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PiHKAL#105 MDDM; SI#80 MDDMA
105
Variant: N α R3,4 skeleton isomers all
Analogues: 29 2 3 28 42 104

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

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

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

PubChem CID: 551630; ChemSpider: 479880; Wikipedia: Methylenedioxydimethylamphetamine

Shulgin Index: #80 MDDMA; Table: 4 Page: 331 Row: 24

See also PiHKAL: #103 MDBZ    

See also Transcripts: 2.244

See also Pharmacology notes II: p. 244, MDDM

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

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

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

Al-Hossaini, AM. GC-MS and GC-IRD studies on ethoxyphenethylamines related to MDEA, MDMMA and MBDB. Ph. D. Thesis, Auburn University, Auburn, AL, USA, 18 Dec 2009. 1195 kB.

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

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

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

29 N analogues:
81
Analogue 1: Substituting Hydroxy and Methyl for Dimethyl at N

FLEA
N-Hydroxy-N-methyl-3,4-methylenedioxyamphetamine

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

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

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

PubChem CID: 44350092; ChemSpider: 21106310; Wikipedia: Methylenedioxyhydroxymethamphetamine

Shulgin Index: See #84 MDOH; Table: 4 Page: 331 Row: 23

See also PiHKAL: #114 MDOH    

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

100
Analogue 2: Removing Dimethyl at N

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

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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

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

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

Baggott, MJ; Siegrist, JD; Galloway, GP; Robertson, LC; Coyle, JR; Mendelson, JE. Investigating the mechanisms of hallucinogen-induced visions using 3,4-methylenedioxyamphetamine (MDA): A randomized controlled trial in humans. PLOS ONE, 2 Dec 2010, 5 (12). 1435 kB. doi:10.1371/journal.pone.0014074

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

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

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.

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

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

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101
Analogue 3: Substituting Allyl for Dimethyl at N

MDAL
N-Allyl-MDA
N-Allyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-allylamphetamine

IUPAC: N-[1-(1,3-Benzodioxol-5-yl)propan-2-yl]prop-2-en-1-amine

Formula: C13H17NO2 Molecular weight: 219.27958 g/mol InChI Key: BMKCDDFQEGYEJC-UHFFFAOYSA-N

InChI=1S/C13H17NO2/c1-3-6-14-10(2)7-11-4-5-12-13(8-11)16-9-15-12/h3-5,8,10,14H,1,6-7,9H2,2H3

PubChem CID: 44719581; ChemSpider: 21106331; Wikipedia: Methylenedioxyallylamphetamine

Shulgin Index: See #77 MDA; Table: 4 Page: 331 Row: 35

See also Transcripts: 2.255

See also Pharmacology notes II: p. 255, MDAL

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

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

102
Analogue 4: Substituting Butyl for Dimethyl at N

MDBU
N-Butyl-MDA
N-Butyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-butylamphetamine

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

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

InChI=1S/C14H21NO2/c1-3-4-7-15-11(2)8-12-5-6-13-14(9-12)17-10-16-13/h5-6,9,11,15H,3-4,7-8,10H2,1-2H3

PubChem CID: 16206440; ChemSpider: 17334605; Wikipedia: Methylenedioxybutylamphetamine

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 1

See also PiHKAL: #103 MDBZ #112 MDMEOET  

See also Transcripts: 2.262

See also Pharmacology notes II: p. 262, MDBU

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

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

Noggle, FT; DeRuiter, J; Coker, ST; Clark, CR. Synthesis, identification, and acute toxicity of some N-alkyl derivatives of 3,4-methylenedioxyamphetamine. J. Assoc. Off. Anal. Chem., 1987, 70 (6), 981–986. 1842 kB.

103
Analogue 5: Substituting Benzyl for Dimethyl at N

MDBZ
N-Benzyl-MDA
N-Benzyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-benzylamphetamine

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

Formula: C17H19NO2 Molecular weight: 269.33826 g/mol InChI Key: DWLUHTUYTBWOLO-UHFFFAOYSA-N

InChI=1S/C17H19NO2/c1-13(18-11-14-5-3-2-4-6-14)9-15-7-8-16-17(10-15)20-12-19-16/h2-8,10,13,18H,9,11-12H2,1H3

PubChem CID: 20507314; ChemSpider: 15110233; Wikipedia: Methylenedioxybenzylamphetamine

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 7

See also PiHKAL: #102 MDBU #106 MDE  

See also Transcripts: 2.308

See also Pharmacology notes II: p. 308, MDBZ

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

Nieddu, M; Burrai, L; Pirisi, MA; Carta, A; Briguglio, I; Dessi, G; Boatto, G. Validated liquid chromatography-mass spectrometry method for the quantitation of N-substituted derivatives of 3,4-methylenedioxyamphetamine in rat urine. Forensic Toxicol., 1 Jul 2013, 31 (2), 204–211. 527 kB. doi:10.1007/s11419-013-0178-5

104
Analogue 6: Substituting Cyclopropylmethyl for Dimethyl at N

MDCPM
Cyclopropylmethyl-MDA
N-Cyclopropylmethyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-cyclopropylmethylamphetamine

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

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

InChI=1S/C14H19NO2/c1-10(15-8-11-2-3-11)6-12-4-5-13-14(7-12)17-9-16-13/h4-5,7,10-11,15H,2-3,6,8-9H2,1H3

PubChem CID: 44719582; ChemSpider: 21106332; Wikipedia: Methylenedioxycyclopropylmethylamphetamine

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 10

See also Transcripts: 2.272

See also Pharmacology notes II: p. 272, MDCPM

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

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

Nieddu, M; Burrai, L; Pirisi, MA; Carta, A; Briguglio, I; Dessi, G; Boatto, G. Validated liquid chromatography-mass spectrometry method for the quantitation of N-substituted derivatives of 3,4-methylenedioxyamphetamine in rat urine. Forensic Toxicol., 1 Jul 2013, 31 (2), 204–211. 527 kB. doi:10.1007/s11419-013-0178-5

106
Analogue 7: Substituting Ethyl for Dimethyl at N

MDE
MDEA
EVE
N-Ethyl-MDA
N-Ethyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-ethylamphetamine

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

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

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

PubChem CID: 105039; ChemSpider: 94775; Erowid: MDE; Wikipedia: MDEA

Shulgin Index: #81 MDE; Table: 4 Page: 331 Row: 28

See also PiHKAL: #57 DME
#77 ETHYL-J
#100 MDA
#108 MDIP
#111 MDMEO
#115 MDPEA
#128 METHYL-J
See also TiHKAL: #8 α,N-DMT    

See also Transcripts: 2.206, 2.274, 2.323.2, 3.376, 3.412, 3.413, 4.453, 4.454

See also Pharmacology notes II: app. 2, Abuse week
p. 206, MDE
p. 274, MDE

Gouzoulis-Mayfrank, E; Hermle, L. Are the “entactogens” a distinct psychoactive substance class? In Heffter Review; Nichols, DE, Ed., Heffter Research Institute, Santa Fe, NM, 1998; Vol. 1, pp 46–51. 44 kB.

