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IBF5MAP; 1-(1,3-Dihydro-2-benzofuran-5-yl)-N-methylpropan-2-amine
6481
Variant: N R3,4 isomers all
Analogues: 1 10 16 27

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

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

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

Shulgin Index: See #77 MDA; Table: 4 Page: 327 Row: 31

One N analogue:
6480
Analogue 1: Removing Methyl at N

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

10 R3,4 analogues:
109
Analogue 1: Substituting Methylenedioxy for 2,5-Dihydrofuro[c] at R3,4

MDMA
XTC
X
MDM
ADAM
Ecstasy
N-Methyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-methylamphetamine

IUPAC: 1-(1,3-Benzodioxol-5-yl)-N-methylpropan-2-amine

Formula: C11H15NO2 Molecular weight: 193.2423 g/mol InChI Key: SHXWCVYOXRDMCX-UHFFFAOYSA-N

InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3

PubChem CID: 1615; ChemSpider: 1556; Drugs Forum: MDMA; Erowid: MDMA; Wikipedia: MDMA

Shulgin Index: #82 MDMA; Table: 4 Page: 331 Row: 21

See also PiHKAL: #14 BOD
#20 2C-B
#34 2C-N
#39 2C-T
#40 2C-T-2
#43 2C-T-7
#58 DMMDA
#67 DOI
#77 ETHYL-J
#81 FLEA
#94 J
#96 M
#98 MADAM-6
#100 MDA
#101 MDAL
#102 MDBU
#103 MDBZ
#104 MDCPM
#105 MDDM
#106 MDE
#107 MDHOET
#108 MDIP
#110 MDMC
#111 MDMEO
#112 MDMEOET
#113 MDMP
#114 MDOH
#116 MDPH
#117 MDPL
#118 MDPR
#119 ME
#122 MEM
#126 METHYL-DMA
#127 METHYL-DOB
#128 METHYL-J
#130 METHYL-MA
#132 MMDA
#133 MMDA-2
#142 PEA
See also TiHKAL: #1 AL-LAD
#4 DIPT
#5 α,O-DMS
#8 α,N-DMT
#11 α-ET
#13 Harmaline
#17 4-HO-DIPT
#18 4-HO-DMT
#22 4-HO-MIPT
#31 5,6-MDO-DMT
#38 5-MeO-DMT
#51 PRO-LAD
#55 α,N,O-TMS
See also Pharmacology notes I: p. 139, The Pseunut Cocktail
p. 186, MDMA
See also Pharmacology notes II: p. 207, MDMA
p. 210, MDMA
p. 230, MDMA
p. 231, MDMA
p. 232, MDMA
p. 233, MDMA: Saturation experiments
p. 234, MDMA: Saturation experiments
p. 235, MDMA
p. 241, MDMA
p. 242, MDMA
p. 243, MDMA
p. 261, MDMA
p. 271, MDMA
p. 275, MDMA: Report of results
p. 284, MDMA: Report of experience
p. 289, MDMA: Report of experience
p. 290, MDMA
p. 295, MDMA: Report of experience
p. 299, MDMA: Report of experience
p. 304, MDMA: Report of experience
p. 306, MDMA: Report of experiment
p. 307, MDMA: Report of experiment
p. 311, MDMA: Report of experience
p. 314, MDMA: Report of experience
p. 320, MDMA: Report of experience

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Steele, TD; Nichols, DE; Yim, GKW. MDMA transiently alters biogenic amines and metabolites in mouse brain and heart. Pharmacol. Biochem. Behav., 1 Jan 1989, 34 (2), 223–227. 477 kB. doi:10.1016/0091-3057(89)90303-1

Johnson, MP; Nichols, DE. Neurotoxic effects of the alpha-ethyl homologue of MDMA following subacute administration. Pharmacol. Biochem. Behav., 1 Jan 1989, 33 (1), 105–108. 399 kB. doi:10.1016/0091-3057(89)90437-1

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

Nash, JF; Nichols, DE. Microdialysis studies on 3,4-methylenedioxyamphetamine and structurally related analogues. Eur. J. Pharmacol., 1 Jan 1991, 200 (1), 53–58. 714 kB. doi:10.1016/0014-2999(91)90664-C

Johnson, MP; Huang, X; Nichols, DE. Serotonin neurotoxicity in rats after combined treatment with a dopaminergic agent followed by a nonneurotoxic 3,4-methylenedioxymethamphetamine (MDMA) analogue. Pharmacol. Biochem. Behav., 1 Jan 1991, 40 (4), 915–922. 845 kB. doi:10.1016/0091-3057(91)90106-C

Steele, TD; Brewster, WK; Johnson, MP; Nichols, DE; Yim, GKW. Assessment of the role of α-methylepinine in the neurotoxicity of MDMA. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (2), 345–351. 723 kB. doi:10.1016/0091-3057(91)90289-E

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

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Shulgin, AT. MDMA (Ecstasy) tolerance. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 10 Apr 2002.

