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UCD0120

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UCD0120
Clinical data
Other namesUCD0120; UCD-0120; "Compound 160a"; des-B-des-C-LSD; Dides-B,C-LSD; 1-Deaza-2,3,4-trinor-LSD; DEMPDHPCA
Drug classSerotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen; Simplified/partial LSD analogue
ATC code
  • None
Identifiers
  • N,N-diethyl-1-methyl-5-phenyl-3,6-dihydro-2H-pyridine-3-carboxamide
PubChem CID
Chemical and physical data
FormulaC17H24N2O
Molar mass272.392 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)C1CN(CC(=C1)C2=CC=CC=C2)C
  • InChI=1S/C17H24N2O/c1-4-19(5-2)17(20)16-11-15(12-18(3)13-16)14-9-7-6-8-10-14/h6-11,16H,4-5,12-13H2,1-3H3
  • Key:DRQYLJPWAXRRHI-UHFFFAOYSA-N

UCD0120, also known as dides-B,C-LSD or as 1-deaza-2,3,4-trinor-LSD, is a psychedelic drug and a cyclized phenethylamine and simplified or partial ergoline that is structurally related to lysergic acid diethylamide (LSD).[1][2][3][4] It is the analogue of LSD in which the carbon and nitrogen atoms at positions 1 through 4 of the ergoline ring system have been removed.[1][2][3][4]

Pharmacology

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Pharmacodynamics

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UCD0120 shows affinity for the serotonin 5-HT2A receptor (Ki = 175 nM).[1][3] It is a potent partial agonist of the serotonin 5-HT2A receptor (EC50Tooltip half-maximal effective concentration = 7.48 nM; EmaxTooltip maximal efficacy = 63%), serotonin 5-HT2B receptor (EC50 = 22.1 nM; Emax = 64%), and serotonin 5-HT2C receptor (EC50 = 18.0 nM; Emax = 89%).[1][3] The drug was 14-fold less potent than LSD as a serotonin 5-HT2A receptor agonist in vitro.[1]

Early research found that UCD0120 produces gross behavioral effects very similar to those of serotonergic psychedelics like LSD in rodents and has been assumed to act as a hallucinogen likewise.[2] However, the drug has not been tested in humans.[2] UCD0120 is much less potent than LSD in rodents, which was active at a dose of 0.16 Όmol/kg by intraperitoneal injection, whereas UCD0120 was active at doses of 10 to 35 Όmol/kg (63- to 219-fold less potent).[2] On the other hand, UCD0120 was more potent than dimethyltryptamine (DMT) and is also more potent than mescaline.[2]

Subsequent research has found that UCD0120 indeed produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[1] The maximally effective dose for the response of the assessed doses was 10 mg/kg, whereas that of LSD was 0.1 mg/kg, suggesting that UCD0120 may be on the order of 100-fold less potent than LSD as a psychedelic drug in rodents.[1]

Pharmacokinetics

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The pharmacokinetics of UCD0120 in rodents have been studied.[1]

Chemistry

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Synthesis

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The chemical synthesis of UCD0120 has been described.[1]

Analogues and derivatives

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A few derivatives of UCD0120 have also been studied and found to produce similar effects and/or amphetamine-like in animals, including the derivatives with 4-methoxy- and 3,4,5-trimethoxy- substitutions on the phenyl ring and the derivative with the phenyl ring replaced with a 1-naphthalene ring.[2] The former two were less potent than UCD0120, whereas the latter was slightly more potent.[2] Another derivative, UCD0120-2C-D, was attempted to be synthesized by David E. Nichols in his PhD thesis.[5] It is the derivative with 4-methyl and 2,5-dimethoxy substitutions on the phenyl ring.[5] These UCD0120 derivatives are cyclized phenethylamine analogues of various psychedelic- and/or stimulant-related phenethylamines and amphetamines including para-methoxyamphetamine (PMA), mescaline (M), 1-naphthylaminopropane (1-NAP), and 2C-D.[2][5] Other analogues of UCD0120 such as UCD0179 have also since been described.[1]

History

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UCD0120 was first described in the scientific literature by Mangner in 1978.[2] It was subsequently patented in 2021 by David E. Olson and colleagues and the patent was assigned to Delix Therapeutics.[3] Later, UCD0120 was described in greater detail by Olson and colleagues 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 Basargin AG, Domokos A, Hennessey JJ, Aarrestad IK, Sambyal R, Khatib YA, KrĂŒger J, Dunlap LE, Carter SJ, Rebek IA, McKee JL, Schalk SS, Liu M, Fettinger JC, Gonzalez MA, Potluri A, Tantillo DJ, Fiehn O, McCorvy JD, Olson DE (September 2026). "Deconstruction of lysergic acid diethylamide" (PDF). Proc Natl Acad Sci U S A. 123 (38): e2603412123. doi:10.1073/pnas.2603412123. PMC 13598156. PMID 42709856.{{cite journal}}: CS1 maint: article number as page number (link)
  2. 1 2 3 4 5 6 7 8 9 10 11 12 13 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 gross behavior of the test animals under the influence of 160a-d was observed during the course of the dose-response study depicted by Figure 7. The gross behavioral signs displayed by rats under the influence of the phenyl (160a) and trimethoxyphenyl (160c) homologs were indistinguishable from those exhibited with LSD, DMT or mescaline, and were characterized by general inactivity, muscle twitching and the occurrence of a Straub tail reaction (a somewhat specific indication of the influence of a psychotomimetic drug in which the tail is held in an upright 191 position ). The naphthyl homolog (160d) produced similar behavioral signs but the rats were more active than with 160a and 160c. The gross behavioral pattern of rats under the influence of the methoxy homolog (160b), in contrast, was not at all similar to that caused by LSD, 160a or 160c. It more closely resembled the pattern exhibited with amphetamine, characterized by very marked hyperactivity. [...] Initial indications, based on the gross behavioral comparisons mentioned previously, are that 160a,c,d possess psychotomimetic activity similar to LSD, while 160b possesses amphetamine-like stimulatory activity. [...] On the other hand, 160a, whose structure more closely resembles that of LSD, seems to have LSD-like activity of greater potency than either 160b or 160c. Since the structure of 160a is very closely related to the structure of LSD and contains no aryl methoxy groups necessary for psychotomimetic activity in the methoxyamphetamine series, it could be inferred that 160a acts via an LSD-like mechanism. [...] SUMMARY [...]
  3. 1 2 3 4 5 WO 2021076572, Olson DE, Dunlap L, Wagner F, Chytil M, Powell NA, "Ergoline-like compounds for promoting neural plasticity", published 22 April 2021, assigned to Delix Therapeutics, Inc. and The Regents of the University of California
  4. 1 2 "N,N-diethyl-1-methyl-5-phenyl-3,6-dihydro-2H-pyridine-3-carboxamide". PubChem. Retrieved 1 April 2025.
  5. 1 2 3 4 Nichols DE (May 1973). Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid (Thesis). University of Iowa. p. 23. OCLC 1194694085.
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