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| Clinical data | |
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| 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 |
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| Chemical and physical data | |
| Formula | C17H21BrN2O2 |
| Molar mass | 365.271 g·mol−1 |
| 3D model (JSmol) | |
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CT-5252 is atryptamine-likeless-rigidanalogue oflysergic acid diethylamide (LSD).[1][2][3][4] It is a10,11-secoergoline; that is, anergoline in which thecovalent bond between the 10 and 11 positions of the ergolinering system has been broken tounconstrain thestructure.[2][3][4] The drug produces specific LSD-like behavioral changes inguinea pigs but with only about 1/48th thepotency of LSD.[1][2][3] It also causesseizures at slightly higher doses than those that cause LSD-like effects.[3] CT-5252 was first described in thescientific literature in 1969.[4][3] Theanalogue of CT-5252 with anN,N-diethyl-carboxamidemoiety on thetetrahydropyridinering instead of thecarboxylategroup (i.e., more analogous to LSD) has also been assessed and described.[3]
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.
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.
[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.
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