Exploring Methcathinone. To explore a different substance…

Names:
METHCATH · Methcathinone · α-Methylaminopropiophenone · Ephedrone
IUPAC name:
2-(Methylamino)-1-phenylpropan-1-one
ID: 2003 · Formula: C10H13NO · Molecular weight: 163.216
InChI: InChI=1S/C10H13NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,11H,1-2H3

Glennon, RA. Bath salts, mephedrone, and methylenedioxypyrovalerone as emerging illicit drugs that will need targeted therapeutic intervention. Advances in Pharmacology, 2014, 69, 581–620. 564 kB. http://dx.doi.org/10.1016/B978-0-12-420118-7.00015-9

Rothman, RB; Vu, N; Partilla, JS; Roth, BL; Hufeisen, SJ; Compton-Toth, BA; Birkes, J; Young, R; Glennon, RA. In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J. Pharmacol. Exp. Ther., 1 Oct 2003, 307 (1), 138–145. 516 kB. http://dx.doi.org/10.1124/jpet.103.053975

LeBelle, MJ; Savard, C; Dawson, BA; Black, DB; Katyal, LK; Zrcek, F; By, AW. Chiral identification and determination of ephedrine, pseudoephedrine, methamphetamine and metecathinone by gas chromatography and nuclear magnetic resonance. Forensic Sci. Int., 28 Feb 1995, 71 (3), 215–223. 405 kB. http://dx.doi.org/10.1016/0379-0738(94)01669-0

Foley, KF; Cozzi, NV. Novel aminopropiophenones as potential antidepressants. Drug Dev. Res., 1 Dec 2003, 60 (4), 252–260. 1.6 MB. http://dx.doi.org/10.1002/ddr.10297

Young, R; Glennon, RA. Cocaine-stimulus generalization to two new designer drugs: Methcathinone and 4-methylaminorex. Pharmacol. Biochem. Behav., 1 May 1993, 45 (1), 209–214. 224 kB. http://dx.doi.org/10.1016/0091-3057(93)90110-F

Cameron, K; Kolanos, R; Vekariya, R; De Felice, L; Glennon, RA. Mephedrone and methylenedioxypyrovalerone (MDPV), major constituents of “bath salts,” produce opposite effects at the human dopamine transporter. Psychopharmacology, 1 Jun 2013, 227 (3), 493–499. 190 kB. http://dx.doi.org/10.1007/s00213-013-2967-2

Eshleman, AJ; Wolfrum, KM; Hatfield, MG; Johnson, RA; Murphy, KV; Janowsky, A. Substituted methcathinones differ in transporter and receptor interactions. Biochem. Pharmacol., 15 Jun 2013, 85 (12), 1803–1815. 2.2 MB. http://dx.doi.org/10.1016/j.bcp.2013.04.004

Dybdal-Hargreaves, NF; Holder, ND; Ottoson, PE; Sweeney, MD; Williams, T. Mephedrone: Public health risk, mechanisms of action, and behavioral effects. Eur. J. Pharmacol., 15 Aug 2013, 714 (1–3), 32–40. 837 kB. http://dx.doi.org/10.1016/j.ejphar.2013.05.024

De Felice, LJ; Glennon, RA; Negus, SS. Synthetic cathinones: Chemical phylogeny, physiology, and neuropharmacology. Life Sci., 27 Feb 2014, 97 (1), 20–26. 697 kB. http://dx.doi.org/10.1016/j.lfs.2013.10.029

Bonano, JS; Glennon, RA; Felice, LJ; Banks, ML; Negus, SS. Abuse-related and abuse-limiting effects of methcathinone and the synthetic “bath salts” cathinone analogs methylenedioxypyrovalerone (MDPV), methylone and mephedrone on intracranial self-stimulation in rats. Psychopharmacology, 1 Jan 2014, 231 (1), 199-207. 285 kB. http://dx.doi.org/10.1007/s00213-013-3223-5

Zuba, D. Identification of cathinones and other active components of ‘legal highs’ by mass spectrometric methods. Trends Anal. Chem., 1 Feb 2012, 32, 15–30. 576 kB. http://dx.doi.org/10.1016/j.trac.2011.09.009

Cozzi, NV; Brandt, SD; Daley, PF; Partilla, JS; Rothman, RB; Tulzer, A; Sitte, HH; Baumann, MH. Pharmacological examination of trifluoromethyl ring-substituted methcathinone analogs. Eur. J. Pharmacol., 15 Jan 2013, 699 (1–3), 180–187. 590 kB. http://dx.doi.org/10.1016/j.ejphar.2012.11.008

Dal Cason, TA; Young, R; Glennon, RA. Cathinone: An investigation of several N-alkyl and methylenedioxy-substituted analogs. Pharmacol. Biochem. Behav., 1 Jan 1997, 58 (4), 1109–1116. 97 kB. http://dx.doi.org/10.1016/S0091-3057(97)00323-7

Foley, KF. Aminopropiophenones at the norepinephrine transporter: Structure-activity relationships and behavioral effects of methcathinone analogs. Ph. D. Thesis, Brody School of Medicine, Greenville, NC, USA, 1 May 2002. 8.6 MB.

Archer, R. Fluoromethcathinone, a new substance of abuse. Forensic Sci. Int., 1 Jan 2009, 185 (1–3), 10–20. 1.4 MB. http://dx.doi.org/10.1016/j.forsciint.2008.11.013

Iversen, LL. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010. 286 kB.

Glennon, RA; Young, R; Martin, BR; Dal Cason, TA. Methcathinone (“Cat”): An enantiomeric potency comparison. Pharmacol. Biochem. Behav., 1 Jan 1995, 50 (4), 601–606. 709 kB. http://dx.doi.org/10.1016/0091-3057(94)00348-3

Cozzi, NV; Shulgin, AT; Ruoho, AE. Methcathinone (MCAT) and 2-methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one (MDMCAT) inhibit [3H]serotonin uptake into human platelets. Amer. Chem. Soc. Div. Med. Chem. Abs., 1 Jan 1998, 215, 152. 11 kB.