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Lieberman, JA; Mailman, RB; Duncan, G; Sikich, L; Chakos, M; Nichols, DE; Kraus, JE. Serotonergic basis of antipsychotic drug effects in schizophrenia. Biol. Psychiat., 1 Dec 1998, 44 (11), 1099–1117. 154 kB. doi:10.1016/S0006-3223(98)00187-5

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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

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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

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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.

Braun, U; Shulgin, AT; Braun, G. Prüfung auf zentrale Aktivität und Analgesia von N-substituierten Analogen des Amphetamin-Derivates 3,4-Methylendioxyphenylisopropylamin. Arzneim. Forsch., 1 Jan 1980, 30 (5), 825–830. 1504 kB.

Shulgin, AT; Jacob, P. Potential misrepresentation of 3,4-methylene-dioxyamphetamine (MDA). A toxicological warning. J. Anal. Toxicol., 1 Jan 1982, 6 (2), 71–75. 5581 kB. doi:10.1093/jat/6.2.71

Nichols, DE; Hoffman, AJ; Oberlender, RA; Jacob, P; Shulgin, AT. Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: Representatives of a novel therapeutic class. J. Med. Chem., 1 Jan 1986, 29 (10), 2009–2015. 1024 kB. doi:10.1021/jm00160a035

Shulgin, AT. The background and chemistry of MDMA. J. Psychoactive Drugs, 1 Jan 1986, 18 (4), 291–304. 13190 kB. doi:10.1080/02791072.1986.10472361

Brown, CR; McKinney, H; Osterloh, JD; Shulgin, AT; Jacob, P; Olson, KR. Severe adverse reaction to 3,4-methylenedioxymethamphetamine (MDMA). Vet. Hum. Toxicol., 1 Oct 1986, 28 (5), 490. 239 kB.

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

Shulgin, AT. History of MDMA. In Ecstasy: The Clinical, Pharmacological and Neurotoxicological Effects of the Drug MDMA; Peroutka, S, Ed., Kluwer Academic Publishers, Norwell, MA, 1 Jan 1990; pp 1–20. 3840 kB.

McKenna, DJ; Guan, AM; Shulgin, AT. 3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 505–12. 783 kB. doi:10.1016/0091-3057(91)90005-M

Sprague, JE; Nichols, DE. Neurotoxicity of MDMA (ecstasy): beyond metabolism. Trends Pharmacol. Sci., 1 Feb 2005, 26 (2), 59–60. 60 kB. doi:10.1016/j.tips.2004.12.001

110
Analogue 2: Substituting Ethylenedioxy for 2,5-Dihydrofuro[c] at R3,4

MDMC
EDMA
N-Methyl-3,4-ethylenedioxyamphetamine
3,4-Ethylenedioxy-N-methylamphetamine

IUPAC: 1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-N-methylpropan-2-amine

Formula: C12H17NO2 Molecular weight: 207.26888 g/mol InChI Key: UJKWLAZYSLJTKA-UHFFFAOYSA-N

InChI=1S/C12H17NO2/c1-9(13-2)7-10-3-4-11-12(8-10)15-6-5-14-11/h3-4,8-9,13H,5-7H2,1-2H3

PubChem CID: 24257269; ChemSpider: 23553090; Wikipedia: EDMA

Shulgin Index: See #65 EDA; Table: 4 Page: 334 Row: 1

See also PiHKAL: #100 MDA      

McKenna, DJ; Guan, AM; Shulgin, AT. 3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 505–12. 783 kB. doi:10.1016/0091-3057(91)90005-M

Shulgin, AT. MDMA and its methylenedioxy ring. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 3 Jun 2003.

