Chemistry:Benzofuranylpropylaminopentane

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Short description: Chemical compound
Benzofuranylpropylaminopentane
BPAP.svg
BPAP.png
Clinical data
Other names(-)-1-(Benzofuran-2-yl)-2-propylaminopentane;
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC16H23NO
Molar mass245.366 g·mol−1
3D model (JSmol)
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Benzofuranylpropylaminopentane (BPAP, (-)-BPAP,[1] BFPAPn, or BFPAP) is a drug with an unusual monoamine-release potentiating mechanism of action. It can loosely be grouped with the stimulant or antidepressant drug families, but its mechanism of action is quite different.[2][3]

BPAP (along with another similar compound PPAP) is classified as a catecholaminergic and serotonergic activity enhancer. This means that it stimulates the impulse propagation mediated transmitter release of the neurotransmitters dopamine, norepinephrine and serotonin in the brain. However, unlike stimulant drugs like amphetamine, which release a flood of these neurotransmitters in an uncontrolled manner, BPAP instead only increases the amount of neurotransmitter that gets released when a neuron is stimulated by receiving an impulse from a neighbouring neuron. So while both amphetamine and BPAP increase the amount of neurotransmitters that get released, amphetamine causes neurons to dump neurotransmitter stores into the synapse regardless of external input, while with BPAP the pattern of neurotransmitter release is not changed, but when the neuron would normally release neurotransmitter, a larger amount than normal is released.[4][5]

Other drugs which produce this effect are the endogenous trace amines phenethylamine and tryptamine, and the neuroprotective MAO-B inhibitor selegiline.[6] However, while selegiline is a potent monoamine oxidase inhibitor, BPAP is only a weak MAO-A inhibitor at high doses, and at low doses produces only the activity enhancer effect.[6]

BPAP has been shown to have neuroprotective effects similar to those of selegiline in some animal models, and has been preclinically researched for the treatment of Alzheimer's disease, Parkinson's disease and clinical depression.[7]

BPAP is a stronger enhancer of dopamine, epinephrine, and serotonin release than PPAP, with more selectivity for serotonin over dopamine and epinephrine.[8] BPAP is a stronger dopamine reuptake inhibitor than cocaine with approx. 28× higher binding affinity as a reuptake inhibitor and 12× higher potency as a dopamine reuptake inhibitor. BPAP is also a strong epinephrine reuptake inhibitor and a weak serotonin reuptake inhibitor.[9]

References

  1. ↑ Yoneda F, Knoll J, Ode H, Sakae H, Katurada M, Moto T, Ando T, Shimazu S, Takahata K, Fujimoto M, "Ethylamine derivatives", US patent 6214859, issued 10 April 2001, assigned to Fujimoto Brothers Co Ltd.
  2. ↑ "(-)-1-(Benzofuran-2-yl)-2-propylaminopentane enhances locomotor activity in rats due to its ability to induce dopamine release". European Journal of Pharmacology 421 (3): 181–9. June 2001. doi:10.1016/S0014-2999(01)01040-8. PMID 11516435. 
  3. ↑ "Transporter-mediated actions of R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane". European Journal of Pharmacology 482 (1–3): 9–16. December 2003. doi:10.1016/j.ejphar.2003.09.044. PMID 14659999. 
  4. ↑ "The fate of (-)1-(benzofuran-2-yl)-2-propylaminopentane . HCl, (-)-BPAP, in rats, a potent enhancer of the impulse-evoked release of catecholamines and serotonin in the brain". European Journal of Drug Metabolism and Pharmacokinetics 27 (3): 157–61. 2002. doi:10.1007/BF03190451. PMID 12365195. 
  5. ↑ "Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane, ((-)-BPAP), a highly potent and selective catecholaminergic activity enhancer". Bioorganic & Medicinal Chemistry 9 (5): 1213–9. May 2001. doi:10.1016/S0968-0896(00)00341-2. PMID 11377179. 
  6. ↑ 6.0 6.1 "Pharmacological studies with endogenous enhancer substances: beta-phenylethylamine, tryptamine, and their synthetic derivatives". Progress in Neuro-Psychopharmacology & Biological Psychiatry 28 (3): 421–7. May 2004. doi:10.1016/j.pnpbp.2003.11.016. PMID 15093948. 
  7. ↑ "Major depression and the synthetic enhancer substances, (-)-deprenyl and R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane". Progress in Neuro-Psychopharmacology & Biological Psychiatry 30 (1): 5–14. January 2006. doi:10.1016/j.pnpbp.2005.06.004. PMID 16023777. 
  8. ↑ "(-)1-(Benzofuran-2-yl)-2-propylaminopentane, [(-)BPAP, a selective enhancer of the impulse propagation mediated release of catecholamines and serotonin in the brain"]. British Journal of Pharmacology 128 (8): 1723–1732. December 1999. doi:10.1038/sj.bjp.0702995. PMID 10588928. 
  9. ↑ "Transporter-mediated actions of R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane". European Journal of Pharmacology 482 (1–3): 9–16. December 2003. doi:10.1016/j.ejphar.2003.09.044. PMID 14659999. 



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