{{Short description|Substituted cathinone stimulant drug}} {{infobox drug | drug_name = BMAPN | image = Bk-methamnetamine.svg | image_class = skin-invert-image | legal_UK = PSA | legal_DE = NpSG | C = 14 | H = 15 | N = 1 | O = 1 | IUPAC_name = 2-(methylamino)-1-(naphthalene-2-yl) propan-1-one | CAS_number = 109453-73-8 | ChemSpiderID = 65998790 | PubChem = 112704365 | UNII = DL8RX8N8NK | synonyms = BMAPN; βk-Methamnetamine | smiles = CC(C(=O)C1=CC2=CC=CC=C2C=C1)NC | StdInChI = 1S/C14H15NO/c1-10(15-2)14(16)13-8-7-11-5-3-4-6-12(11)9-13/h3-10,15H,1-2H3 | StdInChIKey = QIMNQDXLKHGANJ-UHFFFAOYSA-N }}
'''2-Naphthylmethcathinone''' ('''BMAPN'''), also known as '''βk-methamnetamine''', is a stimulant drug of the cathinone and naphthylaminopropane families. It inhibits dopamine reuptake and has rewarding and reinforcing properties in animal studies.<ref name="pmid27737791">{{cite journal | vauthors = Botanas CJ, Yoon SS, de la Peña JB, Dela Peña IJ, Kim M, Woo T, Seo JW, Jang CG, Park KT, Lee YH, Lee YS, Kim HJ, Cheong JH | title = A novel synthetic cathinone, 2-(methylamino)-1-(naphthalen-2-yl) propan-1-one (BMAPN), produced rewarding effects and altered striatal dopamine-related gene expression in mice | journal = Behavioural Brain Research | volume = 317 | issue = | pages = 494–501 | date = January 2017 | pmid = 27737791 | doi = 10.1016/j.bbr.2016.10.016 | s2cid = 3095092 }}</ref><ref>{{cite book | vauthors = Simmons SJ, Kim E, Gentile TA, Murad A, Muschamp JW, Rawls SM | date = 2018 | chapter = Behavioral Profiles and Underlying Transmitters/Circuits of Cathinone-Derived Psychostimulant Drugs of Abuse. | veditors = Zawilska J | title = Synthetic Cathinones | series = Current Topics in Neurotoxicity | volume = 12 | pages = 125–152 | publisher = Springer | location = Cham | doi = 10.1007/978-3-319-78707-7_8| isbn = 978-3-319-78706-0 }}</ref> It is banned under drug analogue legislation in a number of jurisdictions. The drug was at one point marketed under the name '''NRG-3''', although only a minority of samples of substances sold under this name have been found to actually contain BMAPN, with most such samples containing mixtures of other cathinone derivatives.<ref name="pmid21960541">{{cite journal | vauthors = Brandt SD, Freeman S, Sumnall HR, Measham F, Cole J | title = Analysis of NRG 'legal highs' in the UK: identification and formation of novel cathinones | journal = Drug Testing and Analysis | volume = 3 | issue = 9 | pages = 569–75 | date = September 2011 | pmid = 21960541 | doi = 10.1002/dta.204 }}</ref><ref name="pmid24111554">{{cite journal | vauthors = Eiden C, Mathieu O, Cathala P, Debruyne D, Baccino E, Petit P, Peyriere H | title = Toxicity and death following recreational use of 2-pyrrolidino valerophenone | journal = Clinical Toxicology | location = Philadelphia, Pa. | volume = 51 | issue = 9 | pages = 899–903 | date = November 2013 | pmid = 24111554 | doi = 10.3109/15563650.2013.847187 | s2cid = 22826544 }}</ref>
{| class="wikitable" style="font-size:small;" |+ {{Nowrap|Monoamine release of BMAPN and related agents ({{Abbrlink|EC<sub>50</sub>|Half maximal effective concentration}}, nM)}} |- ! Compound !! data-sort-type="number" | {{abbrlink|NE|Norepinephrine}} !! data-sort-type="number" | {{abbrlink|DA|Dopamine}} !! data-sort-type="number" | {{abbrlink|5-HT|Serotonin}} !! Ref |- | ''d''-Amphetamine || 6.6–10.2 || 5.8–24.8 || 698–1,765 || <ref name="RothmanBaumannDersch2001">{{cite journal | vauthors = Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS | title = Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin | journal = Synapse | volume = 39 | issue = 1 | pages = 32–41 | date = January 2001 | pmid = 11071707 | doi = 10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3 | s2cid = 15573624 }}</ref><ref name="BaumannPartillaLehner2013">{{cite journal | vauthors = Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, Rothman RB, Goldberg SR, Lupica CR, Sitte HH, Brandt SD, Tella SR, Cozzi NV, Schindler CW | title = Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products | journal = Neuropsychopharmacology | volume = 38 | issue = 4 | pages = 552–562 | date = March 2013 | pmid = 23072836 | pmc = 3572453 | doi = 10.1038/npp.2012.204 }}</ref><ref name="Blough2008">{{cite book | vauthors = Blough B | chapter = Dopamine-releasing agents | veditors = Trudell ML, Izenwasser S | title = Dopamine Transporters: Chemistry, Biology and Pharmacology | pages = 305–320 | date = July 2008 | isbn = 978-0-470-11790-3 | oclc = 181862653 | ol = OL18589888W | publisher = Wiley | location = Hoboken [NJ] | doi = | url = https://books.google.com/books?id=QCagLAAACAAJ | chapter-url = https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf }}</ref><ref name="GlennonDukat2017">{{cite book | vauthors = Glennon RA, Dukat M | title = Neuropharmacology of New Psychoactive Substances (NPS) | chapter = Structure-Activity Relationships of Synthetic Cathinones | series = Current Topics in Behavioral Neurosciences | volume = 32 | pages = 19–47 | date = 2017 | publisher = Springer | pmid = 27830576 | pmc = 5818155 | doi = 10.1007/7854_2016_41 | isbn = 978-3-319-52442-9 | chapter-url = }}</ref><ref name="PartillaDerschBaumann1999">{{cite book | vauthors = Partilla JS, Dersch CM, Baumann MH, Carroll FI, Rothman RB | chapter = Profiling CNS Stimulants with a High-Throughput Assay for Biogenic Amine Transporter Substrates | title = Problems of Drug Dependence 1999: Proceedings of the 61st Annual Scientific Meeting, The College on Problems of Drug Dependence, Inc | series = NIDA Res Monogr | volume = 180 | pages = 1–476 (252) | date = 1999 | pmid = 11680410 | doi = | url = https://archives.nida.nih.gov/sites/default/files/180.pdf#page=261 | archive-url = https://web.archive.org/web/20230805004105/https://archives.nida.nih.gov/sites/default/files/180.pdf#page=261 | url-status = dead | archive-date = August 5, 2023 | quote = RESULTS. Methamphetamine and amphetamine potently released NE (IC50s = 14.3 and 7.0 nM) and DA (IC50s = 40.4 nM and 24.8 nM), and were much less potent releasers of 5-HT (IC50s = 740 nM and 1765 nM). Phentermine released all three biogenic amines with an order of potency NE (IC50 = 28.8 nM)> DA (IC50 = 262 nM)> 5-HT (IC50 = 2575 nM). Aminorex released NE (IC50 = 26.4 nM), DA (IC50 = 44.8 nM) and 5-HT (IC50 = 193 nM). Chlorphentermine was a very potent 5-HT releaser (IC50 = 18.2 nM), a weaker DA releaser (IC50 = 935 nM) and inactive in the NE release assay. Chlorphentermine was a moderate potency inhibitor of [3H]NE uptake (Ki = 451 nM). Diethylpropion, which is self-administered, was a weak DA uptake inhibitor (Ki = 15 µM) and NE uptake inhibitor (Ki = 18.1 µM) and essentially inactive in the other assays. Phendimetrazine, which is self-administered, was a weak DA uptake inhibitor (IC50 = 19 µM), a weak NE uptake inhibitor (8.3 µM) and essentially inactive in the other assays.