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

Schmidt, WJ; Mayerhofer, A; Meyer, A; Kovar, K. Ecstasy counteracts catalepsy in rats, an anti-parkinsonian effect? Neurosci. Lett., 27 Sep 2002, 330 (3), 251–254. 280 kB. doi:10.1016/S0304-3940(02)00823-6

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

Noggle, FT; DeRuiter, J; Coker, ST; Clark, CR. Synthesis, identification, and acute toxicity of some N-alkyl derivatives of 3,4-methylenedioxyamphetamine. J. Assoc. Off. Anal. Chem., 1987, 70 (6), 981–986. 1842 kB.

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

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

Nieddu, M; Burrai, L; Pirisi, MA; Carta, A; Briguglio, I; Dessi, G; Boatto, G. Validated liquid chromatography-mass spectrometry method for the quantitation of N-substituted derivatives of 3,4-methylenedioxyamphetamine in rat urine. Forensic Toxicol., 1 Jul 2013, 31 (2), 204–211. 527 kB. doi:10.1007/s11419-013-0178-5

Freudenmann, RW; Spitzer, M. Neuropsychopharmacology and toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA). CNS Drug Rev., 1 Jun 2004, 10 (2), 89–216. 187 kB. doi:10.1111/j.1527-3458.2004.tb00007.x

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

Gouzoulis-Mayfrank, E. Differential actions of an entactogen compared to a stimulant and a hallucinogen in healthy humans. In Heffter Review; Nichols, DE, Ed., Heffter Research Institute, Santa Fe, NM, 2001; Vol. 2, pp 64–72. 261 kB.

Al-Hossaini, AM. GC-MS and GC-IRD studies on ethoxyphenethylamines related to MDEA, MDMMA and MBDB. Ph. D. Thesis, Auburn University, Auburn, AL, USA, 18 Dec 2009. 1195 kB.

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

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

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.

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

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

Stone, DM; Johnson, M; Hanson, GR; Gibb, JW. A comparison of the neurotoxic potential of methylenedioxyamphetamine (MDA) and its N-methylated and N-ethylated derivatives. Eur. J. Pharmacol., 10 Feb 1987, 134 (2), 245–248. 316 kB. doi:10.1016/0014-2999(87)90555-8

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

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

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

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

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.

107
Analogue 8: Substituting 2-Hydroxyethyl for Dimethyl at N

MDHOET
Hydroxyethyl-MDA
N-(2-Hydroxyethyl)-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-(2-hydroxyethyl)amphetamine

IUPAC: 2-{[1-(1,3-Benzodioxol-5-yl)propan-2-yl]amino}ethanol

Formula: C12H17NO3 Molecular weight: 223.26828 g/mol InChI Key: SCUUYKMQDUDNBP-UHFFFAOYSA-N

InChI=1S/C12H17NO3/c1-9(13-4-5-14)6-10-2-3-11-12(7-10)16-8-15-11/h2-3,7,9,13-14H,4-6,8H2,1H3

PubChem CID: 21645837; ChemSpider: 15637662; Wikipedia: Methylenedioxyhydroxyethylamphetamine

Shulgin Index: See #77 MDA; Table: 4 Page: 331 Row: 31

See also Transcripts: 2.250

See also Pharmacology notes II: p. 250, MDHOET

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

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

Koper, C; Ali-Tolppa, E; Bozenko, JS; Dufey, V; Puetz, M; Weyermann, C; Zrcek, F. Identification of a new amphetamine type stimulant: 3,4-Methylenedioxy-(2-hydroxyethyl)amphetamine (MDHOET). Microgram J., 1 Jul 2005, 3 (3–4), 166–174. 406 kB.

108
Analogue 9: Substituting Isopropyl for Dimethyl at N

MDIP
N-Isopropyl-MDA
N-Isopropyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-isopropylamphetamine

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

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

InChI=1S/C13H19NO2/c1-9(2)14-10(3)6-11-4-5-12-13(7-11)16-8-15-12/h4-5,7,9-10,14H,6,8H2,1-3H3

PubChem CID: 3057996; ChemSpider: 2319184; Wikipedia: Methylenedioxyisopropylamphetamine

Shulgin Index: See #77 MDA; Table: 4 Page: 331 Row: 34

See also Transcripts: 2.237

See also Pharmacology notes II: p. 237, MDIP

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

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

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

Nieddu, M; Burrai, L; Pirisi, MA; Carta, A; Briguglio, I; Dessi, G; Boatto, G. Validated liquid chromatography-mass spectrometry method for the quantitation of N-substituted derivatives of 3,4-methylenedioxyamphetamine in rat urine. Forensic Toxicol., 1 Jul 2013, 31 (2), 204–211. 527 kB. doi:10.1007/s11419-013-0178-5

Noggle, FT; DeRuiter, J; Coker, ST; Clark, CR. Synthesis, identification, and acute toxicity of some N-alkyl derivatives of 3,4-methylenedioxyamphetamine. J. Assoc. Off. Anal. Chem., 1987, 70 (6), 981–986. 1842 kB.

109
Analogue 10: Substituting Methyl for Dimethyl at N

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 Transcripts: 1.139, 1.186, 2.207, 2.210, 2.230, 2.231, 2.232, 2.233, 2.234, 2.235, 2.241, 2.242, 2.243, 2.261, 2.271, 2.275, 2.284, 2.289, 2.290, 2.295, 2.299, 2.304, 2.306, 2.307, 2.311, 2.314, 2.320, 3.328, 3.331, 3.333, 3.336, 3.340, 3.350, 3.360, 3.362, 3.366, 3.374, 3.375, 3.376, 3.378, 3.379, 3.382, 3.384, 3.385, 3.386, 3.387, 3.388, 3.391, 3.392, 3.393, 3.398, 3.399, 3.403, 3.404, 3.405, 3.408, 3.410, 3.414, 3.415, 3.420, 3.421, 3.423, 3.425, 3.427, 3.435, 3.441, 3.442, 3.444, 4.456, 4.457, 4.458, 4.463, 4.467, 4.467.2, 4.469, 4.473, 4.488, 4.492, 4.493, 4.494, 4.496, 4.503, 4.504, 4.505, 4.506, 4.507, 4.510, 4.520, 5.568, 5.570, 5.572, 5.583, 5.584, 5.594, 5.600, 5.601, 5.608, 5.609, 5.610, 5.611, 5.612, 5.613, 5.614, 5.621, 5.622, 5.623, 5.624, 5.629, 5.630, 5.632, 5.635, 5.636, 5.637, 5.638, 5.640, 5.641, 5.642, 5.643, 5.653, 5.654, 5.655, 5.656, 5.657, 5.658, 5.659, 5.660, 5.663, 5.664

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

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

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

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

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

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.

