N-Methylphenethylamine

From Infogalactic: the planetary knowledge core
Jump to: navigation, search

<templatestyles src="Module:Hatnote/styles.css"></templatestyles>

Not to be confused with amphetamine or β-Methylphenethylamine.
N-Methylphenethylamine[1]
N-methylphenethylamine2DCSD.svg
N-Methylphenethylamine molecule ball.png
Names
IUPAC name
N-Methyl-2-phenylethanamine
Other names
N-Methylphenethylamine
N-Methyl-β-phenethylamine
Identifiers
589-08-2
ChEMBL ChEMBL45763 YesY
ChemSpider 11019 YesY
Jmol 3D model Interactive image
PubChem 11503
  • InChI=1S/C9H13N/c1-10-8-7-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3 YesY
    Key: SASNBVQSOZSTPD-UHFFFAOYSA-N YesY
  • InChI=1/C9H13N/c1-10-8-7-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3
    Key: SASNBVQSOZSTPD-UHFFFAOYAA
  • N(CCc1ccccc1)C
Properties
C9H13N
Molar mass 135.21 g·mol−1
Appearance Colorless liquid
Density 0.93 g/mL
Boiling point 203 °C (397 °F; 476 K)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

N-Methylphenethylamine (NMPEA), a positional isomer of amphetamine,[2] is a naturally occurring trace amine neuromodulator in humans that is derived from the trace amine, phenethylamine (PEA).[3][4] It has been detected (< 1 μg/24 hrs.) in human urine[5] and is produced by phenylethanolamine N-methyltransferase with phenethylamine as a substrate.[3][4] PEA and NMPEA are both alkaloids that are found in a number of different plant species as well.[6] Some Acacia species, such as A. rigidula, contain remarkably high levels of NMPEA (~2300–5300 ppm).[7] NMPEA is also present at low concentrations (< 10 ppm) in a wide range of foodstuffs.[8]

Human biosynthesis pathway for trace amines and catecholamines[4][9]
The image above contains clickable links
N-methylphenethylamine, an endogenous compound in humans,[4] is an isomer of amphetamine with the same biomolecular target, TAAR1, a G protein-coupled receptor which modulates catecholamine neurotransmission.[10]

Chemistry

In appearance, NMPEA is a colorless liquid. NMPEA is a weak base, with pKa = 10.14; pKb = 3.86 (calculated from data given as Kb[11]). It forms a hydrochloride salt, m.p. 162–164°C.[12]

Although NMPEA is available commercially, it may be synthesized by various methods. An early synthesis reported by Carothers and co-workers involved conversion of phenethylamine to its p-toluenesulfonamide, followed by N-methylation using methyl iodide, then hydrolysis of the sulfonamide.[11] A more recent method, similar in principle, and used for making NMPEA radio-labeled with 14C in the N-methyl group, started with the conversion of phenethylamine to its trifluoroacetamide. This was N-methylated (in this particular case using 14C – labeled methyl iodide), and then the amide hydrolyzed.[13]

NMPEA is a substrate for both MAO-A (KM = 58.8 μM) and MAO-B (KM = 4.13 μM) from rat brain mitochondria.[14]

Pharmacology

NMPEA is a pressor, with 1/350 x the potency of epinephrine.[15]

Like its parent compound, PEA, and isomer, amphetamine, NMPEA is a potent agonist of human TAAR1.[4][9] It has comparable pharmacodynamic and toxicodynamic properties to that of phenethylamine, amphetamine, and other methylphenethylamines in rats.[2]

As with PEA, NMPEA is metabolized relatively rapidly by monoamine oxidases during first pass metabolism;[4][9] both compounds are preferentially metabolized by MAO-B.[4][9]

Toxicology

The "minimum lethal dose" (mouse, i.p.) of the HCl salt of NMPEA is 203 mg/kg;[16] the LD50 for oral administration to mice of the same salt is 685 mg/kg.[17]

Acute toxicity studies on NMPEA show an LD50 = 90 mg/kg, after intravenous administration to mice.[18]

References

  1. ↑ N-Methyl-phenethylamine at Sigma-Aldrich
  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ G. P. Reynolds and D. O. Gray (1978) J. Chrom. B: Biomedical Applications 145 137–140.
  6. ↑ T. A. Smith (1977). "Phenethylamine and related compounds in plants." Phytochem. 16 9–18.
  7. ↑ B. A. Clement, C. M. Goff and T. D. A. Forbes (1998) Phytochem. 49 1377–1380.
  8. ↑ G. B. Neurath et al. (1977) Fd. Cosmet. Toxicol. 15 275–282.
  9. ↑ 9.0 9.1 9.2 9.3 Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ 11.0 11.1 W.H. Carothers, C. F. Bickford and G. J. Hurwitz (1927) J. Am. Chem. Soc. 49 2908–2914.
  12. ↑ C. Z. Ding et al. (1993) J. Med. Chem. 36 1711–1715.
  13. ↑ I. Osamu (1983) Eur. J. Nucl. Med. 8 385–388.
  14. ↑ O. Suzuki, M. Oya and Y. Katsumata (1980) Biochem. Pharmacol. 29 2663–2667.
  15. ↑ W. H. Hartung (1945) Ind. Eng. Chem. 37 126–137.
  16. ↑ A. M. Hjort (1934) J. Pharm. Exp. Ther. 52 101–112.
  17. ↑ C. M. Suter and A. W. Weston (1941) J. Am. Chem. Soc. 63 602–605.
  18. ↑ A. M. Lands and J. I. Grant (1952). "The vasopressor action and toxicity of cyclohexylethylamine derivatives." J. Pharmacol. Exp. Ther. 106 341–345.
Retrieved from "https://infogalactic.com/w/index.php?title=N-Methylphenethylamine&oldid=723125396"