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EAP; Ethcathinone
2019
Variant: N α R2 R3 R4 skeleton isomers all
Analogues: 9 1 1 1 3 69 25 109

IUPAC: 2-(Ethylamino)-1-phenylpropan-1-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: LYMHIBZGTAPASQ-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-3-12-9(2)11(13)10-7-5-4-6-8-10/h4-9,12H,3H2,1-2H3

PubChem CID: 458519; ChemSpider: 403504; Erowid: Ethylcathinone; Wikipedia: Ethcathinone

Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 35

Dal Cason, TA. The characterization of some 3,4-methylenedioxycathinone (MDCATH) homologs. Forensic Sci. Int., 1 Jan 1997, 87 (1), 9–53. 909 kB. doi:10.1016/S0379-0738(97)02133-6

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. doi:10.1016/S0091-3057(97)00323-7

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

Tsujikawa, K; Mikuma, T; Kuwayama, K; Miyaguchi, H; Kanamori, T; Iwata, YT; Inoue, H. Degradation pathways of 4-methylmethcathinone in alkaline solution and stability of methcathinone analogs in various pH solutions. Forensic Sci. Int., 10 Jul 2012, 220 (1–3), 103–110. 671 kB. doi:10.1016/j.forsciint.2012.02.005

McDermott, SD; Power, JD; Kavanagh, PV; O’Brien, J. The analysis of substituted cathinones. Part 2: An investigation into the phenylacetone based isomers of 4-methylmethcathinone and N-ethylcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 13–21. 1129 kB. doi:10.1016/j.forsciint.2011.06.030

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. doi:10.1016/j.trac.2011.09.009

Reitzel, LA; Dalsgaard, PW; Müller, IB; Cornett, C. Identification of ten new designer drugs by GC-MS, UPLC-QTOF-MS, and NMR as part of a police investigation of a Danish Internet company. Drug Test. Anal., 1 May 2012, 4 (5), 342–354. 538 kB. doi:10.1002/dta.358

Nine N analogues:
2003
Analogue 1: Substituting Methyl for Ethyl at N

METHCATH
Methcathinone
α-Methylaminopropiophenone
Ephedrone

IUPAC: 2-(Methylamino)-1-phenylpropan-1-one

Formula: C10H13NO Molecular weight: 163.21632 g/mol InChI Key: LPLLVINFLBSFRP-UHFFFAOYSA-N

InChI=1S/C10H13NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,11H,1-2H3

PubChem CID: 1576; ChemSpider: 1519; Erowid: Cathinone & Methcathinone; Wikipedia: Methcathinone

Shulgin Index: #92 METHCATH; Table: 2 Page: 318 Row: 33

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

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. doi:10.1016/j.trac.2011.09.009

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. doi: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. doi:10.1016/0379-0738(94)01669-0

Foley, KF; Cozzi, NV. Novel aminopropiophenones as potential antidepressants. Drug Develop. Res., 1 Dec 2003, 60 (4), 252–260. 1588 kB. doi:10.1002/ddr.10297

Cameron, K; Kolanos, R; Vekariya, R; Felice, LD; 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. doi:10.1007/s00213-013-2967-2

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. doi:10.1016/0091-3057(93)90110-F

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. 2164 kB. doi: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. doi:10.1016/j.ejphar.2013.05.024

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. doi:10.1016/j.ejphar.2012.11.008

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.

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. doi: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. 8573 kB.

Archer, RP. Fluoromethcathinone, a new substance of abuse. Forensic Sci. Int., 1 Jan 2009, 185 (1–3), 10–20. 1355 kB. doi:10.1016/j.forsciint.2008.11.013

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

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. doi: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. doi: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. doi:10.1016/S0014-2999(99)00538-5

2004
Analogue 2: Removing Ethyl at N

Cathinone
β-Keto-amphetamine

IUPAC: 2-Amino-1-phenylpropan-1-one

Formula: C9H11NO Molecular weight: 149.18974 g/mol InChI Key: PUAQLLVFLMYYJJ-UHFFFAOYSA-N

InChI=1S/C9H11NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,10H2,1H3

PubChem CID: 107786; ChemSpider: 96940; Erowid: Cathinone & Methcathinone; Wikipedia: Cathinone

Shulgin Index: Table: 2 Page: 318 Row: 29

See also TiHKAL: #18 4-HO-DMT      

See also Transcripts: 5.652

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

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. doi:10.1016/0091-3057(93)90110-F

Dawson, BA; Black, DB; Lavoie, A; LeBelle, MJ. Nuclear magnetic resonance identification of the phenylalkylamine alkaloids of khat using a chiral solvating agent. J. Forensic Sci., 1 Jul 1994, 39 (4), 1026–1038. 453 kB. doi:10.1520/JFS13681J

LeBelle, MJ; Lauriault, G; Lavoie, A. Gas chromatographic-mass spectrometric identification of chiral derivatives of the alkaloids of KHAT. Forensic Sci. Int., 1 Sep 1993, 61 (1), 53–64. 900 kB. doi:10.1016/0379-0738(93)90249-A

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. doi:10.1124/jpet.103.053975

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. doi:10.1016/j.trac.2011.09.009

Gambaro, V; Arnoldi, S; Colombo, ML; Dell’Acqua, L; Guerrini, K; Roda, G. Determination of the active principles of Catha Edulis: Quali-quantitative analysis of cathinone, cathine, and phenylpropanolamine. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 87–92. 479 kB. doi:10.1016/j.forsciint.2011.09.028

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.

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012

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. doi:10.1016/0091-3057(94)00348-3

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

Archer, RP. Fluoromethcathinone, a new substance of abuse. Forensic Sci. Int., 1 Jan 2009, 185 (1–3), 10–20. 1355 kB. doi:10.1016/j.forsciint.2008.11.013

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. doi:10.1016/S0091-3057(97)00323-7

Shulgin, AT. Cathinone. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 3 Jun 2004.

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. 8573 kB.

2110
Analogue 3: Substituting Dimethyl for Ethyl at N

DMAP
Dimethylcathinone
Dimethylpropion
Metamfepramone

IUPAC: 2-(Dimethylamino)-1-phenylpropan-1-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: KBHMHROOFHVLBA-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9H,1-3H3

PubChem CID: 71872; ChemSpider: 64889; Wikipedia: Metamfepramone

Shulgin Index: #40 DMAP; Table: 2 Page: 318 Row: 34

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. doi:10.1016/S0091-3057(97)00323-7

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

Tsujikawa, K; Mikuma, T; Kuwayama, K; Miyaguchi, H; Kanamori, T; Iwata, YT; Inoue, H. Degradation pathways of 4-methylmethcathinone in alkaline solution and stability of methcathinone analogs in various pH solutions. Forensic Sci. Int., 10 Jul 2012, 220 (1–3), 103–110. 671 kB. doi:10.1016/j.forsciint.2012.02.005

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.

Dal Cason, TA. Synthesis and identification of N,N-dimethylcathinone hydrochloride. Microgram J., 1 Jan 2007, 5 (1–4), 3–12. 93 kB.

2339
Analogue 4: Substituting Diethyl for Ethyl at N

DEAP
Diethylpropion
Diethylcathinone
Amfepramone

IUPAC: 2-(Diethylamino)-1-phenylpropan-1-one

Formula: C13H19NO Molecular weight: 205.29606 g/mol InChI Key: XXEPPPIWZFICOJ-UHFFFAOYSA-N

InChI=1S/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3

PubChem CID: 7029; ChemSpider: 6762; Wikipedia: Amfepramone

Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 36

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

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. doi:10.1016/j.trac.2011.09.009

Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622

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

6051
Analogue 5: Substituting Propyl for Ethyl at N

PAP

IUPAC: 1-Phenyl-2-(propylamino)propan-1-one

Formula: C12H17NO Molecular weight: 191.26948 g/mol InChI Key: GXPFWFAQFTVCDU-UHFFFAOYSA-N

InChI=1S/C12H17NO/c1-3-9-13-10(2)12(14)11-7-5-4-6-8-11/h4-8,10,13H,3,9H2,1-2H3

PubChem CID: 45049; ChemSpider: 40983

Shulgin Index: See #40 DMAP; Table: 2 Page: 319 Row: 1

6052
Analogue 6: Substituting Isopropyl for Ethyl at N

i-PAP

IUPAC: 1-Phenyl-2-(propan-2-ylamino)propan-1-one

Formula: C12H17NO Molecular weight: 191.26948 g/mol InChI Key: LWRDNIQTNMVTBK-UHFFFAOYSA-N

InChI=1S/C12H17NO/c1-9(2)13-10(3)12(14)11-7-5-4-6-8-11/h4-10,13H,1-3H3

PubChem CID: 458522; ChemSpider: 403507

Shulgin Index: See #40 DMAP; Table: 2 Page: 319 Row: 2

Foley, KF; Cozzi, NV. Novel aminopropiophenones as potential antidepressants. Drug Develop. Res., 1 Dec 2003, 60 (4), 252–260. 1588 kB. doi:10.1002/ddr.10297

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. 8573 kB.

6053
Analogue 7: Substituting Butyl for Ethyl at N

BAP

IUPAC: 2-(Butylamino)-1-phenylpropan-1-one

Formula: C13H19NO Molecular weight: 205.29606 g/mol InChI Key: SFTGFCDNBIIGBP-UHFFFAOYSA-N

InChI=1S/C13H19NO/c1-3-4-10-14-11(2)13(15)12-8-6-5-7-9-12/h5-9,11,14H,3-4,10H2,1-2H3

PubChem CID: 423965; ChemSpider: 375254

Shulgin Index: See #40 DMAP; Table: 2 Page: 319 Row: 3

6054
Analogue 8: Substituting tert-Butyl for Ethyl at N

t-BAP

IUPAC: 2-(tert-Butylamino)-1-phenylpropan-1-one

Formula: C13H19NO Molecular weight: 205.29606 g/mol InChI Key: JQNSRSIGKZYQAA-UHFFFAOYSA-N

InChI=1S/C13H19NO/c1-10(14-13(2,3)4)12(15)11-8-6-5-7-9-11/h5-10,14H,1-4H3

PubChem CID: 3047299; ChemSpider: 2309776

Shulgin Index: See #40 DMAP; Table: 2 Page: 319 Row: 4

Foley, KF; Cozzi, NV. Novel aminopropiophenones as potential antidepressants. Drug Develop. Res., 1 Dec 2003, 60 (4), 252–260. 1588 kB. doi:10.1002/ddr.10297

Carroll, FI; Blough, BE; Abraham, P; Mills, AC; Holleman, JA; Wolckenhauer, SA; Decker, AM; Landavazo, A; McElroy, KT; Navarro, HA; Gatch, MB; Forster, MJ. Synthesis and biological evaluation of bupropion analogues as potential pharmacotherapies for cocaine addiction. J. Med. Chem., 2009, 52 (21), 6768–2781. 1104 kB. doi:10.1021/jm901189z

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. 8573 kB.

2576
Analogue 9: Substituting Ethyl and Methyl for Ethyl at N

EMC
N-Ethylmethcathinone

IUPAC: 2-[Ethyl(methyl)amino]-1-phenylpropan-1-one

Formula: C12H17NO Molecular weight: 191.26948 g/mol InChI Key: LOQPFJRCXJZNQV-UHFFFAOYSA-N

InChI=1S/C12H17NO/c1-4-13(3)10(2)12(14)11-8-6-5-7-9-11/h5-10H,4H2,1-3H3

One α analogue:
2430
Analogue 1: Substituting Ethyl for Methyl at α

NEB
N-Ethylbuphedrone

IUPAC: 2-(Ethylamino)-1-phenylbutan-1-one

Formula: C12H17NO Molecular weight: 191.26948 g/mol InChI Key: HEPVRDHGUWFXJS-UHFFFAOYSA-N

InChI=1S/C12H17NO/c1-3-11(13-4-2)12(14)10-8-6-5-7-9-10/h5-9,11,13H,3-4H2,1-2H3

PubChem CID: 20326296

One R2 analogue:
2538
Analogue 1: Adding Fluoro at R2

2-FEC
N-Ethyl-2-fluorocathinone

IUPAC: 2-(Ethylamino)-1-(2-fluorophenyl)propan-1-one

Formula: C11H14FNO Molecular weight: 195.2333632 g/mol InChI Key: HTIPESHOKKKFAV-UHFFFAOYSA-N

InChI=1S/C11H14FNO/c1-3-13-8(2)11(14)9-6-4-5-7-10(9)12/h4-8,13H,3H2,1-2H3

One R3 analogue:
2548
Analogue 1: Adding Fluoro at R3

3-FEC
N-Ethyl-3-fluorocathinone

IUPAC: 2-(Ethylamino)-1-(3-fluorophenyl)propan-1-one

Formula: C11H14FNO Molecular weight: 195.2333632 g/mol InChI Key: DTCAGAIFZCHZFO-UHFFFAOYSA-N

InChI=1S/C11H14FNO/c1-3-13-8(2)11(14)9-5-4-6-10(12)7-9/h4-8,13H,3H2,1-2H3

Westphal, F; Junge, T. Ring positional differentiation of isomeric N-alkylated fluorocathinones by gas chromatography/tandem mass spectrometry. Forensic Sci. Int., 30 Nov 2012, 223 (1–3), 97–105. 470 kB. doi:10.1016/j.forsciint.2012.08.011

Three R4 analogues:
2372
Analogue 1: Adding Methyl at R4

4-MEC
4-Methylethcathinone

IUPAC: 2-(Ethylamino)-1-(4-methylphenyl)propan-1-one

Formula: C12H17NO Molecular weight: 191.26948 g/mol InChI Key: ZOXZWYWOECCBSH-UHFFFAOYSA-N

InChI=1S/C12H17NO/c1-4-13-10(3)12(14)11-7-5-9(2)6-8-11/h5-8,10,13H,4H2,1-3H3

PubChem CID: 52988259; ChemSpider: 25630091; Erowid: 4-Methylethcathinone (4-MEC); Wikipedia: 4-Methylethcathinone