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

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

Benzenhöfer, U; Passie, T. Zur Frühgeschichte von “Ecstasy” Nervenarzt, 2006, 77 (1), 95–96, 98–99. 533 kB. doi:10.1007/s00115-005-2001-y

Capela, JP; Carmo, H; Remião, F; Bastos, ML; Meisel, A; Carvalho, FG. Molecular and cellular mechanisms of ecstasy-induced neurotoxicity: An overview. Mol. Neurobiol., 1 Jun 2009, 39 (3), 210–271. 1946 kB. doi:10.1007/s12035-009-8064-1

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

Stone, DM; Johnson, M; Hanson, GR; Gibb, JW. A comparison of the neurotoxic potential of methylenedioxyamphetamine (MDA) and its N-methylated and N-ethylated derivatives. Eur. J. Pharmacol., 10 Feb 1987, 134 (2), 245–248. 316 kB. doi:10.1016/0014-2999(87)90555-8

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

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

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

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

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

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

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

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

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

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

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

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

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

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111
Analogue 11: Substituting Methoxy for Dimethyl at N

MDMEO
N-Methoxy-MDA
N-Methoxy-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-methyoxyamphetamine

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

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

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

PubChem CID: 44719583; ChemSpider: 21106333; Wikipedia: MDMEO

Shulgin Index: See #77 MDA; Table: 4 Page: 331 Row: 22, See #77 MDA; Table: 4 Page: 332 Row: 11

See also Transcripts: 2.248

See also Pharmacology notes II: p. 248, MDMEO

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

112
Analogue 12: Substituting 2-Methoxyethyl for Dimethyl at N

MDMEOET
N-Methoxyethyl-MDA
N-(2-Methoxyethyl)-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-(2-methoxyethyl)amphetamine

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

Formula: C13H19NO3 Molecular weight: 237.29486 g/mol InChI Key: LOZJEWOZOKSOKA-UHFFFAOYSA-N

InChI=1S/C13H19NO3/c1-10(14-5-6-15-2)7-11-3-4-12-13(8-11)17-9-16-12/h3-4,8,10,14H,5-7,9H2,1-2H3

PubChem CID: 44719584; ChemSpider: 21106334; Wikipedia: Methylenedioxymethoxyethylamphetamine

Shulgin Index: See #77 MDA; Table: 4 Page: 331 Row: 32

See also Transcripts: 2.245

See also Pharmacology notes II: p. 245, MDMEOET

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

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

114
Analogue 13: Substituting Hydroxy for Dimethyl at N

MDOH
N-Hydroxy-MDA
N-Hydroxy-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-hydroxyamphetamine

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

Formula: C10H13NO3 Molecular weight: 195.21512 g/mol InChI Key: FNDCTJYFKOQGTL-UHFFFAOYSA-N

InChI=1S/C10H13NO3/c1-7(11-12)4-8-2-3-9-10(5-8)14-6-13-9/h2-3,5,7,11-12H,4,6H2,1H3

PubChem CID: 98528; ChemSpider: 88979; Wikipedia: Methylenedioxyhydroxyamphetamine

Shulgin Index: #84 MDOH; Table: 4 Page: 332 Row: 9

See also PiHKAL: #81 FLEA #88 HOT-7 #111 MDMEO

See also Transcripts: 2.263, 2.322, 3.324, 3.325, 3.332, 3.422

See also Pharmacology notes II: p. 263, MDOH
p. 322, MDOH: Report of experiment

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

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

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

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

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

117
Analogue 14: Substituting Prop-2-ynyl for Dimethyl at N

MDPL
N-Propargyl-MDA
N-Propynyl-MDA
N-Propargyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-propargylamphetamine

IUPAC: N-[1-(1,3-Benzodioxol-5-yl)propan-2-yl]prop-2-yn-1-amine

Formula: C13H15NO2 Molecular weight: 217.2637 g/mol InChI Key: LRYUTPIBTLEDJJ-UHFFFAOYSA-N

InChI=1S/C13H15NO2/c1-3-6-14-10(2)7-11-4-5-12-13(8-11)16-9-15-12/h1,4-5,8,10,14H,6-7,9H2,2H3

ChemSpider: 21106336; Wikipedia: Methylenedioxypropargylamphetamine

Shulgin Index: See #77 MDA; Table: 4 Page: 331 Row: 36

See also Transcripts: 2.264

See also Pharmacology notes II: p. 264, MDPL

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

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

118
Analogue 15: Substituting Propyl for Dimethyl at N

MDPR
MDPA
N-Propyl-MDA
N-Propyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-propylamphetamine

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

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

InChI=1S/C13H19NO2/c1-3-6-14-10(2)7-11-4-5-12-13(8-11)16-9-15-12/h4-5,8,10,14H,3,6-7,9H2,1-2H3

PubChem CID: 559375; ChemSpider: 486273; Erowid: MDPR; Wikipedia: Methylenedioxypropylamphetamine

Shulgin Index: #86 MDPR; Table: 4 Page: 331 Row: 33

See also PiHKAL: #101 MDAL #111 MDMEO #116 MDPH
See also TiHKAL: #8 α,N-DMT    

See also Transcripts: 2.254, 3.336

See also Pharmacology notes II: p. 254, MDPR

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

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

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

Noggle, FT; DeRuiter, J; Coker, ST; Clark, CR. Synthesis, identification, and acute toxicity of some N-alkyl derivatives of 3,4-methylenedioxyamphetamine. J. Assoc. Off. Anal. Chem., 1987, 70 (6), 981–986. 1842 kB.

276
Analogue 16: Substituting Isobutyl for Dimethyl at N

MDIB
3,4-Methylenedioxy-N-isobutylamphetamine

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

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

InChI=1S/C14H21NO2/c1-10(2)8-15-11(3)6-12-4-5-13-14(7-12)17-9-16-13/h4-5,7,10-11,15H,6,8-9H2,1-3H3

PubChem CID: 3058000; ChemSpider: 2319188

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 2

See also PiHKAL: #103 MDBZ    

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

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

Noggle, FT; DeRuiter, J; Coker, ST; Clark, CR. Synthesis, identification, and acute toxicity of some N-alkyl derivatives of 3,4-methylenedioxyamphetamine. J. Assoc. Off. Anal. Chem., 1987, 70 (6), 981–986. 1842 kB.

