(-)-1-(Benzofuran-2-yl)-2-propylaminopentane

Drugbox
IUPAC_name = (2"R")-1-(1-Benzofuran-2-yl)-"N"-propylpentan-2-amine

---

width= 200
CAS_number= 260550-89-8
ATC_prefix=
ATC_suffix=
PubChem=9859674
DrugBank=
C=16 | H=23 | N=1 | O=1
molecular_weight = 245.37
bioavailability=
metabolism =
elimination_half-life=
excretion =
pregnancy_category =
legal_status =
routes_of_administration=

(-)-1-(Benzofuran-2-yl)-2-propylaminopentane ((-)-BPAP) is a drug with an unusual effects profile. It can loosely be grouped with the stimulant or antidepressant drug families, but its mechanism of action is quite different. [Shimazu S, Takahata K, Katsuki H, Tsunekawa H, Tanigawa A, Yoneda F, Knoll J, Akaike A. (-)-1-(Benzofuran-2-yl)-2-propylaminopentane enhances locomotor activity in rats due to its ability to induce dopamine release. "European Journal of Pharmacology". 2001; 421: 181-189.] [Shimazu S, Tsunekawa H, Yoneda F, Katsuki H, Akaike A, Janowsky A. Transporter Mediated Actions of R-(-)-1-(Benzofuran-2-yl)-2-propylaminopentane. "European Journal of Pharmacology". 2003; 482: 9-16.]

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, noradrenaline and serotonin in the brain. However unlike stimulant drugs like amphetamines, 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 amphetamines and BPAP increase the amount of neurotransmitters that get released, amphetamines cause 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. [Knoll J, Yoneda F, Knoll B, Ohde H, Miklya I. (-)-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" 1999; 128: 1723-1732] [Oka T, Yasusa T, Ando T, Watanabe M, Yoneda F, Ishida T, Knoll J. Enantioselective Synthesis and Absolute Configuration of (-)-1-(Benzofuran-2-yl)-2-propylaminopentane ((-)BPAP), a Highly Potent and Selective Catecholaminergic Activity Enhancer. "Bioorganic and Medicinal Chemistry." 2001; 9: 1213-1219.]

Other drugs which produce this effect are the endogenous trace amines phenethylamine and tryptamine, and the neuroprotective MAO-B inhibitor selegiline. [Shimazu S, Miklya I. Pharmacological studies with endogenous enhancer substances: β-phenethylamine, tryptamine, and their synthetic derivatives. "Progress in Neuropsychopharmacology & Biological Psychiatry". 2004; 28: 421-427.] 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.

BPAP has been shown to have neuroprotective effects similar to those of selegiline, and has been researched for the treatment of Alzheimer's disease, Parkinson's disease and clinical depression. [Gaszner P, Miklya I. Major depression and the synthetic enhancer substances (-)-deprenyl and (-)-1-(Benzofuran-2-yl)-2-propylaminopentane. "Progress in Neuropsychopharmacology & Biological Psychiatry". 2006 Jan;30(1):5-14. ]

References