Methylenedioxyphenylpropylaminopentane

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MPAP
Clinical data
Other names1-(3,4-Methylenedioxyphenyl)-2-propylaminopentane; MPAP; 3,4-Methylenedioxy-α,N-dipropylphenethylamine; 3,4-Methylenedioxy-PPAP; MDPPAP
Drug classMonoaminergic activity enhancer
Chemical and physical data
FormulaC15H25NO2
Molar mass251.370 g·mol−1
3D model (JSmol)
  • CCCNC(CCC)CC1=CC2OCOC2C=C1
  • InChI=1S/C15H25NO2/c1-3-5-13(16-8-4-2)9-12-6-7-14-15(10-12)18-11-17-14/h6-7,10,13-16H,3-5,8-9,11H2,1-2H3
  • Key:MXDWJUBNNVFKKO-UHFFFAOYSA-N

1-(3,4-Methylenedioxyphenyl)-2-propylaminopentane (MPAP), also known as 3,4-methylenedioxy-α,N-dipropylphenethylamine, is a monoaminergic activity enhancer (MAE) of the phenethylamine, amphetamine, and α-propylphenethylamine families that is closely related to phenylpropylaminopentane (PPAP).[1] It is an analogue of PPAP and benzofuranylpropylaminopentane (BPAP) with a benzodioxole ring instead of a phenyl or benzofuran ring, respectively.[1]

MAEs are agents that enhance the action potential-mediated release of monoamine neurotransmitters.[2][3][4] MPAP is a MAE of serotonin, norepinephrine, and dopamine, all with similar potency.[5][1] This is similar to BPAP, but is in contrast to PPAP and selegiline, which act exclusively as catecholaminergic activity enhancers (CAEs) and do not enhance serotonin.[1] Like PPAP and BPAP, but in contrast to amphetamines, MPAP has no classical monoamine releasing agent actions.[1]

MPAP has comparable potency to PPAP and selegiline as a MAE in terms of enhancing the monoamine neurotransmitters in the isolated rat brain stem ex vivo.[1] However, it was 5-fold more potent than PPAP and selegiline as a MAE in rodents in vivo in terms of the minimum dose that significantly antagonized the behavioral depression induced by tetrabenazine in the shuttle box.[1] On the other hand, MPAP was 20-fold less potent than the highly potent BPAP in the shuttle box.[1] As with BPAP and PPAP, the negative enantiomer (i.e., (–)-MPAP) is more biologically active as a MAE.[1] The effects of MAEs seem to be mediated by intracellular TAAR1 agonism coupled with uptake by monoamine transporters into monoaminergic neurons.[5][6]

MPAP is closely structurally related to a number of other phenethylamine drugs.[7][8][9][10][11] These include the entactogen-like drug 1,3-benzodioxolylpentanamine (BDP; K) and its derivatives 1,3-benzodioxolyl-N-methylpentanamine (MBDP; methyl-K) and 1,3-benzodioxolyl-N-ethylpentanamine (EBDP; ethyl-K);[7][8][9] the entactogen-like drug 3,4-methylenedioxy-N-propylamphetamine (MDPR);[7][8][9] and the cathinone stimulants pentylone (βk-MBDP) and methylenedioxypyrovalerone (MDPV).[10][11]

MPAP was first described in the scientific literature in 2001, following BPAP in 1999.[1] It was discovered by József Knoll and colleagues.[1]

See also

References

  1. ^ a b c d e f g h i j k Yoneda F, Moto T, Sakae M, Ohde H, Knoll B, Miklya I, et al. (May 2001). "Structure-activity studies leading to (-)1-(benzofuran-2-yl)-2-propylaminopentane, ((-)BPAP), a highly potent, selective enhancer of the impulse propagation mediated release of catecholamines and serotonin in the brain". Bioorg Med Chem. 9 (5): 1197–212. doi:10.1016/s0968-0896(01)00002-5. PMID 11377178.
  2. ^ Shimazu S, Miklya I (May 2004). "Pharmacological studies with endogenous enhancer substances: beta-phenylethylamine, tryptamine, and their synthetic derivatives". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 28 (3): 421–427. doi:10.1016/j.pnpbp.2003.11.016. PMID 15093948. S2CID 37564231.
  3. ^ Miklya I (November 2016). "The significance of selegiline/(-)-deprenyl after 50 years in research and therapy (1965-2015)". Molecular Psychiatry. 21 (11): 1499–1503. doi:10.1038/mp.2016.127. PMID 27480491. S2CID 205202709.
  4. ^ Knoll J (August 2003). "Enhancer regulation/endogenous and synthetic enhancer compounds: a neurochemical concept of the innate and acquired drives". Neurochemical Research. 28 (8): 1275–1297. doi:10.1023/a:1024224311289. PMID 12834268.
  5. ^ a b Harsing LG, Knoll J, Miklya I (August 2022). "Enhancer Regulation of Dopaminergic Neurochemical Transmission in the Striatum". Int J Mol Sci. 23 (15): 8543. doi:10.3390/ijms23158543. PMC 9369307. PMID 35955676.
  6. ^ Harsing LG, Timar J, Miklya I (August 2023). "Striking Neurochemical and Behavioral Differences in the Mode of Action of Selegiline and Rasagiline". Int J Mol Sci. 24 (17): 13334. doi:10.3390/ijms241713334. PMC 10487936. PMID 37686140.
  7. ^ a b c Shulgin AT, Shulgin A (1991). PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN 9780963009609. OCLC 25627628.
  8. ^ a b c Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
  9. ^ a b c Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German). Solothurn: Nachtschatten-Verlag. p. 556. ISBN 978-3-03788-700-4. OCLC 858805226. Retrieved 29 January 2025.
  10. ^ a b Soares J, Costa VM, Bastos ML, Carvalho F, Capela JP (September 2021). "An updated review on synthetic cathinones" (PDF). Arch Toxicol. 95 (9): 2895–2940. Bibcode:2021ArTox..95.2895S. doi:10.1007/s00204-021-03083-3. PMID 34100120.
  11. ^ a b Kuropka P, Zawadzki M, Szpot P (May 2023). "A narrative review of the neuropharmacology of synthetic cathinones-Popular alternatives to classical drugs of abuse" (PDF). Hum Psychopharmacol. 38 (3): e2866. doi:10.1002/hup.2866. PMID 36866677.


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