CT-5252

CT-5252 is a tryptamine-like less-rigid analogue of lysergic acid diethylamide (LSD).^[1]^[2]^[3]^[4] It is a 10,11-secoergoline; that is, an ergoline in which the covalent bond between the 10 and 11 positions of the ergoline ring system has been broken to unconstrain the structure.^[2]^[3]^[4] The drug produces specific LSD-like behavioral changes in guinea pigs but with only about 1/48th the potency of LSD.^[1]^[2]^[3] It also causes seizures at slightly higher doses than those that cause LSD-like effects.^[3] CT-5252 was first described in the scientific literature in 1969.^[4]^[3] The analogue of CT-5252 with an N,N-diethyl-carboxamide moiety on the tetrahydropyridine ring instead of the carboxylate group (i.e., more analogous to LSD) has also been assessed and described.^[3]

Other namesCT5252; Methyl-12-bromo-8,9-didehydro-2,3β-dihydro-6-methyl-10,11-secoergoline-8-carboxylate

Drug classSimplified/partial LSD analogue

ATC code

None

FormulaC₁₇H₂₁BrN₂O₂

Quick facts Clinical data, Other names ...

CT-5252
Clinical data


Other names	CT5252; Methyl-12-bromo-8,9-didehydro-2,3β-dihydro-6-methyl-10,11-secoergoline-8-carboxylate
Drug class	Simplified/partial LSD analogue
ATC code	None
Chemical and physical data
Formula	C₁₇H₂₁BrN₂O₂
Molar mass	365.271 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC(=O)C1=CCC(CC2CNc3ccc(Br)cc23)N(C)C1
InChI InChI=1S/C17H21BrN2O2/c1-20-10-11(17(21)22-2)3-5-14(20)7-12-9-19-16-6-4-13(18)8-15(12)16/h3-4,6,8,12,14,19H,5,7,9-10H2,1-2H3 Key:POWSHADSWSCVJU-UHFFFAOYSA-N

References

[1]
Nichols DE (May 1973). Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid (Thesis). University of Iowa. pp. 18–19. OCLC 1194694085. The dihydroindole derivative 11 was prepared by Sivajian and found to be 1/48 as active as LSD in studies with guinea pigs (38). Sivajian (38) also reported biological activities in the guinea pig for arecoline 12, 6-methylarecoline 13, and 5-phenyl-6-methylarecoline 14. These compounds were devoid of LSD-like activity in guinea pigs.
[2]
Sankar DV (1975). "Molecular Investigations: Relations Between Molecular Structure and Psychobiological Activity / Molecular Aspects: Structure-Activity Relations". LSD - A Total Study (PDF). Westbury, N.Y.: PJD Publications. pp. 65–106 (70–71). ISBN 978-0-9600290-3-7. LCCN 72-95447. Sivadjian reported in 1970 (15) studies on twelve lysergic acid analogues. These included arecoline-HBr, Methyl-12-bromo-8,9-didehydro-2,3-beta-dihydro-6-methyl-10,11-secoergoline-8-carboxylate, and 1,2,5,6-tetrahydro-5-phenyl-1,6-dimethyldiethylnicotinamide-HCI. Of these compounds only the methyl-12-bromo-8,9-didehydro-2,3-beta-dihydro-6-methyl-10,11-secoergoline-8-carboxylate derivative showed some activity. It disrupted the conditioned avoidance response in guinea pigs into a disorderly reflex movement of varying duration. While acetyl LSD was quite active, the acetyl derivatives obtained by acetylation of the indole nitrogen of the compounds were usually less active.
[3]
Sivadjian J (May 1970). "Étude psychopharmacologique de quelques dérivés analogues à l'acide lysergique" [Psychopharmacological study of some derivatives analogous with lysergic acid]. Comptes Rendus de l'Académie des Sciences, Série D (in French). 270 (20): 2499–2501. PMID 4987582. [Translated:] The guinea pig, placed in a conditioning cage and treated with a dose of 13 mg/kg of the product CT 5252, subcutaneously, manifests a certain number of stereotyped reactions, similar to those described previously for LSD-25. In particular, the conditioned flight reflex is transformed into a disordered reflex movement, which may or may not end with a correct response to the conditioned stimulant. The other derivatives lack this activity. Most of these compounds cause epileptiform convulsions in this animal which may be repeated several times and be followed by calm periods lasting 5 and 10 minutes. [...] PHARMACOLOGICAL PART. — The most active of these products tested is CT 5252 (VI b), whose tartrate, at a dose of 9 mg/kg, administered subcutaneously, causes stereotypical reactions similar to those obtained with LSD. The animal begins to scratch and bite the metal filaments of the cage. Treated with doses of 12.5 and 13.5 mg/kg, the animal begins to move back and forth, without reason, from one compartment of the cage to another, but as soon as it hears the sound signal, it becomes panicked; it advances towards the separation barrier, climbs onto this barrier, but immediately withdraws, then returns to the barrier and jumps. We are thus witnessing the transformation of the flight reflex into that of a disorderly movement at the beginning, but which then ends with the correct jump. From this point of view, the product VI b is 48 times less active than LSD-25. At a dose of 15 mg/kg, VI b gives rise to three epileptic seizures, separated from each other by calm periods of 5 and 10 minutes. Its acetylated derivative (VI a), at the same doses, provokes the same stereotypical reactions: scratching of the muzzle, change of compartment without reason; the animal also bites anything it finds unpleasant in the cage; at a dose of 16 mg/kg, it provokes an epileptic seizure, but this product is distinguished from the deacetylated derivative VI b by its action on the flight reflex, which does not undergo any modification.
[4]
Julia M, Le Goffic F, Igolen J, Baillarge M (1969). "Une nouvelle synthese de l'acide lysergique" [A new synthesis of lysergic acid]. Tetrahedron Letters (in French). 10 (20): 1569–1571. doi:10.1016/S0040-4039(01)87946-6.

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