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homo-MDA; 4-(1,3-Benzodioxol-5-yl)butan-2-amine
610
Variant: N α R3,4 skeleton isomers all
Analogues: 6 1 1 18 36 62

IUPAC: 4-(1,3-Benzodioxol-5-yl)butan-2-amine

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

InChI=1S/C11H15NO2/c1-8(12)2-3-9-4-5-10-11(6-9)14-7-13-10/h4-6,8H,2-3,7,12H2,1H3

PubChem CID: 162424; ChemSpider: 142612

Shulgin Index: #78 homo-MDA; Table: 10 Page: 358 Row: 17

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

Six N analogues:
611
Analogue 1: Adding Methyl at N

homo-MDMA

IUPAC: 4-(1,3-Benzodioxol-5-yl)-N-methylbutan-2-amine

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

InChI=1S/C12H17NO2/c1-9(13-2)3-4-10-5-6-11-12(7-10)15-8-14-11/h5-7,9,13H,3-4,8H2,1-2H3

PubChem CID: 135381; ChemSpider: 119255

Shulgin Index: #83 homo-MDMA; Table: 10 Page: 358 Row: 18

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; 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

615
Analogue 2: Adding Isopropyl at N

homo-MDIP

IUPAC: 4-(1,3-Benzodioxol-5-yl)-N-(propan-2-yl)butan-2-amine

Formula: C14H21NO2 Molecular weight: 235.32204 g/mol InChI Key: XHJBUYYVWFGADS-UHFFFAOYSA-N

InChI=1S/C14H21NO2/c1-10(2)15-11(3)4-5-12-6-7-13-14(8-12)17-9-16-13/h6-8,10-11,15H,4-5,9H2,1-3H3

PubChem CID: 14475863; ChemSpider: 24422991

Shulgin Index: See #78 homo-MDA; Table: 10 Page: 358 Row: 22

613
Analogue 3: Adding Ethyl at N

homo-MDE
HMDE

IUPAC: 4-(1,3-Benzodioxol-5-yl)-N-ethylbutan-2-amine

Formula: C13H19NO2 Molecular weight: 221.29546 g/mol InChI Key: ZEYDYCRKFZQGDI-UHFFFAOYSA-N

InChI=1S/C13H19NO2/c1-3-14-10(2)4-5-11-6-7-12-13(8-11)16-9-15-12/h6-8,10,14H,3-5,9H2,1-2H3

PubChem CID: 14475861; ChemSpider: 24198849

Shulgin Index: See #78 homo-MDA; Table: 10 Page: 358 Row: 20

612
Analogue 4: Adding Dimethyl at N

homo-MDDMA

IUPAC: 4-(1,3-Benzodioxol-5-yl)-N,N-dimethylbutan-2-amine

Formula: C13H19NO2 Molecular weight: 221.29546 g/mol InChI Key: ISSLNPPWKXHUNE-UHFFFAOYSA-N

InChI=1S/C13H19NO2/c1-10(14(2)3)4-5-11-6-7-12-13(8-11)16-9-15-12/h6-8,10H,4-5,9H2,1-3H3

Shulgin Index: See #78 homo-MDA; Table: 10 Page: 358 Row: 19

616
Analogue 5: Adding Hydroxy at N

homo-MDOH
HMDOH

IUPAC: 4-(1,3-Benzodioxol-5-yl)-N-hydroxybutan-2-amine

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

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

Shulgin Index: See #78 homo-MDA; Table: 10 Page: 358 Row: 23

614
Analogue 6: Adding n-Propyl at N

homo-MDPR

IUPAC: 4-(1,3-Benzodioxol-5-yl)-N-propylbutan-2-amine

Formula: C14H21NO2 Molecular weight: 235.32204 g/mol InChI Key: MFFUGTSUAWSESG-UHFFFAOYSA-N

InChI=1S/C14H21NO2/c1-3-8-15-11(2)4-5-12-6-7-13-14(9-12)17-10-16-13/h6-7,9,11,15H,3-5,8,10H2,1-2H3

