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N,N-di-n-propylserotonin: binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin. 1988

R A Glennon, and M Titeler, and R A Lyon, and R M Slusher
Department of Medicinal Chemistry/School of Pharmacy, Medical College of Virginia, Virginia Commonwealth University, Richmond 23298-0581.

8-Hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT) is a serotonergic agonist with high affinity and selectivity for a particular population of central serotonin (5-HT) binding sites (i.e., 5-HT1A sites). Because the selectivity of 8-OH-DPAT may be due to the terminal amine substituents, the di-n-propyl analogue of 5-HT (i.e., 4) and of 5-methoxytryptamine (i.e., 5) were prepared and compared with 8-OH-DPAT with respect to their binding profile. Unlike 8-OH-DPAT, neither compound 4 nor 5 displays selectivity for 5-HT1A vs 5-HT2 sites. Consistent with these results, stimulus generalization occurs with 5 both in rats trained to discriminate 8-OH-DPAT from saline and in rats trained to discriminate the 5-HT2 agonist DOM from saline. The results of this study suggest that it is not the N,N-dipropyl groups that account for selectivity, but, rather, it is some feature associated with the pyrrole portion of the indolylalkanamines that is important.

UI MeSH Term Description Entries
D008297 Male Males
D009281 Naphthalenes Two-ring crystalline hydrocarbons isolated from coal tar. They are used as intermediates in chemical synthesis, as insect repellents, fungicides, lubricants, preservatives, and, formerly, as topical antiseptics.
D011919 Rats, Inbred Strains Genetically identical individuals developed from brother and sister matings which have been carried out for twenty or more generations or by parent x offspring matings carried out with certain restrictions. This also includes animals with a long history of closed colony breeding. August Rats,Inbred Rat Strains,Inbred Strain of Rat,Inbred Strain of Rats,Inbred Strains of Rats,Rat, Inbred Strain,August Rat,Inbred Rat Strain,Inbred Strain Rat,Inbred Strain Rats,Inbred Strains Rat,Inbred Strains Rats,Rat Inbred Strain,Rat Inbred Strains,Rat Strain, Inbred,Rat Strains, Inbred,Rat, August,Rat, Inbred Strains,Rats Inbred Strain,Rats Inbred Strains,Rats, August,Rats, Inbred Strain,Strain Rat, Inbred,Strain Rats, Inbred,Strain, Inbred Rat,Strains, Inbred Rat
D011985 Receptors, Serotonin Cell-surface proteins that bind SEROTONIN and trigger intracellular changes which influence the behavior of cells. Several types of serotonin receptors have been recognized which differ in their pharmacology, molecular biology, and mode of action. 5-HT Receptor,5-HT Receptors,5-Hydroxytryptamine Receptor,5-Hydroxytryptamine Receptors,Receptors, Tryptamine,Serotonin Receptor,Serotonin Receptors,Tryptamine Receptor,Tryptamine Receptors,Receptors, 5-HT,Receptors, 5-Hydroxytryptamine,5 HT Receptor,5 HT Receptors,5 Hydroxytryptamine Receptor,5 Hydroxytryptamine Receptors,Receptor, 5-HT,Receptor, 5-Hydroxytryptamine,Receptor, Serotonin,Receptor, Tryptamine,Receptors, 5 HT,Receptors, 5 Hydroxytryptamine
D004193 Discrimination Learning Learning that is manifested in the ability to respond differentially to various stimuli. Discriminative Learning,Discrimination Learnings,Discriminative Learnings,Learning, Discrimination,Learning, Discriminative
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D001665 Binding Sites The parts of a macromolecule that directly participate in its specific combination with another molecule. Combining Site,Binding Site,Combining Sites,Site, Binding,Site, Combining,Sites, Binding,Sites, Combining
D012701 Serotonin A biochemical messenger and regulator, synthesized from the essential amino acid L-TRYPTOPHAN. In humans it is found primarily in the central nervous system, gastrointestinal tract, and blood platelets. Serotonin mediates several important physiological functions including neurotransmission, gastrointestinal motility, hemostasis, and cardiovascular integrity. Multiple receptor families (RECEPTORS, SEROTONIN) explain the broad physiological actions and distribution of this biochemical mediator. 5-HT,5-Hydroxytryptamine,3-(2-Aminoethyl)-1H-indol-5-ol,Enteramine,Hippophaine,Hydroxytryptamine,5 Hydroxytryptamine
D013764 Tetrahydronaphthalenes Partially saturated 1,2,3,4-tetrahydronaphthalene compounds. Tetralins
D017371 8-Hydroxy-2-(di-n-propylamino)tetralin A serotonin 1A-receptor agonist that is used experimentally to test the effects of serotonin. 8-OH-DPAT,8-Hydroxy-2-(di-n-propylamino)tetralin Hydrobromide,8-Hydroxy-2-(di-n-propylamino)tetralin Hydrobromide, (+-)-Isomer,8-Hydroxy-2-(di-n-propylamino)tetralin Hydrobromide, (R)-Isomer,,8-Hydroxy-2-(di-n-propylamino)tetralin Hydrobromide, (S)-Isomer,,8-Hydroxy-2-(di-n-propylamino)tetralin Hydrochloride, (R)-Isomer,,8-Hydroxy-2-(di-n-propylamino)tetralin Hydrochloride, (S)-Isomer,8-Hydroxy-2-(di-n-propylamino)tetralin, (+-)-Isomer,8-Hydroxy-2-(di-n-propylamino)tetralin, (R)-Isomer,8-Hydroxy-2-(di-n-propylamino)tetralin, (S)-Isomer

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