277
Analogue 17: Substituting tert-Butyl for Dimethyl at N

MDTB
3,4-Methylenedioxy-N-tert-butylamphetamine

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

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

InChI=1S/C14H21NO2/c1-10(15-14(2,3)4)7-11-5-6-12-13(8-11)17-9-16-12/h5-6,8,10,15H,7,9H2,1-4H3

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

See also PiHKAL: #103 MDBZ    
278
Analogue 18: Substituting Pentyl for Dimethyl at N

MDAM
3,4-Methylenedioxy-N-n-amylamphetamine

IUPAC: N-[1-(1,3-Benzodioxol-5-yl)propan-2-yl]pentan-1-amine

Formula: C15H23NO2 Molecular weight: 249.34862 g/mol InChI Key: BSWXDABLQURYGI-UHFFFAOYSA-N

InChI=1S/C15H23NO2/c1-3-4-5-8-16-12(2)9-13-6-7-14-15(10-13)18-11-17-14/h6-7,10,12,16H,3-5,8-9,11H2,1-2H3

PubChem CID: 69396692

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 5

See also PiHKAL: #103 MDBZ    

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

279
Analogue 19: Substituting Hexyl for Dimethyl at N

MDHE
3,4-Methylenedioxy-N-n-hexylamphetamine

IUPAC: N-[1-(1,3-Benzodioxol-5-yl)propan-2-yl]hexan-1-amine

Formula: C16H25NO2 Molecular weight: 263.3752 g/mol InChI Key: XRXCVVZLTOBPNY-UHFFFAOYSA-N

InChI=1S/C16H25NO2/c1-3-4-5-6-9-17-13(2)10-14-7-8-15-16(11-14)19-12-18-15/h7-8,11,13,17H,3-6,9-10,12H2,1-2H3

PubChem CID: 69454836

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 6

See also PiHKAL: #103 MDBZ    

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

280
Analogue 20: Substituting Octyl for Dimethyl at N

MDOC
3,4-Methylenedioxy-N-n-octylamphetamine

IUPAC: N-[1-(1,3-Benzodioxol-5-yl)propan-2-yl]octan-1-amine

Formula: C18H29NO2 Molecular weight: 291.42836 g/mol InChI Key: YJXXZDAZSNJQOR-UHFFFAOYSA-N

InChI=1S/C18H29NO2/c1-3-4-5-6-7-8-11-19-15(2)12-16-9-10-17-18(13-16)21-14-20-17/h9-10,13,15,19H,3-8,11-12,14H2,1-2H3

PubChem CID: 69453458

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 8

See also PiHKAL: #103 MDBZ    

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

281
Analogue 21: Substituting Diethyl for Dimethyl at N

MDDEA
MDDE
3,4-Methylenedioxy-N,N-diethylamphetamine

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

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

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

PubChem CID: 69390377

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

See also PiHKAL: #103 MDBZ    

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

282
Analogue 22: Substituting Cyanomethyl for Dimethyl at N

MDCM
3,4-Methylenedioxy-N-cyanomethylamphetamine

IUPAC: {[1-(1,3-Benzodioxol-5-yl)propan-2-yl]amino}acetonitrile

Formula: C12H14N2O2 Molecular weight: 218.25176 g/mol InChI Key: DKMWTLGWDBRTBN-UHFFFAOYSA-N

InChI=1S/C12H14N2O2/c1-9(14-5-4-13)6-10-2-3-11-12(7-10)16-8-15-11/h2-3,7,9,14H,5-6,8H2,1H3

Shulgin Index: See #77 MDA; Table: 4 Page: 331 Row: 30

See also PiHKAL: #103 MDBZ    

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

283
Analogue 23: Substituting tert-Butylamino for Dimethyl at N

MDBA
3,4-Methylenedioxy-N-tert-butylaminoamphetamine

IUPAC: 1-[1-(1,3-Benzodioxol-5-yl)propan-2-yl]-2-tert-butylhydrazine

Formula: C14H22N2O2 Molecular weight: 250.33668 g/mol InChI Key: FWQFDBQIIWPHOV-UHFFFAOYSA-N

InChI=1S/C14H22N2O2/c1-10(15-16-14(2,3)4)7-11-5-6-12-13(8-11)18-9-17-12/h5-6,8,10,15-16H,7,9H2,1-4H3

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 12

See also PiHKAL: #103 MDBZ    

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

284
Analogue 24: Substituting 2,2,2-Trifluoroethyl for Dimethyl at N

MDTFEA
3,4-Methylenedixoy-N-(2,2,2-trifluoroethyl)amphetamine

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

Formula: C12H14F3NO2 Molecular weight: 261.2402696 g/mol InChI Key: MWFPHJXMCQTNGG-UHFFFAOYSA-N

InChI=1S/C12H14F3NO2/c1-8(16-6-12(13,14)15)4-9-2-3-10-11(5-9)18-7-17-10/h2-3,5,8,16H,4,6-7H2,1H3

See also PiHKAL: #106 MDE    

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

6675
Analogue 25: Substituting Methyl and Ethyl for Dimethyl at N

MDMEA

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

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

InChI=1S/C13H19NO2/c1-4-14(3)10(2)7-11-5-6-12-13(8-11)16-9-15-12/h5-6,8,10H,4,7,9H2,1-3H3

PubChem CID: 6421392; ChemSpider: 4926929

Shulgin Index: See #77 MDA; Table: 4 Page: 331 Row: 25

6676
Analogue 26: Substituting Methyl and Propyl for Dimethyl at N

MDMPA

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

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

InChI=1S/C14H21NO2/c1-4-7-15(3)11(2)8-12-5-6-13-14(9-12)17-10-16-13/h5-6,9,11H,4,7-8,10H2,1-3H3

Shulgin Index: See #77 MDA; Table: 4 Page: 331 Row: 26

6677
Analogue 27: Substituting Methyl and Isopropyl for Dimethyl at N

MDMIPA

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

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

InChI=1S/C14H21NO2/c1-10(2)15(4)11(3)7-12-5-6-13-14(8-12)17-9-16-13/h5-6,8,10-11H,7,9H2,1-4H3

Shulgin Index: See #77 MDA; Table: 4 Page: 331 Row: 27

6703
Analogue 28: Substituting sec-Butyl for Dimethyl at N

MDSB

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

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

InChI=1S/C14H21NO2/c1-4-10(2)15-11(3)7-12-5-6-13-14(8-12)17-9-16-13/h5-6,8,10-11,15H,4,7,9H2,1-3H3

PubChem CID: 3087181; ChemSpider: 2343683

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 3

Noggle, FT; DeRuiter, J; Coker, ST; Clark, CR. Synthesis, identification, and acute toxicity of some N-alkyl derivatives of 3,4-methylenedioxyamphetamine. J. Assoc. Off. Anal. Chem., 1987, 70 (6), 981–986. 1842 kB.