PubChem CID: 14475862; ChemSpider: 24199840

Shulgin Index: See #78 homo-MDA; Table: 10 Page: 358 Row: 21

One α analogue:
272
Analogue 1: Removing Methyl at α

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      
One R3,4 analogue:
608
Analogue 1: Substituting Dimethoxy for Methylenedioxy at R3,4

homo-DMA

IUPAC: 4-(3,4-Dimethoxyphenyl)butan-2-amine

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

InChI=1S/C12H19NO2/c1-9(13)4-5-10-6-7-11(14-2)12(8-10)15-3/h6-9H,4-5,13H2,1-3H3

PubChem CID: 3041177; ChemSpider: 2304482

Shulgin Index: See #38 DMA; Table: 10 Page: 358 Row: 15

18 skeleton analogues:
100
Analogue 1: With 2-Phenylethan-1-amine skeleton

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 Pharmacology notes I: p. 37, MDA: Subacute evaluation
p. 123, MDA: Subjective response
p. 139, The Pseunut Cocktail
See also Pharmacology notes II: app. 3, MDA: Record
p. 202, MDA: Subjective response
p. 203, MDA: Subjective response
p. 246, MDA: Subjective response
p. 278, MDA: Subjective response

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Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1767 kB. doi:10.1111/j.2042-7158.1985.tb03072.x

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Shulgin, AT; Sargent, T; Naranjo, C. The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines. In Ethnopharmacologic Search for Psychoactive Drugs; Efron, DH; Holmstedt, B; Kline, NS, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 28 Jan 1967; pp 202–215. 951 kB.

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115
Analogue 2: With 2-Phenylethan-1-amine skeleton

MDPEA
EA-1297
Homopiperonylamine
3,4-Methylenedioxyphenethylamine

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

Formula: C9H11NO2 Molecular weight: 165.18914 g/mol InChI Key: RRIRDPSOCUCGBV-UHFFFAOYSA-N Properties: Peyote alkaloid

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

PubChem CID: 73874; ChemSpider: 66508; Wikipedia: Methylenedioxyphenethylamine

Shulgin Index: #85 MDPEA; Table: 4 Page: 331 Row: 10

See also PiHKAL: #10 B
#15 BOH
#16 BOHD
#57 DME
#100 MDA
#128 METHYL-J
 
See also Chemistry notes VIII: p. 186, MDPEA: Synthesis
p. 187, MDPEA: Synthesis
p. 188, MDPEA: Synthesis
p. 189, MDPEA: Synthesis
p. 190, MDPEA: Synthesis
p. 192, MDPEA: GC-MS
p. 193, MDPEA: GC-MS
p. 208, MDPEA: Synthesis

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. 36161 kB. Rhodium.

Dal Cason, TA. An evaluation of the potential for clandestine manufacture of 3,4-methylenedioxyamphetamine (MDA) analogs and homologs. J. Forensic Sci., 1 May 1990, 35 (3), 675–697. 2235 kB. doi:10.1520/JFS12874J

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. doi:10.1002/jps.2600680733

Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1767 kB. doi:10.1111/j.2042-7158.1985.tb03072.x

Bruhn, JG; EI-Seedi, HR; Stephanson, N; Beck, O; Shulgin, AT. Ecstasy analogues found in cacti. J. Psychoactive Drugs, 1 Jun 2008, 40 (2), 219–222. 874 kB. doi:10.1080/02791072.2008.10400635

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

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

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

1031
Analogue 3: With Prop-2-en-1-ylbenzene skeleton

Safrole
3,4-Methylenedioxyphenylprop-2-ene

IUPAC: 5-(Prop-2-en-1-yl)-1,3-benzodioxole

Formula: C10H10O2 Molecular weight: 162.1852 g/mol InChI Key: ZMQAAUBTXCXRIC-UHFFFAOYSA-N Properties: Essential oil

InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2

PubChem CID: 5144; ChemSpider: 13848731; Wikipedia: Safrole

See also PiHKAL: #100 MDA #157 TMA    

Shulgin, AT. The separation and identification of the components of the aromatic ether fraction of essential oils by gas-liquid chromatography. J. Chromatogr., 1 Jan 1967, 30, 54–61. 769 kB. doi:10.1016/S0021-9673(00)84112-6

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

Shulgin, AT. Composition of the myristicin fraction from oil of nutmeg. Nature, 1 Jan 1963, 197, 379. 107 kB. doi:10.1038/197379a0 Rhodium.

Dal Cason, TA. An evaluation of the potential for clandestine manufacture of 3,4-methylenedioxyamphetamine (MDA) analogs and homologs. J. Forensic Sci., 1 May 1990, 35 (3), 675–697. 2235 kB. doi:10.1520/JFS12874J

Shulgin, AT; Sargent, T; Naranjo, C. The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines. In Ethnopharmacologic Search for Psychoactive Drugs; Efron, DH; Holmstedt, B; Kline, NS, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 28 Jan 1967; pp 202–215. 951 kB.