}}</ref> |- | Naphthylaminopropane (NAP; PAL-287) || 11.1 || 12.6 || 3.4 || <ref name="RothmanBloughWoolverton2005">{{cite journal | vauthors = Rothman RB, Blough BE, Woolverton WL, Anderson KG, Negus SS, Mello NK, Roth BL, Baumann MH | title = Development of a rationally designed, low abuse potential, biogenic amine releaser that suppresses cocaine self-administration | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 313 | issue = 3 | pages = 1361–1369 | date = June 2005 | pmid = 15761112 | doi = 10.1124/jpet.104.082503 | s2cid = 19802702 }}</ref><ref name="Blough2008" /> |- | ''d''-Methamphetamine || 12.3–14.3 || 8.5–40.4 || 736–1,292 || <ref name="RothmanBaumannDersch2001" /><ref name="BaumannAyestasPartilla2012">{{cite journal | vauthors = Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho AE, Cozzi NV | title = The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue | journal = Neuropsychopharmacology | volume = 37 | issue = 5 | pages = 1192–1203 | date = April 2012 | pmid = 22169943 | pmc = 3306880 | doi = 10.1038/npp.2011.304 }}</ref><ref name="Blough2008" /><ref name="PartillaDerschBaumann1999" /> |- | Methylnaphthylaminopropane (MNAP; PAL-1046) || 34 || 10 || 13 || <ref name="RothmanPartillaBaumann2012">{{cite journal | vauthors = Rothman RB, Partilla JS, Baumann MH, Lightfoot-Siordia C, Blough BE | title = Studies of the biogenic amine transporters. 14. Identification of low-efficacy "partial" substrates for the biogenic amine transporters | journal = J Pharmacol Exp Ther | volume = 341 | issue = 1 | pages = 251–262 | date = April 2012 | pmid = 22271821 | pmc = 3364510 | doi = 10.1124/jpet.111.188946 | url = }}</ref><ref name="ReithBloughHong2015">{{cite journal | vauthors = Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, Partilla JS, Rothman RB, Katz JL | title = Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter | journal = Drug Alcohol Depend | volume = 147 | issue = | pages = 1–19 | date = February 2015 | pmid = 25548026 | pmc = 4297708 | doi = 10.1016/j.drugalcdep.2014.12.005 | url = }}</ref> |- | ''l''-Methcathinone || 13.1 || 14.8 || 1,772 || <ref name="RothmanVuPartilla2003">{{cite journal | vauthors = Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA | title = In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 307 | issue = 1 | pages = 138–145 | date = October 2003 | pmid = 12954796 | doi = 10.1124/jpet.103.053975 | s2cid = 19015584 }}</ref><ref name="GlennonDukat2017" /> |- | 2-Naphthylmethcathinone (BMAPN; βk-MNAP) || 94% at 10{{nbsp}}μM || 34 || 27 || <ref name="BloughDeckerLandavazo2019">{{cite journal | vauthors = Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RB | title = The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes | journal = Psychopharmacology (Berl) | volume = 236 | issue = 3 | pages = 915–924 | date = March 2019 | pmid = 30341459 | pmc = 6475490 | doi = 10.1007/s00213-018-5063-9 | url = }}</ref><ref name="Yadav2019">{{cite thesis | last=Yadav | first=Barkha J | title=Understanding Structure–Activity Relationship of Synthetic Cathinones (Bath Salts) Utilizing Methylphenidate | website=VCU Scholars Compass | date=16 July 2019 | doi=10.25772/MJQW-8C64 | url=https://scholarscompass.vcu.edu/etd/5955/ | access-date=24 November 2024 }}</ref> |- | ''d''-Ethylamphetamine || 28.8 || 44.1 || 333.0 || <ref name="FitzgeraldGannonWalther2024">{{cite journal | vauthors = Fitzgerald LR, Gannon BM, Walther D, Landavazo A, Hiranita T, Blough BE, Baumann MH, Fantegrossi WE | title = Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones | journal = Neuropharmacology | volume = 245 | issue = | article-number = 109827 | date = March 2024 | pmid = 38154512 | doi = 10.1016/j.neuropharm.2023.109827 | pmc = 10842458 | url = }}</ref><ref name="Nicole2022">{{cite web | last=Nicole | first=Lauren | title=In vivo Structure-Activity Relationships of Substituted Amphetamines and Substituted Cathinones | date=2022 | website=ProQuest | url=https://www.proquest.com/openview/a207e98868b4a9c5ac9296fb24abbcd8/ | access-date=5 December 2024 | quote = FIGURE 2-6: Release: Effects of the specified test drug on monoamine release by DAT (red circles), NET (blue squares), and SERT (black traingles) in rat brain tissue. [...] EC50 values determined for the drug indicated within the panel. [...]