Benzofuranylpropylaminopentane

For the mode of mechanical ventilation known as BPAP, see bilevel positive airway pressure.
BPAP
Clinical data
Other names(–)-1-(Benzofuran-2-yl)-2-propylaminopentane; (–)-BPAP; R-(–)-BPAP; BFPAPn; BFPAP; (αR)-N,α-Dipropyl-2-benzofuranethanamine;[1] FPFS-1169[2]
Routes of
administration		By mouth[3]
Drug classMonoaminergic activity enhancer
Identifiers
IUPAC name
  • (2R)-1-(1-Benzofuran-2-yl)-N-propylpentan-2-amine; (-)-BPAP; BFPAPn; BFPAP
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC16H23NO
Molar mass245.366 g·mol−1
3D model (JSmol)
SMILES
  • CCC[C@@H](NCCC)CC1=CC2=C(C=CC=C2)O1
InChI
  • InChI=1S/C16H23NO/c1-3-7-14(17-10-4-2)12-15-11-13-8-5-6-9-16(13)18-15/h5-6,8-9,11,14,17H,3-4,7,10,12H2,1-2H3/t14-/m1/s1 Y
  • Key:LJHIBIVAYHQPBT-CQSZACIVSA-N Y
  (verify)

(–)-Benzofuranylpropylaminopentane (BPAP; developmental code name FPFS-1169) is an experimental drug related to selegiline which acts as a monoaminergic activity enhancer (MAE).[4][5][6][2] It is orally active in animals.[3]

BPAP is a highly potent MAE and enhances the nerve impulse propagation-mediated release of serotonin, norepinephrine, and dopamine.[4][7][5][6] At much higher concentrations, BPAP is also a monoamine reuptake inhibitor, specifically of dopamine and norepinephrine and to a much lesser extent of serotonin.[8] BPAP produces psychostimulant-like effects in animals, with these effects mediated by its MAE actions.[7][9][10] The drug is a substituted benzofuran derivative and tryptamine relative structurally related to phenylpropylaminopentane (PPAP).[5][7][11]

BPAP was first described in 1999.[12][11] There has been interest in BPAP for potential clinical use in humans, including in the treatment of Parkinson's disease, Alzheimer's disease, and depression.[4][12][7] There has also been interest in BPAP to help slow aging.[4][13]

  1. ^ "R-(-)-BPAP". CAS Common Chemistry. Chemical Abstract Service, American Chemical Society. 12 August 2024. 260550-89-8. Retrieved 12 August 2024.
  2. ^ a b Maruyama W, Yi H, Takahashi T, Shimazu S, Ohde H, Yoneda F, et al. (May 2004). "Neuroprotective function of R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane, [R-(-)-BPAP], against apoptosis induced by N-methyl(R)salsolinol, an endogenous dopaminergic neurotoxin, in human dopaminergic neuroblastoma SH-SY5Y cells". Life Sci. 75 (1): 107–117. doi:10.1016/j.lfs.2003.12.001. PMID 15102525. Among catecholaminergic-serotonergic enhancers, (–)-1-phenyl-2-propylaminopentane [(–)-PPAP] and R-(–)-(benzofuran-2-yl)-2-propylaminopentane [R-(–)-BPAP, the development number; FPFS-1169] are the most promising agents (Knoll et al., 1999). [...] Fig. 1. Chemical structure and abbreviations of used BPAP derivatives. FPFS-1169 and FPFS-1170: R-(–)- and S-(+)-1-(benzofuran-2-yl)-2-propylamino-pentane hydrochloride, [...]
  3. ^ a b Cite error: The named reference MagyarLengyelBolehovszky2002 was invoked but never defined (see the help page).
  4. ^ a b c d Cite error: The named reference Knoll2001 was invoked but never defined (see the help page).
  5. ^ a b c Cite error: The named reference ShimazuMiklya2004 was invoked but never defined (see the help page).
  6. ^ a b Miklya I (November 2016). "The significance of selegiline/(-)-deprenyl after 50 years in research and therapy (1965-2015)". Mol Psychiatry. 21 (11): 1499–1503. doi:10.1038/mp.2016.127. PMID 27480491.
  7. ^ a b c d Cite error: The named reference Knoll2003 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference ShimazuTsunekawaYoneda2003 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference ShimazuTakahataKatsuki2001 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference ShimazuTamashiroYoneda2003 was invoked but never defined (see the help page).
  11. ^ a b Cite error: The named reference KnollYonedaKnoll1999 was invoked but never defined (see the help page).
  12. ^ a b Cite error: The named reference GasznerMiklya2006 was invoked but never defined (see the help page).
  13. ^ Knoll J, Miklya I (December 2016). "Longevity study with low doses of selegiline/(-)-deprenyl and (2R)-1-(1-benzofuran-2-yl)-N-propylpentane-2-amine (BPAP)". Life Sci. 167: 32–38. doi:10.1016/j.lfs.2016.10.023. PMID 27777099.
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