Shulgin, AT. Concerning the pharmacology of nutmeg. Mind, 1 Jan 1963, 1, 299–302. 578 kB.

Shulgin, AT. Making MDMA (II): “Ecstasy”, MDMA, & Safrole. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 1 May 2002.

Weil, AT. The use of nutmeg as a psychotropic agent. Bull. Narc., United Nations Office on Drugs and Crime, 1 Jan 1966.

1032
Analogue 4: With (1Z)-Prop-1-en-1-ylbenzene skeleton

α-Isosafrole
cis-3,4-Methylenedioxyphenylprop-1-ene

IUPAC: 5-[(1Z)-Prop-1-en-1-yl]-1,3-benzodioxole

Formula: C10H10O2 Molecular weight: 162.1852 g/mol InChI Key: VHVOLFRBFDOUSH-IHWYPQMZSA-N Properties: Essential oil

InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2-

PubChem CID: 1549044; ChemSpider: 1266029

See also PiHKAL: #100 MDA      

Shulgin, AT. The separation and identification of the components of the aromatic ether fraction of essential oils by gas-liquid chromatography. J. Chromatogr., 1 Jan 1967, 30, 54–61. 769 kB. doi:10.1016/S0021-9673(00)84112-6

Dal Cason, TA. An evaluation of the potential for clandestine manufacture of 3,4-methylenedioxyamphetamine (MDA) analogs and homologs. J. Forensic Sci., 1 May 1990, 35 (3), 675–697. 2235 kB. doi:10.1520/JFS12874J

1033
Analogue 5: With (1E)-Prop-1-en-1-ylbenzene skeleton

β-Isosafrole
trans-3,4-Methylenedioxyphenylprop-1-ene

IUPAC: 5-[(1E)-Prop-1-en-1-yl]-1,3-benzodioxole

Formula: C10H10O2 Molecular weight: 162.1852 g/mol InChI Key: VHVOLFRBFDOUSH-NSCUHMNNSA-N Properties: Essential oil

InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2+

PubChem CID: 637796; ChemSpider: 21106329

Shulgin, AT. The separation and identification of the components of the aromatic ether fraction of essential oils by gas-liquid chromatography. J. Chromatogr., 1 Jan 1967, 30, 54–61. 769 kB. doi:10.1016/S0021-9673(00)84112-6

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

Dal Cason, TA. An evaluation of the potential for clandestine manufacture of 3,4-methylenedioxyamphetamine (MDA) analogs and homologs. J. Forensic Sci., 1 May 1990, 35 (3), 675–697. 2235 kB. doi:10.1520/JFS12874J

2122
Analogue 6: With 2-Amino-1-phenylethanone skeleton

ONE
MDC
bk-MDA
3,4-Methylenedioxycathinone
β-Keto-3,4-methylenedioxyamphetamine

IUPAC: 2-Amino-1-(1,3-benzodioxol-5-yl)propan-1-one

Formula: C10H11NO3 Molecular weight: 193.19924 g/mol InChI Key: XDEZOLVDJWWXRG-UHFFFAOYSA-N

InChI=1S/C10H11NO3/c1-6(11)10(12)7-2-3-8-9(4-7)14-5-13-8/h2-4,6H,5,11H2,1H3

PubChem CID: 57465250; ChemSpider: 25524469; Wikipedia: Methylenedioxycathinone

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 14

Zaitsu, K; Katagi, M; Tatsuno, M; Sato, T; Tsuchihashi, H; Suzuki, K. Recently abused β-keto derivatives of 3,4-methylenedioxyphenylalkylamines: a review of their metabolisms and toxicological analysis. Forensic Toxicol., 1 Jul 2011, 29 (2), 73–84. 971 kB. doi:10.1007/s11419-011-0111-8

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

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

Jacob, P; Shulgin, AT. Preparation of novel N-substituted-2-amino-3′,4′-methylenedioxypropiophenones as anti-depressant and anti-parkinsonism agents. International patent WO 96/39133, 12 Dec 1996. 941 kB.

