PHENETH-LAD

PHENETH-LAD
Clinical data
Other names	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
ATC code	None;
Identifiers
	IUPAC name (6aR,9R)-N,N-diethyl-7-(2-phenylethyl)-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;
PubChem CID	44457779;
ChemSpider	23120272;
ChEMBL	ChEMBL23046;
Chemical and physical data
Formula	C27H31N3O
Molar mass	413.565 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)CCC5=CC=CC=C5;
	InChI 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, 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).¹²³⁴⁵ It is the derivative of LSD in which the methyl group at the 6 position has been replaced with a phenyl ethyl moiety.¹²³

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.¹⁴⁵ Unlike other 6-substituted lysergamides, PHENETH-LAD was not assessed at the serotonin receptors.¹⁵ 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 μg.³ He has specified the potentially active dose as being >350 μg and its hallucinogenic potency being less than 30% of that of LSD.²⁶

PHENETH-LAD was first described in the scientific literature by Andrew Joseph Hoffman of the lab of David E. Nichols at Purdue University in 1985.⁴ Its effects in humans were first described by Shulgin by 1994.⁶³

References

Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994). "Lysergamides revisited". NIDA Research Monograph. 146: 52–73. PMID 8742794.
Shulgin 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.
Shulgin 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."
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): 1252–1255. doi:10.1021/jm00147a022. PMID 4032428.
Hoffman AJ (1987). Synthesis and pharmacological evaluation of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives (Ph.D. thesis). Purdue University. Retrieved 30 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. [...]
Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Research Monograph. 146: 74–91. PMID 8742795.

External links

PHENETH-LAD - Isomer Design

[Pfaff_1994-1] Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994). "Lysergamides revisited". NIDA Research Monograph. 146: 52–73. PMID 8742794.

[Shulgin_2003-2] Shulgin 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.

[TiHKAL-3] Shulgin 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."

[Hoffman_1985-4] 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): 1252–1255. doi:10.1021/jm00147a022. PMID 4032428.

[Hoffman_1987-5] Hoffman AJ (1987). Synthesis and pharmacological evaluation of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives (Ph.D. thesis). Purdue University. Retrieved 30 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. [...]

[Jacob_1994-6] Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Research Monograph. 146: 74–91. PMID 8742795.

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References

External links