Movatterモバイル変換


[0]ホーム

URL:


Jump to content
WikipediaThe Free Encyclopedia
Search

Methamnetamine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Methamnetamine
Clinical data
Other namesMethylnaphetamine; MNA; MNT; MNAP; PAL-1046; MY-10;[1]N-Methylnaphthylaminopropane;N-Methylnaphthylisopropylamine
Legal status
Legal status
Identifiers
  • N-Methyl-1-(naphthalen-2-yl)propan-2-amine
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC14H17N
Molar mass199.297 g·mol−1
3D model (JSmol)
  • CNC(C)Cc1ccc2ccccc2c1
  • InChI=1S/C14H17N/c1-11(15-2)9-12-7-8-13-5-3-4-6-14(13)10-12/h3-8,10-11,15H,9H2,1-2H3
  • Key:BWWWOLYZMKACSB-UHFFFAOYSA-N

Methamnetamine (also known asmethylnaphetamine,MNA,MNT,MNAP,PAL-1046, andMY-10) is atriple monoamine releasing agent of theamphetamine andnaphthylaminopropane families. It is theN-methylanalog of the non-neurotoxic experimental drugnaphthylaminopropane and thenaphthalene analog ofmethamphetamine.[2][3][4] It has been sold online as adesigner drug between 2015 and 2016.[5][6][7]

Pharmacology

[edit]

Pharmacodynamics

[edit]

Methamnetamine acts as areleasing agent ofserotonin,norepinephrine, anddopamine, withEC50 values of 13 nM, 34 nM, and 10 nM, respectively.[2] It is also a lower-potencypartial agonist of theserotonin5-HT2A receptor.[8]

Monoamine release of methamnetamine and related agents (EC50Tooltip Half maximal effective concentration, nM)
CompoundNETooltip NorepinephrineDATooltip Dopamine5-HTTooltip SerotoninRef
d-Amphetamine6.6–10.25.8–24.8698–1,765[9][10][11][12][13]
Naphthylaminopropane (NAP; PAL-287)11.112.63.4[14][11]
d-Methamphetamine12.3–14.38.5–40.4736–1,292[9][15][11][13]
Methylnaphthylaminopropane (MNAP; PAL-1046)341013[16][17]
l-Methcathinone13.114.81,772[18][12]
2-Naphthylmethcathinone (BMAPN; βk-MNAP)94% at 10 μM3427[19][20]
d-Ethylamphetamine28.844.1333.0[21][22]
Ethylnaphthylaminopropane (ENAP; PAL-1045)13746a12a[16]
Phenmetrazine29–50.470–1317,765–>10,000[23][11][24][25]
Naphthylmetrazine (PAL-704)203111RI (105)[25]
Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. Theassays were done in rat brainsynaptosomes and humanpotencies may be different. See alsoMonoamine releasing agent § Activity profiles for a larger table with more compounds.Footnotes:aENAPTooltip Ethylnaphthylaminopropane is apartial releaser of serotonin (EmaxTooltip maximal efficacy = 66%) and dopamine (Emax = 78%).Refs:[26][27]

Society and culture

[edit]

Legal status

[edit]

Methamnetamine is illegal in Japan.[28]

See also

[edit]

