 | |
| Names | |
|---|---|
| IUPAC name 3-(piperidin-2-ylmethyl)-1H-indole | |
| Other names 3-(2-Piperidylmethyl)indole; α,N-Tetramethylenetryptamine; α,N-Piperidinyltryptamine; α,N-Pip-T | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
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| Properties | |
| C14H18N2 | |
| Molar mass | 214.31 g/mol |
| Pharmacology | |
| Drug class | Simplified/partial ergoline |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
10,11-Secoergoline, also known as3-(2-piperidylmethyl)indole or asα,N-tetramethylenetryptamine, is thestructure ofergoline in which thebond between the 10 and 11 positions of thering system has been broken tounconstrain themolecule.[1][2] It is also atryptamine with theaminecyclized into apiperidinering connected to the α position.[1][2]
A notablederivative of 10,11-secoergoline isCT-5252 (methyl-12-bromo-8,9-didehydro-2,3β-dihydro-6-methyl-10,11-secoergoline-8-carboxylate), which is ananalogue oflysergic acid diethylamide (LSD) with some of the same behavioral effects in animals but with much lowerpotency.[3][4][5]
10,11-Secoergoline (3-{(2S)-[(piperidin-2-yl)methyl]}-1H-indole). The name ergoline is ultimately from ergot (Claviceps purpurea).
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.
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