2477
Analogue 29: Substituting Formyl and Methyl for Dimethyl at N

N-Formyl-MDMA

IUPAC: N-[1-(1,3-Benzodioxol-5-yl)propan-2-yl]-N-methylformamide

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

InChI=1S/C12H15NO3/c1-9(13(2)7-14)5-10-3-4-11-12(6-10)16-8-15-11/h3-4,6-7,9H,5,8H2,1-2H3

PubChem CID: 559857; ChemSpider: 486685

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

Two α analogues:
326
Analogue 1: Removing Methyl at α

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

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

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

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

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. 884 kB. doi:10.1080/02791072.2008.10400635

6736
Analogue 2: Substituting Ethyl for Methyl at α

MMBDB

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

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

InChI=1S/C13H19NO2/c1-4-11(14(2)3)7-10-5-6-12-13(8-10)16-9-15-12/h5-6,8,11H,4,7,9H2,1-3H3

PubChem CID: 53734518

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 36

Three R3,4 analogues:
6530
Analogue 1: Substituting Dihydroxy for Methylenedioxy at R3,4

N,N-Me-DHA

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

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

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

PubChem CID: 21151685

Shulgin Index: See #33 DHA; Table: 4 Page: 328 Row: 30

6621
Analogue 2: Substituting Dimethoxy for Methylenedioxy at R3,4

N,N-Me-DMA

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

Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: KRNRFVKFPWEACF-UHFFFAOYSA-N

InChI=1S/C13H21NO2/c1-10(14(2)3)8-11-6-7-12(15-4)13(9-11)16-5/h6-7,9-10H,8H2,1-5H3

Shulgin Index: See #38 DMA; Table: 4 Page: 330 Row: 21

6802
Analogue 3: Substituting Ethylenedioxy for Methylenedioxy at R3,4

ED-NDMA

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

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

InChI=1S/C13H19NO2/c1-10(14(2)3)8-11-4-5-12-13(9-11)16-7-6-15-12/h4-5,9-10H,6-8H2,1-3H3

PubChem CID: 4547996; ChemSpider: 3741932

Shulgin Index: See #65 EDA; Table: 4 Page: 334 Row: 2

28 skeleton analogues:
272
Analogue 1: With 3-Phenylpropan-1-amine skeleton

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    
1031
Analogue 2: 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.

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

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

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

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.

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

1032
Analogue 3: 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 4: 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

2041
Analogue 5: With 2-Amino-1-phenylethanone skeleton

bk-MDMA
MDMC
M1
Methylone
3,4-Methylenedioxymethcathinone

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

Formula: C11H13NO3 Molecular weight: 207.22582 g/mol InChI Key: VKEQBMCRQDSRET-UHFFFAOYSA-N

InChI=1S/C11H13NO3/c1-7(12-2)11(13)8-3-4-9-10(5-8)15-6-14-9/h3-5,7,12H,6H2,1-2H3

PubChem CID: 45789647; ChemSpider: 21106350; Drugs Forum: Methylone; Erowid: Methylone; Wikipedia: Methylone

Shulgin Index: #93 Methylone; Table: 4 Page: 332 Row: 15

See also Chemistry notes VIII: p. 10, Methylone: GC-MS
p. 11, Methylone: GC-MS

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

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

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

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

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

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

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.

Rösner, P; Zechlin, L; Junge, T. N-Ethyl-2-(3,4-methylenedioxyphenyl)-propan-1-amin eine neue Designerdroge mit der Struktur eines beta-isomeren MDE. Toxichem Krimtech, 2003, 70 (2), 82–86. 42 kB.

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

Eshleman, AJ; Wolfrum, KM; Hatfield, MG; Johnson, RA; Murphy, KV; Janowsky, A. Substituted methcathinones differ in transporter and receptor interactions. Biochem. Pharmacol., 15 Jun 2013, 85 (12), 1803–1815. 2164 kB. doi:10.1016/j.bcp.2013.04.004

Dybdal-Hargreaves, NF; Holder, ND; Ottoson, PE; Sweeney, MD; Williams, T. Mephedrone: Public health risk, mechanisms of action, and behavioral effects. Eur. J. Pharmacol., 15 Aug 2013, 714 (1–3), 32–40. 837 kB. doi:10.1016/j.ejphar.2013.05.024

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

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

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

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.

Kavanagh, PV; O’Brien, J; Fox, J; O’Donnell, C; Christie, R; Power, JD; McDermott, SD. The analysis of substituted cathinones. Part 3. Synthesis and characterisation of 2,3-methylenedioxy substituted cathinones. Forensic Sci. Int., 10 Mar 2012, 216 (1–2), 19–28. 1580 kB. doi:10.1016/j.forsciint.2011.08.011

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

Shulgin, AT. 4-Hydroxy-5-methoxy-N,N-dimethyltryptamine, Psilocybe mushrooms, psilocin. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 7 Dec 2005.

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

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

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

Cozzi, NV; Shulgin, AT; Ruoho, AE. Methcathinone (MCAT) and 2-methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one (MDMCAT) inhibit [3H]serotonin uptake into human platelets. Amer. Chem. Soc. Div. Med. Chem. Abs., 1 Jan 1998, 215, 152. 11 kB.

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

Russell, MJ; Bogun, B. New “party pill” components in New Zealand: The synthesis and analysis of some β-ketone analogues of 3,4-methylenedioxymethamphetamine (MDMA) including βk-DMBDB (β-ketone-N,N-dimethyl-1-(1,3-benzodioxol-5-yl)-2-butanamine). Forensic Sci. Int., 15 Jul 2011, 210 (1–3), 174–181. 1161 kB. doi:10.1016/j.forsciint.2011.03.005

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

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

Bossong, MG; Dijk, JP; Niesink, RJM. Methylone and mCPP, two new drugs of abuse? Addict. Biol., 1 Dec 2005, 10 (4), 321–323. 69 kB. doi:10.1080/13556210500350794

Warrick, BJ; Wilson, J; Hedge, M; Freeman, S; Leonard, K; Aaron, C. Lethal serotonin syndrome after methylone and butylone ingestion. J. Med. Toxicol., 1 Mar 2012, 8 (1), 65–68. 150 kB. doi:10.1007/s13181-011-0199-6

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

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

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

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.