Brandt, SD; Sumnall, HR; Measham, F; Cole, JC. Analyses of second-generation ‘legal highs’ in the UK: Initial findings. Drug Test. Anal., 1 Aug 2010, 2 (8), 377–382. 317 kB. doi:10.1002/dta.155

Jankovics, P; Váradi, A; Tölgyesi, L; Lohner, S; Németh-Palotás, J; Kőszegi-Szalai, H. Identification and characterization of the new designer drug 4′-methylethcathinone (4-MEC) and elaboration of a novel liquid chromatography-tandem mass spectrometry (LC-MS/MS) screening method for seven different methcathinone analogs. Forensic Sci. Int., 15 Jul 2011, 210 (1–3), 213–220. 899 kB. doi:10.1016/j.forsciint.2011.03.019

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. doi:10.1016/j.trac.2011.09.009

Zuba, D; Byrska, B. Prevalence and co-existence of active components of ‘legal highs’ Drug Test. Anal., 1 Jun 2013, 5 (6), 420–429. 1294 kB. doi:10.1002/dta.1365

Kanu, AB; Brandt, SD; Williams, MD; Zhang, N; Hill, HH. Analysis of psychoactive cathinones and tryptamines by electrospray ionization atmospheric pressure ion mobility time-of-flight mass spectrometry. Anal. Chem., 17 Sep 2013, 85 (18), 8535–8542. 1636 kB. doi:10.1021/ac401951a

Gil, D; Adamowicz, P; Skulska, A; Tokarczyk, B; Stanaszek, R. Analysis of 4-MEC in biological and non-biological material—Three case reports. Forensic Sci. Int., 10 May 2013, 228 (1–3), e11–e15. 554 kB. doi:10.1016/j.forsciint.2013.03.011

Iversen, L; Gibbons, S; Treble, R; Setola, V; Huang, X; Roth, BL. Neurochemical profiles of some novel psychoactive substances. Eur. J. Pharmacol., 30 Jan 2013, 700 (1–3), 147–151. 490 kB. doi:10.1016/j.ejphar.2012.12.006

567
Analogue 2: Adding Ethyl at R4

4-EEC
4-Ethylethcathinone

IUPAC: 2-(Ethylamino)-1-(4-ethylphenyl)propan-1-one

Formula: C13H19NO Molecular weight: 205.29606 g/mol InChI Key: FAXVCSOMTSWQNT-UHFFFAOYSA-N

InChI=1S/C13H19NO/c1-4-11-6-8-12(9-7-11)13(15)10(3)14-5-2/h6-10,14H,4-5H2,1-3H3

ChemSpider: 25630221

570
Analogue 3: Adding Fluoro at R4

4-FEC
4-Fluoroethcathinone

IUPAC: 2-(Ethylamino)-1-(4-fluorophenyl)propan-1-one

Formula: C11H14FNO Molecular weight: 195.2333632 g/mol InChI Key: KBNVGQPMFGSPPT-UHFFFAOYSA-N

InChI=1S/C11H14FNO/c1-3-13-8(2)11(14)9-4-6-10(12)7-5-9/h4-8,13H,3H2,1-2H3

ChemSpider: 25630443; Wikipedia: 4-Fluoroethcathinone

Westphal, F; Junge, T. Ring positional differentiation of isomeric N-alkylated fluorocathinones by gas chromatography/tandem mass spectrometry. Forensic Sci. Int., 30 Nov 2012, 223 (1–3), 97–105. 470 kB. doi:10.1016/j.forsciint.2012.08.011

69 skeleton analogues:
142
Analogue 1: With 2-Phenylethan-1-amine skeleton

PEA
β-PEA
2-PEA
β-Phenethylamine
Phenethylamine

IUPAC: 2-Phenylethan-1-amine

Formula: C8H11N Molecular weight: 121.17964 g/mol InChI Key: BHHGXPLMPWCGHP-UHFFFAOYSA-N

InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2

PubChem CID: 1001; ChemSpider: 13856352; Wikipedia: Phenethylamine

Shulgin Index: #107 PEA; Table: 2 Page: 318 Row: 1

See also TiHKAL: #2 DBT
#5 α,O-DMS
#8 α,N-DMT
#11 α-ET
#30 4,5-MDO-DMT
#32 5,6-MDO-MIPT
#37 5-MeO-DIPT
#46 5-MeS-DMT
#53 T
#55 α,N,O-TMS

Suter, CM; Weston, AW. Some fluorinated amines of the pressor type. J. Am. Chem. Soc., 1 Feb 1941, 63 (2), 602–605. 444 kB. doi:10.1021/ja01847a069

Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

Horn, AS. Structure-activity relations for the inhibition of catecholamine uptake into synaptosomes from noradrenaline and dopaminergic neurones in rat brain homogenates. Br. J. Pharmacol., 1 Feb 1973, 47 (2), 332–338. 903 kB. doi:10.1111/j.1476-5381.1973.tb08331.x

Krawczeniuk, AS. Identification of phenethylamines and methylenedioxyamphetamines using liquid chromatography atmospheric pressure electrospray ionization mass spectrometry. Microgram J., 1 Jan 2005, 3 (1–2), 78–100. 979 kB.

Baker, GB; Coutts, RT; Rao, TS. Neuropharmacological and neurochemical properties of N- (2-cyanoethyl)-2-phenylethylamine, a prodrug of 2-phenylethylamine. Br. J. Pharmacol., 1 Oct 1987, 92 (2), 243–255. 1932 kB. doi:10.1111/j.1476-5381.1987.tb11318.x

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Bailey, K; By, AW. The conformation of β-phenylethylamines in solution. Can. J. Pharm. Sci., 1975, 10 (1), 31–32. 117 kB.

Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622

Repke, DB; Ferguson, WJ; Bates, DK. Synthesis of secondary methylalkylamines. Tetrahedron Lett., 1979, 20 (43), 4183–4184. 149 kB. doi:10.1016/S0040-4039(01)86538-2

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Fontanilla, D; Johannessen, M; Hajipour, AR; Cozzi, NV; Jackson, MB; Ruoho, AE. The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator. Science, 13 Feb 2009, 323 (5916):,934–937. 529 kB. doi:10.1126/science.1166127

Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012

Meyers-Riggs, B. Phenethylamine and amphetamine. countyourculture: rational exploration of the underground, 2 Nov 2010.

2006
Analogue 2: With 2-Phenylethan-1-amine skeleton

Amphetamine

IUPAC: 1-Phenylpropan-2-amine

Formula: C9H13N Molecular weight: 135.20622 g/mol InChI Key: KWTSXDURSIMDCE-UHFFFAOYSA-N

InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3

PubChem CID: 3007; ChemSpider: 13852819; Drugs Forum: Amphetamine; Erowid: Amphetamines; Wikipedia: Amphetamine

See also TiHKAL: #5 α,O-DMS
#8 α,N-DMT
#13 Harmaline
#48 α-MT
#55 α,N,O-TMS  

See also Transcripts: 1.133

See also Pharmacology notes I: p. 133, Amphetamine

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Warren, RJ; Begosh, PP; Zarembo, JE. Identification of amphetamines and related sympathomimetic amines. J. Assoc. Off. Anal. Chem., 1971, 54 (5), 1179–1191. 3851 kB.

Ho, B; McIsaac, WM; An, R; Tansey, LW; Walker, KE; Englert, LF; Noel, MB. Analogs of α-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs. J. Med. Chem., 1 Jan 1970, 13 (1), 26–30. 601 kB. doi:10.1021/jm00295a007

Lurie, IS; Bozenko, JS; Li, L; Miller, EE; Greenfield, SJ. Chiral separation of methamphetamine and related compounds using capillary electrophoresis with dynamically coated capillaries. Microgram J., 1 Jan 2011, 8 (1), 24–28. 786 kB.

Krawczeniuk, AS. Identification of phenethylamines and methylenedioxyamphetamines using liquid chromatography atmospheric pressure electrospray ionization mass spectrometry. Microgram J., 1 Jan 2005, 3 (1–2), 78–100. 979 kB.

Bustamante, D; Diaz-Véliz, G; Paeile, C; Zapata-Torres, G; Cassels, BK. Analgesic and behavioral effects of amphetamine enantiomers, p-methoxyamphetamine and N-alkyl-p-methoxyamphetamine derivatives. Pharmacol. Biochem. Behav., 1 Oct 2004, 79 (2), 199–212. 404 kB. doi:10.1016/j.pbb.2004.06.017

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Bailey, K; Legault, D. Analysis of the 13C-NMR spectra of mono- and dimethylamphetamines. Anal. Chim. Acta., 1 Jan 1981, 123, 75–82. 654 kB. doi:10.1016/S0003-2670(01)83160-3

Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622

Reviriego, F; Navarro, P; Domènech, A; García-España, E. Effective complexation of psychotropic phenethylammonium salts from a disodium dipyrazolate salt of macrocyclic structure. J. Chem. Soc. Perkin Trans. 2, 2002, 1634–1638. 115 kB. doi:10.1039/b200607c

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Horn, AS. Structure-activity relations for the inhibition of catecholamine uptake into synaptosomes from noradrenaline and dopaminergic neurones in rat brain homogenates. Br. J. Pharmacol., 1 Feb 1973, 47 (2), 332–338. 903 kB. doi:10.1111/j.1476-5381.1973.tb08331.x

Benington, F; Morin, RD; Clark, LC. Behavioral and neuropharmacological actions of N-aralkylhydroxylamines and their O-methyl ethers. J. Med. Chem., 1 Jan 1965, 8 (1), 100–104. 634 kB. doi:10.1021/jm00325a020

Aceto, MD; Rosecrans, JA; Young, R; Glennon, RA. Similarity between (+)-amphetamine and amfonelic acid. Pharmacol. Biochem. Behav., 1 Apr 1984, 20 (4), 635–637. 184 kB. doi:10.1016/0091-3057(84)90316-2

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

Suter, CM; Weston, AW. Some fluorinated amines of the pressor type. J. Am. Chem. Soc., 1 Feb 1941, 63 (2), 602–605. 444 kB. doi:10.1021/ja01847a069

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

Stojanovska, N; Fu, S; Tahtouh, M; Kelly, T; Beavis, A; Kirkbride, KP. A review of impurity profiling and synthetic route of manufacture of methylamphetamine, 3,4-methylenedioxymethylamphetamine, amphetamine, dimethylamphetamine and p-methoxyamphetamine. Forensic Sci. Int., 10 Jan 2013, 224 (1–3), 8–26. 813 kB. doi:10.1016/j.forsciint.2012.10.040

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of α-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-X

Heal, DJ; Smith, SL; Gosden, J; Nutt, DJ. Amphetamine, past and present—a pharmacological and clinical perspective. J. Psychopharmacol., 1 Jun 2013, 27 (6), 479–496. 740 kB. doi:10.1177/0269881113482532

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

Rasmussen, N. Making the first anti-depressant: Amphetamine in American medicine, 1929-1950. J. Hist. Med. Allied Sci., 1 Jul 2006, 61 (3), 288–323. 175 kB. doi:10.1093/jhmas/jrj039

Worsham, JN. 5-HT3 receptor ligands and their effect on psychomotor stimulants. M. Sc. Thesis, Virginia Commonwealth University, Richmond, VA, USA, 1 May 2008. 956 kB.

Oberlender, R; Nichols, DE. Drug discrimination studies with MDMA and amphetamine. Psychopharmacology, 1 May 1988, 95 (1), 71–26. 674 kB. doi:10.1007/BF00212770

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

Thunhorst, M; Holzgrabe, U. Utilizing NMR spectroscopy for assessing drug enantiomeric composition. Magn. Reson. Chem., 1 Mar 1998, 36 (3), 211–216. 237 kB. doi:10.1002/(SICI)1097-458X(199803)363211AID-OMR2463.0.CO;2-Y

Ögren, S; Ross, SB. Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones. Acta Pharmacol. Toxicol., 1 Oct 1977, 41 (4), 353–368. 1335 kB. doi:10.1111/j.1600-0773.1977.tb02674.x

Anderson, GM; Braun, G; Braun, U; Nichols, DE; Shulgin, AT. Absolute configuration and psychotomimetic activity. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 8–15. 457 kB.

Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. doi:10.1016/j.pbb.2007.06.001

McGraw, NP; Callery, PS; Castagnoli, N. In vitro stereoselective metabolism of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane. An apparent enantiomeric interaction. J. Med. Chem., 1 Jan 1977, 20 (2), 185–189. 661 kB. doi:10.1021/jm00212a001

Rothman, RB; Blough, BE; Baumann, MH. Dual dopamine-5-HT releasers: potential treatment agents for cocaine addiction. Trends Pharmacol. Sci., 1 Dec 2006, 27 (12), 612–618. 519 kB. doi:10.1016/j.tips.2006.10.006

Marona-Lewicka, D; Kurrasch-Orbaugh, DM; Selken, JR; Cumbay, MG; Lisnicchia, JG; Nichols, DE. Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioural effects overlap its other properties in rats. Psychopharmacology, 1 Oct 2002, 164 (1), 93–107. 293 kB. doi:10.1007/s00213-002-1141-z

Vilches-Herrera, M; Miranda-Sepúlveda, J; Rebolledo-Fuentes, M; Fierro, A; Lühr, S; Iturriaga-Vasquez, P; Cassels, BK; Reyes-Parada, M. Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors. Bioorg. Med. Chem., 15 Mar 2009, 17 (6), 2452–2460. 509 kB. doi:10.1016/j.bmc.2009.01.074

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012

Meyers-Riggs, B. Phenethylamine and amphetamine. countyourculture: rational exploration of the underground, 2 Nov 2010.