Baumann, MH; Ayestas, MA; Partilla, JS; Sink, JR; Shulgin, AT; Daley, PF; Brandt, SD; Rothman, RB; Ruoho, AE; Cozzi, NV. The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue. Neuropsychopharmacology, 1 Apr 2012, 37, 1192–1203. 763 kB. http://dx.doi.org/10.1038/npp.2011.304

Cozzi, NV; Sievert, MK; Shulgin, AT; Jacob, P; Ruoho, AE. Inhibition of plasma membrane monoamine transporters by β-ketoamphetamines. Eur. J. Pharmacol., 1 Jan 1999, 381 (1), 63–69. 111 kB. http://dx.doi.org/10.1016/S0014-2999(99)00538-5

Toole, KE; Fu, S; Shimmon, RG; Kraymen, M; Taflaga, S. Color tests for the preliminary identification of methcathinone and analogues of methcathinone. Microgram J., 2012, 9 (1), 27–32. 496 kB.

Cathinone
EAP · Ethcathinone
DMAP · Dimethylcathinone
DEAP · Diethylpropion
PAP · Propylcathinone
i-PAP
BAP
t-BAP
EMC
MABP · Buphedrone
Pentedrone
MAA
2-FMC
2-MMA-βk
3-FMC
3-BMC
3-MeOMC · 3-MMA-βk
3-TFMAP
4-MMC · Mephedrone
PMMA-βk · Methedrone
4-FMC
4-BMC
4-EMC · 4-Ethylmethcathinone
4-CMC
4-TFMAP
4-IMC
PEA
Ephedrine
Pseudoephedrine
MA · Methamphetamine
A · Amphetamine
α-PPP
2-AI
2-AT
N-MePEA
β-Me-PEA
β-Methoxyamphetamine
Norephedrine
Phenibut
PP
MBZP
BZP
1-PEA · α-PEA
Benzylamine
homo-β,N-MePEA
homo-PEA
pip-PEA
β,N-MePEA · Phenpromethamine
β-HO-PEA
Norpseudoephedrine
Phenmetrazine
PIAP
PZAP
cPr-PEA · Tranylcypromine
β-Aminoamphetamine
β-DFA
β-FA
bk-2-AT
2463
2465
2-ADN
2-DPMP · Desoxypipradrol
Pipradrol
Desoxy-D2PM
D2PM · Diphenylprolinol
Aminorex
4-MAR · 4-Methylaminorex
MPH · Methylphenidate
EPH · Ethylphenidate
Phendimetrazine
P2P
1141
1307
N-Methyl-2-aminotetralin
NM-2-AI
1-Phenyl-2-propanol
Cyclazodone
Fenozolone
Pemoline
Thozalinone
N-M-1-PEA
1471
1482
1497
1498
1499
1500
1502
1511
1512
β,β-Me-PEA
β-iPr-PEA
DPEA
Isoethcathinone
Isopentedrone
2759
Levamisole
Homoamphetamine
W-15
Phenylpropanolmethylamine
Phenylpropanolamine
N-Et-Benzylamine
10825
10824
7-HAT
MeO-AI
4-MC · 4-Methylcathinone
DMAA
HHAT
1481
HOT-2-AT
Cathinone
EAP · Ethcathinone
DMAP · Dimethylcathinone
DEAP · Diethylpropion
PAP · Propylcathinone
i-PAP
BAP
t-BAP
EMC
MABP · Buphedrone
Pentedrone
MAA
2-FMC
2-MMA-βk
3-FMC
3-BMC
3-MeOMC · 3-MMA-βk
3-TFMAP
4-MMC · Mephedrone
PMMA-βk · Methedrone
4-FMC
4-BMC
4-EMC · 4-Ethylmethcathinone
4-CMC
4-TFMAP
4-IMC
PEA
Ephedrine
Pseudoephedrine
MA · Methamphetamine
A · Amphetamine
α-PPP
2-AI
2-AT
N-MePEA
β-Me-PEA
β-Methoxyamphetamine
Norephedrine
Phenibut
PP
MBZP
BZP
1-PEA · α-PEA
Benzylamine
homo-β,N-MePEA
homo-PEA
pip-PEA
β,N-MePEA · Phenpromethamine
β-HO-PEA
Norpseudoephedrine
Phenmetrazine
PIAP
PZAP
cPr-PEA · Tranylcypromine
β-Aminoamphetamine
β-DFA
β-FA
bk-2-AT
2463
2465
2-ADN
2-DPMP · Desoxypipradrol
Pipradrol
Desoxy-D2PM
D2PM · Diphenylprolinol
Aminorex
4-MAR · 4-Methylaminorex
MPH · Methylphenidate
EPH · Ethylphenidate
Phendimetrazine
P2P
1141
1307
N-Methyl-2-aminotetralin
NM-2-AI
1-Phenyl-2-propanol
Cyclazodone
Fenozolone
Pemoline
Thozalinone
N-M-1-PEA
1471
1482
1497
1498
1499
1500
1502
1511
1512
β,β-Me-PEA
β-iPr-PEA
DPEA
Isoethcathinone
Isopentedrone
2759
Levamisole
Homoamphetamine
W-15
Phenylpropanolmethylamine
Phenylpropanolamine
N-Et-Benzylamine
10825
10824
7-HAT
MeO-AI
4-MC · 4-Methylcathinone
DMAA
HHAT
1481
HOT-2-AT
19 November 2017 · Creative Commons BY-NC-SA ·