2315
Analogue 3: Substituting 1,1-Difluoromethylenedioxy for 2,5-Dihydrofuro[c] at R3,4

F2-MDMA
DFMDMA
3,4-(1,1-Difluoromethylenedioxy)-N-methylamphetamine

IUPAC: 1-(2,2-Difluoro-1,3-benzodioxol-5-yl)-N-methylpropan-2-amine

Formula: C11H13F2NO2 Molecular weight: 229.2232264 g/mol InChI Key: YZYZCMNVUDUELW-UHFFFAOYSA-N

InChI=1S/C11H13F2NO2/c1-7(14-2)5-8-3-4-9-10(6-8)16-11(12,13)15-9/h3-4,6-7,14H,5H2,1-2H3

Shulgin Index: See #82 MDMA; Table: 4 Page: 333 Row: 27

Trachsel, D; Hadorn, M; Baumberger, F. Synthesis of fluoro analogues of 3,4-(methylenedioxy)amphetamine (MDA) and Its derivatives. Chem. Biodiv., 23 Mar 2006, 3 (3), 326–336. 106 kB. doi:10.1002/cbdv.200690035

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

5555
Analogue 4: Substituting Trimethylene for 2,5-Dihydrofuro[c] at R3,4

IMA
IMP
Indanylmethylaminopropane
N-Methyl-3,4-trimethyleneamphetamine

IUPAC: 1-(2,3-Dihydro-1H-inden-5-yl)-N-methylpropan-2-amine

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

InChI=1S/C13H19N/c1-10(14-2)8-11-6-7-12-4-3-5-13(12)9-11/h6-7,9-10,14H,3-5,8H2,1-2H3

PubChem CID: 57461970; ChemSpider: 26679339

Shulgin Index: See #42 DMeA; Table: 4 Page: 327 Row: 27

6528
Analogue 5: Substituting Dihydroxy for 2,5-Dihydrofuro[c] at R3,4

DHMA

IUPAC: 4-[2-(Methylamino)propyl]benzene-1,2-diol

Formula: C10H15NO2 Molecular weight: 181.2316 g/mol InChI Key: NTCPGTZTPGFNOM-UHFFFAOYSA-N

InChI=1S/C10H15NO2/c1-7(11-2)5-8-3-4-9(12)10(13)6-8/h3-4,6-7,11-13H,5H2,1-2H3

PubChem CID: 161126; ChemSpider: 141547

Shulgin Index: See #33 DHA; Table: 4 Page: 328 Row: 28

Torre, R; Farré, M. Neurotoxicity of MDMA (ecstasy): the limitations of scaling from animals to humans. Trends Pharmacol. Sci., 1 Oct 2004, 25 (10), 505–508. 104 kB. doi:10.1016/j.tips.2004.08.001

Steele, TD; Brewster, WK; Johnson, MP; Nichols, DE; Yim, GKW. Assessment of the role of α-methylepinine in the neurotoxicity of MDMA. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (2), 345–351. 723 kB. doi:10.1016/0091-3057(91)90289-E

Capela, JP; Macedo, C; Branco, PS; Ferreira, LM; Lobo, AM; Fernandes, E; Remião, F; Bastos, ML; Dirnagl, U; Meisel, A; Carvalho, FG. Neurotoxicity mechanisms of thioether Ecstasy metabolites. Neuroscience, 1 Jan 2007, 146, 1743–1757. 995 kB. doi:10.1016/j.neuroscience.2007.03.028

Felim, A; Herrera, G; Neudörffer, A; Blanco, M; O’Connor, J; Largeron, M. Synthesis and in vitro cytotoxicity profile of the R-enantiomer of 3,4-dihydroxymethamphetamine (R-(-)-HHMA): Comparison with related catecholamines. Chem. Res. Toxicol., 2010, 23 (1), 211–219. 349 kB. doi:10.1021/tx9003374

6620
Analogue 6: Substituting Dimethoxy for 2,5-Dihydrofuro[c] at R3,4

DMMA

IUPAC: 1-(3,4-Dimethoxyphenyl)-N-methylpropan-2-amine

Formula: C12H19NO2 Molecular weight: 209.28476 g/mol InChI Key: BUWHCARWGYFQPE-UHFFFAOYSA-N

InChI=1S/C12H19NO2/c1-9(13-2)7-10-5-6-11(14-3)12(8-10)15-4/h5-6,8-9,13H,7H2,1-4H3

PubChem CID: 12235308; ChemSpider: 10467995

Felim, A; Herrera, G; Neudörffer, A; Blanco, M; O’Connor, J; Largeron, M. Synthesis and in vitro cytotoxicity profile of the R-enantiomer of 3,4-dihydroxymethamphetamine (R-(-)-HHMA): Comparison with related catecholamines. Chem. Res. Toxicol., 2010, 23 (1), 211–219. 349 kB. doi:10.1021/tx9003374