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. doi:10.1016/0091-3057(94)00348-3

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. doi:10.1021/jm00263a013

Hathaway, BA; Nichols, DE; Nichols, MB; Yim, GKW. A new, potent, conformationally-restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene. J. Med. Chem., 1 Jan 1982, 25 (5), 535–538. 563 kB. doi:10.1021/jm00347a011

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Woolverton, WL; Shybut, G; Johanson, CE. Structure-activity relationships among some d-N-alkylated amphetamines. Pharmacol. Biochem. Behav., 1 Jan 1980, 13 (6), 869–876. 783 kB. doi:10.1016/0091-3057(80)90221-X

Rothman, RB; Blough, BE; Baumann, MH. Dual dopamine/serotonin releasers as potential medications for stimulant and alcohol addictions. AAPS J., 2007, 9 (1), E1–E10. 999 kB. doi:10.1208/aapsj0901001

Guy, M; Freeman, S; Alder, JF; Brandt, SD. The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines. Cent. Eur. J. Chem., 1 Dec 2008, 6 (4), 526–534. 982 kB. doi:10.2478/s11532-008-0054-z

Alles, GA; Feigen, GA. Comparative physiological actions of phenyl-, thienyl- and furylisopropylamines. J. Pharmacol. Exp. Ther., 1 Jul 1941, 72 (3), 265–275. 1459 kB.

Huang, X; Nichols, DE. 5-HT2 receptor-mediated potentiation of dopamine synthesis and central serotonergic deficits. Eur. J. Pharmacol., 1 Jan 1993, 238 (2–3), 291–296. 553 kB. doi:10.1016/0014-2999(93)90859-G

Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 581–586. 586 kB. doi:10.1016/0091-3057(91)90017-V

Nichols, DE. Differences between the mechanism of action of MDMA, MBDB, and the classic hallucinogens. Identification of a new therapeutic class: Entactogens. J. Psychoactive Drugs, 1 Jan 1986, 18 (4), 305–313. 10675 kB. doi:10.1080/02791072.1986.10472362

2114
Analogue 3: With 2-Cyclic-amine-1-phenylethanone skeleton

α-PPP
PPP
α-Pyrrolidinopropiophenone

IUPAC: 1-Phenyl-2-(pyrrolidin-1-yl)propan-1-one

Formula: C13H17NO Molecular weight: 203.28018 g/mol InChI Key: KPUJAQRFIJAORQ-UHFFFAOYSA-N

InChI=1S/C13H17NO/c1-11(14-9-5-6-10-14)13(15)12-7-3-2-4-8-12/h2-4,7-8,11H,5-6,9-10H2,1H3

PubChem CID: 209045; ChemSpider: 181124; Wikipedia: Alpha-Pyrrolidinopropiophenone

Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 30

Maurer, HH; Kraemer, T; Springer, D; Staack, RF. Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (Ecstasy), piperazine, and pyrrolidinophenone types. A synopsis. Ther. Drug Monit., 1 Apr 2004, 26 (2), 127–131. 121 kB.

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

Staack, RF; Maurer, HH. Metabolism of designer drugs of abuse. Curr. Drug Metab., 1 Jun 2005, 6 (3), 259–274. 104 kB. doi:10.2174/1389200054021825

Reitzel, LA; Dalsgaard, PW; Müller, IB; Cornett, C. Identification of ten new designer drugs by GC-MS, UPLC-QTOF-MS, and NMR as part of a police investigation of a Danish Internet company. Drug Test. Anal., 1 May 2012, 4 (5), 342–354. 538 kB. doi:10.1002/dta.358

Rösner, P; Junge, T; Fritschi, G; Klein, B; Thielert, K; Kozlowski, M. Neue synthetische Drogen: Piperazin-, propicyclidin- und α-aminopropiophenonderivate. Toxichem Krimtech, 1999, 66 (2), 81–90. 1202 kB.

2357
Analogue 4: With 2,3-Dihydro-1H-inden-2-amine skeleton

2-AI
2-Aminoindane

IUPAC: 2,3-Dihydro-1H-inden-2-amine

Formula: C9H11N Molecular weight: 133.19034 g/mol InChI Key: LMHHFZAXSANGGM-UHFFFAOYSA-N

InChI=1S/C9H11N/c10-9-5-7-3-1-2-4-8(7)6-9/h1-4,9H,5-6,10H2

PubChem CID: 76310; ChemSpider: 68787; Erowid: 2-Aminoindan; Wikipedia: 2-Aminoindane

Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 581–586. 586 kB. doi:10.1016/0091-3057(91)90017-V

Cannon, JG; Perez, JA; Pease, JP; Long, JP; Flynn, JR; Rusterholz, DB; Dryer., SE. Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene. J. Med. Chem., 1 Jan 1980, 23 (7), 745–749. 731 kB. doi:10.1021/jm00181a009

400
Analogue 5: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

2-AT
2-Aminotetralin

IUPAC: 1,2,3,4-Tetrahydronaphthalen-2-amine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: LCGFVWKNXLRFIF-UHFFFAOYSA-N

InChI=1S/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2

PubChem CID: 34677; ChemSpider: 31912; Wikipedia: 2-Aminotetralin

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of α-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-X

Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 581–586. 586 kB. doi:10.1016/0091-3057(91)90017-V

Nichols, DE; Pfister, WR; Yim, GKW; Cosgrove, RJ. A new view of the structural relationship between LSD and mescaline. Brain Res. Bull., 1 May 1977, 2 (3), 169–171. 338 kB. doi:10.1016/0361-9230(77)90034-X

Cannon, JG; Perez, JA; Pease, JP; Long, JP; Flynn, JR; Rusterholz, DB; Dryer., SE. Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene. J. Med. Chem., 1 Jan 1980, 23 (7), 745–749. 731 kB. doi:10.1021/jm00181a009

Barfknecht, CF; Nichols, DE; Rusterholz, DB; Long, JP; Engelbrecht, JA; Beaton, JM; Bradley, RJ; Dyer, DC. Potential psychotomimetics. 2-Amino-1,2,3,4-tetrahydronaphthalene analogs. J. Med. Chem., 1 Jan 1973, 16, (7), 804–808. 614 kB. doi:10.1021/jm00265a013

Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012

5554
Analogue 6: With 2-Phenylethan-1-amine skeleton

β-Me-PEA
β-Methylphenethylamine

IUPAC: 2-Phenylpropan-1-amine

Formula: C9H13N Molecular weight: 135.20622 g/mol InChI Key: AXORVIZLPOGIRG-UHFFFAOYSA-N

InChI=1S/C9H13N/c1-8(7-10)9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3

PubChem CID: 11398; ChemSpider: 10920; Wikipedia: Beta-Methylphenethylamine

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

2405
Analogue 7: With 2-Phenylethan-1-amine skeleton

β-Methoxyamphetamine

IUPAC: 1-Methoxy-1-phenylpropan-2-amine

Formula: C10H15NO Molecular weight: 165.2322 g/mol InChI Key: XNYRQJJPTRMQBG-UHFFFAOYSA-N

InChI=1S/C10H15NO/c1-8(11)10(12-2)9-6-4-3-5-7-9/h3-8,10H,11H2,1-2H3

PubChem CID: 12843489; ChemSpider: 28169264

2393
Analogue 8: With 2-Phenylethan-1-amine skeleton

Norephedrine
nor-Ephedrine

IUPAC: (1R,2S)-2-Amino-1-phenylpropan-1-ol

Formula: C9H13NO Molecular weight: 151.20562 g/mol InChI Key: DLNKOYKMWOXYQA-CBAPKCEASA-N

InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1

PubChem CID: 4786; ChemSpider: 4622

Shulgin Index: Table: 2 Page: 318 Row: 23

Thunhorst, M; Holzgrabe, U. Utilizing NMR spectroscopy for assessing drug enantiomeric composition. Magn. Reson. Chem., 1 Mar 1998, 36 (3), 211–216. 237 kB. doi:10.1002/(SICI)1097-458X(199803)363211AID-OMR2463.0.CO;2-Y

Osorio-Olivares, M; Rezende, MC; Sepúlveda-Boza, S; Cassels, BK; Fierro, A. MAO inhibition by arylisopropylamines: the effect of oxygen substituents at the β-position. Bioorg. Med. Chem., 1 Jan 2004, 12 (15), 4055–4066. 412 kB. doi:10.1016/j.bmc.2004.05.033

Gambaro, V; Arnoldi, S; Colombo, ML; Dell’Acqua, L; Guerrini, K; Roda, G. Determination of the active principles of Catha Edulis: Quali-quantitative analysis of cathinone, cathine, and phenylpropanolamine. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 87–92. 479 kB. doi:10.1016/j.forsciint.2011.09.028

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

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. doi:10.1124/jpet.103.053975

Dawson, BA; Black, DB; Lavoie, A; LeBelle, MJ. Nuclear magnetic resonance identification of the phenylalkylamine alkaloids of khat using a chiral solvating agent. J. Forensic Sci., 1 Jul 1994, 39 (4), 1026–1038. 453 kB. doi:10.1520/JFS13681J

2378
Analogue 9: With 2-Phenylethan-1-amine skeleton

Phenibut

IUPAC: 4-Amino-3-phenylbutanoic acid

Formula: C10H13NO2 Molecular weight: 179.21572 g/mol InChI Key: DAFOCGYVTAOKAJ-UHFFFAOYSA-N

InChI=1S/C10H13NO2/c11-7-9(6-10(12)13)8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)

PubChem CID: 14113; ChemSpider: 13491; Erowid: Phenibut; Wikipedia: Phenibut

801
Analogue 10: With 1-Phenylpiperazine skeleton

PP

IUPAC: 1-Phenylpiperazine

Formula: C10H14N2 Molecular weight: 162.23156 g/mol InChI Key: YZTJYBJCZXZGCT-UHFFFAOYSA-N

InChI=1S/C10H14N2/c1-2-4-10(5-3-1)12-8-6-11-7-9-12/h1-5,11H,6-9H2

PubChem CID: 7096; ChemSpider: 6829; Wikipedia: Phenylpiperazine

Shulgin Index: See #24 oCPP; Table: 8 Page: 357 Row: 1

Schoenwald, RD; Gadiraju, RR; Barfknecht, CF. Serotonin antagonists for use as antiglaucoma agents and their ocular penetration. Eur. J. Pharm. Biopharm., 1 Jun 1997, 43 (3), 273–281. 688 kB. doi:10.1016/S0939-6411(97)00055-6

903
Analogue 11: With 1-Benzylpiperazine skeleton

BZP

IUPAC: 1-Benzylpiperazine

Formula: C11H16N2 Molecular weight: 176.25814 g/mol InChI Key: IQXXEPZFOOTTBA-UHFFFAOYSA-N

InChI=1S/C11H16N2/c1-2-4-11(5-3-1)10-13-8-6-12-7-9-13/h1-5,12H,6-10H2

PubChem CID: 75994; ChemSpider: 68493; Wikipedia: Benzylpiperazine

Shulgin Index: Table: 9 Page: 357 Row: 19

Rösner, P; Junge, T; Fritschi, G; Klein, B; Thielert, K; Kozlowski, M. Neue synthetische Drogen: Piperazin-, propicyclidin- und α-aminopropiophenonderivate. Toxichem Krimtech, 1999, 66 (2), 81–90. 1202 kB.

Zuba, D; Byrska, B. Prevalence and co-existence of active components of ‘legal highs’ Drug Test. Anal., 1 Jun 2013, 5 (6), 420–429. 1294 kB. doi:10.1002/dta.1365

Krawczeniuk, AS. Identification of phenethylamines and methylenedioxyamphetamines using liquid chromatography atmospheric pressure electrospray ionization mass spectrometry. Microgram J., 1 Jan 2005, 3 (1–2), 78–100. 979 kB.

Maurer, HH. Mass spectra of select benzyl- and phenyl- piperazine designer drugs. Microgram J., 1 Jan 2004, 2 (1–4), 22–26. 326 kB.

Wood, DM; Button, J; Lidder, S; Ramsey, J; Holt, DW; Dargan, PI. Dissociative and sympathomimetic toxicity associated with recreational use of 1-(3-trifluoromethylphenyl)piperazine (TFMPP) and 1-benzylpiperzine (BZP). J. Med. Toxicol., 1 Dec 2008, 4 (4), 254–257. 334 kB. doi:10.1007/BF03161209

Byrska, B; Zuba, D; Stanaszek, R. Determination of piperazine derivatives in “legal highs” Probl. Forensic Sci., 2010, 81, 101–113. 852 kB.

Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Schep, LJ; Slaughter, RJ; Temple, WA; Gee, P. Comments on BZP and New Zealand’s alternative approach to prohibition. Drug Test. Anal., 1 Jan 2012, 4 (1), 57. 47 kB. doi:10.1002/dta.356

Anon. Report on the risk assessment of BZP, European Monitoring Centre for Drugs and Drug Addiction, Feb 2009.

