| Revision as of 22:58, 6 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'StdInChI', 'StdInChIKey').← Previous edit |
Latest revision as of 05:17, 8 December 2024 edit undo76.174.0.57 (talk) See also. |
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{{Short description|Chemical compound}} |
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{{Use dmy dates|date=April 2015}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 332825898 |
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| verifiedrevid = 449584722 |
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| IUPAC_name = 2-phenylpropan-1-amine |
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| IUPAC_name = 2-Phenylpropan-1-amine |
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| image = Beta-methylphenethylamine.png |
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| image = Beta-methylphenethylamine.png |
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| image2 = Beta-Methylphenethylamine molecule ball.png |
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| width = 200px |
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| drug_name = β-Methylphenethylamine |
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| InChI = 1/C9H13N/c1-8(7-10)9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3 |
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<!--Clinical data--> |
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| tradename = |
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| pregnancy_category = |
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| legal_status = |
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| legal_US = Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in ]s, ], or ] is unlawful; otherwise uncontrolled.<ref>{{Cite web |date=February 22, 2023 |title=BMPEA in Dietary Supplements |url=https://www.fda.gov/food/dietary-supplement-ingredient-directory/bmpea-dietary-supplements |access-date=June 9, 2023 |website=]}}</ref> |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|PubChem}} |
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| CAS_number = 582-22-9 |
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| ATC_prefix = none |
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| ATC_suffix = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 6XL7O3V13L |
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| ChEMBL = 158578 |
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| ChEBI = 229522 |
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| PubChem = 11398 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10920 |
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<!--Chemical data--> |
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| C=9 | H=13 | N=1 |
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| smiles = NCC(c1ccccc1)C |
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| smiles = NCC(c1ccccc1)C |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChIKey = AXORVIZLPOGIRG-UHFFFAOYAK |
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| CASNo_Ref = {{cascite}} |
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| CAS_number = |
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| ATC_prefix = |
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| ATC_suffix = |
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| StdInChI = 1S/C9H13N/c1-8(7-10)9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3 |
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| StdInChI = 1S/C9H13N/c1-8(7-10)9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = AXORVIZLPOGIRG-UHFFFAOYSA-N |
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| StdInChIKey = AXORVIZLPOGIRG-UHFFFAOYSA-N |
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| PubChem = 11398 |
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| density = 0.93 |
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| DrugBank = |
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| boiling_point = 80 |
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| boiling_notes = (at 10 mm Hg) |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10920 |
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| chemical_formula = C<sub>9</sub>H<sub>13</sub>N |
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| molecular_weight = 135.21 g/mol |
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| bioavailability = |
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| pregnancy_category= |
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| legal_status = Uncontrolled |
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| routes_of_administration = |
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'''β-Methylphenethylamine''' ('''β-Me-PEA''', '''BMPEA''', or '''1-amino-2-phenylpropane''') is an ] of the ] class, and a ] of the drug ], with which it shares some properties. In particular, both amphetamine and β-methylphenethylamine are human ] agonists.<ref name="pmid17038507">{{cite journal | vauthors = Wainscott DB, Little SP, Yin T, Tu Y, Rocco VP, He JX, Nelson DL | title = Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1 | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 320 | issue = 1 | pages = 475–485 | date = January 2007 | pmid = 17038507 | doi = 10.1124/jpet.106.112532 | quote = 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. | s2cid = 10829497 }}</ref> In appearance, it is a colorless or yellowish liquid. |
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'''β-Methylphenethylamine''' ('''β-Me-PEA''') is a ] ] of the ] ] that is related to ] (which is α-methylphenethylamine). It is found in many '']'' species{{Fact|date=March 2009}}, notably '']'' (guajillo)<ref></ref>. β-Me-PEA is ] in humans as the β-] ] slows ] by the ] ] (MAO).{{Fact|date=March 2009}} |
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Relatively little information has been published about this substance. Hartung and Munch reported that it had good ] (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.).<ref name = Hartung>{{ cite journal | vauthors = Hartung WH, Munch JC | title = Amino alcohols. VI. The preparation and pharmacodynamic activity of four isomeric phenylpropylamines | journal = J. Am. Chem. Soc. | year = 1931 | volume = 53 | issue = 5 | pages = 1875–9 | doi = 10.1021/ja01356a036 }}</ref> |
