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2,3-MDA; 2,3-Methylenedioxyamphetamine
275
Variant: N α R4 R5 R6 R2,3 skeleton isomers all
Analogues: 3 3 1 1 1 7 1 16 33

IUPAC: 1-(1,3-Benzodioxol-4-yl)propan-2-amine

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

InChI=1S/C10H13NO2/c1-7(11)5-8-3-2-4-9-10(8)13-6-12-9/h2-4,7H,5-6,11H2,1H3

PubChem CID: 152655; ChemSpider: 134547; Wikipedia: 2,3-Methylenedioxyamphetamine

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 10

See also PiHKAL: #100 MDA      
See also TiHKAL: #28 4,5-MDO-DIPT      

See also Transcripts: 4.462

Casale, JF; Hays, PA; Klein, RFX. Synthesis and characterization of the 2,3-methylenedioxyamphetamines. J. Forensic Sci., 1 May 1995, 40 (3), 391–400. 500 kB. doi:10.1520/JFS13793J

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Three N analogues:
6411
Analogue 1: Adding Methyl at N

2,3-MDMA

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

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

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

ChemSpider: 23255735

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 11

Casale, JF; Hays, PA; Klein, RFX. Synthesis and characterization of the 2,3-methylenedioxyamphetamines. J. Forensic Sci., 1 May 1995, 40 (3), 391–400. 500 kB. doi:10.1520/JFS13793J

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC–IRD methods for the identification of some tertiary amines related to MDMA. Forensic Sci. Int., 15 Jun 2010, 199 (1–3), 18–28. 877 kB. doi:10.1016/j.forsciint.2010.02.022

6412
Analogue 2: Adding Dimethyl at N

2,3-MDDMA

IUPAC: 1-(1,3-Benzodioxol-4-yl)-N,N-dimethylpropan-2-amine

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

InChI=1S/C12H17NO2/c1-9(13(2)3)7-10-5-4-6-11-12(10)15-8-14-11/h4-6,9H,7-8H2,1-3H3

ChemSpider: 23254904

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 12

Casale, JF; Hays, PA; Klein, RFX. Synthesis and characterization of the 2,3-methylenedioxyamphetamines. J. Forensic Sci., 1 May 1995, 40 (3), 391–400. 500 kB. doi:10.1520/JFS13793J

Thigpen, AL; DeRuiter, J; Clark, CR. GC-MS studies on the regioisomeric 2,3- and 3,4-methylenedioxyphenethylamines related to MDEA, MDMMA, and MBDB. J. Chromatogr. Sci., 1 May 2007, 45 (5), 229–235. 332 kB. doi:10.1093/chromsci/45.5.229

Thigpen, AL; Awad, T; DeRuiter, J; Clark, CR. GC-MS studies on the regioisomeric methoxy-methyl-phenethylamines related to MDEA, MDMMA, and MBDB. J. Chromatogr. Sci., 1 Nov 2008, 46 (10), 900–206. 448 kB. doi:10.1093/chromsci/46.10.900

6413
Analogue 3: Adding Ethyl at N

2,3-MDE

IUPAC: 1-(1,3-Benzodioxol-4-yl)-N-ethylpropan-2-amine

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

InChI=1S/C12H17NO2/c1-3-13-9(2)7-10-5-4-6-11-12(10)15-8-14-11/h4-6,9,13H,3,7-8H2,1-2H3

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 13

Casale, JF; Hays, PA; Klein, RFX. Synthesis and characterization of the 2,3-methylenedioxyamphetamines. J. Forensic Sci., 1 May 1995, 40 (3), 391–400. 500 kB. doi:10.1520/JFS13793J

Thigpen, AL; DeRuiter, J; Clark, CR. GC-MS studies on the regioisomeric 2,3- and 3,4-methylenedioxyphenethylamines related to MDEA, MDMMA, and MBDB. J. Chromatogr. Sci., 1 May 2007, 45 (5), 229–235. 332 kB. doi:10.1093/chromsci/45.5.229