Elie, L; Baron, M; Croxton, R; Elie, M. Microcrystalline identification of selected designer drugs. Forensic Sci. Int., 10 Jan 2012, 214 (1–3),. 1364 kB. doi:10.1016/j.forsciint.2011.08.005

Staack, RF; Maurer, HH. Metabolism of designer drugs of abuse. Curr. Drug Metab., 1 Jun 2005, 6 (3), 259–274. 104 kB. doi:10.2174/1389200054021825

Baumann, MH; Clark, RD; Budzynski, AG; Partilla, JS; Blough, BE; Rothman, RB. N-Substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or ‘Ecstasy’). Neuropsychopharmacology, 1 Mar 2005, 30 (3), 550–560. 184 kB. doi:10.1038/sj.npp.1300585

902
Analogue 12: With Phenylmethanamine skeleton

1-PEA
α-PEA
α-Me-benzylamine

IUPAC: 1-Phenylethan-1-amine

Formula: C8H11N Molecular weight: 121.17964 g/mol InChI Key: RQEUFEKYXDPUSK-UHFFFAOYSA-N

InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3

PubChem CID: 7408; ChemSpider: 7130; Wikipedia: 1-Phenylethylamine

Shulgin Index: See #107 PEA; Table: 9 Page: 357 Row: 18

King, LA; Meer, AJP; Huizer, H. 1-Phenylethylamines: a new series of illicit drugs? Forensic Sci. Int., 9 Feb 1996, 77 (3), 141–149. 491 kB. doi:10.1016/0379-0738(95)01852-2

901
Analogue 13: With Phenylmethanamine skeleton

Benzylamine

IUPAC: 1-Phenylmethanamine

Formula: C7H9N Molecular weight: 107.15306 g/mol InChI Key: WGQKYBSKWIADBV-UHFFFAOYSA-N

InChI=1S/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2

PubChem CID: 7504; ChemSpider: 7223; Wikipedia: Benzylamine

Shulgin Index: See #107 PEA; Table: 9 Page: 357 Row: 17

601
Analogue 14: With 3-Phenylpropan-1-amine skeleton

homo-PEA

IUPAC: 3-Phenylpropan-1-amine

Formula: C9H13N Molecular weight: 135.20622 g/mol InChI Key: LYUQWQRTDLVQGA-UHFFFAOYSA-N

InChI=1S/C9H13N/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8,10H2

PubChem CID: 16259; ChemSpider: 15427

Shulgin Index: See #107 PEA; Table: 10 Page: 358 Row: 8

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

6004
Analogue 15: With 2-Phenylethan-1-amine skeleton

N-EtPEA

IUPAC: N-Ethyl-2-phenylethan-1-amine

Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: WOHOHPONCSKXSQ-UHFFFAOYSA-N

InChI=1S/C10H15N/c1-2-11-9-8-10-6-4-3-5-7-10/h3-7,11H,2,8-9H2,1H3

PubChem CID: 547324; ChemSpider: 476381

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 4

6007
Analogue 16: With Phenylethyl-cyclic-amine skeleton

pip-PEA

IUPAC: 1-(2-Phenylethyl)piperidine

Formula: C13H19N Molecular weight: 189.29666 g/mol InChI Key: DBDVAKGHPZJLTH-UHFFFAOYSA-N

InChI=1S/C13H19N/c1-3-7-13(8-4-1)9-12-14-10-5-2-6-11-14/h1,3-4,7-8H,2,5-6,9-12H2

PubChem CID: 9513; ChemSpider: 9141

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 7

6009
Analogue 17: With 2-Phenylethan-1-amine skeleton

β-Me-N-Et-PEA

IUPAC: N-Ethyl-2-phenylpropan-1-amine

Formula: C11H17N Molecular weight: 163.25938 g/mol InChI Key: YRJYTEMOKSUBHJ-UHFFFAOYSA-N

InChI=1S/C11H17N/c1-3-12-9-10(2)11-7-5-4-6-8-11/h4-8,10,12H,3,9H2,1-2H3

PubChem CID: 15788198; ChemSpider: 10617484

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 9

6010
Analogue 18: With 2-Phenylethan-1-amine skeleton

β-HO-PEA

IUPAC: 2-Amino-1-phenylethanol

Formula: C8H11NO Molecular weight: 137.17904 g/mol InChI Key: ULSIYEODSMZIPX-UHFFFAOYSA-N

InChI=1S/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2

PubChem CID: 1000; ChemSpider: 975

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 10

Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012

Horn, AS. Structure-activity relations for the inhibition of catecholamine uptake into synaptosomes from noradrenaline and dopaminergic neurones in rat brain homogenates. Br. J. Pharmacol., 1 Feb 1973, 47 (2), 332–338. 903 kB. doi:10.1111/j.1476-5381.1973.tb08331.x

6018
Analogue 19: With 2-Phenylethan-1-amine skeleton

EA
N-Ethylamphetamine

IUPAC: N-Ethyl-1-phenylpropan-2-amine

Formula: C11H17N Molecular weight: 163.25938 g/mol InChI Key: YAGBSNMZQKEFCO-UHFFFAOYSA-N

InChI=1S/C11H17N/c1-3-12-10(2)9-11-7-5-4-6-8-11/h4-8,10,12H,3,9H2,1-2H3

PubChem CID: 9982; ChemSpider: 9588

Shulgin Index: Table: 2 Page: 318 Row: 18

Woolverton, WL; Shybut, G; Johanson, CE. Structure-activity relationships among some d-N-alkylated amphetamines. Pharmacol. Biochem. Behav., 1 Jan 1980, 13 (6), 869–876. 783 kB. doi:10.1016/0091-3057(80)90221-X

Glennon, RA; Yousif, M; Patrick, G. Stimulus properties of 1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDA) analogs. Pharmacol. Biochem. Behav., 1 Mar 1988, 29 (3), 443–449. 551 kB. doi:10.1016/0091-3057(88)90001-9

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Musshoff, F. Illegal or legitimate use? Precursor compounds to amphetamine and methamphetamine. Drug Metab. Rev., 2000, 32 (1), 15–44. 345 kB. doi:10.1081/DMR-100100562

Krawczeniuk, AS. Identification of phenethylamines and methylenedioxyamphetamines using liquid chromatography atmospheric pressure electrospray ionization mass spectrometry. Microgram J., 1 Jan 2005, 3 (1–2), 78–100. 979 kB.

6024
Analogue 20: With 2-Phenylethan-1-amine skeleton

Norpseudoephdrine
nor-Pseudoephdrine

IUPAC: (1S,2S)-2-Amino-1-phenylpropan-1-ol

Formula: C9H13NO Molecular weight: 151.20562 g/mol InChI Key: DLNKOYKMWOXYQA-IONNQARKSA-N

InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9+/m0/s1

PubChem CID: 54463712; ChemSpider: 390189

Shulgin Index: Table: 2 Page: 318 Row: 24

Gambaro, V; Arnoldi, S; Colombo, ML; Dell’Acqua, L; Guerrini, K; Roda, G. Determination of the active principles of Catha Edulis: Quali-quantitative analysis of cathinone, cathine, and phenylpropanolamine. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 87–92. 479 kB. doi:10.1016/j.forsciint.2011.09.028

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Horn, AS. Structure-activity relations for the inhibition of catecholamine uptake into synaptosomes from noradrenaline and dopaminergic neurones in rat brain homogenates. Br. J. Pharmacol., 1 Feb 1973, 47 (2), 332–338. 903 kB. doi:10.1111/j.1476-5381.1973.tb08331.x

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. doi:10.1124/jpet.103.053975

Dawson, BA; Black, DB; Lavoie, A; LeBelle, MJ. Nuclear magnetic resonance identification of the phenylalkylamine alkaloids of khat using a chiral solvating agent. J. Forensic Sci., 1 Jul 1994, 39 (4), 1026–1038. 453 kB. doi:10.1520/JFS13681J

6028
Analogue 21: With Phenyl-cyclic-amine skeleton

Phenmetrazine

IUPAC: 3-Methyl-2-phenylmorpholine

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: OOBHFESNSZDWIU-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-9-11(13-8-7-12-9)10-5-3-2-4-6-10/h2-6,9,11-12H,7-8H2,1H3

PubChem CID: 4762; ChemSpider: 4598

Shulgin Index: Table: 2 Page: 318 Row: 28

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

Banks, ML; Blough, BE; Fennell, TR; Snyder, RW; Negus, SS. Role of phenmetrazine as an active metabolite of phendimetrazine: Evidence from studies of drug discrimination and pharmacokinetics in rhesus monkeys. Drug Alcohol Depend., 1 Jun 2013, 130 (1–3), 158–166. 520 kB. doi:10.1016/j.drugalcdep.2012.10.026

Clarke, FH. cis- and trans-3-methyl-2-phenylmorpholine. J. Org. Chem., 1 Sep 1962, 27 (9), 3251–3253. 409 kB. doi:10.1021/jo01056a063

Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622

6031
Analogue 22: With 2-Cyclic-amine-1-phenylethanone skeleton

PIAP

IUPAC: 1-Phenyl-2-(piperidin-1-yl)propan-1-one

Formula: C14H19NO Molecular weight: 217.30676 g/mol InChI Key: GEHIWZFQDZBTBY-UHFFFAOYSA-N

InChI=1S/C14H19NO/c1-12(15-10-6-3-7-11-15)14(16)13-8-4-2-5-9-13/h2,4-5,8-9,12H,3,6-7,10-11H2,1H3

PubChem CID: 458526; ChemSpider: 403511

Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 31

6032
Analogue 23: With 2-Cyclic-amine-1-phenylethanone skeleton

PZAP

IUPAC: 2-(4-Methylpiperazin-1-yl)-1-phenylpropan-1-one

Formula: C14H20N2O Molecular weight: 232.3214 g/mol InChI Key: VJYLTZJATFKDGJ-UHFFFAOYSA-N

InChI=1S/C14H20N2O/c1-12(16-10-8-15(2)9-11-16)14(17)13-6-4-3-5-7-13/h3-7,12H,8-11H2,1-2H3

PubChem CID: 43227278

Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 32

6055
Analogue 24: With 2-Phenylcyclopropan-1-amine skeleton

cPr-PEA

IUPAC: 2-Phenylcyclopropanamine

Formula: C9H11N Molecular weight: 133.19034 g/mol InChI Key: AELCINSCMGFISI-UHFFFAOYSA-N

InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2

PubChem CID: 5530; ChemSpider: 5329

Shulgin Index: See #107 PEA; Table: 2 Page: 319 Row: 5

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

Arvidsson, L; Johansson, AM; Hacksell, U; Nilsson, JLG; Svensson, K; Hjorth, S; Magnusson, T; Carlsson, A; Lindberg, P; Andersson, B; Sanchez, D; Wikström, H; Sundell, S. N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: Novel central 5-hydroxytryptamine receptor agonists. J. Med. Chem., 1 Jan 1988, 31 (1), 92–99. 1162 kB. doi:10.1021/jm00396a014

Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018

Walters, GC; Cooper, PD. Alicyclic analogue of mescaline. Nature, 20 Apr 1968, 218 (5138), 298–300. 3141 kB. doi:10.1038/218298a0

2461
Analogue 25: With 2-Phenylethan-1-amine skeleton

β-Aminoamphetamine

IUPAC: 1-Phenylpropane-1,2-diamine

Formula: C9H14N2 Molecular weight: 150.22086 g/mol InChI Key: PRCXGQJVEKZKQR-UHFFFAOYSA-N

InChI=1S/C9H14N2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9H,10-11H2,1H3

PubChem CID: 12475829; ChemSpider: 13341018

Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012

461
Analogue 26: With 2-Phenylethan-1-amine skeleton

β-DFA

IUPAC: 1,1-Difluoro-1-phenylpropan-2-amine

Formula: C9H11F2N Molecular weight: 171.1871464 g/mol InChI Key: CTOGXYQJJYYTRC-UHFFFAOYSA-N

InChI=1S/C9H11F2N/c1-7(12)9(10,11)8-5-3-2-4-6-8/h2-7H,12H2,1H3

PubChem CID: 12570687; ChemSpider: 10324996

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

460
Analogue 27: With 2-Phenylethan-1-amine skeleton

β-FA

IUPAC: 1-Fluoro-1-phenylpropan-2-amine

Formula: C9H12FN Molecular weight: 153.1966832 g/mol InChI Key: PPZYDZIZQRVGPE-UHFFFAOYSA-N

InChI=1S/C9H12FN/c1-7(11)9(10)8-5-3-2-4-6-8/h2-7,9H,11H2,1H3

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

2462
Analogue 28: With 2-Amino-3,4-dihydronaphthalen-1(2H)-one skeleton

bk-2-AT

IUPAC: 2-Amino-3,4-dihydronaphthalen-1(2H)-one

Formula: C10H11NO Molecular weight: 161.20044 g/mol InChI Key: MUGWUYGVUZLWRB-UHFFFAOYSA-N

InChI=1S/C10H11NO/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-4,9H,5-6,11H2

PubChem CID: 412890; ChemSpider: 365595

Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012

2463
Analogue 29: With 1-(3,4-Dihydronaphthalen-1-yl)methanamine skeleton

IUPAC: 1-(3,4-Dihydronaphthalen-1-yl)methanamine

Formula: C11H13N Molecular weight: 159.22762 g/mol InChI Key: WNFNQSTXHLQIED-UHFFFAOYSA-N

InChI=1S/C11H13N/c12-8-10-6-3-5-9-4-1-2-7-11(9)10/h1-2,4,6-7H,3,5,8,12H2

PubChem CID: 12914860; ChemSpider: 14442059

Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012

2465
Analogue 30: With 1-(2H-Chromen-4-yl)methanamine skeleton

IUPAC: 1-(2H-Chromen-4-yl)methanamine

Formula: C10H11NO Molecular weight: 161.20044 g/mol InChI Key: WRQGQTBQEWMFLP-UHFFFAOYSA-N

InChI=1S/C10H11NO/c11-7-8-5-6-12-10-4-2-1-3-9(8)10/h1-5H,6-7,11H2

PubChem CID: 12914869

Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012

544
Analogue 31: With 1,2-Dihydronaphthalen-2-amine skeleton

2-ADN

IUPAC: 1,2-Dihydronaphthalen-2-amine

Formula: C10H11N Molecular weight: 145.20104 g/mol InChI Key: SHLZSYAMFQNEOF-UHFFFAOYSA-N

InChI=1S/C10H11N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-6,10H,7,11H2

PubChem CID: 133605; ChemSpider: 117856; Wikipedia: 2-Amino-1,2-dihydronaphthalene

Hathaway, BA; Nichols, DE; Nichols, MB; Yim, GKW. A new, potent, conformationally-restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene. J. Med. Chem., 1 Jan 1982, 25 (5), 535–538. 563 kB. doi:10.1021/jm00347a011

Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 581–586. 586 kB. doi:10.1016/0091-3057(91)90017-V

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of α-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-X

557
Analogue 32: With Benzyl-cyclic-amine skeleton

Desoxypipradrol
2-DPMP
2-Diphenylmethylpiperidine;

IUPAC: 2-(Diphenylmethyl)piperidine

Formula: C18H21N Molecular weight: 251.36604 g/mol InChI Key: RWTNXJXZVGHMGI-UHFFFAOYSA-N

InChI=1S/C18H21N/c1-3-9-15(10-4-1)18(16-11-5-2-6-12-16)17-13-7-8-14-19-17/h1-6,9-12,17-19H,7-8,13-14H2

PubChem CID: 160506; ChemSpider: 141045

Iversen, L; Gibbons, S; Treble, R; Setola, V; Huang, X; Roth, BL. Neurochemical profiles of some novel psychoactive substances. Eur. J. Pharmacol., 30 Jan 2013, 700 (1–3), 147–151. 490 kB. doi:10.1016/j.ejphar.2012.12.006

Corkery, JM; Elliott, S; Schifano, F; Corazza, O; Ghodse, AH. 2-DPMP (desoxypipradrol, 2-benzhydrylpiperidine, 2-phenylmethylpiperidine) and D2PM (diphenyl-2-pyrrolidin-2-yl-methanol, diphenylprolinol): A preliminary review. Prog. Neuro-Psychopharmacol. Biol. Psych., 3 Dec 2012, 39 (2), 253–258. 347 kB. doi:10.1016/j.pnpbp.2012.05.021

Wood, DM; Dargan, PI. Use and acute toxicity associated with the novel psychoactive substances diphenylprolinol (D2PM) and desoxypipradrol (2-DPMP). Clin. Toxicol., 1 Sep 2012, 50 (8), 727–732. 117 kB. doi:10.3109/15563650.2012.716158

Iversen, LL. Consideration of desoxypipradrol (2-DPMP) and related pipradrol compounds, Advisory Council on the Misuse of Drugs, 13 Sep 2011.

