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.
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.[1]
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]
β-Methylphenethylamine can be made by the catalytichydrogenation of 2-phenylpropionitrile with Pd/C in pure anhydrous ethanol containing three equivalents of HCl; the finished product is extracted as the HCl salt, m.p. 123-124°.[3]
Presenceedit
In 2015, 52% of supplements labeled as containing Acacia rigidula were found to contain BMPEA.[5][6] Consumers following recommended maximum daily servings would consume a maximum of 94 mg of BMPEA per day.[5] In 2012, however, the FDA determined that BMPEA was not naturally present in Acacia rigidula leaves.[7] This question was litigated during the trial of Hi Tech Pharmaceuticals Inc vs. Cohen.[8][9] Despite US Food and Drug Administration warning letters, BMPEA remains present in dietary supplements.[10]
Safetyedit
β-Methylphenethylamine was associated with a case of cerebral hemorrhage in a Swedish athlete and first time user. The female victim with no medical history had taken a Swedish food supplement with 290 mg β-methylphenethylamine per serving before commencing her usual exercises. After about 30 minutes the first symptoms appeared. The presence of the active ingredient was not declared on the label.[11] Use of β-Methylphenethylamine is also prohibited in sports.[12]
^"BMPEA in Dietary Supplements". FDA. 22 February 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.
^ abHartung 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.
^ abCohen PA, Bloszies C, Yee C, Gerona R (2016). "An amphetamine isomer whose efficacy and safety in humans has never been studied, β-methylphenylethylamine (BMPEA), is found in multiple dietary supplements". Drug Testing and Analysis. 8 (3–4): 328–333. doi:10.1002/dta.1793. PMID 25847603.
^The Editorial Board (13 April 2015). "Conflicts of Interest at the F.D.A." The New York Times. Retrieved 13 April 2015. they identified BMPEA in 11 of 21 brands of supplements with acacia rigidula listed as an ingredient.
^Goodman B (7 April 2015). "Untested Stimulant Still in Dietary Supplements". WebMD.
^Bagley N, Carroll AE, Cohen PA (January 2018). "Scientific Trials-In the Laboratories, Not the Courts". JAMA Internal Medicine. 178 (1): 7–8. doi:10.1001/jamainternmed.2017.5730. PMID 29114742.
^"BMPEA and Acacia Rigidula: Hi-Tech Pharmaceuticals Fights Back". PricePlow. 26 October 2015. Retrieved 27 October 2015.
^Cohen PA, Wen A, Gerona R (December 2018). "Prohibited Stimulants in Dietary Supplements After Enforcement Action by the US Food and Drug Administration". JAMA Internal Medicine. 178 (12): 1721–1723. doi:10.1001/jamainternmed.2018.4846. PMC6583602. PMID 30422217.
^Cohen PA, Zeijlon R, Nardin R, Keizers PH, Venhuis B (June 2015). "Hemorrhagic Stroke Probably Caused by Exercise Combined With a Sports Supplement Containing β-Methylphenyl-ethylamine (BMPEA): A Case Report". Annals of Internal Medicine. 162 (12): 879–880. doi:10.7326/L15-5101. PMID 26075771.
^Chołbiński P, Wicka M, Kowalczyk K, Jarek A, Kaliszewski P, Pokrywka A, et al. (June 2014). "Detection of β-methylphenethylamine, a novel doping substance, by means of UPLC/MS/MS". Analytical and Bioanalytical Chemistry. 406 (15): 3681–3688. doi:10.1007/s00216-014-7728-5. PMC4026626. PMID 24633566.