Thigpen, AL; Awad, T; DeRuiter, J; Clark, CR. GC-MS studies on the regioisomeric methoxy-methyl-phenethylamines related to MDEA, MDMMA, and MBDB. J. Chromatogr. Sci., 1 Nov 2008, 46 (10), 900–206. 448 kB. doi:10.1093/chromsci/46.10.900

Three α analogues:
6405
Analogue 1: Removing Methyl at α

2,3-MDPEA

IUPAC: 2-(1,3-Benzodioxol-4-yl)ethan-1-amine

Formula: C9H11NO2 Molecular weight: 165.18914 g/mol InChI Key: WGQBCGOHTNBZHW-UHFFFAOYSA-N

InChI=1S/C9H11NO2/c10-5-4-7-2-1-3-8-9(7)12-6-11-8/h1-3H,4-6,10H2

PubChem CID: 15234962; ChemSpider: 13690984

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 5

6414
Analogue 2: Substituting Dimethyl for Methyl at α

α,α-Me-2,3-MDPEA

IUPAC: 1-(1,3-Benzodioxol-4-yl)-2-methylpropan-2-amine

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

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

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 14

6415
Analogue 3: Substituting Ethyl for Methyl at α

2,3-BDB

IUPAC: 1-(1,3-Benzodioxol-4-yl)butan-2-amine

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

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

PubChem CID: 55254953; ChemSpider: 26493196

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 15

One R4 analogue:
135
Analogue 1: Adding Methoxy at R4

MMDA-3b
4-Methoxy-2,3-methylenedioxyamphetamine

IUPAC: 1-(7-Methoxy-1,3-benzodioxol-4-yl)propan-2-amine

Formula: C11H15NO3 Molecular weight: 209.2417 g/mol InChI Key: CLRZDDLQTLKYFH-UHFFFAOYSA-N

InChI=1S/C11H15NO3/c1-7(12)5-8-3-4-9(13-2)11-10(8)14-6-15-11/h3-4,7H,5-6,12H2,1-2H3

PubChem CID: 44374894; ChemSpider: 23231727; Wikipedia: MMDA (drug)

Shulgin Index: See #97 MMDA; Table: 5 Page: 338 Row: 19

See also PiHKAL: #134 MMDA-3a      

See also Transcripts: 1.150

See also Pharmacology notes I: p. 150, MMDA-3b

Shulgin, AT. Psychotomimetic amphetamines: Methoxy 3,4-dialkoxyamphetamines. Experientia, 1 Jan 1964, 20 (7), 366–367. 240 kB. doi:10.1007/BF02147960

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

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

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

One R5 analogue:
2153
Analogue 1: Adding Methoxy at R5

MMDA-4
5-Methoxy-2,3-methylenedioxyamphetamine

IUPAC: 1-(6-Methoxy-1,3-benzodioxol-4-yl)propan-2-amine

Formula: C11H15NO3 Molecular weight: 209.2417 g/mol InChI Key: FHGQWKADRLDGMI-UHFFFAOYSA-N

InChI=1S/C11H15NO3/c1-7(12)3-8-4-9(13-2)5-10-11(8)15-6-14-10/h4-5,7H,3,6,12H2,1-2H3

Shulgin Index: See #97 MMDA; Table: 5 Page: 339 Row: 25

See also PiHKAL: #135 MMDA-3b #160 TMA-4    

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Shulgin, AT. MMDA (MMDA-4). Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 11 Apr 2003.

One R6 analogue:
301
Analogue 1: Adding Methoxy at R6

MMDA-5
6-Methoxy-2,3-methylenedioxyamphetamine

IUPAC: 1-(5-Methoxy-1,3-benzodioxol-4-yl)propan-2-amine

Formula: C11H15NO3 Molecular weight: 209.2417 g/mol InChI Key: CMLBFORYSUACKE-UHFFFAOYSA-N

InChI=1S/C11H15NO3/c1-7(12)5-8-9(13-2)3-4-10-11(8)15-6-14-10/h3-4,7H,5-6,12H2,1-2H3