558
Analogue 33: With Benzyl-cyclic-amine skeleton

Pipradrol

IUPAC: Diphenyl(piperidin-2-yl)methanol

Formula: C18H21NO Molecular weight: 267.36544 g/mol InChI Key: XSWHNYGMWWVAIE-UHFFFAOYSA-N

InChI=1S/C18H21NO/c20-18(15-9-3-1-4-10-15,16-11-5-2-6-12-16)17-13-7-8-14-19-17/h1-6,9-12,17,19-20H,7-8,13-14H2

PubChem CID: 10083; ChemSpider: 9681

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

559
Analogue 34: With Benzyl-cyclic-amine skeleton

Desoxy-D2PM
2-Diphenylmethylpyrrolidine

IUPAC: 2-(Diphenylmethyl)pyrrolidine

Formula: C17H19N Molecular weight: 237.33946 g/mol InChI Key: OXOBKZZXZVFOBB-UHFFFAOYSA-N

InChI=1S/C17H19N/c1-3-8-14(9-4-1)17(16-12-7-13-18-16)15-10-5-2-6-11-15/h1-6,8-11,16-18H,7,12-13H2

PubChem CID: 1295; ChemSpider: 1256

Paoli, GD; Brandt, SD; Pounder, DJ. Analytical characterization and rapid determination of 2-(diphenylmethyl)pyrrolidine in blood and application to an internet product. J. Chromatogr. B, 1 Dec 2011, 879 (31), 3771–3774. 353 kB. doi:10.1016/j.jchromb.2011.10.014

560
Analogue 35: With Benzyl-cyclic-amine skeleton

D2PM
Diphenylprolinol

IUPAC: Diphenyl(pyrrolidin-2-yl)methanol

Formula: C17H19NO Molecular weight: 253.33886 g/mol InChI Key: OGCGXUGBDJGFFY-UHFFFAOYSA-N

InChI=1S/C17H19NO/c19-17(16-12-7-13-18-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,18-19H,7,12-13H2

PubChem CID: 204386; ChemSpider: 177034

Corkery, JM; Elliott, S; Schifano, F; Corazza, O; Ghodse, AH. 2-DPMP (desoxypipradrol, 2-benzhydrylpiperidine, 2-phenylmethylpiperidine) and D2PM (diphenyl-2-pyrrolidin-2-yl-methanol, diphenylprolinol): A preliminary review. Prog. Neuro-Psychopharmacol. Biol. Psych., 3 Dec 2012, 39 (2), 253–258. 347 kB. doi:10.1016/j.pnpbp.2012.05.021

Lidder, S; Dargan, PI; Sexton, M; Button, J; Ramsey, J; Holt, DW; Wood, DM. Cardiovascular toxicity associated with recreational use of diphenylprolinol (diphenyl-2-pyrrolidinemethanol [D2PM]). J. Med. Toxicol., 1 Sep 2008, 4 (3), 167–169. 164 kB. doi:10.1007/BF03161195

Wood, DM; Dargan, PI. Use and acute toxicity associated with the novel psychoactive substances diphenylprolinol (D2PM) and desoxypipradrol (2-DPMP). Clin. Toxicol., 1 Sep 2012, 50 (8), 727–732. 117 kB. doi:10.3109/15563650.2012.716158

Zuba, D; Byrska, B. Prevalence and co-existence of active components of ‘legal highs’ Drug Test. Anal., 1 Jun 2013, 5 (6), 420–429. 1294 kB. doi:10.1002/dta.1365

561
Analogue 36: With Phenyl-cyclic-amine skeleton

Aminorex

IUPAC: 5-Phenyl-4,5-dihydro-1,3-oxazol-2-amine

Formula: C9H10N2O Molecular weight: 162.1885 g/mol InChI Key: SYAKTDIEAPMBAL-UHFFFAOYSA-N

InChI=1S/C9H10N2O/c10-9-11-6-8(12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H2,10,11)

PubChem CID: 16630; Wikipedia: Aminorex

Hess, C; Ritke, N; Sydow, K; Mehling, L; Ruehs, H; Madea, B; Musshoff, F. Determination of levamisole, aminorex, and pemoline in plasma by means of liquid chromatography-mass spectrometry and application to a pharmacokinetic study of levamisole. Drug Test. Anal., 20 Feb 2014. 451 kB. doi:10.1002/dta.1619

Brandt, SD; Baumann, MH; Partilla, JS; Kavanagh, PV; Power, JD; Talbot, B; Twamley, B; Mahony, O; O’Brien, J; Elliott, SP; Archer, RP; Patrick, J; Singh, K; Dempster, NM; Cosbey, SH. Characterization of a novel and potentially lethal designer drug (±)-cis-para-methyl-4-methylaminorex (4,4′-DMAR, or ‘Serotoni’). Drug Test. Anal., 2014. 1068 kB. doi:10.1002/dta.1668

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. doi:10.1016/0091-3057(93)90110-F

Woolverton, WL; Massey, BW; Winger, G; Patrick, GA; Harris, LS. Evaluation of the abuse liability of aminorex. Drug Alcohol Depend., 1 Dec 1994, 36 (3), 187–192. 711 kB. doi:10.1016/0376-8716(94)90144-9

562
Analogue 37: With Phenyl-cyclic-amine skeleton

4-MAR
4-Methylaminorex

IUPAC: 4-Methyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine

Formula: C10H12N2O Molecular weight: 176.21508 g/mol InChI Key: LJQBMYDFWFGESC-UHFFFAOYSA-N

InChI=1S/C10H12N2O/c1-7-9(13-10(11)12-7)8-5-3-2-4-6-8/h2-7,9H,1H3,(H2,11,12)

PubChem CID: 92196; ChemSpider: 83237; Wikipedia: 4-Methylaminorex

Brandt, SD; Baumann, MH; Partilla, JS; Kavanagh, PV; Power, JD; Talbot, B; Twamley, B; Mahony, O; O’Brien, J; Elliott, SP; Archer, RP; Patrick, J; Singh, K; Dempster, NM; Cosbey, SH. Characterization of a novel and potentially lethal designer drug (±)-cis-para-methyl-4-methylaminorex (4,4′-DMAR, or ‘Serotoni’). Drug Test. Anal., 2014. 1068 kB. doi:10.1002/dta.1668

Rodriguez, WR; Allred, RA. Synthesis of trans-4-methylaminorex from norephedrine and potassium cyanate. Microgram J., 1 Jul 2005, 3 (3–4), 154–165. 559 kB.

565
Analogue 38: With Benzyl-cyclic-amine skeleton

Methylphenidate

IUPAC: Methyl phenyl(piperidin-2-yl)acetate

Formula: C14H19NO2 Molecular weight: 233.30616 g/mol InChI Key: DUGOZIWVEXMGBE-UHFFFAOYSA-N

InChI=1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3

PubChem CID: 4158; ChemSpider: 4015

Griffiths, RR; Richards, WA; McCann, U; Jesse, R. Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance. Psychopharmacology, 1 Aug 2006, 187 (3), 268–283. 342 kB. doi:10.1007/s00213-006-0457-5

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

566
Analogue 39: With Benzyl-cyclic-amine skeleton

Ethylphenidate

IUPAC: Ethyl phenyl(piperidin-2-yl)acetate

Formula: C15H21NO2 Molecular weight: 247.33274 g/mol InChI Key: AIVSIRYZIBXTMM-UHFFFAOYSA-N

InChI=1S/C15H21NO2/c1-2-18-15(17)14(12-8-4-3-5-9-12)13-10-6-7-11-16-13/h3-5,8-9,13-14,16H,2,6-7,10-11H2,1H3

PubChem CID: 3080846; ChemSpider: 2338571

Casale, JF; Hays, PA. Ethylphenidate: An analytical profile. Microgram J., 2011, 8 (2), 58–61. 906 kB.

1235
Analogue 40: With Phenyl-cyclic-amine skeleton

Phendimetrazine

IUPAC: 3,4-Dimethyl-2-phenylmorpholine

Formula: C12H17NO Molecular weight: 191.26948 g/mol InChI Key: MFOCDFTXLCYLKU-UHFFFAOYSA-N

InChI=1S/C12H17NO/c1-10-12(14-9-8-13(10)2)11-6-4-3-5-7-11/h3-7,10,12H,8-9H2,1-2H3

PubChem CID: 12460; ChemSpider: 11950

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

Banks, ML; Blough, BE; Fennell, TR; Snyder, RW; Negus, SS. Role of phenmetrazine as an active metabolite of phendimetrazine: Evidence from studies of drug discrimination and pharmacokinetics in rhesus monkeys. Drug Alcohol Depend., 1 Jun 2013, 130 (1–3), 158–166. 520 kB. doi:10.1016/j.drugalcdep.2012.10.026

Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622

542
Analogue 41: With Phenylacetaldehyde skeleton

P2P

IUPAC: 1-Phenylpropan-2-one

Formula: C9H10O Molecular weight: 134.1751 g/mol InChI Key: QCCDLTOVEPVEJK-UHFFFAOYSA-N

InChI=1S/C9H10O/c1-8(10)7-9-5-3-2-4-6-9/h2-6H,7H2,1H3

PubChem CID: 7678; ChemSpider: 21106366

Barfknecht, CF; Smith, RV; Nichols, DE; Leseney, JL; Long, JP; Engelbrecht, JA. Chemistry and pharmacological evaluation of 1-phenyl-2-propanols and 1-phenyl-2-propanones. J. Pharm. Sci., 1 May 1971, 60 (5), 799–801. 352 kB. doi:10.1002/jps.2600600533

1141
Analogue 42: With Prop-2-en-1-ylbenzene skeleton

IUPAC: Prop-2-en-1-ylbenzene

Formula: C9H10 Molecular weight: 118.1757 g/mol InChI Key: HJWLCRVIBGQPNF-UHFFFAOYSA-N

InChI=1S/C9H10/c1-2-6-9-7-4-3-5-8-9/h2-5,7-8H,1,6H2

PubChem CID: 9309; ChemSpider: 8950

Nichols, DE; Mason, DL; Jacobsen, LB. Allylbenzene analogs of Δ9-tetrahydrocannabinol as tumor growth inhibitors. Life Sci., 1 Nov 1977, 21 (9), 1245–1247. 150 kB. doi:10.1016/0024-3205(77)90004-2

1307
Analogue 43: With 6,7,8,9-Tetrahydro-5H-benzo[7]annulen-6-amine skeleton

IUPAC: 6,7,8,9-Tetrahydro-5H-benzo[7]annulen-6-amine

Formula: C11H15N Molecular weight: 161.2435 g/mol InChI Key: MDVRGZASGHPBAG-UHFFFAOYSA-N

InChI=1S/C11H15N/c12-11-7-3-6-9-4-1-2-5-10(9)8-11/h1-2,4-5,11H,3,6-8,12H2

PubChem CID: 41896; ChemSpider: 38228

Cannon, JG; Perez, JA; Pease, JP; Long, JP; Flynn, JR; Rusterholz, DB; Dryer., SE. Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene. J. Med. Chem., 1 Jan 1980, 23 (7), 745–749. 731 kB. doi:10.1021/jm00181a009

1318
Analogue 44: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

N-Ethyl-2-aminotetralin

IUPAC: N-Ethyl-1,2,3,4-tetrahydronaphthalen-2-amine

Formula: C12H17N Molecular weight: 175.27008 g/mol InChI Key: RDDGNJSHYAVRDT-UHFFFAOYSA-N

InChI=1S/C12H17N/c1-2-13-12-8-7-10-5-3-4-6-11(10)9-12/h3-6,12-13H,2,7-9H2,1H3

PubChem CID: 12843074; ChemSpider: 12956378

Cannon, JG; Perez, JA; Pease, JP; Long, JP; Flynn, JR; Rusterholz, DB; Dryer., SE. Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene. J. Med. Chem., 1 Jan 1980, 23 (7), 745–749. 731 kB. doi:10.1021/jm00181a009

1328
Analogue 45: With 2,3-Dihydro-1H-inden-2-amine skeleton

NE-2-AI
N-Ethyl-2-aminoindane

IUPAC: N-Ethyl-2,3-dihydro-1H-inden-2-amine

Formula: C11H15N Molecular weight: 161.2435 g/mol InChI Key: RAJHFMSNMQFOPU-UHFFFAOYSA-N