Clark, CC. The identification of methoxy-N-methylamphetamines. J. Forensic Sci., 1 Oct 1984, 29 (4), 1056–1071. 423 kB. doi:10.1520/JFS11772J

1288
Analogue 7: Substituting Furo[d] for 2,5-Dihydrofuro[c] at R3,4

6-MAPB

IUPAC: 1-(1-Benzofuran-6-yl)-N-methylpropan-2-amine

Formula: C12H15NO Molecular weight: 189.2536 g/mol InChI Key: QLAAURQYEAEHBO-UHFFFAOYSA-N

InChI=1S/C12H15NO/c1-9(13-2)7-10-3-4-11-5-6-14-12(11)8-10/h3-6,8-9,13H,7H2,1-2H3

Wikipedia: 6-MAPB

1289
Analogue 8: Substituting Furo[b] for 2,5-Dihydrofuro[c] at R3,4

5-MAPB

IUPAC: 1-(1-Benzofuran-5-yl)-N-methylpropan-2-amine

Formula: C12H15NO Molecular weight: 189.2536 g/mol InChI Key: ZOVRTIPCNFERHY-UHFFFAOYSA-N

InChI=1S/C12H15NO/c1-9(13-2)7-10-3-4-12-11(8-10)5-6-14-12/h3-6,8-9,13H,7H2,1-2H3

Wikipedia: 5-MAPB

1428
Analogue 9: Substituting 2,3-Dihydrofuro[d] for 2,5-Dihydrofuro[c] at R3,4

6-MAPDB

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

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

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

Wikipedia: 6-MAPDB

1429
Analogue 10: Substituting 2,3-Dihydrofuro[b] for 2,5-Dihydrofuro[c] at R3,4

5-MAPDB

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

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

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

Wikipedia: 5-MAPDB

16 isomers:
2360
Isomer 1

3,4-DMMC
3,4-Dimethylmethcathinone

IUPAC: 1-(3,4-Dimethylphenyl)-2-(methylamino)propan-1-one

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

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

PubChem CID: 52988261; ChemSpider: 25630192

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.

2362
Isomer 2

4-Me-MABP
4-Methylbuphedrone

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

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

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

ChemSpider: 26702147

Uchiyama, N; Matsuda, S; Kawamura, M; Kikura-Hanajiri, R; Goda, Y. Identification of two new-type designer drugs, piperazine derivative MT-45 (I-C6) and synthetic peptide Noopept (GVS-111), with synthetic cannabinoid A-834735, cathinone derivative 4-methoxy-α-PVP, and phenethylamine derivative 4-methylbuphedrine from illegal products. Forensic Toxicol., 1 Jan 2014, 32 (1), 9–18. 678 kB. doi:10.1007/s11419-013-0194-5

2372
Isomer 3

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

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

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

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

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

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

2373
Isomer 4

4-EMC
4-Ethylmethcathinone

IUPAC: 1-(4-Ethylphenyl)-2-(methylamino)propan-1-one

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

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

ChemSpider: 25630253

416
Isomer 5

7,6-MMAT
2-Amino-7-methoxy-6-methyltetralin

IUPAC: 7-Methoxy-6-methyl-1,2,3,4-tetrahydronaphthalen-2-amine

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

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

PubChem CID: 36245; ChemSpider: 33329

Shulgin Index: See #105 PAT; Table: 4 Page: 337 Row: 6, See #96 3,4-MMA; Table: 5 Page: 342 Row: 7

2430
Isomer 6

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

2434
Isomer 7

Pentedrone

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

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

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

PubChem CID: 57501499; ChemSpider: 26286729

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

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

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

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

6051
Isomer 8

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
Isomer 9

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. 4162 kB.

6956
Isomer 10

MMAT

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

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

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

PubChem CID: 15629515; ChemSpider: 14106459

6957
Isomer 11

EHAT

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

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

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

PubChem CID: 21689038; ChemSpider: 14106470

Shulgin Index: See #105 PAT; Table: 4 Page: 337 Row: 7

1235
Isomer 12

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

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

2527
Isomer 13

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

1428
Isomer 14

6-MAPDB

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

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

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

Wikipedia: 6-MAPDB

1429
Isomer 15

5-MAPDB

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

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

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

Wikipedia: 5-MAPDB

2576
Isomer 16

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

Show all 27 analogues and isomers Show only the one N analogues Show only the 10 R3,4 analogues
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