PubChem CID: 44374985; ChemSpider: 23231801

Shulgin Index: See #97 MMDA; Table: 5 Page: 353 Row: 4

See also PiHKAL: #135 MMDA-3b      

See also Transcripts: 1.166

See also Pharmacology notes I: p. 166, MMDA-5: Subacute evaluation

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Seven R2,3 analogues:
2162
Analogue 1: Substituting Dimethoxy for Methylenedioxy at R2,3

2,3-DMA
2,3-Dimethoxyamphetamine

IUPAC: 1-(2,3-Dimethoxyphenyl)propan-2-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: DHLWJXGSZDJWKK-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(12)7-9-5-4-6-10(13-2)11(9)14-3/h4-6,8H,7,12H2,1-3H3

PubChem CID: 91255; ChemSpider: 82404

Shulgin Index: #34 2,3-DMA; Table: 4 Page: 325 Row: 30

See also PiHKAL: #55 3,4-DMA #124 META-DOB    

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

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

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

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

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

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

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

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Bailey, K; Legauld, D; Verner, D. Spectroscopic and chromatographic identification of dimethoxyamphetamines. J. Assoc. Anal. Chem., 1974, 57 (1), 70–78. 426 kB.

2448
Analogue 2: Substituting Benzo for Methylenedioxy at R2,3

IUPAC: 1-(Naphthalen-1-yl)propan-2-amine

Formula: C13H15N Molecular weight: 185.2649 g/mol InChI Key: ODTJDLMNBKMVGR-UHFFFAOYSA-N

InChI=1S/C13H15N/c1-10(14)9-12-7-4-6-11-5-2-3-8-13(11)12/h2-8,10H,9,14H2,1H3

PubChem CID: 413939; ChemSpider: 366505

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

2447
Analogue 3: Substituting Pyrrolo[b] for Methylenedioxy at R2,3

α-Me-isoT
4-IT

IUPAC: 1-(1H-Indol-4-yl)propan-2-amine

Formula: C11H14N2 Molecular weight: 174.24226 g/mol InChI Key: FSNFARLFBCWJMF-UHFFFAOYSA-N

InChI=1S/C11H14N2/c1-8(12)7-9-3-2-4-11-10(9)5-6-13-11/h2-6,8,13H,7,12H2,1H3

PubChem CID: 55254455; ChemSpider: 26495445

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

2445
Analogue 4: Substituting Furo[b] for Methylenedioxy at R2,3

4-APB

IUPAC: 1-(1-Benzofuran-4-yl)propan-2-amine

Formula: C11H13NO Molecular weight: 175.22702 g/mol InChI Key: XROLBZOMVNMIFN-UHFFFAOYSA-N

InChI=1S/C11H13NO/c1-8(12)7-9-3-2-4-11-10(9)5-6-13-11/h2-6,8H,7,12H2,1H3

PubChem CID: 10130546; ChemSpider: 8306061

Casale, JF; Hays, PA. The characterization of 6-(2-aminopropyl)benzofuran and differentiation from its 4-, 5-, and 7-positional analogues. Microgram J., 1 Jan 2012, 9 (2), 61–74. 1652 kB.

Stanczuk, A; Morris, N; Gardner, EA; Kavanagh, PV. Identification of (2-aminopropyl)benzofuran (APB) phenyl ring positional isomers in Internet purchased products. Drug Test. Anal., 1 Apr 2013, 5 (4), 270–276. 1304 kB. doi:10.1002/dta.1451

1284
Analogue 5: Substituting Pyrrolo[d] for Methylenedioxy at R2,3

7-IT

IUPAC: 1-(1H-Indol-7-yl)propan-2-amine

Formula: C11H14N2 Molecular weight: 174.24226 g/mol InChI Key: JRCRPUGDMKLCQO-UHFFFAOYSA-N