2125
Analogue 7: With 2-Cyclic-amine-1-phenylethanone skeleton

MDPPP
3′,4′-Methylenedioxy-α-pyrrolidinopropiophenone

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

Formula: C14H17NO3 Molecular weight: 247.28968 g/mol InChI Key: NIYQOTCYXGXMPI-UHFFFAOYSA-N

InChI=1S/C14H17NO3/c1-10(15-6-2-3-7-15)14(16)11-4-5-12-13(8-11)18-9-17-12/h4-5,8,10H,2-3,6-7,9H2,1H3

PubChem CID: 6430845; ChemSpider: 4936183; Wikipedia: 3',4'-Methylenedioxy-α-pyrrolidinopropiophenone

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 28

Abiedalla, YFH; Abdel-Hay, KM; DeRuiter, J; Clark, CR. Synthesis and GC-MS analysis of a series of homologs and regioisomers of 3,4-methylenedioxypyrovalerone (MDPV). Forensic Sci. Int., 30 Nov 2012, 223 (1–3), 189–197. 657 kB. doi:10.1016/j.forsciint.2012.08.040

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

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

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.

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.

2149
Analogue 8: With 2,3-Dihydro-1H-inden-2-amine skeleton

5,6-MDAI
2-Amino-5,6-methylenedioxyindane

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

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

InChI=1S/C10H11NO2/c11-8-1-6-3-9-10(13-5-12-9)4-7(6)2-8/h3-4,8H,1-2,5,11H2

PubChem CID: 125558; ChemSpider: 111694; Drugs Forum: MDAI; Erowid: MDAI; Wikipedia: MDAI

Shulgin Index: See #77 MDA; Table: 5 Page: 347 Row: 24

See also PiHKAL: #100 MDA      

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

Oberlender, R; Nichols, DE. (+)-N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a discriminative stimulus in studies of 3,4-methylenedioxymethamphetamine-like behavioral activity. J. Pharmacol. Exp. Ther., 1 Dec 1990, 255 (3), 1098–1106. 1876 kB.

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

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

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

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

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

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

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

402
Analogue 9: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

6,7-MDAT
2-Amino-6,7-methylenedioxytetralin

IUPAC: 5,6,7,8-Tetrahydronaphtho[2,3-d][1,3]dioxol-6-amine

Formula: C11H13NO2 Molecular weight: 191.22642 g/mol InChI Key: AWSBQWZZLBPUQH-UHFFFAOYSA-N

InChI=1S/C11H13NO2/c12-9-2-1-7-4-10-11(14-6-13-10)5-8(7)3-9/h4-5,9H,1-3,6,12H2

PubChem CID: 36483; ChemSpider: 33531; Drugs Forum: MDAT; Wikipedia: MDAT

Shulgin Index: See #77 MDA; Table: 5 Page: 347 Row: 26

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

913
Analogue 10: With Phenylmethanamine skeleton

α-MMDBA

IUPAC: 1-(1,3-Benzodioxol-5-yl)ethanamine

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

InChI=1S/C9H11NO2/c1-6(10)7-2-3-8-9(4-7)12-5-11-8/h2-4,6H,5,10H2,1H3

PubChem CID: 129498; ChemSpider: 114677

Shulgin Index: See #45 α,N-DMMDBA; Table: 9 Page: 357 Row: 29

910
Analogue 11: With 1-Benzylpiperazine skeleton

MDBP

IUPAC: 1-(1,3-Benzodioxol-5-ylmethyl)piperazine

Formula: C12H16N2O2 Molecular weight: 220.26764 g/mol InChI Key: NBOOZXVYXHATOW-UHFFFAOYSA-N

InChI=1S/C12H16N2O2/c1-2-11-12(16-9-15-11)7-10(1)8-14-5-3-13-4-6-14/h1-2,7,13H,3-6,8-9H2

PubChem CID: 94426; ChemSpider: 85214; Wikipedia: Methylenedioxybenzylpiperazine

Shulgin Index: #79 MDBP; Table: 9 Page: 357 Row: 26

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

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

6729
Analogue 12: With 2-Phenylcyclopropan-1-amine skeleton

MDCPA

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

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

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

PubChem CID: 21190569; ChemSpider: 25467371

Shulgin Index: See #41 DMCPA; Table: 4 Page: 332 Row: 29

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

499
Analogue 13: With Phenyl-cyclic-amine skeleton

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

Formula: C12H15NO3 Molecular weight: 221.2524 g/mol InChI Key: JMABLCPXWZOLCW-UHFFFAOYSA-N

InChI=1S/C12H15NO3/c1-8-12(14-5-4-13-8)9-2-3-10-11(6-9)16-7-15-10/h2-3,6,8,12-13H,4-5,7H2,1H3

ChemSpider: 26709739

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

564
Analogue 14: With Phenyl-cyclic-amine skeleton

3,4-Methylenedioxyaminorex

IUPAC: 5-(1,3-Benzodioxol-5-yl)-4,5-dihydro-1,3-oxazol-2-amine

Formula: C10H10N2O3 Molecular weight: 206.198 g/mol InChI Key: LOFGJCSNVFFVRE-UHFFFAOYSA-N

InChI=1S/C10H10N2O3/c11-10-12-4-9(15-10)6-1-2-7-8(3-6)14-5-13-7/h1-3,9H,4-5H2,(H2,11,12)

Anon. Personal communication of unpublished research. 1 Jun 2012.

