Structure via PubChem · Public domain (PubChem)
N-methylphenethylamine
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'''N-Methylphenethylamine (NMPEA''') is a naturally occurring trace amine neuromodulator in humans that is derived from the trace amine, phenethylamine (PEA). It has been detected in human urine (<1 μg over 24 hours) and is produced by phenylethanolamine N-methyltransferase with phenethylamine as a substrate, which significantly increases PEA's effects. PEA breaks down into phenylacetaldehyde which is further broken down into phenylacetic acid by monoamine oxidase. When this is inhibited by monoamine oxidase inhibitors, it allows more of the PEA to remain present and produce psychoac
Key facts
- Drug.verifiedrevid
- 415845541
- Drug.drug_name
- N-Methylphenethylamine
- Drug.image
- N-Methylphenethylamine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
- Drug.image2
- N-Methylphenethylamine_3D_Structure_Xtal.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 235px
- Drug.legal_CA
- Schedule 1 as an isomer of amphetamine
- Drug.CAS_number
- 589-08-2
- Drug.PubChem
- 11503
- Drug.ChemSpiderID
- 11019
- Drug.UNII
- 02N4V81704
- Drug.ChEMBL
- 45763
- Drug.synonyms
- NMPEA; N-Methyl-2-phenylethanamine; N-Methylphenethylamine; N-Methyl-β-phenethylamine
- Drug.IUPAC_name
- N-methyl-2-phenylethan-1-amine
- Drug.C
- 9
- Drug.H
- 13
via Wikipedia infobox
Chemical data
- Formula
- C9H13N
- Molecular weight
- 135.21 g/mol
- IUPAC name
- N-methyl-2-phenylethanamine
- SMILES
- CNCCC1=CC=CC=C1
- InChIKey
- SASNBVQSOZSTPD-UHFFFAOYSA-N
- XLogP
- 1.9
- Polar surface area
- 12 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 135.105
Show 4 more facts
- found in taxon
- Senegalia berlandieri
- chemical formula
- C₉H₁₃N
- canonical SMILES
- CNCCC1=CC=CC=C1
- Commons category
- N-Methylphenethylamine
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Biosynthesis
- Chemistry
- Pharmacology
- Toxicology
- References
'''N-Methylphenethylamine (NMPEA''') is a naturally occurring trace amine neuromodulator in humans that is derived from the trace amine, phenethylamine (PEA). It has been detected in human urine (a = 10.14; pKb = 3.86 (calculated from data given as Kb). It forms a hydrochloride salt, m.p. 162–164 °C.
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. 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.
Excerpted from Wikipedia’s “N-methylphenethylamine” article, available under the CC BY-SA 4.0 licence.