10,11-Secoergoline

10,11-Secoergoline structure.svg skin-invert-image 115px 10,11-Secoergoline 3-[(Piperidin-2-yl)methyl]-1H-indole 3-(2-Piperidylmethyl)indole; α,N-Tetramethylenetryptamine; α,N-Piperidinyltryptamine; α,N-Pip-T 5275-05-8 20064 1S/C14H18N2/c1-2-7-14-13(6-1)11(10-16-14)9-12-5-3-4-8-15-12/h1-2,6-7,10,12,15-16H,3-5,8-9H2 NQAIQKCDQAOHIA-UHFFFAOYSA-N 21346 C1CCNC(C1)CC2=CNC3=CC=CC=C32 14 18 2 214.31 g/mol Simplified/partial ergoline 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.Alexander Senning The Etymology of Chemical Names: Tradition and Convenience vs. Rationality in Chemical Nomenclature 4. The IUPAC systematic nomenclature De Gruyter 8 October 2019 978-3-11-061271-4 10.1515/9783110612714-004 167–236 10,11-Secoergoline (3-{(2S)-[(piperidin-2-yl)methyl]}-1H-indole). The name ergoline is ultimately from ergot (Claviceps purpurea).Indole, 3-(2-piperidylmethyl)- PubChem https://pubchem.ncbi.nlm.nih.gov/compound/21346 18 March 2025 It is also a tryptamine with the amine cyclized into a piperidine ring connected to the α position. 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. David E. Nichols Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid May 1973 University of Iowa 18–19 1194694085 https://bitnest.netfirms.com/external/Theses/Nichols1973 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 Molecular Investigations: Relations Between Molecular Structure and Psychobiological Activity / Molecular Aspects: Structure-Activity Relations 65–106 (70–71) LSD - A Total Study 1975 72-95447 978-0-9600290-3-7 PJD Publications Westbury, N.Y. 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. Sivadjian J Psychopharmacological study of some derivatives analogous with lysergic acid Etude psychopharmacologique de quelques dérivés analogues à l'acide lysergique French Comptes Rendus de l'Académie des Sciences, Série D 270 20 2499–2501 May 1970 4987582 https://erowid.org/references/texts/show/5057docid4847 Another notable derivative is 10,11-seco-LSD (UCD0121). Basargin AG, Domokosa A, Hennessey JJ, Aarrestad IK, Sambyal R, Khatib YA, Krüger J, Dunlap LE, Carter SJ, Rebek IA, McKee JL, Schalk SS, Liu M, Fettinger JC, Gonzalez MA, Potluri A, Tantillo DJ, Fiehn O, McCorvy JD, Olson DE Deconstruction of lysergic acid diethylamide Proc Natl Acad Sci U S A 123 38 e2603412123 September 2026 42709856 10.1073/pnas.2603412123 free See also 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-24969 EMD-386088 Mefloquine References Category:N-Monoalkyltryptamines Category:Partial ergolines Category:Piperidines