1586
Analogue 15: With 1,3-Diphenylpropan-2-amine skeleton

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

Formula: C17H17NO4 Molecular weight: 299.32118 g/mol InChI Key: WGDBJUJJRWABLD-UHFFFAOYSA-N

InChI=1S/C17H17NO4/c18-13(5-11-1-3-14-16(7-11)21-9-19-14)6-12-2-4-15-17(8-12)22-10-20-15/h1-4,7-8,13H,5-6,9-10,18H2

PubChem CID: 24258016; ChemSpider: 23900827

McNamara, YM; Cloonan, SM; Knox, AJS; Keating, JJ; Butler, SG; Peters, GH; Meegan, MJ; Williams, DC. Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents. Bioorg. Med. Chem., 1 Feb 2011, 19 (3), 1328–1348. 3938 kB. doi:10.1016/j.bmc.2010.11.054

2563
Analogue 16: With 2-Cyclic-amine-1-phenylethanone skeleton

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

Formula: C15H19NO3 Molecular weight: 261.31626 g/mol InChI Key: LOMJQDFXMNGXHU-UHFFFAOYSA-N

InChI=1S/C15H19NO3/c1-11(16-7-3-2-4-8-16)15(17)12-5-6-13-14(9-12)19-10-18-13/h5-6,9,11H,2-4,7-8,10H2,1H3

Abiedalla, YFH; Abdel-Hay, KM; DeRuiter, J; Clark, CR. Synthesis and GC-MS analysis of a series of homologs and regioisomers of 3,4-methylenedioxypyrovalerone (MDPV). Forensic Sci. Int., 30 Nov 2012, 223 (1–3), 189–197. 657 kB. doi:10.1016/j.forsciint.2012.08.040

2566
Analogue 17: With 2-Cyclic-amine-1-phenylethanone skeleton

IUPAC: 2-(Azepan-1-yl)-1-(1,3-benzodioxol-5-yl)propan-1-one

Formula: C16H21NO3 Molecular weight: 275.34284 g/mol InChI Key: GALZJEJBJWTZBZ-UHFFFAOYSA-N

InChI=1S/C16H21NO3/c1-12(17-8-4-2-3-5-9-17)16(18)13-6-7-14-15(10-13)20-11-19-14/h6-7,10,12H,2-5,8-9,11H2,1H3

Abiedalla, YFH; Abdel-Hay, KM; DeRuiter, J; Clark, CR. Synthesis and GC-MS analysis of a series of homologs and regioisomers of 3,4-methylenedioxypyrovalerone (MDPV). Forensic Sci. Int., 30 Nov 2012, 223 (1–3), 189–197. 657 kB. doi:10.1016/j.forsciint.2012.08.040

1049
Analogue 18: With Phenyl-cyclic-amine skeleton

IUPAC: 5-(1,3-Benzodioxol-5-yl)-4-ethyl-4,5-dihydro-1,3-oxazol-2-amine

Formula: C12H14N2O3 Molecular weight: 234.25116 g/mol InChI Key: QPTGXBCYJABHMA-UHFFFAOYSA-N

InChI=1S/C12H14N2O3/c1-2-8-11(17-12(13)14-8)7-3-4-9-10(5-7)16-6-15-9/h3-5,8,11H,2,6H2,1H3,(H2,13,14)

Anon. Personal communication of unpublished research. 6 Dec 2013.

36 isomers:
94
Isomer 1

J
BDB
Benzodioxolylbutanamine
2-Amino-1-(3,4-methylenedioxyphenyl)butane
1-(1,3-Benzodioxol-5-yl)-2-butanamine
α-Ethyl-3,4-methylenedioxyphenethylamine

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

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

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

PubChem CID: 129870; ChemSpider: 114963; Wikipedia: Benzodioxolylbutanamine

Shulgin Index: #9 BDB; Table: 4 Page: 332 Row: 33

See also PiHKAL: #77 ETHYL-J #100 MDA #106 MDE #128 METHYL-J

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

Johnson, MP; Hoffman, AJ; Nichols, DE. Effects of the enantiomers of MDA, MDMA and related analogues on [3H]serotonin and [3H]dopamine release from superfused rat brain slices. Eur. J. Pharmacol., 16 Dec 1986, 132 (2–3), 269–276. 559 kB. doi:10.1016/0014-2999(86)90615-1

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

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

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

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.

