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α-Propylphenethylamine

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α-Propylphenethylamine
Clinical data
Other names1-Phenyl-2-aminopentane; 1-Benzylbutylamine; α-Propylphenethylamine; α-Pr-PEA; APPEA; α-Phenyl-β-aminopentane; PAL-550; PAL550
Drug classMonoamine reuptake inhibitor; Stimulant
Identifiers
  • 1-phenylpentan-2-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H17N
Molar mass163.264 g·mol−1
3D model (JSmol)
  • CCCC(CC1=CC=CC=C1)N
  • InChI=1S/C11H17N/c1-2-6-11(12)9-10-7-4-3-5-8-10/h3-5,7-8,11H,2,6,9,12H2,1H3
  • Key:VXGQDFOHLMAZIV-UHFFFAOYSA-N

α-Propylphenethylamine (APPEA or α-Pr-PEA), also known as 1-phenyl-2-aminopentane, is a stimulant drug of the phenethylamine and amphetamine families.[1][2] It is the analogue of the β-phenethylamine (PEA) derivatives amphetamine (α-methylphenethylamine; "AMPEA") and phenylisobutylamine (α-ethylphenethylamine; AEPEA) in which the α-alkyl chain has been further lengthened to be a propyl group.[1][2]

APPEA is known to act as a low-potency dopamine reuptake inhibitor.[1][2] Conversely, the drug was inactive as a serotonin reuptake inhibitor and was not assessed in terms of norepinephrine reuptake inhibition.[1][2] It was similarly inactive as a releasing agent of either dopamine or serotonin, being predominantly a reuptake inhibitor.[1][2] APPEA's IC50Tooltip half-maximal inhibitory concentration values for inhibition of monoamine reuptake were 2,596 nM for dopamine and >10,000 nM for serotonin.[1][2] Analogues of APPEA like phenylisobutylamine (AEPEA) are norepinephrine–dopamine releasing agents (NDRAs) and norepinephrine–dopamine reuptake inhibitors (NDRIs) and have been found to produce stimulant-like and reinforcing effects in rodents.[3]

Numerous derivatives of APPEA exist.[4][5][6] These include 1,3-benzodioxolylpentanamine (BDP; K) and its derivatives like MBDP (methyl-K) and EBDP (ethyl-K); pentedrone (α-propyl-β-keto-N-methylphenethylamine) and its derivatives like ephylone (N-ethylpentedrone), 4-methylpentedrone, pentylone, and dipentylone; and prolintane and its derivatives like α-pyrrolidinopentiophenone (α-PVP), pyrovalerone, methylenedioxypyrovalerone (MDPV), and naphyrone, among others.[4][5][6] Another notable analogue, instead with a thiophene ring, is α-pyrrolidinopentiothiophenone (α-PVT).[5] 1-Phenyl-2-propylaminopentane (PPAP; α,N-dipropylphenethylamine) is the combined derivative of APPEA and propylamphetamine (N-propylamphetamine).[7][8][9][10] Methylenedioxyphenylpropylaminopentane (MPAP) is the 3,4-methylenedioxy derivative of PPAP.[11]

See also

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References

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  1. ^ a b c d e f Blough BE, Landavazo A, Partilla JS, Baumann MH, Decker AM, Page KM, et al. (June 2014). "Hybrid dopamine uptake blocker-serotonin releaser ligands: a new twist on transporter-focused therapeutics". ACS Medicinal Chemistry Letters. 5 (6): 623–627. doi:10.1021/ml500113s. PMC 4060932. PMID 24944732.
  2. ^ a b c d e f Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, et al. (February 2015). "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug and Alcohol Dependence. 147: 1–19. doi:10.1016/j.drugalcdep.2014.12.005. PMC 4297708. PMID 25548026.
  3. ^ Schindler CW, Thorndike EB, Partilla JS, Rice KC, Baumann MH (January 2021). "Amphetamine-like Neurochemical and Cardiovascular Effects of α-Ethylphenethylamine Analogs Found in Dietary Supplements". The Journal of Pharmacology and Experimental Therapeutics. 376 (1): 118–126. doi:10.1124/jpet.120.000129. PMC 7788351. PMID 33082158.
  4. ^ a b Soares J, Costa VM, Bastos ML, Carvalho F, Capela JP (September 2021). "An updated review on synthetic cathinones". Archives of Toxicology. 95 (9): 2895–2940. doi:10.1007/s00204-021-03083-3. PMID 34100120.
  5. ^ a b c Kuropka P, Zawadzki M, Szpot P (May 2023). "A narrative review of the neuropharmacology of synthetic cathinones-Popular alternatives to classical drugs of abuse". Human Psychopharmacology. 38 (3): e2866. doi:10.1002/hup.2866. PMID 36866677.
  6. ^ a b Shulgin AT, Shulgin A (1991). PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN 9780963009609. OCLC 25627628.
  7. ^ Knoll J, Knoll B, Török Z, Timár J, Yasar S (1992). "The pharmacology of 1-phenyl-2-propylamino-pentane (PPAP), a deprenyl-derived new spectrum psychostimulant". Archives Internationales de Pharmacodynamie et de Therapie. 316: 5–29. PMID 1356324.
  8. ^ Knoll J (2001). "Antiaging compounds: (-)deprenyl (selegeline) and (-)1-(benzofuran-2-yl)-2-propylaminopentane, [(-)BPAP], a selective highly potent enhancer of the impulse propagation mediated release of catecholamine and serotonin in the brain". CNS Drug Reviews. 7 (3): 317–345. doi:10.1111/j.1527-3458.2001.tb00202.x. PMC 6494119. PMID 11607046.
  9. ^ 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.
  10. ^ Harsing LG, Knoll J, Miklya I (August 2022). "Enhancer Regulation of Dopaminergic Neurochemical Transmission in the Striatum". International Journal of Molecular Sciences. 23 (15): 8543. doi:10.3390/ijms23158543. PMC 9369307. PMID 35955676.
  11. ^ 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.
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