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

References

  1. ^ a b 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. p. 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).
  2. ^ a b "Indole, 3-(2-piperidylmethyl)-". PubChem. Retrieved 18 March 2025.
  3. ^ 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.
  4. ^ 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.
  5. ^ Sivadjian J (May 1970). "Etude psychopharmacologique de quelques dérivés analogues à l'acide lysergique" [Psychopharmacological study of some derivatives analogous with lysergic acid]. C R Acad Hebd Seances Acad Sci D (in French). 270 (20): 2499–2501. PMID 4987582.



Allikas: https://en.wikipedia.org/wiki/10,11-Secoergoline
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