2124
Analogue 7: With 2-Amino-1-phenylethanone skeleton

bk-MDDMA
DMONE
N,N-Dimethyl MDCATH
N,N-Dimethyl-3,4-methylenedioxycathinone
Dimethylone
N,N-Dimethyl-β-keto-3,4-methylenedioxyamphetamine

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

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

InChI=1S/C12H15NO3/c1-8(13(2)3)12(14)9-4-5-10-11(6-9)16-7-15-10/h4-6,8H,7H2,1-3H3

PubChem CID: 9794472; ChemSpider: 7970239

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 16

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. 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

Russell, MJ; Bogun, B. New “party pill” components in New Zealand: The synthesis and analysis of some β-ketone analogues of 3,4-methylenedioxymethamphetamine (MDMA) including βk-DMBDB (β-ketone-N,N-dimethyl-1-(1,3-benzodioxol-5-yl)-2-butanamine). Forensic Sci. Int., 15 Jul 2011, 210 (1–3), 174–181. 1161 kB. doi:10.1016/j.forsciint.2011.03.005

2125
Analogue 8: 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

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

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

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

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

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 9: 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    

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

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.

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

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

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

2151
Analogue 10: With 2,3-Dihydro-1H-inden-2-amine skeleton

5,6-MDMAI
MDMAI
2-Amino-N-methyl-5,6-methylenedioxyindane

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

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

InChI=1S/C11H13NO2/c1-12-9-2-7-4-10-11(14-6-13-10)5-8(7)3-9/h4-5,9,12H,2-3,6H2,1H3

PubChem CID: 125559; ChemSpider: 111695; Wikipedia: 5,6-Methylenedioxy-N-methyl-2-aminoindane

Shulgin Index: See #77 MDA; Table: 5 Page: 347 Row: 25

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

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.

Shulgin, AT. MDMA variations & freedom of inquiry. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 24 Apr 2003.

402
Analogue 11: 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

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

415
Analogue 12: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

6,7-MDMAT
MDMAT
2-Amino-N-methyl-6,7-methylenedioxytetralin

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

Formula: C12H15NO2 Molecular weight: 205.253 g/mol InChI Key: MTRLJTZQUZHTJI-UHFFFAOYSA-N

InChI=1S/C12H15NO2/c1-13-10-3-2-8-5-11-12(15-7-14-11)6-9(8)4-10/h5-6,10,13H,2-4,7H2,1H3

PubChem CID: 23324601; Wikipedia: MDMAT

Shulgin Index: See #77 MDA; Table: 5 Page: 347 Row: 27

918
Analogue 13: With Phenylmethanamine skeleton

α,N,N-TMMDBA

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

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

917
Analogue 14: With Phenylmethanamine skeleton

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

913
Analogue 15: With Phenylmethanamine skeleton

α-MMDBA

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

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

912
Analogue 16: With Phenylmethanamine skeleton

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

911
Analogue 17: With Phenylmethanamine skeleton

N-MMDBA
N-Methylpiperonylamine

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

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

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

PubChem CID: 421238; ChemSpider: 372890

Shulgin Index: See #45 α,N-DMMDBA; Table: 9 Page: 357 Row: 27

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

910
Analogue 18: 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.

611
Analogue 19: With 3-Phenylpropan-1-amine skeleton

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

610
Analogue 20: With 3-Phenylpropan-1-amine skeleton

homo-MDA

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

612
Analogue 21: With 3-Phenylpropan-1-amine skeleton

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

6729
Analogue 22: 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 23: 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 24: 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 25: 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 26: 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 27: 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 28: 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.

42 isomers:
56
Isomer 1

DMCPA
2-(2,5-Dimethoxy-4-methylphenyl)cyclopropylamine

IUPAC: 2-(2,5-Dimethoxy-4-methylphenyl)cyclopropanamine

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

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

PubChem CID: 3017965; ChemSpider: 2285590; Wikipedia: 4-Methyl-2,5-methoxyphenylcyclopropylamine

Shulgin Index: #41 DMCPA; Table: 5 Page: 342 Row: 27

See also PiHKAL: #142 PEA    
See also TiHKAL: #8 α,N-DMT    

See also Transcripts: 4.497

Nichols, DE; Woodard, R; Hathaway, BA; Lowy, MT; Yim, GKW. Resolution and absolute configuration of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, a potent hallucinogen analogue. J. Med. Chem., 1 Jan 1979, 22 (4), 458–460. 464 kB. doi:10.1021/jm00190a021

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Nichols, DE; Pfister, WR; Yim, GKW. LSD and phenethylamine hallucinogens: New structural analogy and implications for receptor geometry. Life Sci., 1 Jan 1978, 22 (24), 2165–2170. 323 kB. doi:10.1016/0024-3205(78)90567-2

Jacob, JN; Nichols, DE. Isomeric cyclopropyl ring-methylated homologues of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, an hallucinogen analogue. J. Med. Chem., 1 Jan 1982, 25 (5), 526–530. 732 kB. doi:10.1021/jm00347a009

Nichols, DE; Jadhav, KP; Oberlender, RA; Zabik, JE; Bossart, JF; Hamada, A; Miller, DD. Synthesis and evaluation of substituted 2-phenylcyclobutylamines as analogues of hallucinogenic phenethylamines: Lack of LSD-like biological activity. J. Med. Chem., 1 Jan 1984, 27 (9), 1108–1111. 617 kB. doi:10.1021/jm00375a004

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

98
Isomer 2

MADAM-6
2,N-Dimethyl-4,5-methylenedioxyamphetamine

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

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

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

PubChem CID: 44719578; ChemSpider: 21106340; Wikipedia: MADAM-6

Shulgin Index: See #77 MDA; Table: 5 Page: 347 Row: 16

106
Isomer 3

MDE
MDEA
EVE
N-Ethyl-MDA
N-Ethyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-ethylamphetamine

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

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

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

PubChem CID: 105039; ChemSpider: 94775; Erowid: MDE; Wikipedia: MDEA

Shulgin Index: #81 MDE; Table: 4 Page: 331 Row: 28

See also PiHKAL: #57 DME
#77 ETHYL-J
#100 MDA
#108 MDIP
#111 MDMEO
#115 MDPEA
#128 METHYL-J
See also TiHKAL: #8 α,N-DMT    

See also Transcripts: 2.206, 2.274, 2.323.2, 3.376, 3.412, 3.413, 4.453, 4.454

See also Pharmacology notes II: app. 2, Abuse week
p. 206, MDE
p. 274, MDE

Gouzoulis-Mayfrank, E; Hermle, L. Are the “entactogens” a distinct psychoactive substance class? In Heffter Review; Nichols, DE, Ed., Heffter Research Institute, Santa Fe, NM, 1998; Vol. 1, pp 46–51. 44 kB.