InChI=1S/C11H14N2/c1-8(12)7-10-4-2-3-9-5-6-13-11(9)10/h2-6,8,13H,7,12H2,1H3

PubChem CID: 55254240; ChemSpider: 26495376

1046
Analogue 6: Substituting 2,3-Dihydrofuro[d] for Methylenedioxy at R2,3

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

1040
Analogue 7: Substituting Furo[d] for Methylenedioxy at R2,3

7-APB

IUPAC: 1-(1-Benzofuran-7-yl)propan-2-amine

Formula: C11H13NO Molecular weight: 175.22702 g/mol InChI Key: YVMDMFRZSDUZLK-UHFFFAOYSA-N

InChI=1S/C11H13NO/c1-8(12)7-10-4-2-3-9-5-6-13-11(9)10/h2-6,8H,7,12H2,1H3

PubChem CID: 10130548; ChemSpider: 8306063

Casale, JF; Hays, PA. The characterization of 6-(2-aminopropyl)benzofuran and differentiation from its 4-, 5-, and 7-positional analogues. Microgram J., 1 Jan 2012, 9 (2), 61–74. 1652 kB.

Stanczuk, A; Morris, N; Gardner, EA; Kavanagh, PV. Identification of (2-aminopropyl)benzofuran (APB) phenyl ring positional isomers in Internet purchased products. Drug Test. Anal., 1 Apr 2013, 5 (4), 270–276. 1304 kB. doi:10.1002/dta.1451

One skeleton analogue:
405
Analogue 1: With 2,3-Dihydro-1H-inden-2-amine skeleton

4,5-MDAI
2-Amino-4,5-methylenedioxyindane

IUPAC: 7,8-Dihydro-6H-indeno[4,5-d][1,3]dioxol-7-amine

Formula: C10H11NO2 Molecular weight: 177.19984 g/mol InChI Key: AHYFDWHTTFREHS-UHFFFAOYSA-N

InChI=1S/C10H11NO2/c11-7-3-6-1-2-9-10(8(6)4-7)13-5-12-9/h1-2,7H,3-5,11H2

PubChem CID: 44375435; ChemSpider: 23232252

Shulgin Index: See #77 MDA; Table: 5 Page: 338 Row: 25

Nichols, DE; Brewster, WK; Johnson, MP; Oberlender, R; Riggs, RM. Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA). J. Med. Chem., 1 Jan 1990, 33 (2), 703–710. 1078 kB. doi:10.1021/jm00164a037

Casale, JF; Hays, PA. Characterization of the “methylenedioxy-2-aminoindans” Microgram J., 2011, 8 (2), 43–52. 1303 kB.

16 isomers:
100
Isomer 1

MDA
EA-1298
Amphedoxamine
3,4-Methylenedioxyamphetamine

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

Formula: C10H13NO2 Molecular weight: 179.21572 g/mol InChI Key: NGBBVGZWCFBOGO-UHFFFAOYSA-N Properties: Essential amphetamine

InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3

PubChem CID: 1614; ChemSpider: 1555; Erowid: MDA; Wikipedia: 3,4-Methylenedioxyamphetamine

Shulgin Index: #77 MDA; Table: 4 Page: 331 Row: 20

See also PiHKAL: #8 ARIADNE
#19 2-Br-4,5-MDA
#55 3,4-DMA
#58 DMMDA
#59 DMMDA-2
#62 DOB
#67 DOI
#77 ETHYL-J
#81 FLEA
#88 HOT-7
#94 J
#96 M
#97 4-MA
#102 MDBU
#103 MDBZ
#106 MDE
#107 MDHOET
#109 MDMA
#111 MDMEO
#114 MDOH
#115 MDPEA
#116 MDPH
#120 MEDA
#124 META-DOB
#127 METHYL-DOB
#128 METHYL-J
#133 MMDA-2
#135 MMDA-3b
#142 PEA
#157 TMA
See also TiHKAL: #5 α,O-DMS
#6 DMT
#8 α,N-DMT
#28 4,5-MDO-DIPT
#31 5,6-MDO-DMT
#47 MIPT
#55 α,N,O-TMS

See also Transcripts: 1.37, 1.123, 1.139, 2.202, 2.203, 2.246, 2.278, 2.323.1, 2.323.3, 3.377, 3.390, 3.406

