5-MeO-DPAC

5-MeO-DPAC
Clinical data
Other names5-Methoxy-3-(dipropylamino)chroman; 5-Methoxy-3-(di-n-propylamino)chroman; 5-Methoxy-3,4-dihydro-N,N-dipropyl-2H-1-benzopyran-3-amine
Drug classSerotonin 5-HT1A receptor agonist
ATC code
  • None
Legal status
Legal status
  • Generally not controlled
Identifiers
  • 5-methoxy-N,N-dipropyl-3,4-dihydro-2H-chromen-3-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H25NO2
Molar mass263.381 g·mol−1
3D model (JSmol)
  • CCCN(CCC)C1CC2=C(C=CC=C2OC)OC1
  • InChI=1S/C16H25NO2/c1-4-9-17(10-5-2)13-11-14-15(18-3)7-6-8-16(14)19-12-13/h6-8,13H,4-5,9-12H2,1-3H3
  • Key:GOWYIQOIWRLZLO-UHFFFAOYSA-N

5-MeO-DPAC, also known as 5-methoxy-3-(dipropylamino)chroman, is a potent and highly selective serotonin 5-HT1A receptor full agonist related to 8-OH-DPAT. It is a derivative of 3-aminochroman, in which in the 5th position of the benzene ring there is a methoxy group, and in the 3rd position of dipropylamine.

The drug shows no affinity for other serotonin receptors or for the dopamine D2 receptor. It acts at very low concentrations, albeit with lower potency than 8-OH-DPAT, and unlike 8-OH-DPAT, does not bind to presynaptic serotonin 5-HT1A receptors in the striatum.[1][2][3][4]

The mechanism of action of 5-MeO-DPAC is to reduce the synthesis and turnover of serotonin in the brain through selective activation of serotonin 5-HT1A autoreceptors, which is mediated through a negative feedback system without a direct effect on striatal binding sites.[5]

5-MeO-DPAC was first described in the scientific literature by 1987.[1]

See also

References

  1. ^ a b Cossery JM, Gozlan H, Spampinato U, Perdicakis C, Guillaumet G, Pichat L, et al. (August 1987). "The selective labelling of central 5-HT1A receptor binding sites by [3H]5-methoxy-3-(di-n-propylamino)chroman". European Journal of Pharmacology. 140 (2): 143–155. doi:10.1016/0014-2999(87)90800-4. PMID 2959487.
  2. ^ Comoy C, Marot C, Podona T, Baudin ML, Morin-Allory L, Guillaumet G, et al. (October 1996). "3-amino-3,4-dihydro-2H-1-benzopyran derivatives as 5-HT1A receptor ligands and potential anxiolytic agents. 2. Synthesis and quantitative structure-activity relationship studies of spiro[pyrrolidine- and piperidine-2,3'(2'H)-benzopyrans]". Journal of Medicinal Chemistry. 39 (21): 4285–4298. doi:10.1021/jm950861w. PMID 8863806.
  3. ^ Podona T, Guardiola-Lemaître B, Caignard DH, Adam G, Pfeiffer B, Renard P, et al. (June 1994). "3,4-Dihydro-3-amino-2H-1-benzopyran derivatives as 5-HT1A receptor ligands and potential anxiolytic agents. 1. Synthesis and structure--activity relationship studies". Journal of Medicinal Chemistry. 37 (12): 1779–1793. doi:10.1021/jm00038a007. PMID 7912735.
  4. ^ Uphouse L, Caldarola-Pastuszka M, Moore N (July 1993). "Inhibitory effects of the 5-HT1A agonists, 5-hydroxy- and 5-methoxy-(3-di-n-propylamino)chroman, on female lordosis behavior". Neuropharmacology. 32 (7): 641–651. doi:10.1016/0028-3908(93)90077-g. PMID 8361579.
  5. ^ Fuller RW, Perry KW, Ward JS (November 1989). "Decreased 5-hydroxytryptamine turnover in striatum and other brain regions after administration of 5-methoxy-3-(di-n-propylamino)chroman to rats". The Journal of Pharmacy and Pharmacology. 41 (11): 805–806. doi:10.1111/j.2042-7158.1989.tb06375.x. PMID 2576058.
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