References

[edit]
  1. ^U.S. patent 6,057,371
  2. ^abRothman RB, Partilla JS, Baumann MH, Lightfoot-Siordia C, Blough BE (April 2012)."Studies of the biogenic amine transporters. 14. Identification of low-efficacy "partial" substrates for the biogenic amine transporters".The Journal of Pharmacology and Experimental Therapeutics.341 (1):251–262.doi:10.1124/jpet.111.188946.PMC 3364510.PMID 22271821.
  3. ^Youn DH, Kim JM, Hong YK, Park SI, Lee JM, Kim YH, et al. (August 2021). "Assessment of the abuse potential of methamnetamine in rodents: a behavioral pharmacology study".Psychopharmacology.238 (8):2155–2165.doi:10.1007/s00213-021-05840-9.PMID 33811503.S2CID 232773019.
  4. ^Hong YK, Kim YH, Lee JM, Yoo HH, Choi SO, Kang MS (July 2021). "Characterization of in vitro phase I metabolites of methamnetamine in human liver microsomes by liquid chromatography-quadrupole time-of-flight mass spectrometry".International Journal of Legal Medicine.135 (4):1471–1476.doi:10.1007/s00414-021-02594-z.PMID 33928430.S2CID 233451101.
  5. ^"Methamnetamine".WEDINOS.
  6. ^Jonas Reinhardt, med (9 November 2023)."Methamnetamine". New Synthetic Drugs Database.
  7. ^Milton Trott, Dominic."2.7.8 MNA (Methamnetamine)".Drug Users Bible. Retrieved14 July 2025.
  8. ^Stalberga, D., Kronstrand, R., Schranz, B., van Zijl, N., Karlman, S., Aref, S., ... & Gréen, H. (2025). Comprehensive in vitro profiling of traditional and emerging stimulants at monoamine transporters and the 5HT2A receptor.https://doi.org/10.22541/au.176253891.19158813/v1
  9. ^abRothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS (January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin".Synapse.39 (1):32–41.doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3.PMID 11071707.S2CID 15573624.
  10. ^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 (March 2013)."Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products".Neuropsychopharmacology.38 (4):552–562.doi:10.1038/npp.2012.204.PMC 3572453.PMID 23072836.
  11. ^abcdBlough B (July 2008)."Dopamine-releasing agents"(PDF). In Trudell ML, Izenwasser S (eds.).Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. pp. 305–320.ISBN 978-0-470-11790-3.OCLC 181862653.OL 18589888W.
  12. ^abGlennon RA, Dukat M (2017). "Structure-Activity Relationships of Synthetic Cathinones".Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. Vol. 32. Springer. pp. 19–47.doi:10.1007/7854_2016_41.ISBN 978-3-319-52442-9.PMC 5818155.PMID 27830576.
  13. ^abPartilla JS, Dersch CM, Baumann MH, Carroll FI, Rothman RB (1999). "Profiling CNS Stimulants with a High-Throughput Assay for Biogenic Amine Transporter Substractes".Problems of Drug Dependence 1999: Proceedings of the 61st Annual Scientific Meeting, The College on Problems of Drug Dependence, Inc(PDF). NIDA Res Monogr. Vol. 180. pp. 1–476 (252).PMID 11680410. Archived fromthe original(PDF) on August 5, 2023.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.
  14. ^Rothman RB, Blough BE, Woolverton WL, Anderson KG, Negus SS, Mello NK, Roth BL, Baumann MH (June 2005). "Development of a rationally designed, low abuse potential, biogenic amine releaser that suppresses cocaine self-administration".The Journal of Pharmacology and Experimental Therapeutics.313 (3):1361–1369.doi:10.1124/jpet.104.082503.PMID 15761112.S2CID 19802702.
  15. ^Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho AE, Cozzi NV (April 2012)."The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue".Neuropsychopharmacology.37 (5):1192–1203.doi:10.1038/npp.2011.304.PMC 3306880.PMID 22169943.
  16. ^abRothman RB, Partilla JS, Baumann MH, Lightfoot-Siordia C, Blough BE (April 2012)."Studies of the biogenic amine transporters. 14. Identification of low-efficacy "partial" substrates for the biogenic amine transporters".J Pharmacol Exp Ther.341 (1):251–262.doi:10.1124/jpet.111.188946.PMC 3364510.PMID 22271821.
