10,11-Secoergoline
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| Names | |
|---|---|
| IUPAC name
10,11-Secoergoline | |
| Systematic IUPAC name
3-[(Piperidin-2-yl)methyl]-1H-indole | |
| Other names
3-(2-Piperidylmethyl)indole; α,N-Tetramethylenetryptamine; α,N-Piperidinyltryptamine; α,N-Pip-T | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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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 their standard state (at 25°C [77°F], 100kPa).
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Chemical compound
10,11-Secoergoline, also known as 3-(2-piperidylmethyl)indole or as α,N-tetramethylenetryptamine, is the structure of ergoline in which the bond between the 10 and 11 positions of the ring system has been broken to unconstrain the molecule.[1] [2] It is also a tryptamine with the amine cyclized into a piperidine ring connected to the α position.[1] [2]
A notable derivative of 10,11-secoergoline is CT-5252 (methyl-12-bromo-8,9-didehydro-2,3β-dihydro-6-methyl-10,11-secoergoline-8-carboxylate), which is an analogue of lysergic acid diethylamide (LSD) with some of the same behavioral effects in animals but with much lower potency.[3] [4] [5]
See also
[edit ]- Partial ergoline
- Secoergoline
- Seco-LSD
- Pyr-T (N,N-tetramethylenetryptamine)
- SN-22 (3-(1-methyl-4-piperidinyl)indole)
- MPMI (3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole)
- RU-24,969
- EMD-386088
- Mefloquine
References
[edit ]- 1 2 Alexander Senning (8 October 2019). "4. The IUPAC systematic nomenclature". The Etymology of Chemical Names: Tradition and Convenience vs. Rationality in Chemical Nomenclature. De Gruyter. pp. 167–236. doi:10.1515/9783110612714-004. ISBN 978-3-11-061271-4.
10,11-Secoergoline (3-{(2S)-[(piperidin-2-yl)methyl]}-1H-indole). The name ergoline is ultimately from ergot (Claviceps purpurea).
- 1 2 "Indole, 3-(2-piperidylmethyl)-". PubChem. Retrieved 18 March 2025.
- ↑ David E. Nichols (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.
- ↑ D. V. Siva Sankar (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.
- ↑ Sivadjian J (May 1970). "Etude 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.
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