N-Metilfenetilamin

N-Metilfenetilamin
Nazivi
	Preferisani IUPAC naziv N-Metil-2-feniletan-1-amin
	Drugi nazivi N-Metil-2-feniletanamin; N-Metilfenetilamin; N-Metil-β-fenetilamin
Identifikacija
CAS broj	589-08-2 ;
3D model (Jmol)	interaktivna slika;
ChemSpider	11019 ;
ECHA InfoCard	100.008.758
PubChem C ID	11503;
	SMILES CNCCc1ccccc1; ; ; ; ; ;
Svojstva
Hemijska formula	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

N-metilfenetilamin, endogeno jedinjenje kod ljudi,^[5] je izomer amfetamina sa istim biološkim ciljem, TAAR1, G protein spregnutim receptorom koji modulira kateholaminsku neurotransmisiju.^[13]

Osobine[уреди | уреди извор]

N-Metilfenetilamin je organsko jedinjenje, koje sadrži 9 atoma ugljenika i ima molekulsku masu od 135,206 Da.

Osobina	Vrednost
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[уреди | уреди извор]

^ 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[уреди | уреди извор]

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[уреди | уреди извор]

N-Methylphenethylamine

[1] 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

[2] 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.

[NMPH-3] 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.

[Pendleton_263–8-4] 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.

[Trace_Amines-5] 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.

[6] G. P. Reynolds and D. O. Gray (1978) J. Chrom. B: Biomedical Applications 145 137–140.

[7] T. A. Smith (1977). "Phenethylamine and related compounds in plants." Phytochem. 16 9–18.

[8] B. A. Clement, C. M. Goff and T. D. A. Forbes (1998) Phytochem. 49 1377–1380.

[9] G. B. Neurath et al. (1977) Fd. Cosmet. Toxicol. 15 275–282.

[Trace_amine_template_1-10] 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.

[Trace_amine_template_2-11] 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.

[CYP2D6_tyramine-dopamine_metabolism-12] 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-13] 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.

[14] 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.

[15] 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.

[16] 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.

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