{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = | image = PHENETH-LAD.svg | image_class = skin-invert-image | width = 200px
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<!-- Identifiers --> | CAS_number = | CAS_supplemental = | PubChem = 44457779 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 23120272 | UNII = | KEGG = | ChEBI = | ChEMBL = 23046 | NIAID_ChemDB = | PDB_ligand = | synonyms = PHENETHLAD; 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
<!-- Chemical data --> | IUPAC_name = (6''aR'',9''R'')-''N'',''N''-diethyl-7-(2-phenylethyl)-6,6''a'',8,9-tetrahydro-4''H''-indolo[4,3-fg]quinoline-9-carboxamide | C=27 | H=31 | N=3 | O=1 | SMILES = CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)CCC5=CC=CC=C5 | StdInChI = 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 | StdInChIKey = YCWXYUACPTXUEC-PXDATVDWSA-N }}
'''PHENETH-LAD''', or '''PHENETHY-LAD''', also known as '''6-(β-phenethyl)-6-nor-LSD''', is a drug of the lysergamide family related to lysergic acid diethylamide (LSD).<ref name="Pfaff_1994" /><ref name="Shulgin_2003">{{cite book | vauthors = Shulgin AT | veditors = Laing RR | chapter = Basic Pharmacology and Effects | title = Hallucinogens: A Forensic Drug Handbook | pages = 67–137 | year = 2003 | publisher = Elsevier Science | series = Forensic Drug Handbook Series | isbn = 978-0-12-433951-4 | url = https://books.google.com/books?id=l1DrqgobbcwC | chapter-url = https://web.archive.org/web/20250223164514/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6 }}</ref><ref name="TiHKAL">{{CiteTiHKAL }} "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."</ref><ref name="Hoffman_1985">{{cite journal | vauthors = Hoffman AJ, Nichols DE | title = Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives | journal = Journal of Medicinal Chemistry | volume = 28 | issue = 9 | pages = 1252–1255 | date = September 1985 | pmid = 4032428 | doi = 10.1021/jm00147a022 }}</ref><ref name="Hoffman_1987">{{cite thesis | vauthors = Hoffman AJ | title = Synthesis and pharmacological evaluation of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives | date = 1987 | degree = Ph.D. | publisher = Purdue University | via = ProQuest | url = https://www.proquest.com/openview/3097b1429fad4318d34a8ee7204f9f93 | access-date = 30 June 2025 | quote = 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. [...] }}</ref> It is the derivative of LSD in which the methyl group at the 6 position has been replaced with a phenylethyl moiety.<ref name="Pfaff_1994" /><ref name="Shulgin_2003" /><ref name="TiHKAL" />
The drug failed to substitute for LSD in rodent drug discrimination tests, with a maximum of 25 or 50% LSD-appropriate responding at the highest assessed dose.<ref name="Pfaff_1994" /><ref name="Hoffman_1985" /><ref name="Hoffman_1987" /> Unlike other 6-substituted lysergamides, PHENETH-LAD was not assessed at the serotonin receptors.<ref name="Pfaff_1994">{{cite journal | vauthors = Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE | title = Lysergamides revisited | journal = NIDA Research Monograph | volume = 146 | pages = 52–73 | date = 1994 | pmid = 8742794 | url = https://bitnest.netfirms.com/external/Books/NIDA146.52 }}</ref><ref name="Hoffman_1987" /> According to Alexander Shulgin in his book ''TiHKAL'' (''Tryptamines I Have Known and Loved''), PHENETH-LAD produced no effects in humans at a dose of 500{{nbsp}}μg.<ref name="TiHKAL" /> He has specified the potentially active dose as being >350{{nbsp}}μg and its hallucinogenic potency being less than 30% of that of LSD.<ref name="Shulgin_2003" /><ref name="Jacob_1994">{{cite journal | vauthors = Jacob P, Shulgin AT | title = Structure-activity relationships of the classic hallucinogens and their analogs | journal = NIDA Research Monograph | volume = 146 | pages = 74–91 | date = 1994 | pmid = 8742795 | url = https://bitnest.netfirms.com/external/Books/NIDA146.74 }}</ref>
PHENETH-LAD was first described in the scientific literature by Andrew Joseph Hoffman of the lab of David E. Nichols at Purdue University in 1985.<ref name="Hoffman_1985" /> Its effects in humans were first described by Shulgin by 1994.<ref name="Jacob_1994" /><ref name="TiHKAL" />
==See also== * Substituted lysergamide * NBOMe-LAD
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/5345 PHENETH-LAD - Isomer Design]
{{Ergolines}}
Category:David E. Nichols Category:Carboxamides Category:Diethylamino compounds Category:Lysergamides Category:Phenethylamines
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