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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 ], 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 LD<sub>50</sub> of 50 mg/kg (rat, i.v.).<ref>{{ cite journal | vauthors = Graham BE, Cartland GF, Woodruff EH | title = Phenyl propyl and phenyl isopropyl amines. Changes in pharmacological action on substitution of phenyl nucleus and amino nitrogen | journal = Ind. Eng. Chem. | year = 1945 | volume = 37 | issue = 2 | pages = 149–51 | doi = 10.1021/ie50422a010 }}</ref> |
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==Synthesis== |
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β-Methylphenethylamine can be made by the ] ] of 2-phenylpropionitrile with ] in pure anhydrous ethanol containing three equivalents of HCl; the finished product is extracted as the HCl salt, m.p. 123-124°.<ref name = Hartung/> |
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== Presence == |
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In 2015, 52% of supplements labeled as containing '']'' were found to contain BMPEA.<ref name=cohen2015>{{cite journal | vauthors = Cohen PA, Bloszies C, Yee C, Gerona R | title = An amphetamine isomer whose efficacy and safety in humans has never been studied, β-methylphenylethylamine (BMPEA), is found in multiple dietary supplements | journal = Drug Testing and Analysis | volume = 8 | issue = 3–4 | pages = 328–333 | year = 2016 | pmid = 25847603 | doi = 10.1002/dta.1793 | doi-access = free }}</ref><ref>{{cite news | vauthors = ((The Editorial Board)) |title=Conflicts of Interest at the F.D.A. |url=https://www.nytimes.com/2015/04/13/opinion/conflicts-of-interest-at-the-fda.html |quote= they identified BMPEA in 11 of 21 brands of supplements with acacia rigidula listed as an ingredient.|newspaper=] |date=April 13, 2015 |access-date=2015-04-13 }}</ref> Consumers following recommended maximum daily servings would consume a maximum of 94 mg of BMPEA per day.<ref name=cohen2015/> In 2012, however, the FDA determined that BMPEA was not naturally present in ''Acacia rigidula'' leaves.<ref>{{cite web|url=http://www.webmd.com/vitamins-and-supplements/news/20150407/bmpea-acacia-rigidula-supplments|title=Untested Stimulant Still in Dietary Supplements| vauthors = Goodman B |website=WebMD|date=7 April 2015}}</ref> This question was litigated during the trial of ''Hi Tech Pharmaceuticals Inc vs. Cohen''.<ref>{{cite journal | vauthors = Bagley N, Carroll AE, Cohen PA | title = Scientific Trials-In the Laboratories, Not the Courts | journal = JAMA Internal Medicine | volume = 178 | issue = 1 | pages = 7–8 | date = January 2018 | pmid = 29114742 | doi = 10.1001/jamainternmed.2017.5730 | url = http://nrs.harvard.edu/urn-3:HUL.InstRepos:34902783 }}</ref><ref>{{cite web|title=BMPEA and Acacia Rigidula: Hi-Tech Pharmaceuticals Fights Back|url=https://blog.priceplow.com/bmpea#natural|website=PricePlow|access-date=27 October 2015|date=26 October 2015}}</ref> Despite US Food and Drug Administration warning letters, BMPEA remains present in dietary supplements.<ref>{{cite journal | vauthors = Cohen PA, Wen A, Gerona R | title = Prohibited Stimulants in Dietary Supplements After Enforcement Action by the US Food and Drug Administration | journal = JAMA Internal Medicine | volume = 178 | issue = 12 | pages = 1721–1723 | date = December 2018 | pmid = 30422217 | pmc = 6583602 | doi = 10.1001/jamainternmed.2018.4846 }}</ref> |
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== Safety == |
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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 ] 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.<ref name = Cohen>{{cite journal | vauthors = Cohen PA, Zeijlon R, Nardin R, Keizers PH, Venhuis B | title = Hemorrhagic Stroke Probably Caused by Exercise Combined With a Sports Supplement Containing β-Methylphenyl-ethylamine (BMPEA): A Case Report | journal = Annals of Internal Medicine | volume = 162 | issue = 12 | pages = 879–880 | date = June 2015 | pmid = 26075771 | doi = 10.7326/L15-5101 | url = http://nrs.harvard.edu/urn-3:HUL.InstRepos:40997747 }}</ref> Use of β-Methylphenethylamine is also prohibited in sports.<ref name = Cholbinski>{{cite journal | vauthors = Chołbiński P, Wicka M, Kowalczyk K, Jarek A, Kaliszewski P, Pokrywka A, Bulska E, Kwiatkowska D | display-authors = 6 | title = Detection of β-methylphenethylamine, a novel doping substance, by means of UPLC/MS/MS | journal = Analytical and Bioanalytical Chemistry | volume = 406 | issue = 15 | pages = 3681–3688 | date = June 2014 | pmid = 24633566 | pmc = 4026626 | doi = 10.1007/s00216-014-7728-5 }}</ref> |
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== See also == |
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== See also == |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] (''N''-methyl-β-methylphenethylamine) |
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== References == |
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== References == |
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{{Reflist|2}} |
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{{Reflist}} |
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{{Monoamine releasing agents}} |
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{{Stimulants}} |
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{{Adrenergics}} |
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{{TAAR ligands}} |
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{{Dopaminergics}} |
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{{Phenethylamines}} |
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{{Phenethylamines}} |
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{{DEFAULTSORT:Methylphenethylamine, Beta-}} |
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{{DEFAULTSORT:Methylphenethylamine, Beta-}} |
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{{pharmacology-stub}} |
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