N-Metilfenetilamin
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Nazivi | |
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Preferisani IUPAC naziv N-Metil-2-feniletan-1-amin | |
Drugi nazivi N-Metil-2-feniletanamin N-Metilfenetilamin N-Metil-β-fenetilamin | |
Identifikacija | |
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3D model (Jmol) |
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ChemSpider |
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ECHA InfoCard | 100.008.758 |
PubChem[1][2] C ID |
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SMILES
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Svojstva | |
C9H13N | |
Molarna masa | 135,206 |
Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa). | |
Reference infokutije | |
N-Metilfenetilamin (NMPEA), pozicioni izomer amfetamina,[3] je prirodni trag aminski neuromodulator kod ljudi koji je izveden iz trag amina, fenetilamina (PEA).[4][5] On je prisutan (< 1 μg/24 hrs.) u ljudskom urinu[6] i formira se posredstvom feniletanolamin N-metiltransferazae sa fenetilaminom kao supstratom.[4][5] PEA i NMPEA su alkaloidi koji su prisutni i u brojnim vrstama biljki.[7] Neke od Acacia vrsta, kao što su A. rigidula, sadrže veoma visoke nivoe NMPEA (~2300–5300 ppm).[8] NMPEA je takođe prisutan u niskim koncentracijama (< 10 ppm) u širokom opsegu namirnica.[9]
Biosintetički putevi za kateholamine i trag amine u ljudskom mozgu[10][11][12] ![]() N-Metilfenetilamin primarni put manje zastupljeni put ![]() |
Osobine
N-Metilfenetilamin je organsko jedinjenje, koje sadrži 9 atoma ugljenika i ima molekulsku masu od 135,206 Da.
Osobina | Vrednost |
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Broj akceptora vodonika | 1 |
Broj donora vodonika | 1 |
Broj rotacionih veza | 3 |
Particioni koeficijent[14] (ALogP) | 1,7 |
Rastvorljivost[15] (logS, log(mol/L)) | -2,4 |
Polarna površina[16] (PSA, Å2) | 12,0 |
Reference
- ^ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди
- ^ Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.
- ^ Mosnaim AD, Callaghan OH, Hudzik T, Wolf ME (2013). „Rat brain-uptake index for phenylethylamine and various monomethylated derivatives”. Neurochem. Res. 38 (4): 842—6. PMID 23389662. doi:10.1007/s11064-013-0988-1.
- ^ а б Pendleton RG, Gessner G, Sawyer J (1980). „Studies on lung N-methyltransferases, a pharmacological approach”. Naunyn Schmiedebergs Arch. Pharmacol. 313 (3): 263—8. PMID 7432557. doi:10.1007/bf00505743.
- ^ а б в Broadley KJ (2010). „The vascular effects of trace amines and amphetamines”. Pharmacol. Ther. 125 (3): 363—375. PMID 19948186. doi:10.1016/j.pharmthera.2009.11.005.
- ^ G. P. Reynolds and D. O. Gray (1978) J. Chrom. B: Biomedical Applications 145 137–140.
- ^ T. A. Smith (1977). "Phenethylamine and related compounds in plants." Phytochem. 16 9–18.
- ^ B. A. Clement, C. M. Goff and T. D. A. Forbes (1998) Phytochem. 49 1377–1380.
- ^ G. B. Neurath et al. (1977) Fd. Cosmet. Toxicol. 15 275–282.
- ^ Broadley KJ (2010). „The vascular effects of trace amines and amphetamines”. Pharmacol. Ther. 125 (3): 363—375. PMID 19948186. doi:10.1016/j.pharmthera.2009.11.005.
- ^ Lindemann L, Hoener MC (2005). „A renaissance in trace amines inspired by a novel GPCR family”. Trends Pharmacol. Sci. 26 (5): 274—281. PMID 15860375. doi:10.1016/j.tips.2005.03.007.
- ^ Wang X, Li J, Dong G, Yue J (2014). „The endogenous substrates of brain CYP2D”. Eur. J. Pharmacol. 724: 211—218. PMID 24374199. doi:10.1016/j.ejphar.2013.12.025.
- ^ Miller GM (2011). „The emerging role of trace amine-associated receptor 1 in the functional regulation of monoamine transporters and dopaminergic activity”. J. Neurochem. 116 (2): 164—176. PMC 3005101
. PMID 21073468. doi:10.1111/j.1471-4159.2010.07109.x.
- ^ Ghose, A.K.; Viswanadhan V.N. & Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A. 102: 3762—3772. doi:10.1021/jp980230o.
- ^ Tetko IV, Tanchuk VY, Kasheva TN, Villa AE (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488—1493. PMID 11749573. doi:10.1021/ci000392t.
- ^ Ertl P.; Rohde B.; Selzer P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties”. J. Med. Chem. 43: 3714—3717. PMID 11020286. doi:10.1021/jm000942e.
Literatura
- Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (I изд.). Oxford University Press. ISBN 978-0-19-850346-0.
- Smith, Michael B.; March, Jerry (2007). Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th изд.). New York: Wiley-Interscience. ISBN 0-471-72091-7.
- Katritzky A.R.; Pozharskii A.F. (2000). Handbook of Heterocyclic Chemistry (Second изд.). Academic Press. ISBN 0080429882.
Spoljašnje veze
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N-Metilfenetilamin на Викимедијиној остави.
- N-Methylphenethylamine