See also Pharmacology notes I: p. 37, MDA: Subacute evaluation
p. 123, MDA: Subjective response
p. 139, The Pseunut Cocktail
See also Pharmacology notes II: app. 1, MDA: Record
p. 202, MDA: Subjective response
p. 203, MDA: Subjective response
p. 246, MDA: Subjective response
p. 278, MDA: Subjective response

Benzenhöfer, U; Passie, T. Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin. Addiction, 1 Aug 2010, 105 (8), 1355–1361. 794 kB. doi:10.1111/j.1360-0443.2010.02948.x

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

Thiessen, PN; Cook, DA. The properties of 3,4-methylenedioxyamphetamine (MDA). I. A review of the literature. Clin. Toxicol., 1973, 6 (1), 45–52. 367 kB. doi:10.3109/15563657308991042

Vohlken, BA; Layton, SM. Instrumental separation of 3,4-methylenedioxyamphetamine (MDA) from 1-(3,4- methylenedioxyphenyl)-2-propanol, a co-eluting compound. Microgram J., 1 Jan 2003, 1 (1–2), 32–36. 208 kB.

Glennon, RA; Young, R. MDA: A psychoactive agent with dual stimulus effects. Life Sci., 23 Jan 1984, 34 (4), 379–383. 283 kB. doi:10.1016/0024-3205(84)90627-1

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

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270
Isomer 2

ALPHA
1-Amino-1-(3,4-methylenedioxyphenyl)propane

IUPAC: 1-(1,3-Benzodioxol-5-yl)propan-1-amine

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

InChI=1S/C10H13NO2/c1-2-8(11)7-3-4-9-10(5-7)13-6-12-9/h3-5,8H,2,6,11H2,1H3

PubChem CID: 14647596; ChemSpider: 11853242

See also PiHKAL: #100 MDA      

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

272
Isomer 3

homo-MDPEA
GAMMA
1-Amino-3-(3,4-methylenedioxyphenyl)propane

IUPAC: 3-(1,3-Benzodioxol-5-yl)propan-1-amine

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

InChI=1S/C10H13NO2/c11-5-1-2-8-3-4-9-10(6-8)13-7-12-9/h3-4,6H,1-2,5,7,11H2

PubChem CID: 413015; ChemSpider: 365714

Shulgin Index: See #78 homo-MDA; Table: 10 Page: 358 Row: 16

See also PiHKAL: #100 MDA      
285
Isomer 4

N-Me-MDPEA
METHYL-H
METHYL-MDPEA
N-Methyl-3,4-methylenedixoyphenethylamine
3,4-Methylenedixoy-N-methylphenethylamine

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

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

InChI=1S/C10H13NO2/c1-11-5-4-8-2-3-9-10(6-8)13-7-12-9/h2-3,6,11H,4-5,7H2,1H3

PubChem CID: 10776; ChemSpider: 10321

Shulgin Index: See #85 MDPEA; Table: 4 Page: 331 Row: 11

See also PiHKAL: #115 MDPEA      

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

2382
Isomer 5

PMA-βk
4-Methoxycathinone

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

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

InChI=1S/C10H13NO2/c1-7(11)10(12)8-3-5-9(13-2)6-4-8/h3-7H,11H2,1-2H3

PubChem CID: 12626564; ChemSpider: 23188095

Shulgin Index: See #110 PMA; Table: 3 Page: 324 Row: 12

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

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; 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