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

Schmidt, WJ; Mayerhofer, A; Meyer, A; Kovar, K. Ecstasy counteracts catalepsy in rats, an anti-parkinsonian effect? Neurosci. Lett., 27 Sep 2002, 330 (3), 251–254. 280 kB. doi:10.1016/S0304-3940(02)00823-6

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

Noggle, FT; DeRuiter, J; Coker, ST; Clark, CR. Synthesis, identification, and acute toxicity of some N-alkyl derivatives of 3,4-methylenedioxyamphetamine. J. Assoc. Off. Anal. Chem., 1987, 70 (6), 981–986. 1842 kB.

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

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

Nieddu, M; Burrai, L; Pirisi, MA; Carta, A; Briguglio, I; Dessi, G; Boatto, G. Validated liquid chromatography-mass spectrometry method for the quantitation of N-substituted derivatives of 3,4-methylenedioxyamphetamine in rat urine. Forensic Toxicol., 1 Jul 2013, 31 (2), 204–211. 527 kB. doi:10.1007/s11419-013-0178-5

Freudenmann, RW; Spitzer, M. Neuropsychopharmacology and toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA). CNS Drug Rev., 1 Jun 2004, 10 (2), 89–216. 187 kB. doi:10.1111/j.1527-3458.2004.tb00007.x

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

Gouzoulis-Mayfrank, E. Differential actions of an entactogen compared to a stimulant and a hallucinogen in healthy humans. In Heffter Review; Nichols, DE, Ed., Heffter Research Institute, Santa Fe, NM, 2001; Vol. 2, pp 64–72. 261 kB.

Al-Hossaini, AM. GC-MS and GC-IRD studies on ethoxyphenethylamines related to MDEA, MDMMA and MBDB. Ph. D. Thesis, Auburn University, Auburn, AL, USA, 18 Dec 2009. 1195 kB.

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

Braun, U; Shulgin, AT; Braun, G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci., 1 Jan 1980, 69 (2), 192–195. 513 kB. doi:10.1002/jps.2600690220

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.

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

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

Stone, DM; Johnson, M; Hanson, GR; Gibb, JW. A comparison of the neurotoxic potential of methylenedioxyamphetamine (MDA) and its N-methylated and N-ethylated derivatives. Eur. J. Pharmacol., 10 Feb 1987, 134 (2), 245–248. 316 kB. doi:10.1016/0014-2999(87)90555-8

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

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

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

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

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.

110
Isomer 4

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

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

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

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

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

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

See also PiHKAL: #100 MDA    

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

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

113
Isomer 5

MDMP
Methylenedioxymephentermine
α,α,N-Trimethyl-3,4-methylenedioxyphenethylamine

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

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

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

PubChem CID: 44366836; ChemSpider: 21106335; Wikipedia: MDMP

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 31

See also PiHKAL: #116 MDPH    

See also Transcripts: 3.373

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

128
Isomer 6

METHYL-J
MBDB
Eden
2-Methylamino-1-(3,4-methylenedioxyphenyl)butane
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine
N-Methyl-α-ethyl-3,4-methylenedioxyphenethylamine

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

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

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

PubChem CID: 124844; ChemSpider: 111153; Erowid: MBDB; Wikipedia: Methylbenzodioxolylbutanamine

Shulgin Index: #76 MBDB; Table: 4 Page: 332 Row: 34

See also PiHKAL: #77 ETHYL-J
#94 J
#100 MDA
#106 MDE
#115 MDPEA
#129 METHYL-K

See also Transcripts: 5.605

Al-Hossaini, AM. GC-MS and GC-IRD studies on ethoxyphenethylamines related to MDEA, MDMMA and MBDB. Ph. D. Thesis, Auburn University, Auburn, AL, USA, 18 Dec 2009. 1195 kB.

Schmidt, WJ; Mayerhofer, A; Meyer, A; Kovar, K. Ecstasy counteracts catalepsy in rats, an anti-parkinsonian effect? Neurosci. Lett., 27 Sep 2002, 330 (3), 251–254. 280 kB. doi:10.1016/S0304-3940(02)00823-6

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.

Anon. Report on the risk assessment of MBDB, European Monitoring Centre for Drugs and Drug Addiction, Jun 1999.

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

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

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

Gandy, MN; Mclldowie, M; Lewis, K; Wasik, AM; Salomonczyk, D; Wagg, K; Millar, ZA; Tindiglia, D; Huot, P; Johnston, T; Thiele, S; Nguyen, B; Barnes, NM; Brotchie, JM; Martin-Iverson, MT. Redesigning the designer drug ecstasy: non-psychoactive MDMA analogues exhibiting Burkitt’s lymphoma cytotoxicity. Med. Chem. Comm., 2010, 1 (4), 287–293. 177 kB. doi:10.1039/c0md00108b

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

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

Johnson, MP; 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

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.

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

Shulgin, AT; Manning, T; Daley, PF. The Shulgin Index, Vol. 1, #76. MBDB. Erowid, 1 Jun 2011.

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

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

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

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

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

247
Isomer 7

F
Benzofuran-2,3-dihydro-5-methoxy-6-(2-aminopropane)

IUPAC: 1-(5-Methoxy-2,3-dihydro-1-benzofuran-6-yl)propan-2-amine

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

InChI=1S/C12H17NO2/c1-8(13)5-10-7-12-9(3-4-15-12)6-11(10)14-2/h6-8H,3-5,13H2,1-2H3

PubChem CID: 13553507; ChemSpider: 23183074

Shulgin Index: #66 F; Table: 5 Page: 347 Row: 1

See also PiHKAL: #79 F-2    

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Nichols, DE; Snyder, SE; Oberlender, R; Johnson, MP; Huang, X. 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines. J. Med. Chem., 1 Jan 1991, 34 (1), 276–281. 833 kB. doi:10.1021/jm00105a043

Nichols, DE; Hoffman, AJ; Oberlender, RA; Riggs, RM. Synthesis and evaluation of 2,3-dihydrobenzofuran analogues of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: Drug discrimination studies in rats. J. Med. Chem., 1 Jan 1986, 29 (2), 302–304. 441 kB. doi:10.1021/jm00152a022