April 15, 2024
methylphenethylamine, bmpea, amino, phenylpropane, organic, compound, phenethylamine, class, positional, isomer, drug, amphetamine, with, which, shares, some, properties, particular, both, amphetamine, methylphenethylamine, human, taar1, agonists, appearance, . b Methylphenethylamine b 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 b methylphenethylamine are human TAAR1 agonists 2 In appearance it is a colorless or yellowish liquid b MethylphenethylamineClinical dataATC codenoneLegal statusLegal statusUS Unapproved New Drug as defined by 21 U S Code 321 p 1 Use in dietary supplements food or medicine is unlawful otherwise uncontrolled 1 IdentifiersIUPAC name 2 Phenylpropan 1 amineCAS Number582 22 9 Y PubChem PubChem CID11398ChemSpider10920 YUNII6XL7O3V13LChEBICHEBI 229522ChEMBLChEMBL158578ECHA InfoCard100 008 619Chemical and physical dataFormulaC 9H 13NMolar mass135 210 g mol 13D model JSmol Interactive imageDensity0 93 g cm3Boiling point80 C 176 F at 10 mm Hg SMILES NCC c1ccccc1 CInChI InChI 1S C9H13N c1 8 7 10 9 5 3 2 4 6 9 h2 6 8H 7 10H2 1H3 YKey AXORVIZLPOGIRG UHFFFAOYSA N Y verify 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 b methylphenethylamines substituted on the benzene ring showed that b methylphenethylamine itself had 1 700 x the pressor activity of epinephrine corresponding to 1 3 the potency of amphetamine The b 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 Contents 1 Synthesis 2 Presence 3 Safety 4 See also 5 ReferencesSynthesis editb Methylphenethylamine can be made by the catalytic hydrogenation of 2 phenylpropionitrile with Pd C in pure anhydrous ethanol containing three equivalents of HCl the finished product is extracted as the HCl salt m p 123 124 3 Presence editIn 2015 52 of supplements labeled as containing Acacia rigidula were found to contain BMPEA 5 6 Consumers following recommended maximum daily servings would consume a maximum of 94 mg of BMPEA per day 5 In 2012 however the FDA determined that BMPEA was not naturally present in Acacia rigidula leaves 7 This question was litigated during the trial of Hi Tech Pharmaceuticals Inc vs Cohen 8 9 Despite US Food and Drug Administration warning letters BMPEA remains present in dietary supplements 10 Safety editb Methylphenethylamine was associated with a case of cerebral hemorrhage in a Swedish athlete and first time user The female victim with no medical history had taken a Swedish food supplement with 290 mg b methylphenethylamine per serving before commencing her usual exercises After about 30 minutes the first symptoms appeared The presence of the active ingredient was not declared on the label 11 Use of b Methylphenethylamine is also prohibited in sports 12 See also editAmphetamine b Methylamphetamine PhenethylamineReferences edit BMPEA in Dietary Supplements FDA 22 February 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 b carbon substitution on the phenylethylamine side chain was also investigated Table 3 A b methyl substituent was well tolerated compared with b PEA In fact S b methyl b PEA was as potent as b PEA at human TAAR1 a b 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 a b Cohen PA Bloszies C Yee C Gerona R 2016 An amphetamine isomer whose efficacy and safety in humans has never been studied b methylphenylethylamine BMPEA is found in multiple dietary supplements Drug Testing and Analysis 8 3 4 328 333 doi 10 1002 dta 1793 PMID 25847603 The Editorial Board 13 April 2015 Conflicts of Interest at the F D A The New York Times Retrieved 13 April 2015 they identified BMPEA in 11 of 21 brands of supplements with acacia rigidula listed as an ingredient Goodman B 7 April 2015 Untested Stimulant Still in Dietary Supplements WebMD Bagley N Carroll AE Cohen PA January 2018 Scientific Trials In the Laboratories Not the Courts JAMA Internal Medicine 178 1 7 8 doi 10 1001 jamainternmed 2017 5730 PMID 29114742 BMPEA and Acacia Rigidula Hi Tech Pharmaceuticals Fights Back PricePlow 26 October 2015 Retrieved 27 October 2015 Cohen PA Wen A Gerona R December 2018 Prohibited Stimulants in Dietary Supplements After Enforcement Action by the US Food and Drug Administration JAMA Internal Medicine 178 12 1721 1723 doi 10 1001 jamainternmed 2018 4846 PMC 6583602 PMID 30422217 Cohen PA Zeijlon R Nardin R Keizers PH Venhuis B June 2015 Hemorrhagic Stroke Probably Caused by Exercise Combined With a Sports Supplement Containing b Methylphenyl ethylamine BMPEA A Case Report Annals of Internal Medicine 162 12 879 880 doi 10 7326 L15 5101 PMID 26075771 Cholbinski P Wicka M Kowalczyk K Jarek A Kaliszewski P Pokrywka A et al June 2014 Detection of b methylphenethylamine a novel doping substance by means of UPLC MS MS Analytical and Bioanalytical Chemistry 406 15 3681 3688 doi 10 1007 s00216 014 7728 5 PMC 4026626 PMID 24633566 Retrieved from https en wikipedia org w index php title B Methylphenethylamine amp oldid 1201780920, wikipedia, wiki, book, books, library,
