β-Methylphenethylamine

β-Methylphenethylamine
Clinical data
ATC code	none;
Legal status
Legal status	US: Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in dietary supplements, food, or medicine is unlawful; otherwise uncontrolled.;
Identifiers
	IUPAC name 2-Phenylpropan-1-amine;
CAS Number	582-22-9 [PubChem];
PubChem CID	11398;
ChemSpider	10920 ;
UNII	6XL7O3V13L;
ChEBI	CHEBI:229522;
ChEMBL	ChEMBL158578;
CompTox Dashboard (EPA)	DTXSID10870630 ;
ECHA InfoCard	100.008.619
Chemical and physical data
Formula	C9H13N
Molar mass	135.210 g·mol−1
3D model (JSmol)	Interactive image;
Density	0.93 g/cm3
Boiling point	80 °C (176 °F) (at 10 mm Hg)
	SMILES NCC(c1ccccc1)C;
	InChI InChI=1S/C9H13N/c1-8(7-10)9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3 ; Key:AXORVIZLPOGIRG-UHFFFAOYSA-N ;
	(verify)

β-Methylphenethylamine (β-Me-PEA, BMPEA, or 1-amino-2-phenylpropane) is an organic compound of the phenethylamine class, and a positional isomer of the drug amphetamine, with which it shares some properties. In particular, both amphetamine and β-methylphenethylamine are human TAAR1 agonists.^[2] In appearance, it is a colorless or yellowish liquid.

Relatively little information has been published about this substance. Hartung and Munch reported that it had good antihypotensive (pressor) activity in experimental animals, and that it was orally active. The MLD (minimum lethal dose) for the HCl salt was given as 500 mg/kg (rat, s.c.) and 50 mg/kg (rabbit, i.v.).^[3]

A study by Graham and co-workers at the Upjohn Co., comparing many β-methylphenethylamines substituted on the benzene ring showed that β-methylphenethylamine itself had 1/700 x the pressor activity of epinephrine, corresponding to ~ 1/3 the potency of amphetamine. The β-methyl compound also had ~ 2 x the broncho-dilating power of amphetamine (as measured using the isolated rabbit lung), and an LD₅₀ of 50 mg/kg (rat, i.v.).^[4]

^ "BMPEA in Dietary Supplements". FDA. 22 February 2023. Archived from the original on 26 March 2023. Retrieved 9 June 2023.
^ Wainscott DB, Little SP, Yin T, Tu Y, Rocco VP, He JX, Nelson DL (January 2007). "Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1". The Journal of Pharmacology and Experimental Therapeutics. 320 (1): 475–485. doi:10.1124/jpet.106.112532. PMID 17038507. S2CID 10829497. The effect of β-carbon substitution on the phenylethylamine side chain was also investigated (Table 3). A β-methyl substituent was well tolerated compared with β-PEA. In fact, S-(–)-β-methyl-β-PEA was as potent as β-PEA at human TAAR1.
^ Hartung WH, Munch JC (1931). "Amino alcohols. VI. The preparation and pharmacodynamic activity of four isomeric phenylpropylamines". J. Am. Chem. Soc. 53 (5): 1875–9. doi:10.1021/ja01356a036.
^ Graham BE, Cartland GF, Woodruff EH (1945). "Phenyl propyl and phenyl isopropyl amines. Changes in pharmacological action on substitution of phenyl nucleus and amino nitrogen". Ind. Eng. Chem. 37 (2): 149–51. doi:10.1021/ie50422a010.

[1] "BMPEA in Dietary Supplements". FDA. 22 February 2023. Archived from the original on 26 March 2023. Retrieved 9 June 2023.

[pmid17038507-2] Wainscott DB, Little SP, Yin T, Tu Y, Rocco VP, He JX, Nelson DL (January 2007). "Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1". The Journal of Pharmacology and Experimental Therapeutics. 320 (1): 475–485. doi:10.1124/jpet.106.112532. PMID 17038507. S2CID 10829497. The effect of β-carbon substitution on the phenylethylamine side chain was also investigated (Table 3). A β-methyl substituent was well tolerated compared with β-PEA. In fact, S-(–)-β-methyl-β-PEA was as potent as β-PEA at human TAAR1.

[Hartung-3] Hartung WH, Munch JC (1931). "Amino alcohols. VI. The preparation and pharmacodynamic activity of four isomeric phenylpropylamines". J. Am. Chem. Soc. 53 (5): 1875–9. doi:10.1021/ja01356a036.

[4] Graham BE, Cartland GF, Woodruff EH (1945). "Phenyl propyl and phenyl isopropyl amines. Changes in pharmacological action on substitution of phenyl nucleus and amino nitrogen". Ind. Eng. Chem. 37 (2): 149–51. doi:10.1021/ie50422a010.

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