Chemistry:10,11-Secoergoline

From HandWiki

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. ↑ 1.0 1.1 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)." 
  2. ↑ 2.0 2.1 "Indole, 3-(2-piperidylmethyl)-". https://pubchem.ncbi.nlm.nih.gov/compound/21346. 
  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. Westbury, N.Y.: PJD Publications. pp. 65–106 (70–71). ISBN 978-0-9600290-3-7. https://www.samorini.it/doc1/alt_aut/sz/sankar-lsd-a-total-study.pdf#page=69. "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. ↑ "Etude psychopharmacologique de quelques dérivés analogues à l'acide lysergique" (in French). Comptes Rendus de l'Académie des Sciences, Série D 270 (20): 2499–2501. May 1970. PMID 4987582. https://erowid.org/references/texts/show/5057docid4847. 





Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:10,11-Secoergoline&oldid=4031475"