109
Isomer 2

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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116
Isomer 3

MDPH
3,4-Methylenedioxyphentermine
α,α-Dimethyl-3,4-methylenedioxyphenethylamine

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

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

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

PubChem CID: 13020598; ChemSpider: 15204207; Wikipedia: Methylenedioxyphentermine

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 30

See also PiHKAL: #8 ARIADNE #113 MDMP    

Nichols, DE; Lloyd, DH; Hoffman, AJ; Nichols, MB; Yim, GKW. Effects of certain hallucinogenic amphetamine analogues on the release of [3H]-serotonin from rat brain synaptosomes. J. Med. Chem., 1 Jan 1982, 25 (5), 530–535. 804 kB. doi:10.1021/jm00347a010

271
Isomer 4

M-ALPHA
α-Ethyl-N-methylpiperonylamine
1-Methylamino-1-(3,4-methylenedioxyphenyl)propane

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

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

InChI=1S/C11H15NO2/c1-3-9(12-2)8-4-5-10-11(6-8)14-7-13-10/h4-6,9,12H,3,7H2,1-2H3

PubChem CID: 14647597

See also PiHKAL: #100 MDA      
273
Isomer 5

7-Me-MDA
EDA
3,4-Ethylidenedioxyamphetamine

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

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

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

PubChem CID: 130542; ChemSpider: 115478

Shulgin Index: See #77 MDA; Table: 4 Page: 333 Row: 31, #65 EDA; Table: 4 Page: 333 Row: 37

See also PiHKAL: #100 MDA #120 MEDA    

Nichols, DE; Oberlender, R; Burris, K; Hoffman, AJ; Johnson, MP. Studies of dioxole ring substituted 3,4-methylenedioxyamphetamine (MDA) analogues. Pharmacol. Biochem. Behav., 1 Jan 1989, 34 (3), 571–576. 680 kB. doi:10.1016/0091-3057(89)90560-1

Nichols, DE; Kostuba, LJ. Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring. J. Med. Chem., 1 Jan 1979, 22 (10), 1264–1267. 606 kB. doi:10.1021/jm00196a022

326
Isomer 6

N,N-Me-MDPEA
Lobivine
N,N-Dimethyl-3,4-methylenedioxyphenethylamine

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

Formula: C11H15NO2 Molecular weight: 193.2423 g/mol InChI Key: GWQGGJKNIBZRAG-UHFFFAOYSA-N Properties: Peyote alkaloid

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

ChemSpider: 26485734

Shulgin Index: See #85 MDPEA; Table: 4 Page: 331 Row: 12

See also Chemistry notes VIII: p. 195, Lobivine: Synthesis

Bruhn, JG; EI-Seedi, HR; Stephanson, N; Beck, O; Shulgin, AT. Ecstasy analogues found in cacti. J. Psychoactive Drugs, 1 Jun 2008, 40 (2), 219–222. 874 kB. doi:10.1080/02791072.2008.10400635

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

2111
Isomer 7

PMMA-βk
bk-PMMA
PMMC
Methedrone
4-Methoxymethcathinone
Para-methoxymethcathinone

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

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

InChI=1S/C11H15NO2/c1-8(12-2)11(13)9-4-6-10(14-3)7-5-9/h4-8,12H,1-3H3

PubChem CID: 216281; ChemSpider: 187475; Drugs Forum: Methedrone; Wikipedia: Para-Methoxymethcathinone

Shulgin Index: See #112 PMMA; Table: 3 Page: 324 Row: 13

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

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

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

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

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

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

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.

