TRALA-12

TRALA-12
Clinical data
Other namesTRALA12; N-Ethenyl-N-ethyllysergamide; N-Vinyl-N-ethyllysergamide; Lysergic acid ethenylethylamide; Lysergic acid vinylethylamide; N-Ethenyl-N-ethyl-6-methyl-9,10-didehydroergoline-8β-carboxamide; "Compound 2l"
Routes of
administration		Oral or intravenous[1][2]
Drug classSerotonin receptor modulator; Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Possible serotonergic psychedelic or hallucinogen
ATC code
  • None
Identifiers
  • (6aR,9R)-N-ethenyl-N-ethyl-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC20H23N3O
Molar mass321.424 g·mol−1
3D model (JSmol)
  • CCN(C=C)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
  • InChI=1S/C20H23N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h4,6-9,11,14,18,21H,1,5,10,12H2,2-3H3/t14-,18-/m1/s1
  • Key:MQCCUHBPZPBYDB-RDTXWAMCSA-N

TRALA-12, also known as N-ethenyl-N-ethyllysergamide or as lysergic acid vinylethylamide, is a serotonin receptor modulator and possible psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD).[1] It is the analogue of LSD in which one of the ethyl groups on the amide has been replaced with an ethenyl (vinyl) group.[1] Didehydro-LSD (DDH-LSD), which is structurally and pharmacologically compatible with TRALA-12, is being developed by Matthias Liechti and colleagues as a shorter-lasting LSD analogue for potential medical use.[2]

Pharmacology

Pharmacodynamics

TRALA-12 is a potent agonist of the serotonin 5-HT2 receptors similarly to LSD.[1] Its affinities (Ki) were 0.09 nM for the serotonin 5-HT2A receptor, 0.67 nM for the serotonin 5-HT2B receptor, and 3.8 nM for the serotonin 5-HT2C receptor.[1] Conversely, its activational potencies and efficacies (EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy)) were 0.93 nM (79%) at the serotonin 5-HT2A receptor and 1.7 nM (42%) at the serotonin 5-HT2B receptor, whereas values for the serotonin 5-HT2C receptor were not reported.[1] TRALA-12 showed 19-fold higher affinity for the serotonin 5-HT2A receptor than LSD, though it had only 1.5-fold higher activational potency at the receptor and had slightly lower efficacy (Emax = 79% and 90%, respectively).[1] It similarly showed greatly increased affinities for the serotonin 5-HT2B and 5-HT2C receptors compared to LSD.[1]

Pharmacokinetics

TRALA-12 shows dramatically faster metabolism than LSD in human liver microsomes in vitro.[1] Whereas about 75% remained in the case of LSD following incubation after 4 hours, only about 10% of TRALA-12 remained with incubation after 1 hour.[1] It was concluded that due to its very fast metabolism, TRALA-12 is likely not orally active, but may be active via intravenous infusion with short-lasting effects that can be rapidly terminated upon cessation of infusion.[1]

Chemistry

Synthesis

The chemical synthesis of TRALA-12 has been described.[1]

History

TRALA-12 was patented by Daniel Trachsel and Matthias Liechti and colleagues in association with MindMed (Mind Medicine; now Definium Therapeutics) in 2023.[1]

Research

An LSD analogue called didehydro-LSD (DDH-LSD), which has a name that is structurally compatible with TRALA-12, is being developed by Matthias Liechti and colleagues as a potential novel psychedelic drug for medical applications.[2] It is described as having similar receptor activity as LSD in vitro but as having faster in-vitro metabolism and hence as potentially having a shorter duration in comparison, similarly to the case of TRALA-12.[2] A pharmacokinetic clinical study of DDH-LSD comparing it with LSD is underway at University Hospital Basel in Basel, Switzerland as of March 2026, with both drugs given orally (following an initial dose-finding substudy in the case of DDH-LSD).[2]

See also

References

  1. ^ a b c d e f g h i j k l m US 2023/0414583, Trachsel D, Liechti ME, Lustenberger F, "Lysergic acid derivatives with modified LSD-like action", published 28 December 2023, assigned to Mind Medicine Inc. 
  2. ^ a b c d e "Pharmacokinetics of Didehydro-LSD (DDH-LSD) Compared With LSD (DDH-LSD)". ClinicalTrials.gov. 9 March 2026. Retrieved 15 April 2026.

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