PiHKAL • info | explore | homo-MDA; 4-(1,3-Benzodioxol-5-yl)butan-2-amine

Six N analogues:
homo-MDMA 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 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. 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
homo-MDIP 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
homo-MDE 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
homo-MDDMA 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
homo-MDOH 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
homo-MDPR 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:

homo-MDPEA; GAMMA

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

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:
homo-DMA 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

14 skeleton analogues:

MDA

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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MDPEA

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

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Safrole

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

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α-Isosafrole

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

β-Isosafrole

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

ONE; MDC

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

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

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

MDPPP

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

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

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

Abiedalla, YFH; Abdel-Hay, K; 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

5,6-MDAI

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

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; 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

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

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

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

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.

6,7-MDAT

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

α-MMDBA

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

MDBP

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

MDCPA

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

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

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

3,4-Methylenedioxyaminorex

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.

31 isomers:

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

MDMA

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 II:

Shulgin, AT. Ecstasy pill testing. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 12 Sep 2002.

Shulgin, AT. Roadblocks to entheogen research. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 12 Sep 2001.

Shulgin, AT. Thought policing MDMA users (AB 1416). Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 20 Apr 2001.

Shulgin, AT. MDMA (Ecstasy) v. Methamphetamine. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 15 Feb 2001.

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

Shulgin, AT. Taking MDMA (Ecstasy) and other drugs when pregnant. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 28 Jan 2003.

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

Shulgin, AT. Making MDA, MDEA, MDMA. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 15 Mar 2001.

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

Shulgin, AT; Nichols, DE. Characterization of three new psychotomimetics. In The Psychopharmacology of Hallucinogens; Stillman, RC; Willette, RE, Eds., Pergamon Press, New York, 1 Jan 1978; pp 74–84. 547 kB.

Shulgin, AT. Drug testing hair for MDMA (Ecstasy). Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 4 Mar 2005.

Sprague, JE; Huang, X; Kanthasamy, A; Nichols, DE. Attenuation of 3,4-methylenedioxymethamphetamine (MDMA) induced neurotoxicity with the serotonin precursors tryptophan and 5-hydroxytryptophan. Life Sci., 1 Jan 1994, 55 (15), 1193–1198. 336 kB. doi:10.1016/0024-3205(94)00658-X

Galloway, G; Shulgin, AT; Kornfeld, H; Frederick, SL. Amphetamine, not MDMA, is associated with intracranial hemorrhage. J. Accid Emerg Med., 1 Jan 1995, 12 (3), 231–2. 428 kB. doi:10.1136/emj.12.3.231 The target of Sasha’s critique: Intracranial haemorrhage associated with ingestion of ‘Ecstasy’.

Ray, TS. Psychedelics and the human receptorome. PLoS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

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

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

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Baumgarten, HG; Lachenmayer, L. Serotonin neurotoxins—past and present. Neurotox. Res., 1 Jan 2004, 6 (7–8), 589–614. 402 kB. doi:10.1007/BF03033455

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

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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

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

Selken, J; Nichols, DE. α1-Adrenergic receptors mediate the locomotor response to systemic administration of (±)-3,4-methylenedioxymethamphetamine (MDMA) in rats. Pharmacol. Biochem. Behav., 1 Jan 2007, 86 (4), 622–630. 1005 kB. doi:10.1016/j.pbb.2007.02.006

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

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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.

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

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

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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Falk, EM; Cook, VJ; Nichols, DE; Sprague, JE. An antisense oligonucleotide targeted at MAO-B attenuates rat striatal serotonergic neurotoxicity induced by MDMA. Pharmacol. Biochem. Behav., 1 Jan 2002, 72 (3), 617–622. 120 kB. doi:10.1016/S0091-3057(02)00728-1

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MDPH

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

M-ALPHA

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

7-Me-MDA; EDA

7-Me-MDA; 3,4-Ethylidenedioxyamphetamine

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; 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

N,N-Me-MDPEA; Lobivine

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; El-Seedi, HR; Stephanson, N; Beck, O; Shulgin, AT. Ecstasy analogues found in cacti. J. Psychoactive Drugs, 1 Jan 2008, 40 (2), 219–222. 223 kB.

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. 864 kB. doi:10.1080/02791072.2008.10400635

PMMA-βk; Methedrone

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

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

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

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

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.

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

2-Me-MDA; 2-Methyl-MDA

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

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

5-Me-MDA; 5-Methyl-MDA

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

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

6-Me-MDA; 6-Methyl MDA

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

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

4-Ethoxycathinone

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

α-Me-N-Et-MDBA

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

α,N,N-TMMDBA

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

α,α,N-TMMDBA

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

2-MMA-βk

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

3-MMA-βk

6179

Isomer 16

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

AcO-MePEA

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

N,N-Me-2,3-MDPEA

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

N-Et-2,3-MDPEA

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

2,3-MDMA

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

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

α,α-Me-2,3-MDPEA

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

2,3-BDB

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

3,4-DMCPA

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

N-Et-MDPEA

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

β,N-Me-MDPEA

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

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

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

2C-G-1

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

S-MDMA

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.

R-MDMA

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.

N-Ethyl-N-methylpiperonylamine

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

2,5-DMAI

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