2378
Isomer 6

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

917
Isomer 7

α,N-DMMDBA

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

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

InChI=1S/C10H13NO2/c1-7(11-2)8-3-4-9-10(5-8)13-6-12-9/h3-5,7,11H,6H2,1-2H3

PubChem CID: 6424509; ChemSpider: 4930000

Shulgin Index: #45 α,N-DMMDBA; Table: 9 Page: 358 Row: 2

914
Isomer 8

α,α-DMMDBA

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

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

InChI=1S/C10H13NO2/c1-10(2,11)7-3-4-8-9(5-7)13-6-12-8/h3-5H,6,11H2,1-2H3

PubChem CID: 20811520; ChemSpider: 19649962

Shulgin Index: See #45 α,N-DMMDBA; Table: 9 Page: 357 Row: 30

912
Isomer 9

N,N-DMMDBA
N,N-Dimethylpiperonylamine

IUPAC: 1-(1,3-Benzodioxol-5-yl)-N,N-dimethylmethanamine

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

InChI=1S/C10H13NO2/c1-11(2)6-8-3-4-9-10(5-8)13-7-12-9/h3-5H,6-7H2,1-2H3

PubChem CID: 584596; ChemSpider: 508143

Shulgin Index: See #45 α,N-DMMDBA; Table: 9 Page: 357 Row: 28

Świst, M; Wilamowski, J; Zuba, D; Kochana, J; Parczewski, A. Determination of synthesis route of 1-(3,4-methylenedioxyphenyl)-2-propanone (MDP-2-P) based on impurity profiles of MDMA. Forensic Sci. Int., 10 May 2005, 149 (2–3), 181–192. 594 kB. doi:10.1016/j.forsciint.2004.06.016

6406
Isomer 10

2,3-MDMPEA

IUPAC: 2-(1,3-Benzodioxol-4-yl)-N-methylethan-1-amine

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

InChI=1S/C10H13NO2/c1-11-6-5-8-3-2-4-9-10(8)13-7-12-9/h2-4,11H,5-7H2,1H3

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 6

6667
Isomer 11

β-Me-MDPEA

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

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

InChI=1S/C10H13NO2/c1-7(5-11)8-2-3-9-10(4-8)13-6-12-9/h2-4,7H,5-6,11H2,1H3

PubChem CID: 15764472; ChemSpider: 15383063

Shulgin Index: See #85 MDPEA; Table: 4 Page: 331 Row: 17

6783
Isomer 12

EDPEA

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

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

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

PubChem CID: 3747027; ChemSpider: 2976686

Shulgin Index: See #65 EDA; Table: 4 Page: 333 Row: 33

6815
Isomer 13

2-HO-5,N-MePEA-βk

IUPAC: 1-(2-Hydroxy-5-methylphenyl)-2-(methylamino)ethanone

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

InChI=1S/C10H13NO2/c1-7-3-4-9(12)8(5-7)10(13)6-11-2/h3-5,11-12H,6H2,1-2H3

Shulgin Index: See #22 2C-H; Table: 4 Page: 334 Row: 15

6822
Isomer 14

2-M-5-MePEA-βk

IUPAC: 2-Amino-1-(2-methoxy-5-methylphenyl)ethanone

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

InChI=1S/C10H13NO2/c1-7-3-4-10(13-2)8(5-7)9(12)6-11/h3-5H,6,11H2,1-2H3

PubChem CID: 24260972; ChemSpider: 23903821

Shulgin Index: See #22 2C-H; Table: 4 Page: 334 Row: 22

2455
Isomer 15

2-Methoxycathinone

IUPAC: 2-Amino-1-(2-methoxyphenyl)propan-1-one

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

InChI=1S/C10H13NO2/c1-7(11)10(12)8-5-3-4-6-9(8)13-2/h3-7H,11H2,1-2H3

PubChem CID: 12914879; ChemSpider: 23208219

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

1260
Isomer 16

ADTN

IUPAC: 6-Amino-5,6,7,8-tetrahydronaphthalene-2,3-diol

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

InChI=1S/C10H13NO2/c11-8-2-1-6-4-9(12)10(13)5-7(6)3-8/h4-5,8,12-13H,1-3,11H2

PubChem CID: 3153; ChemSpider: 3041

Kohli, JD; Goldberg, LI; Nichols, DE. Dopamine vascular actions of N-substituted derivatives of 2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene (ADTN). Eur. J. Pharmacol., Jun 1979, 56 (1–2), 39–44. 454 kB. doi:10.1016/0014-2999(79)90430-8

Show all 33 analogues and isomers Show only the three N analogues Show only the three α analogues Show only the one R4 analogues Show only the one R5 analogues Show only the one R6 analogues Show only the seven R2,3 analogues Show only the one skeleton analogues
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