl)-9,10-didehydroergoline-8β-carboxamide
ATC code
  • None
Identifiers
  • (6aR,9R)-N,N-diethyl-7-(2-phenylethyl)-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChemCID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC27H31N3O
Molar mass413.565 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)CCC5=CC=CC=C5
  • InChI=1S/C27H31N3O/c1-3-29(4-2)27(31)21-15-23-22-11-8-12-24-26(22)20(17-28-24)16-25(23)30(18-21)14-13-19-9-6-5-7-10-19/h5-12,15,17,21,25,28H,3-4,13-14,16,18H2,1-2H3/t21-,25-/m1/s1
  • Key:YCWXYUACPTXUEC-PXDATVDWSA-N

PHENETH-LAD, orPHENETHY-LAD, also known as6-(β-phenethyl)-6-nor-LSD, is adrug of thelysergamide family related tolysergic acid diethylamide (LSD).[1][2][3][4][5] It is thederivative of LSD in which themethyl group at the 6 position has been replaced with aphenylethylmoiety.[1][2][3]

The drug failed to substitute for LSD in rodentdrug discrimination tests, with a maximum of 25 or 50% LSD-appropriate responding at the highest assessed dose.[1][4][5] Unlike other 6-substituted lysergamides, PHENETH-LAD was not assessed at theserotonin receptors.[1][5] According toAlexander Shulgin in his bookTiHKAL (Tryptamines I Have Known and Loved), PHENETH-LAD produced no effects in humans at a dose of 500 μg.[3] He has specified the potentially active dose as being >350 μg and itshallucinogenicpotency being less than 30% of that of LSD.[2][6]

PHENETH-LAD was first described in thescientific literature by Andrew Joseph Hoffman of the lab ofDavid E. Nichols atPurdue University in 1985.[4] Its effects in humans were first described by Shulgin by 1994.[6][3]

See also

[edit]

References

[edit]
  1. ^abcdPfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994)."Lysergamides revisited".NIDA Research Monograph.146:52–73.PMID 8742794.
  2. ^abcShulgin AT (2003)."Basic Pharmacology and Effects". In Laing RR (ed.).Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137.ISBN 978-0-12-433951-4.
  3. ^abcdShulgin A,Shulgin A (September 1997).TiHKAL: The Continuation.Berkeley, California:Transform Press.ISBN 0-9630096-9-9.OCLC 38503252. "With success in the preparation of the rather stable nor-LSD intermediate, any number of 6-substituted nor-LSD homologues and analogues can be synthesized. [...] Several analogues are in the chemical literature, and some of them have been explored in direct comparison to LSD. Here are a few examples: [...] N-Phenethyl-nor-LSD (PHENETH-LAD). Nothing at 500 μg."
  4. ^abcHoffman 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):1252–1255.doi:10.1021/jm00147a022.PMID 4032428.
  5. ^abcHoffman AJ (1987).Synthesis and pharmacological evaluation of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives (Ph.D. thesis). Purdue University. Retrieved30 June 2025 – via ProQuest.only partial generalization occurred to norLSD and the N(6)-2-phenethyl derivative at the doses tested. [...] Table 6. 5-HT1 binding affinity of N(6)-alkyl norLSD derivatives. [...] Table 7. 5-HT2 binding affinity of N(6)-alkyl norLSD derivatives. [...] Table 9. Drug discrimination testing results. [...]
  6. ^abJacob P, Shulgin AT (1994)."Structure-activity relationships of the classic hallucinogens and their analogs".NIDA Research Monograph.146:74–91.PMID 8742795.

External links

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Ergolines
(incl.lysergines)
Clavines
(6,8-dimethylergolines)
Lysergamides
(lysergic acid amides)
Ergopeptines
(peptide ergolines)
Partial ergolines
Related compounds
Natural sources
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