InChI=1S/C11H15N/c1-2-12-11-7-9-5-3-4-6-10(9)8-11/h3-6,11-12H,2,7-8H2,1H3

PubChem CID: 12452138; ChemSpider: 10635088

Cannon, JG; Perez, JA; Pease, JP; Long, JP; Flynn, JR; Rusterholz, DB; Dryer., SE. Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene. J. Med. Chem., 1 Jan 1980, 23 (7), 745–749. 731 kB. doi:10.1021/jm00181a009

1339
Analogue 46: With 2-Phenylethanol skeleton

1-Phenyl-2-propanol

IUPAC: 1-Phenylpropan-2-ol

Formula: C9H12O Molecular weight: 136.19098 g/mol InChI Key: WYTRYIUQUDTGSX-UHFFFAOYSA-N

InChI=1S/C9H12O/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8,10H,7H2,1H3

PubChem CID: 94185; ChemSpider: 84999

Barfknecht, CF; Smith, RV; Nichols, DE; Leseney, JL; Long, JP; Engelbrecht, JA. Chemistry and pharmacological evaluation of 1-phenyl-2-propanols and 1-phenyl-2-propanones. J. Pharm. Sci., 1 May 1971, 60 (5), 799–801. 352 kB. doi:10.1002/jps.2600600533

1434
Analogue 47: With Phenyl-cyclic-amine skeleton

Cyclazodone

IUPAC: 2-(Cyclopropylamino)-5-phenyl-1,3-oxazol-4(5H)-one

Formula: C12H12N2O2 Molecular weight: 216.23588 g/mol InChI Key: DNRKTAYPGADPGW-UHFFFAOYSA-N

InChI=1S/C12H12N2O2/c15-11-10(8-4-2-1-3-5-8)16-12(14-11)13-9-6-7-9/h1-5,9-10H,6-7H2,(H,13,14,15)

PubChem CID: 26701; ChemSpider: 24875; Wikipedia: Cyclazodone

1435
Analogue 48: With Phenyl-cyclic-amine skeleton

Fenozolone

IUPAC: 2-(Ethylamino)-5-phenyl-1,3-oxazol-4(5H)-one

Formula: C11H12N2O2 Molecular weight: 204.22518 g/mol InChI Key: RXOIEVSUURELPG-UHFFFAOYSA-N

InChI=1S/C11H12N2O2/c1-2-12-11-13-10(14)9(15-11)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,12,13,14)

PubChem CID: 71682; ChemSpider: 64736; Wikipedia: Fenozolone

1437
Analogue 49: With Phenyl-cyclic-amine skeleton

Pemoline

IUPAC: 2-Imino-5-phenyl-1,3-oxazolidin-4-one

Formula: C9H8N2O2 Molecular weight: 176.17202 g/mol InChI Key: NRNCYVBFPDDJNE-UHFFFAOYSA-N

InChI=1S/C9H8N2O2/c10-9-11-8(12)7(13-9)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12)

PubChem CID: 4723; ChemSpider: 4561; Wikipedia: Pemoline

Hess, C; Ritke, N; Sydow, K; Mehling, L; Ruehs, H; Madea, B; Musshoff, F. Determination of levamisole, aminorex, and pemoline in plasma by means of liquid chromatography-mass spectrometry and application to a pharmacokinetic study of levamisole. Drug Test. Anal., 20 Feb 2014. 451 kB. doi:10.1002/dta.1619

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

1438
Analogue 50: With Phenyl-cyclic-amine skeleton

Thozalinone

IUPAC: 2-(Dimethylamino)-5-phenyl-1,3-oxazol-4(5H)-one

Formula: C11H12N2O2 Molecular weight: 204.22518 g/mol InChI Key: JJSHYECKYLDYAR-UHFFFAOYSA-N

InChI=1S/C11H12N2O2/c1-13(2)11-12-10(14)9(15-11)8-6-4-3-5-7-8/h3-7,9H,1-2H3

PubChem CID: 12602; ChemSpider: 12082; Wikipedia: Thozalinone

1471
Analogue 51: With 2-Phenylcyclobutan-1-amine skeleton

IUPAC: 2-Phenylcyclobutanamine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: PKMQLQANCCIABY-UHFFFAOYSA-N

InChI=1S/C10H13N/c11-10-7-6-9(10)8-4-2-1-3-5-8/h1-5,9-10H,6-7,11H2

PubChem CID: 19703781

Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018

1484
Analogue 52: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: N-Ethyl-2-phenylcyclopropanamine

Formula: C11H15N Molecular weight: 161.2435 g/mol InChI Key: LTJUNOMOONBAHB-UHFFFAOYSA-N

InChI=1S/C11H15N/c1-2-12-11-8-10(11)9-6-4-3-5-7-9/h3-7,10-12H,2,8H2,1H3

PubChem CID: 61813376; ChemSpider: 28173221

Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018

1497
Analogue 53: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 2-Methyl-2-phenylcyclopropanamine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: DZOORLACDVEKJC-UHFFFAOYSA-N

InChI=1S/C10H13N/c1-10(7-9(10)11)8-5-3-2-4-6-8/h2-6,9H,7,11H2,1H3

PubChem CID: 54595265; ChemSpider: 27909807

Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018

1498
Analogue 54: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 1-Methyl-2-phenylcyclopropanamine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: MHQDTOHVMGQLTE-UHFFFAOYSA-N

InChI=1S/C10H13N/c1-10(11)7-9(10)8-5-3-2-4-6-8/h2-6,9H,7,11H2,1H3

PubChem CID: 54072774

Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018

1499
Analogue 55: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 2,2-Diphenylcyclopropanamine

Formula: C15H15N Molecular weight: 209.2863 g/mol InChI Key: WVRNJJILWVMIRA-UHFFFAOYSA-N

InChI=1S/C15H15N/c16-14-11-15(14,12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H,11,16H2

PubChem CID: 12345941; ChemSpider: 13566302

Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018

1500
Analogue 56: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 2-Methyl-3-phenylcyclopropanamine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: VYDUHLWMQFOCQJ-UHFFFAOYSA-N

InChI=1S/C10H13N/c1-7-9(10(7)11)8-5-3-2-4-6-8/h2-7,9-10H,11H2,1H3

PubChem CID: 55289096

Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018

1502
Analogue 57: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 2,3-Diphenylcyclopropanamine

Formula: C15H15N Molecular weight: 209.2863 g/mol InChI Key: RYTXAPKVNHVKAX-UHFFFAOYSA-N

InChI=1S/C15H15N/c16-15-13(11-7-3-1-4-8-11)14(15)12-9-5-2-6-10-12/h1-10,13-15H,16H2

PubChem CID: 12523667

Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018

1511
Analogue 58: With 1-Benzylcyclopropan-1-amine skeleton

IUPAC: 1-Benzylcyclopropanamine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: GEQRCQKFLCJFEC-UHFFFAOYSA-N

InChI=1S/C10H13N/c11-10(6-7-10)8-9-4-2-1-3-5-9/h1-5H,6-8,11H2

PubChem CID: 152923; ChemSpider: 134782

1559
Analogue 59: With 2-Phenylethan-1-amine skeleton

β,β-Me-PEA

IUPAC: 2-Methyl-2-phenylpropan-1-amine

Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: CWSGTPMVOJFVIF-UHFFFAOYSA-N

InChI=1S/C10H15N/c1-10(2,8-11)9-6-4-3-5-7-9/h3-7H,8,11H2,1-2H3

PubChem CID: 210602; ChemSpider: 182543

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

1561
Analogue 60: With 2-Phenylethan-1-amine skeleton

β-iPr-PEA

IUPAC: 3-Methyl-2-phenylbutan-1-amine

Formula: C11H17N Molecular weight: 163.25938 g/mol InChI Key: VDMAQVANUGNDOM-UHFFFAOYSA-N

InChI=1S/C11H17N/c1-9(2)11(8-12)10-6-4-3-5-7-10/h3-7,9,11H,8,12H2,1-2H3

PubChem CID: 9880217; ChemSpider: 8055893

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

1562
Analogue 61: With 2-Phenylethan-1-amine skeleton

DPEA

IUPAC: 2,2-Diphenylethan-1-amine

Formula: C14H15N Molecular weight: 197.2756 g/mol InChI Key: RXMTUVIKZRXSSM-UHFFFAOYSA-N

InChI=1S/C14H15N/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H,11,15H2

PubChem CID: 77575; ChemSpider: 69980

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

2526
Analogue 62: With Phenylacetaldehyde skeleton

Isoethcathinone

IUPAC: 1-(Ethylamino)-1-phenylpropan-2-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: GHVCNLDRNVGRJP-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-3-12-11(9(2)13)10-7-5-4-6-8-10/h4-8,11-12H,3H2,1-2H3

PubChem CID: 12403217

McDermott, SD; Power, JD; Kavanagh, PV; O’Brien, J. The analysis of substituted cathinones. Part 2: An investigation into the phenylacetone based isomers of 4-methylmethcathinone and N-ethylcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 13–21. 1129 kB. doi:10.1016/j.forsciint.2011.06.030

2527
Analogue 63: With Phenylacetaldehyde skeleton

Isopentedrone

IUPAC: 1-(Methylamino)-1-phenylpentan-2-one

Formula: C12H17NO Molecular weight: 191.26948 g/mol InChI Key: ILGRTMNCRBDXBI-UHFFFAOYSA-N

InChI=1S/C12H17NO/c1-3-7-11(14)12(13-2)10-8-5-4-6-9-10/h4-6,8-9,12-13H,3,7H2,1-2H3

Westphal, F; Junge, T; Girreser, U; Greibl, W; Doering, C. Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 157–167. 853 kB. doi:10.1016/j.forsciint.2011.10.045

2759
Analogue 64: With Phenylmethanamine skeleton

IUPAC: N′-[4-(Dimethylamino)-2-methoxy-5-nitrobenzyl]-N,N-diethylethane-1,2-diamine

Formula: C16H28N4O3 Molecular weight: 324.41852 g/mol InChI Key: GDOQXLINNITIBE-UHFFFAOYSA-N

InChI=1S/C16H28N4O3/c1-6-19(7-2)9-8-17-12-13-10-15(20(21)22)14(18(3)4)11-16(13)23-5/h10-11,17H,6-9,12H2,1-5H3

Dawson, BA; Black, DB; Cyr, TD; Ethier, J; By, AW; Beckstead, HD; Neville, GA. Structural elucidation of unusual police exhibits. I. Dimethpramide ('Dimetcarb'). Forensic Sci. Int., 28 Feb 1995, 71 (3), 169–179. 1376 kB. doi:10.1016/0379-0738(94)01664-X

1047
Analogue 65: With Phenyl-cyclic-amine skeleton

Levamisole

IUPAC: 6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole

Formula: C11H12N2S Molecular weight: 204.29138 g/mol InChI Key: HLFSDGLLUJUHTE-UHFFFAOYSA-N

InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2

PubChem CID: 3913; ChemSpider: 3776

Hess, C; Ritke, N; Sydow, K; Mehling, L; Ruehs, H; Madea, B; Musshoff, F. Determination of levamisole, aminorex, and pemoline in plasma by means of liquid chromatography-mass spectrometry and application to a pharmacokinetic study of levamisole. Drug Test. Anal., 20 Feb 2014. 451 kB. doi:10.1002/dta.1619

1045
Analogue 66: With 3-Phenylpropan-1-amine skeleton

Homoamphetamine

IUPAC: 4-Phenylbutan-2-amine

Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: WECUIGDEWBNQJJ-UHFFFAOYSA-N

InChI=1S/C10H15N/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6,9H,7-8,11H2,1H3

PubChem CID: 31160; ChemSpider: 28910

King, LA. New phenethylamines in Europe. Drug Test. Anal., 20 Nov 2013. 472 kB. doi:10.1002/dta.1570

1027
Analogue 67: With Phenylethyl-cyclic-amine skeleton

W-15

IUPAC: 4-Chloro-N-[(2E)-1-(2-phenylethyl)piperidin-2-ylidene]benzenesulfonamide

Formula: C19H21ClN2O2S Molecular weight: 376.90024 g/mol InChI Key: VJHXSSVOCOBVMI-XUTLUUPISA-N

InChI=1S/C19H21ClN2O2S/c20-17-9-11-18(12-10-17)25(23,24)21-19-8-4-5-14-22(19)15-13-16-6-2-1-3-7-16/h1-3,6-7,9-12H,4-5,8,13-15H2/b21-19+

ChemSpider: 10544257

1017
Analogue 68: With 2-Phenylethan-1-amine skeleton

Phenylpropanolamine

IUPAC: 2-Amino-1-phenylpropan-1-ol

Formula: C9H13NO Molecular weight: 151.20562 g/mol InChI Key: DLNKOYKMWOXYQA-UHFFFAOYSA-N

InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3

PubChem CID: 4786; ChemSpider: 4622

Warren, RJ; Begosh, PP; Zarembo, JE. Identification of amphetamines and related sympathomimetic amines. J. Assoc. Off. Anal. Chem., 1971, 54 (5), 1179–1191. 3851 kB.

Krawczeniuk, AS. Identification of phenethylamines and methylenedioxyamphetamines using liquid chromatography atmospheric pressure electrospray ionization mass spectrometry. Microgram J., 1 Jan 2005, 3 (1–2), 78–100. 979 kB.

930
Analogue 69: With Phenylmethanamine skeleton

N-IPr-Benzylamine
N-iPr-Benzylamine

IUPAC: N-Benzylpropan-2-amine

Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: LYBKPDDZTNUNNM-UHFFFAOYSA-N

InChI=1S/C10H15N/c1-9(2)11-8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3

PubChem CID: 66024; ChemSpider: 59415

Sanderson, RM. Identification of N-methylbenzylamine hydrochloride, N-ethylbenzylamine hydrochloride, and N-isopropylbenzylamine hydrochloride. Microgram J., 1 Jan 2008, 6 (1–2), 36–45. 495 kB.