}}</ref> |- | Ethylnaphthylaminopropane (ENAP; PAL-1045) || 137 || 46 <sup>a</sup> || 12 <sup>a</sup> || <ref name="RothmanPartillaBaumann2012" /> |- | Phenmetrazine || 29–50.4 || 70–131 || 7,765–>10,000 || <ref name="RothmanKatsnelsonVu2002">{{cite journal | vauthors = Rothman RB, Katsnelson M, Vu N, Partilla JS, Dersch CM, Blough BE, Baumann MH | title = Interaction of the anorectic medication, phendimetrazine, and its metabolites with monoamine transporters in rat brain | journal = European Journal of Pharmacology | volume = 447 | issue = 1 | pages = 51–57 | date = June 2002 | pmid = 12106802 | doi = 10.1016/s0014-2999(02)01830-7 }}</ref><ref name="Blough2008" /><ref name="McLaughlinBaumannKavanagh2018">{{cite journal | vauthors = McLaughlin G, Baumann MH, Kavanagh PV, Morris N, Power JD, Dowling G, Twamley B, O'Brien J, Hessman G, Westphal F, Walther D, Brandt SD | title = Synthesis, analytical characterization, and monoamine transporter activity of the new psychoactive substance 4-methylphenmetrazine (4-MPM), with differentiation from its ortho- and meta- positional isomers | journal = Drug Test Anal | volume = 10 | issue = 9 | pages = 1404–1416 | date = September 2018 | pmid = 29673128 | pmc = 7316143 | doi = 10.1002/dta.2396 | url = }}</ref><ref name="WO2011146850A1">{{cite web | title=Phenylmorpholines and analogues thereof | website=Google Patents | date=20 May 2011 | url=https://patents.google.com/patent/WO2011146850A1/en | access-date=7 December 2024}}</ref> |- | Naphthylmetrazine (PAL-704) || 203 || 111 || {{Abbr|RI|Reuptake inhibitor}} (105) || <ref name="WO2011146850A1" /> |- | colspan="5" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Notes:''' The smaller the value, the more strongly the drug releases the neurotransmitter. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. '''Footnotes:''' <sup>a</sup> {{Abbrlink|ENAP|Ethylnaphthylaminopropane}} is a partial releaser of serotonin ({{Abbrlink|E<sub>max</sub>|maximal efficacy}} = 66%) and dopamine ({{Abbr|E<sub>max</sub>|maximal efficacy}} = 78%). '''Refs:''' <ref name="RothmanBaumann2003">{{cite journal | vauthors = Rothman RB, Baumann MH | title = Monoamine transporters and psychostimulant drugs | journal = European Journal of Pharmacology | volume = 479 | issue = 1–3 | pages = 23–40 | date = October 2003 | pmid = 14612135 | doi = 10.1016/j.ejphar.2003.08.054 }}</ref><ref name="RothmanBaumann2006">{{cite journal | vauthors = Rothman RB, Baumann MH | title = Balance between dopamine and serotonin release modulates behavioral effects of amphetamine-type drugs | journal = Annals of the New York Academy of Sciences | volume = 1074 | issue = 1 | pages = 245–260 | date = August 2006 | pmid = 17105921 | doi = 10.1196/annals.1369.064 | bibcode = 2006NYASA1074..245R | s2cid = 19739692 }}</ref> |}
== See also == * 1-Naphthylmethcathinone (AMAPN) * βk-Ephenidine * Methamnetamine * Methylnaphthidate * Methylone * Naphyrone * WF-23
== References == {{Reflist}}
{{Stimulants}} {{Monoamine releasing agents}} {{Phenethylamines}}
{{DEFAULTSORT:Naphthylmethcathinone, 2-}} Category:Cathinones Category:Designer drugs Category:Methamphetamines Category:2-Naphthyl compounds Category:Naphthylethylamines Category:Serotonin-norepinephrine-dopamine releasing agents