2144
Isomer 8

2-Me-MDA
2-Methyl-MDA
2-Methyl-3,4-methylenedioxyamphetamine

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

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

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

PubChem CID: 10104064; ChemSpider: 8279591; Wikipedia: 2-Methyl-MDA

Shulgin Index: See #77 MDA; Table: 5 Page: 338 Row: 24

Parker, MA; Marona-Lewicka, D; Kurrasch, D; Shulgin, AT; Nichols, DE. Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA). J. Med. Chem., 1 Jan 1998, 41 (6), 1001–1005. 117 kB. doi:10.1021/jm9705925

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

2145
Isomer 9

5-Me-MDA
5-Methyl-MDA
3-Methyl-4,5-methylenedioxyamphetamine

IUPAC: 1-(7-Methyl-1,3-benzodioxol-5-yl)propan-2-amine

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

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

PubChem CID: 10012829; ChemSpider: 8188403; Wikipedia: 5-Methyl-MDA

Shulgin Index: See #77 MDA; Table: 5 Page: 348 Row: 19

Parker, MA; Marona-Lewicka, D; Kurrasch, D; Shulgin, AT; Nichols, DE. Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA). J. Med. Chem., 1 Jan 1998, 41 (6), 1001–1005. 117 kB. doi:10.1021/jm9705925

2146
Isomer 10

6-Me-MDA
6-Methyl MDA
2-Methyl-4,5-methylenedioxyamphetamine

IUPAC: 1-(6-Methyl-1,3-benzodioxol-5-yl)propan-2-amine

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

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

PubChem CID: 10511982; ChemSpider: 8687383; Wikipedia: 6-Methyl-MDA

Shulgin Index: See #77 MDA; Table: 5 Page: 347 Row: 15

Parker, MA; Marona-Lewicka, D; Kurrasch, D; Shulgin, AT; Nichols, DE. Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA). J. Med. Chem., 1 Jan 1998, 41 (6), 1001–1005. 117 kB. doi:10.1021/jm9705925