25 isomers:
2018
Isomer 1

4-Me-MCAT
4-MMC
Mephedrone
4-Methylmethcathinone

IUPAC: 2-(Methylamino)-1-(4-methylphenyl)propan-1-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: YELGFTGWJGBAQU-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8-4-6-10(7-5-8)11(13)9(2)12-3/h4-7,9,12H,1-3H3

PubChem CID: 45266826; ChemSpider: 21485694; Drugs Forum: Mephedrone; Erowid: 4-Methylmethcathinone; Wikipedia: Mephedrone

Shulgin Index: See #92 METHCATH; Table: 3 Page: 323 Row: 2

Morris, K. UK places generic ban on mephedrone drug family. Lancet, 17 Apr 2010, 375 (9723), 1333–1334. 52 kB. doi:10.1016/S0140-6736(10)60559-4

Spiller, HA; Ryan, ML; Weston, RG; Jansen, J. Clinical experience with and analytical confirmation of “bath salts” and “legal highs” (synthetic cathinones) in the United States. Clin. Toxicol., 1 Jul 2011, 49 (6), 499–505. 130 kB. doi:10.3109/15563650.2011.590812

Anon. Report on the risk assessment of mephedrone, European Monitoring Centre for Drugs and Drug Addiction, May 2011.

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. doi:10.1016/j.trac.2011.09.009

Reitzel, LA; Dalsgaard, PW; Müller, IB; Cornett, C. Identification of ten new designer drugs by GC-MS, UPLC-QTOF-MS, and NMR as part of a police investigation of a Danish Internet company. Drug Test. Anal., 1 May 2012, 4 (5), 342–354. 538 kB. doi:10.1002/dta.358

Zuba, D; Byrska, B. Prevalence and co-existence of active components of ‘legal highs’ Drug Test. Anal., 1 Jun 2013, 5 (6), 420–429. 1294 kB. doi:10.1002/dta.1365

Westphal, F; Junge, T; Rösner, P; Girreser, U; Fritsch, R. Massenspektrometrische, infrarotspektroskopische und NMR-spekstroskopische Daten von Mephedron, Butylon und Methylon sowie einigen ihrer Derivate. Toxichem Krimtech, 2010, 77 (2), 95–116. 380 kB.

Cameron, K; Kolanos, R; Vekariya, R; Felice, LD; 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. doi:10.1007/s00213-013-2967-2

Kanu, AB; Brandt, SD; Williams, MD; Zhang, N; Hill, HH. Analysis of psychoactive cathinones and tryptamines by electrospray ionization atmospheric pressure ion mobility time-of-flight mass spectrometry. Anal. Chem., 17 Sep 2013, 85 (18), 8535–8542. 1636 kB. doi:10.1021/ac401951a

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. 2164 kB. doi: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. doi:10.1016/j.ejphar.2013.05.024

Gregg, RA; Rawls, SM. Behavioral pharmacology of designer cathinones: A review of the preclinical literature. Life Sci., 27 Feb 2014, 97 (1), 27–30. 249 kB. doi:10.1016/j.lfs.2013.10.033

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

German, CL; Fleckenstein, AE; Hanson, GR. Bath salts and synthetic cathinones: An emerging designer drug phenomenon. Life Sci., 27 Feb 2014, 97 (1), 2–8. 390 kB. doi:10.1016/j.lfs.2013.07.023

Angoa-Pérez, M; Kane, MJ; Herrera-Mundo, N; Francescutti, DM; Kuhn, DM. Effects of combined treatment with mephedrone and methamphetamine or 3,4-methylenedioxymethamphetamine on serotonin nerve endings of the hippocampus. Life Sci., 27 Feb 2014, 97 (1), 31–36. 888 kB. doi:10.1016/j.lfs.2013.07.015

Iversen, L; Gibbons, S; Treble, R; Setola, V; Huang, X; Roth, BL. Neurochemical profiles of some novel psychoactive substances. Eur. J. Pharmacol., 30 Jan 2013, 700 (1–3), 147–151. 490 kB. doi:10.1016/j.ejphar.2012.12.006

Prosser, JM; Nelson, LS. The toxicology of bath salts: a review of synthetic cathinones. J. Med. Toxicol., 1 Nov 2011, 8 (1), 33–22. 267 kB. doi:10.1007/s13181-011-0193-z

Khreit, OIG; Grant, MH; Zhang, T; Henderson, C; Watson, DG; Sutcliffe, OB. Elucidation of the Phase I and Phase II metabolic pathways of (±)-4′-methylmethcathinone (4-MMC) and (±)-4′-(trifluoromethyl)methcathinone (4-TFMMC) in rat liver hepatocytes using LC–MS and LC–MS2. J. Pharm. Biomed. Anal., 18 Jan 2013, 72, 177–185. 800 kB. doi:10.1016/j.jpba.2012.08.015

McDermott, SD; Power, JD; Kavanagh, PV; O’Brien, J. The analysis of substituted cathinones. Part 2: An investigation into the phenylacetone based isomers of 4-methylmethcathinone and N-ethylcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 13–21. 1129 kB. doi:10.1016/j.forsciint.2011.06.030

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.

Archer, RP. Fluoromethcathinone, a new substance of abuse. Forensic Sci. Int., 1 Jan 2009, 185 (1–3), 10–20. 1355 kB. doi:10.1016/j.forsciint.2008.11.013

Camilleri, A; Johnston, MR; Brennan, M; Davis, S; Caldicott, DGE. Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine, α-phthalimidopropiophenone and N-ethylcathinone. Forensic Sci. Int., 1 Jan 2010, in press. 736 kB. doi:10.1016/j.forsciint.2009.12.048

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

Maheux, CR; Copeland, CR; Pollard, MM. Characterization of three methcathinone analogs: 4-methylmethcathinone, methylone, and bk-MBDB. Microgram J., 1 Dec 2010, 7 (2), 43–49. 765 kB.

Angoa-Pérez, M; Kane, MJ; Francescutti, DM; Sykes, KE; Shah, MM; Mohammed, AM; Thomas, DM; Kuhn, DM. Mephedrone, an abused psychoactive component of ‘bath salts’ and methamphetamine congener, does not cause neurotoxicity to dopamine nerve endings of the striatum. J. Neurochem., 1 Mar 2012, 120 (6), 1097–1107. 777 kB. doi:10.1111/j.1471-4159.2011.07632.x

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. doi:10.1038/npp.2011.304

Meyers-Riggs, B. AIRCR jumps the shark. countyourculture: rational exploration of the underground, 30 Dec 2010.

Santali, EY; Cadogan, A; Daeid, NN; Savage, KA; Sutcliffe, OB. Synthesis, full chemical characterisation and development of validated methods for the quantification of (±)-4′-methylmethcathinone (mephedrone): a new “legal high” J. Pharm. Biomed. Anal., 10 Sep 2011, 56 (2), 246–255. 705 kB. doi:10.1016/j.jpba.2011.05.022

Brandt, SD; Sumnall, HR; Measham, F; Cole, JC. Analyses of second-generation ‘legal highs’ in the UK: Initial findings. Drug Test. Anal., 1 Aug 2010, 2 (8), 377–382. 317 kB. doi:10.1002/dta.155

Wood, DM; Dargan, PI. Mephedrone (4-methylmethcathinone): What is new in our understanding of its use and toxicity. Prog. Neuro-Psychopharmacol. Biol. Psychiatry, 3 Dec 2012. 251 kB. doi:10.1016/j.pnpbp.2012.04.020

Dargan, PI; Sedefov, R; Gallegos, A; Wood, DM. The pharmacology and toxicology of the synthetic cathinone mephedrone (4-methylmethcathinone). Drug Test. Anal., 1 Jul 2011, 3 (7–8), 454–463. 149 kB. doi:10.1002/dta.312

Brunt, TM; Poortman, A; Niesink, RJM; Brink, W. Instability of the ecstasy market and a new kid on the block: mephedrone. J. Psychopharmacol., 1 Nov 2011, 25 (11), 1543–1547. 238 kB. doi:10.1177/0269881110378370

Elie, L; Baron, M; Croxton, R; Elie, M. Microcrystalline identification of selected designer drugs. Forensic Sci. Int., 10 Jan 2012, 214 (1–3),. 1364 kB. doi:10.1016/j.forsciint.2011.08.005

Tsujikawa, K; Mikuma, T; Kuwayama, K; Miyaguchi, H; Kanamori, T; Iwata, YT; Inoue, H. Degradation pathways of 4-methylmethcathinone in alkaline solution and stability of methcathinone analogs in various pH solutions. Forensic Sci. Int., 10 Jul 2012, 220 (1–3), 103–110. 671 kB. doi:10.1016/j.forsciint.2012.02.005

Power, JD; McGlynn, P; Clarke, K; McDermott, S; Kavanagh, PV; O’Brien, J. The analysis of substituted cathinones. Part 1: Chemical analysis of 2-, 3-, and 4-methylmethcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 6–12. 1032 kB. doi:10.1016/j.forsciint.2011.04.020

Jankovics, P; Váradi, A; Tölgyesi, L; Lohner, S; Németh-Palotás, J; Kőszegi-Szalai, H. Identification and characterization of the new designer drug 4′-methylethcathinone (4-MEC) and elaboration of a novel liquid chromatography-tandem mass spectrometry (LC-MS/MS) screening method for seven different methcathinone analogs. Forensic Sci. Int., 15 Jul 2011, 210 (1–3), 213–220. 899 kB. doi:10.1016/j.forsciint.2011.03.019

Sanchez, MJSB. Sur un homologue de l’éphédrine. Bull. Soc. Chim. Fr., 1929, 45, 284–286. 600 kB.

2110
Isomer 2

DMAP
Dimethylcathinone
Dimethylpropion
Metamfepramone

IUPAC: 2-(Dimethylamino)-1-phenylpropan-1-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: KBHMHROOFHVLBA-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9H,1-3H3

PubChem CID: 71872; ChemSpider: 64889; Wikipedia: Metamfepramone

Shulgin Index: #40 DMAP; Table: 2 Page: 318 Row: 34

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. doi:10.1016/S0091-3057(97)00323-7

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

Tsujikawa, K; Mikuma, T; Kuwayama, K; Miyaguchi, H; Kanamori, T; Iwata, YT; Inoue, H. Degradation pathways of 4-methylmethcathinone in alkaline solution and stability of methcathinone analogs in various pH solutions. Forensic Sci. Int., 10 Jul 2012, 220 (1–3), 103–110. 671 kB. doi:10.1016/j.forsciint.2012.02.005

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.

Dal Cason, TA. Synthesis and identification of N,N-dimethylcathinone hydrochloride. Microgram J., 1 Jan 2007, 5 (1–4), 3–12. 93 kB.

2150
Isomer 3

MMAI
2-Amino-5-methoxy-6-methylindane

IUPAC: 5-Methoxy-6-methyl-2,3-dihydro-1H-inden-2-amine

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: JLESVLCTIOAHPT-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-7-3-8-4-10(12)5-9(8)6-11(7)13-2/h3,6,10H,4-5,12H2,1-2H3

PubChem CID: 131575; ChemSpider: 116274; Wikipedia: MMAI

Shulgin Index: See #96 3,4-MMA; Table: 5 Page: 342 Row: 6

Rodríguez, GJ; Roman, DL; White, KJ; Nichols, DE; Barker, EL. Distinct recognition of substrates by the human and Drosophila serotonin transporters. J. Pharmacol. Exp. Ther., 1 Jan 2004, 306 (1), 338–346. 452 kB. doi:10.1124/jpet.103.048751

Marona-Lewicka, D; Rhee, G; Sprague, JE; Nichols, DE. Reinforcing effects of certain serotonin-releasing amphetamine derivatives. Pharmacol. Biochem. Behav., 1 Jan 1996, 53 (1), 99–105. 1028 kB. doi:10.1016/0091-3057(95)00205-7

Huang, X; Nichols, DE. 5-HT2 receptor-mediated potentiation of dopamine synthesis and central serotonergic deficits. Eur. J. Pharmacol., 1 Jan 1993, 238 (2–3), 291–296. 553 kB. doi:10.1016/0014-2999(93)90859-G

Johnson, MP; Conarty, PF; Nichols, DE. [3H]Monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues. Eur. J. Pharmacol., 1 Jan 1991, 200 (1), 9–16. 1107 kB. doi:10.1016/0014-2999(91)90659-E

Marona-Lewicka, D; Kurrasch-Orbaugh, DM; Selken, JR; Cumbay, MG; Lisnicchia, JG; Nichols, DE. Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioural effects overlap its other properties in rats. Psychopharmacology, 1 Oct 2002, 164 (1), 93–107. 293 kB. doi:10.1007/s00213-002-1141-z

Marona-Lewicka, D; Nichols, DE. Behavioral effects of the highly selective serotonin releasing agent 5-methoxy-6-methyl-2-aminoindan. Eur. J. Pharmacol., 1 Jan 1994, 258 (1–2), 1–13. 1252 kB. doi:10.1016/0014-2999(94)90051-5

Monte, AP; Marona-Lewicka, D; Cozzi, NV; Nichols, DE. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine. J. Med. Chem., 1 Jan 1993, 36 (23), 3700–3706. 1026 kB. doi:10.1021/jm00075a027

Johnson, MP; Frescas, SP; Oberlender, R; Nichols, DE. Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: Similarities to 3,4-(methylenedioxy)methamphetamine (MDMA). J. Med. Chem., 1 Jan 1991, 34 (5), 1662–1668. 975 kB. doi:10.1021/jm00109a020

Roman, DL; Saldaña, SN; Nichols, DE; Carroll, FI; Barker, EL. Distinct molecular recognition of psychostimulants by human and Drosophila serotonin transporters. J. Pharmacol. Exp. Ther., 1 Jan 2004, 308 (2), 679–687. 519 kB. doi:10.1124/jpet.103.057836

2340
Isomer 4

MABP
Buphedrone
α-(Methylamino)butyrophenone

IUPAC: 2-(Methylamino)-1-phenylbutan-1-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: DDPMGIMJSRUULN-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-3-10(12-2)11(13)9-7-5-4-6-8-9/h4-8,10,12H,3H2,1-2H3

PubChem CID: 53249194; ChemSpider: 26286946; Wikipedia: Buphedrone

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

Maheux, CR; Copeland, CR. Chemical analysis of two new designer drugs: Buphedrone and pentedrone. Drug Test. Anal., 1 Jan 2012, 4 (1), 17–23. 314 kB. doi:10.1002/dta.385

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. doi:10.1016/j.trac.2011.09.009

Zuba, D; Byrska, B. Prevalence and co-existence of active components of ‘legal highs’ Drug Test. Anal., 1 Jun 2013, 5 (6), 420–429. 1294 kB. doi:10.1002/dta.1365

2351
Isomer 5

BF6AP
6-APDB
4-Desoxy-MDA

IUPAC: 1-(2,3-Dihydro-1-benzofuran-6-yl)propan-2-amine

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: VRNGXHJGMCJRSQ-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-3,7-8H,4-6,12H2,1H3

PubChem CID: 192599; ChemSpider: 167141; Wikipedia: 6-APDB

Shulgin Index: See #77 MDA; Table: 4 Page: 327 Row: 29, See #77 MDA; Table: 4 Page: 331 Row: 9

Monte, AP; Marona-Lewicka, D; Cozzi, NV; Nichols, DE. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine. J. Med. Chem., 1 Jan 1993, 36 (23), 3700–3706. 1026 kB. doi:10.1021/jm00075a027

Casale, JF; Hays, PA. The characterization of 5- and 6-(2-aminopropyl)-2,3-dihydrobenzofuran. Microgram J., 2011, 8 (2), 62–74. 1031 kB.