  17. ^Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, Partilla JS, Rothman RB, Katz JL (February 2015)."Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter".Drug Alcohol Depend.147:1–19.doi:10.1016/j.drugalcdep.2014.12.005.PMC 4297708.PMID 25548026.
  18. ^Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA (October 2003). "In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates".The Journal of Pharmacology and Experimental Therapeutics.307 (1):138–145.doi:10.1124/jpet.103.053975.PMID 12954796.S2CID 19015584.
  19. ^Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RB (March 2019)."The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes".Psychopharmacology (Berl).236 (3):915–924.doi:10.1007/s00213-018-5063-9.PMC 6475490.PMID 30341459.
  20. ^Yadav, Barkha J (16 July 2019).Understanding Structure–Activity Relationship of Synthetic Cathinones (Bath Salts) Utilizing Methylphenidate.VCU Scholars Compass (Thesis).doi:10.25772/MJQW-8C64. Retrieved24 November 2024.
  21. ^Fitzgerald LR, Gannon BM, Walther D, Landavazo A, Hiranita T, Blough BE, Baumann MH, Fantegrossi WE (March 2024)."Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones".Neuropharmacology.245 109827.doi:10.1016/j.neuropharm.2023.109827.PMC 10842458.PMID 38154512.
  22. ^Nicole, Lauren (2022)."In vivo Structure-Activity Relationships of Substituted Amphetamines and Substituted Cathinones".ProQuest. Retrieved5 December 2024.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. [...]
  23. ^Rothman RB, Katsnelson M, Vu N, Partilla JS, Dersch CM, Blough BE, Baumann MH (June 2002). "Interaction of the anorectic medication, phendimetrazine, and its metabolites with monoamine transporters in rat brain".European Journal of Pharmacology.447 (1):51–57.doi:10.1016/s0014-2999(02)01830-7.PMID 12106802.
  24. ^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 (September 2018)."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".Drug Test Anal.10 (9):1404–1416.doi:10.1002/dta.2396.PMC 7316143.PMID 29673128.
  25. ^ab"Phenylmorpholines and analogues thereof".Google Patents. 20 May 2011. Retrieved7 December 2024.
  26. ^Rothman RB, Baumann MH (October 2003). "Monoamine transporters and psychostimulant drugs".European Journal of Pharmacology.479 (1–3):23–40.doi:10.1016/j.ejphar.2003.08.054.PMID 14612135.
  27. ^Rothman RB, Baumann MH (August 2006). "Balance between dopamine and serotonin release modulates behavioral effects of amphetamine-type drugs".Annals of the New York Academy of Sciences.1074 (1):245–260.Bibcode:2006NYASA1074..245R.doi:10.1196/annals.1369.064.PMID 17105921.S2CID 19739692.
  28. ^"指定薬物名称・構造式一覧(平成27年9月16日現在)" [List of designated drug names and structural formulas (as of September 16, 2015)](PDF).厚生労働省 [Ministry of Health, Labour and Welfare] (in Japanese). 16 September 2015. Retrieved8 October 2015.
Phenethylamines
Non-ring-extended
Benzodioxoles
(methylenedioxy- or MDxx)
Benzodioxines
(ethylenedioxy-)
Benzofurans
Dihydrobenzofurans
Benzothiophenes
Benzothiazoles
Benzoxathioles
Indanes
Indoles
Naphthalenes
Tetralins
Others
Cyclized
phenethylamines
2-Aminoindanes
1-Aminomethylindanes
2-Aminotetralins
Aminorexes
Tryptamines
α-Alkyltryptamines
Others
Benzofurans
Benzothiophenes
Indolizines
Isotryptamines
Others
Adamantanes
Adenosine antagonists
Alkylamines
Ampakines
Arylcyclohexylamines
Benzazepines
Cathinones
Cholinergics
Convulsants
Eugeroics
Oxazolines
Phenethylamines
Phenylmorpholines
Piperazines
Piperidines
Phenethylpyrrolidines
Racetams
Psychedelics
Tropanes
Tryptamines
Others
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT37
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
(and further-extended)
Catecholamines
(and close relatives)
Cyclized
phenethylamines
Phenylalkylpyrrolidines
2-Benzylpiperidines
(phenidates)
Phenylmorpholines
(phenmetrazines)
Phenyloxazolamines
(aminorexes)
Isoquinolines and
tetrahydroisoquinolines
2-Aminoindanes
2-Aminotetralins
Others / unsorted
Related compounds
Retrieved from "https://en.wikipedia.org/w/index.php?title=Methamnetamine&oldid=1323720553"
Categories:
Hidden categories:

[8]ページ先頭

©2009-2025 Movatter.jp