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

2383
Isomer 11

4-Ethoxycathinone

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

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

InChI=1S/C11H15NO2/c1-3-14-10-6-4-9(5-7-10)11(13)8(2)12/h4-8H,3,12H2,1-2H3

PubChem CID: 45121978; ChemSpider: 24222876

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

919
Isomer 12

α-Me-N-Et-MDBA

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

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

InChI=1S/C11H15NO2/c1-3-12-8(2)9-4-5-10-11(6-9)14-7-13-10/h4-6,8,12H,3,7H2,1-2H3

PubChem CID: 6424841; ChemSpider: 4930331

Shulgin Index: See #45 α,N-DMMDBA; Table: 9 Page: 358 Row: 4

918
Isomer 13

α,N,N-TMMDBA

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

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

InChI=1S/C11H15NO2/c1-8(12(2)3)9-4-5-10-11(6-9)14-7-13-10/h4-6,8H,7H2,1-3H3

Shulgin Index: See #45 α,N-DMMDBA; Table: 9 Page: 358 Row: 3

915
Isomer 14

α,α,N-TMMDBA

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

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

InChI=1S/C11H15NO2/c1-11(2,12-3)8-4-5-9-10(6-8)14-7-13-9/h4-6,12H,7H2,1-3H3

PubChem CID: 19939161; ChemSpider: 14248439

Shulgin Index: See #45 α,N-DMMDBA; Table: 9 Page: 357 Row: 31

6104
Isomer 15

2-MMA-βk

IUPAC: 1-(2-Methoxyphenyl)-2-(methylamino)propan-1-one

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

InChI=1S/C11H15NO2/c1-8(12-2)11(13)9-6-4-5-7-10(9)14-3/h4-8,12H,1-3H3

ChemSpider: 25631051

Shulgin Index: See #74 2-MA; Table: 3 Page: 320 Row: 4

6179
Isomer 16

3-MeOMC
3-MMA-βk

IUPAC: 1-(3-Methoxyphenyl)-2-(methylamino)propan-1-one

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

InChI=1S/C11H15NO2/c1-8(12-2)11(13)9-5-4-6-10(7-9)14-3/h4-8,12H,1-3H3

ChemSpider: 26702454

Shulgin Index: See #75 3-MA; Table: 3 Page: 321 Row: 29

6280
Isomer 17

AcO-MePEA

IUPAC: 4-[2-(Methylamino)ethyl]phenyl acetate

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

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

Shulgin Index: See #71 Hordenine; Table: 3 Page: 323 Row: 30

6407
Isomer 18

N,N-Me-2,3-MDPEA

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

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

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

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 7

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

6408
Isomer 19

N-Et-2,3-MDPEA

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

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

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

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 8

6411
Isomer 20

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

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

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

6414
Isomer 21

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
Isomer 22

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

6618
Isomer 23

3,4-DMCPA

IUPAC: 2-(3,4-Dimethoxyphenyl)cyclopropanamine

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

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

PubChem CID: 13972273; ChemSpider: 24205354

Shulgin Index: See #41 DMCPA; Table: 4 Page: 330 Row: 18

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

6664
Isomer 24

N-Et-MDPEA

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

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

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

PubChem CID: 19894326

Shulgin Index: See #85 MDPEA; Table: 4 Page: 331 Row: 14

6668
Isomer 25

β,N-Me-MDPEA

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

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

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

PubChem CID: 62088; ChemSpider: 55925

Shulgin Index: See #85 MDPEA; Table: 4 Page: 331 Row: 18

6787
Isomer 26

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

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

InChI=1S/C11H15NO2/c1-8(12)6-9-2-3-10-11(7-9)14-5-4-13-10/h2-3,7-8H,4-6,12H2,1H3

PubChem CID: 5017291; ChemSpider: 4196440

7819
Isomer 27

2C-G-1

IUPAC: 2-(2,5-Dimethoxybicyclo[4.1.0]hepta-1,3,5-trien-3-yl)ethanamine

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

InChI=1S/C11H15NO2/c1-13-10-5-7(3-4-12)11(14-2)9-6-8(9)10/h5H,3-4,6,12H2,1-2H3

Shulgin Index: See #114 TeMPEA; Table: 6 Page: 354 Row: 19

2475
Isomer 28

S-MDMA

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

Formula: C11H15NO2 Molecular weight: 193.2423 g/mol InChI Key: SHXWCVYOXRDMCX-QMMMGPOBSA-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/t8-/m0/s1

PubChem CID: 854031; ChemSpider: 746417

Shulgin, AT. MDMA isomers. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 27 Aug 2001.

2476
Isomer 29

R-MDMA

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

Formula: C11H15NO2 Molecular weight: 193.2423 g/mol InChI Key: SHXWCVYOXRDMCX-MRVPVSSYSA-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/t8-/m1/s1

PubChem CID: 667458; ChemSpider: 580842

Shulgin, AT. MDMA isomers. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 27 Aug 2001.

503
Isomer 30

N-Ethyl-N-methylpiperonylamine

IUPAC: N-(1,3-Benzodioxol-5-ylmethyl)-N-methylethanamine

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

InChI=1S/C11H15NO2/c1-3-12(2)7-9-4-5-10-11(6-9)14-8-13-10/h4-6H,3,7-8H2,1-2H3

PubChem CID: 584519; ChemSpider: 508078

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

193
Isomer 31

2,5-DMAI

IUPAC: 4,7-Dimethoxy-2,3-dihydro-1H-inden-2-amine

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

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

PubChem CID: 11264016; ChemSpider: 9439028

2520
Isomer 32

IUPAC: 2-(Dimethylamino)-1-(2-methoxyphenyl)ethanone

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

InChI=1S/C11H15NO2/c1-12(2)8-10(13)9-6-4-5-7-11(9)14-3/h4-7H,8H2,1-3H3

PubChem CID: 546953; ChemSpider: 476074

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

2521
Isomer 33

IUPAC: 2-(Dimethylamino)-1-(3-methoxyphenyl)ethanone

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

InChI=1S/C11H15NO2/c1-12(2)8-11(13)9-5-4-6-10(7-9)14-3/h4-7H,8H2,1-3H3

PubChem CID: 546935; ChemSpider: 476060

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

2522
Isomer 34

IUPAC: 2-(Dimethylamino)-1-(4-methoxyphenyl)ethanone

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

InChI=1S/C11H15NO2/c1-12(2)8-11(13)9-4-6-10(14-3)7-5-9/h4-7H,8H2,1-3H3

PubChem CID: 546931; ChemSpider: 476056

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

1094
Isomer 35

IUPAC: N-[1-(4-Hydroxyphenyl)propan-2-yl]acetamide

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

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

PubChem CID: 584229; ChemSpider: 507820

Foster, BC; Litster, DL; Lodge, BA. Biotransformation of 2-, 3-, and 4-methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1991, 21 (10), 1337–1346. 553 kB. doi:10.3109/00498259109043208

1007
Isomer 36

IUPAC: N-[1-(2-Hydroxyphenyl)propan-2-yl]acetamide

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

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

PubChem CID: 71341767; ChemSpider: 28682657

Foster, BC; Litster, DL; Lodge, BA. Biotransformation of 2-, 3-, and 4-methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1991, 21 (10), 1337–1346. 553 kB. doi:10.3109/00498259109043208

Show all 62 analogues and isomers Show only the six N analogues Show only the one α analogues Show only the one R3,4 analogues Show only the 18 skeleton analogues
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