Casale, JF. Letter to the editor regarding: Abbreviations for 5- and 6-(2-aminopropyl)-2,3-dihydrobenzofuran vs. 5- and 6-(2-aminopropyl)benzofuran: A clarification of “APB” and “APDB” Microgram J., 2012, 9 (1), 46. 220 kB.

Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB.

2352
Isomer 6

BF5AP
5-APDB
3-Desoxy-MDA
5-(2-Aminopropyl)-2,3-dihydrobenzofuran

IUPAC: 1-(2,3-Dihydro-1-benzofuran-5-yl)propan-2-amine

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: PZTJXZKNTPCPJL-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11/h2-3,7-8H,4-6,12H2,1H3

PubChem CID: 192601; ChemSpider: 167143; Wikipedia: 5-APDB

Monte, AP; Marona-Lewicka, D; Cozzi, NV; Nichols, DE. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine. J. Med. Chem., 1 Jan 1993, 36 (23), 3700–3706. 1026 kB. doi:10.1021/jm00075a027

Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB.

Casale, JF; Hays, PA. The characterization of 5- and 6-(2-aminopropyl)-2,3-dihydrobenzofuran. Microgram J., 2011, 8 (2), 62–74. 1031 kB.

Casale, JF. Letter to the editor regarding: Abbreviations for 5- and 6-(2-aminopropyl)-2,3-dihydrobenzofuran vs. 5- and 6-(2-aminopropyl)benzofuran: A clarification of “APB” and “APDB” Microgram J., 2012, 9 (1), 46. 220 kB.

2375
Isomer 7

4-Ethylcathinone

IUPAC: 2-Amino-1-(4-ethylphenyl)propan-1-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: KACGTMNGFPBVPZ-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-3-9-4-6-10(7-5-9)11(13)8(2)12/h4-8H,3,12H2,1-2H3

PubChem CID: 24260973; ChemSpider: 23903822

408
Isomer 8

6-MAT
2-Amino-6-methoxytetralin

IUPAC: 6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-amine

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: WASIYUSITZITPW-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-13-11-5-3-8-6-10(12)4-2-9(8)7-11/h3,5,7,10H,2,4,6,12H2,1H3

PubChem CID: 19907; ChemSpider: 18753

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of α-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-X

409
Isomer 9

7-MAT
2-Amino-7-methoxytetralin

IUPAC: 7-Methoxy-1,2,3,4-tetrahydronaphthalen-2-amine

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: ZNWNWWLWFCCREO-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-13-11-5-3-8-2-4-10(12)6-9(8)7-11/h3,5,7,10H,2,4,6,12H2,1H3

PubChem CID: 11608015; ChemSpider: 9782770

6028
Isomer 10

Phenmetrazine

IUPAC: 3-Methyl-2-phenylmorpholine

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: OOBHFESNSZDWIU-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-9-11(13-8-7-12-9)10-5-3-2-4-6-10/h2-6,9,11-12H,7-8H2,1H3

PubChem CID: 4762; ChemSpider: 4598

Shulgin Index: Table: 2 Page: 318 Row: 28

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

Banks, ML; Blough, BE; Fennell, TR; Snyder, RW; Negus, SS. Role of phenmetrazine as an active metabolite of phendimetrazine: Evidence from studies of drug discrimination and pharmacokinetics in rhesus monkeys. Drug Alcohol Depend., 1 Jun 2013, 130 (1–3), 158–166. 520 kB. doi:10.1016/j.drugalcdep.2012.10.026

Clarke, FH. cis- and trans-3-methyl-2-phenylmorpholine. J. Org. Chem., 1 Sep 1962, 27 (9), 3251–3253. 409 kB. doi:10.1021/jo01056a063

Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622

6480
Isomer 11

IBF5AP

IUPAC: 1-(1,3-Dihydro-2-benzofuran-5-yl)propan-2-amine

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: SLAQRQKVPQBGDF-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8(12)4-9-2-3-10-6-13-7-11(10)5-9/h2-3,5,8H,4,6-7,12H2,1H3

Shulgin Index: See #77 MDA; Table: 4 Page: 327 Row: 30

6955
Isomer 12

MHAT

IUPAC: 7-(Methylamino)-5,6,7,8-tetrahydronaphthalen-1-ol

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: RKQNQEQRWHOAOX-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-12-9-6-5-8-3-2-4-11(13)10(8)7-9/h2-4,9,12-13H,5-7H2,1H3

PubChem CID: 21689037; ChemSpider: 14106514

Shulgin Index: See #105 PAT; Table: 4 Page: 337 Row: 5

507
Isomer 13

2-HO-CPDMA

IUPAC: 2-[2-(Dimethylamino)cyclopropyl]phenol

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: BVUOMRJSZWYZMF-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-12(2)10-7-9(10)8-5-3-4-6-11(8)13/h3-6,9-10,13H,7H2,1-2H3

PubChem CID: 13972218; ChemSpider: 14106507

Arvidsson, L; Johansson, AM; Hacksell, U; Nilsson, JLG; Svensson, K; Hjorth, S; Magnusson, T; Carlsson, A; Lindberg, P; Andersson, B; Sanchez, D; Wikström, H; Sundell, S. N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: Novel central 5-hydroxytryptamine receptor agonists. J. Med. Chem., 1 Jan 1988, 31 (1), 92–99. 1162 kB. doi:10.1021/jm00396a014

513
Isomer 14

3-HO-CPDMA

IUPAC: 3-[2-(Dimethylamino)cyclopropyl]phenol

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: LYTWDOIYZATBOZ-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-12(2)11-7-10(11)8-4-3-5-9(13)6-8/h3-6,10-11,13H,7H2,1-2H3

PubChem CID: 13972242; ChemSpider: 14120168

Arvidsson, L; Johansson, AM; Hacksell, U; Nilsson, JLG; Svensson, K; Hjorth, S; Magnusson, T; Carlsson, A; Lindberg, P; Andersson, B; Sanchez, D; Wikström, H; Sundell, S. N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: Novel central 5-hydroxytryptamine receptor agonists. J. Med. Chem., 1 Jan 1988, 31 (1), 92–99. 1162 kB. doi:10.1021/jm00396a014

2479
Isomer 15

2-Methylmethcathinone

IUPAC: 2-(Methylamino)-1-(2-methylphenyl)propan-1-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: PRGXFAWAMOFULD-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8-6-4-5-7-10(8)11(13)9(2)12-3/h4-7,9,12H,1-3H3

PubChem CID: 56603536

Power, JD; McGlynn, P; Clarke, K; McDermott, S; Kavanagh, PV; O’Brien, J. The analysis of substituted cathinones. Part 1: Chemical analysis of 2-, 3-, and 4-methylmethcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 6–12. 1032 kB. doi:10.1016/j.forsciint.2011.04.020

2480
Isomer 16

3-Methylmethcathinone
3-Methylmethcathinone

IUPAC: 2-(Methylamino)-1-(3-methylphenyl)propan-1-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: QDNXSIYWHYGMCD-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8-5-4-6-10(7-8)11(13)9(2)12-3/h4-7,9,12H,1-3H3

Power, JD; McGlynn, P; Clarke, K; McDermott, S; Kavanagh, PV; O’Brien, J. The analysis of substituted cathinones. Part 1: Chemical analysis of 2-, 3-, and 4-methylmethcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 6–12. 1032 kB. doi:10.1016/j.forsciint.2011.04.020

1443
Isomer 17

IUPAC: 8-Methoxy-1,2,3,4-tetrahydronaphthalen-2-amine

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: RVKOHSCTEHZRRT-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-13-11-4-2-3-8-5-6-9(12)7-10(8)11/h2-4,9H,5-7,12H2,1H3

PubChem CID: 10197933; ChemSpider: 8373433

Naiman, N; Lyon, RA; Bullock, AE; Rydelek, LT; Teitler, M; Glennon, RA. 2-(Alkylamino)tetralin derivatives: interaction with 5-HT1A serotonin binding sites. J. Med. Chem., 1 Jan 1989, 32 (1), 253–256. 597 kB. doi:10.1021/jm00121a045

2525
Isomer 18

Isomephedrone

IUPAC: 1-(Methylamino)-1-(4-methylphenyl)propan-2-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: YYAJPXVZVYGQIQ-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8-4-6-10(7-5-8)11(12-3)9(2)13/h4-7,11-12H,1-3H3

McDermott, SD; Power, JD; Kavanagh, PV; O’Brien, J. The analysis of substituted cathinones. Part 2: An investigation into the phenylacetone based isomers of 4-methylmethcathinone and N-ethylcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 13–21. 1129 kB. doi:10.1016/j.forsciint.2011.06.030

2526
Isomer 19

Isoethcathinone

IUPAC: 1-(Ethylamino)-1-phenylpropan-2-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: GHVCNLDRNVGRJP-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-3-12-11(9(2)13)10-7-5-4-6-8-10/h4-8,11-12H,3H2,1-2H3

PubChem CID: 12403217

McDermott, SD; Power, JD; Kavanagh, PV; O’Brien, J. The analysis of substituted cathinones. Part 2: An investigation into the phenylacetone based isomers of 4-methylmethcathinone and N-ethylcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 13–21. 1129 kB. doi:10.1016/j.forsciint.2011.06.030

1046
Isomer 20

7-APDB

IUPAC: 1-(2,3-Dihydro-1-benzofuran-7-yl)propan-2-amine

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: FVHLRYWNSYCTAK-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8(12)7-10-4-2-3-9-5-6-13-11(9)10/h2-4,8H,5-7,12H2,1H3

1039
Isomer 21

3,5-DMMC

IUPAC: 1-(3,5-Dimethylphenyl)-2-(methylamino)propan-1-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: YTRQMRHTZKRCDY-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8-4-9(2)6-10(5-8)11(13)7-12-3/h4-6,12H,7H2,1-3H3

ChemSpider: 27070709

Casale, JF; Hays, PA. Differentiation of 3,4-dimethylmethcathinone (3,4-DMMC) from its dimethyl aryl-positional isomers. Microgram J., 1 Jan 2012, 9 (2), 75–83. 1330 kB.

1038
Isomer 22

2,6-DMMC

IUPAC: 1-(2,6-Dimethylphenyl)-2-(methylamino)propan-1-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: PQTYKAMJXVYLEA-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8-5-4-6-9(2)11(8)10(13)7-12-3/h4-6,12H,7H2,1-3H3

Casale, JF; Hays, PA. Differentiation of 3,4-dimethylmethcathinone (3,4-DMMC) from its dimethyl aryl-positional isomers. Microgram J., 1 Jan 2012, 9 (2), 75–83. 1330 kB.

1037
Isomer 23

2,5-DMMC

IUPAC: 1-(2,5-Dimethylphenyl)-2-(methylamino)propan-1-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: GTWAMSQUORREOM-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8-4-5-9(2)10(6-8)11(13)7-12-3/h4-6,12H,7H2,1-3H3

ChemSpider: 25619844

Casale, JF; Hays, PA. Differentiation of 3,4-dimethylmethcathinone (3,4-DMMC) from its dimethyl aryl-positional isomers. Microgram J., 1 Jan 2012, 9 (2), 75–83. 1330 kB.

1036
Isomer 24

2,4-DMMC

IUPAC: 1-(2,4-Dimethylphenyl)-2-(methylamino)propan-1-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: XHXWLZIXSQEFPP-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8-4-5-10(9(2)6-8)11(13)7-12-3/h4-6,12H,7H2,1-3H3

ChemSpider: 25619846

Casale, JF; Hays, PA. Differentiation of 3,4-dimethylmethcathinone (3,4-DMMC) from its dimethyl aryl-positional isomers. Microgram J., 1 Jan 2012, 9 (2), 75–83. 1330 kB.

1020
Isomer 25

2,3-DMMC

IUPAC: 1-(2,3-Dimethylphenyl)-2-(methylamino)propan-1-one

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: VYFJEXMNCCCWHF-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8-5-4-6-10(9(8)2)11(13)7-12-3/h4-6,12H,7H2,1-3H3

ChemSpider: 27070710

Casale, JF; Hays, PA. Differentiation of 3,4-dimethylmethcathinone (3,4-DMMC) from its dimethyl aryl-positional isomers. Microgram J., 1 Jan 2012, 9 (2), 75–83. 1330 kB.

Show all 109 analogues and isomers Show only the nine N analogues Show only the one α analogues Show only the one R2 analogues Show only the one R3 analogues Show only the three R4 analogues Show only the 69 skeleton analogues
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