274
Isomer 8

IDA
3,4-Isopropylidenedioxyamphetamine

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

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

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

PubChem CID: 130544; ChemSpider: 115480

Shulgin Index: See #77 MDA; Table: 4 Page: 333 Row: 32

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

291
Isomer 9

K
2-Amino-1-(3,4-methylenedioxyphenyl)pentane

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

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

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

PubChem CID: 22007048; ChemSpider: 13616549

Shulgin Index: See #77 MDA; Table: 4 Page: 333 Row: 9

See also PiHKAL: #100 MDA #128 METHYL-J #129 METHYL-K
2062
Isomer 10

2C-G-2
2,5-Dimethoxy-3,4-(ethylene)phenethylamine
2,5-Dimethoxy-3,4-(dimethylene)phenethylamine

IUPAC: 2-(2,5-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-3-yl)ethan-1-amine

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

InChI=1S/C12H17NO2/c1-14-11-7-8(5-6-13)12(15-2)10-4-3-9(10)11/h7H,3-6,13H2,1-2H3

Shulgin Index: See #114 TeMPEA; Table: 6 Page: 354 Row: 21

See also PiHKAL: #28 2C-G-3    
2147
Isomer 11

MADAM-2
N,2-Dimethyl-3,4-methylenedioxyamphetamine

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

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

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

PubChem CID: 69396224

See also PiHKAL: #98 MADAM-6    
2198
Isomer 12

2C-VI
2C-V
4-Ethenyl-2,5-dimethoxyphenethylamine

IUPAC: 2-(4-Ethenyl-2,5-dimethoxyphenyl)ethan-1-amine

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

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

PubChem CID: 57474284

Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 19

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 3. 4-Ethynyl-2,5-dimethoxyphenethylamine (= 4-Ethynyl-2,5-dimethoxybenzeneethanamine; 2C-YN). Helv. Chim. Acta, 28 Aug 2003, 86 (8), 2754–2759. 84 kB. doi:10.1002/hlca.200390224

407
Isomer 13

DOMAI
DOM-AI
2-Amino-4,7-dimethoxy-5-methylindane

IUPAC: 4,7-Dimethoxy-5-methyl-2,3-dihydro-1H-inden-2-amine

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

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

PubChem CID: 3016787; ChemSpider: 2284673

Shulgin Index: See #60 DOM; Table: 6 Page: 355 Row: 19

Nichols, DE; Barfknecht, CF; Long, JP; Standridge, RT; Howell, HG; Partyka, RA; Dyer, DC. Potential psychotomimetics. 2. Rigid analogs of 2,5-dimethoxy-4-methylphenylisopropylamine (DOM, STP). J. Med. Chem., 1 Jan 1974, 17 (2), 161–166. 718 kB. doi:10.1021/jm00248a004

Coutts, RT; Malicky, JL. The synthesis of analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). II. Some ring-methoxylated 1-amino- and 2-aminoindanes. Can. J. Chem., 1 Feb 1974, 52 (3), 381–389. 615 kB. doi:10.1139/v74-061

2369
Isomer 14

4-MeO-3-Me-MCAT
4-Methoxy-3-methylmethcathinone

IUPAC: 1-(4-Methoxy-3-methylphenyl)-2-(methylamino)propan-1-one

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

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

ChemSpider: 25630736

412
Isomer 15

5,8-ADT
2-Amino-5,8-dimethoxytetralin

IUPAC: 5,8-Dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine

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

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

PubChem CID: 12924821; ChemSpider: 23128139

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

Rusterholz, DB; Dryer, SE; Long, JP; Barfknecht, CF; Mott, J. Sedative and analgesic actions of methoxylated 2-aminotetralins; involvement of α1- and α2-adrenoreceptors. Eur. J. Pharmacol., 25 Jul 1980, 65 (2–3), 201–211. 870 kB. doi:10.1016/0014-2999(80)90393-3

363
Isomer 16

MeO-B
4-Methoxybuphedrone

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

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

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

ChemSpider: 26705218

439
Isomer 17

DMA-2-hemiFLY

IUPAC: 1-(5-Methoxy-2,3-dihydro-1-benzofuran-7-yl)propan-2-amine

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

InChI=1S/C12H17NO2/c1-8(13)5-10-7-11(14-2)6-9-3-4-15-12(9)10/h6-8H,3-5,13H2,1-2H3

2384
Isomer 18

4-Propoxycathinone

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

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

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

ChemSpider: 24222873

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

920
Isomer 19

α-Me-N-Pr-MDBA

IUPAC: N-[1-(1,3-Benzodioxol-5-yl)ethyl]propan-1-amine

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

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

PubChem CID: 14325226; ChemSpider: 24014617

Shulgin Index: See #45 α,N-DMMDBA; Table: 9 Page: 358 Row: 5

916
Isomer 20

α,α,N,N-TMMDBA

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

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

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

Shulgin Index: See #45 α,N-DMMDBA; Table: 9 Page: 358 Row: 1

611
Isomer 21

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

921
Isomer 22

α-Me-N-iPr-MDBA

IUPAC: N-[1-(1,3-Benzodioxol-5-yl)ethyl]propan-2-amine

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

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

PubChem CID: 14325227; ChemSpider: 24422984

Shulgin Index: See #45 α,N-DMMDBA; Table: 9 Page: 358 Row: 6

6205
Isomer 23

BO3A

IUPAC: 2-Methoxy-2-[3-(prop-2-en-1-yloxy)phenyl]ethan-1-amine

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

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

Shulgin Index: See #101 3-MPEA; Table: 3 Page: 322 Row: 5

6281
Isomer 24

Hordenine acetate

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

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

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

PubChem CID: 13539073; ChemSpider: 12283417

Shulgin Index: See #71 Hordenine; Table: 3 Page: 323 Row: 31

6412
Isomer 25

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
Isomer 26

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

6416
Isomer 27

2,3-MBDB

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

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

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

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 16

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

6657
Isomer 28

MAPEA

IUPAC: 2-[3-Methoxy-4-(prop-2-en-1-yloxy)phenyl]ethan-1-amine

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

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

PubChem CID: 14622431; ChemSpider: 15382929

Shulgin Index: See #90 MEPEA; Table: 4 Page: 331 Row: 7

See also PiHKAL: #123 MEPEA    

Meyers-Riggs, B. Leminger’s scalines. countyourculture: rational exploration of the underground, 4 May 2012.

6663
Isomer 29

N-Me-N-Et-MDPEA

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

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

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

Shulgin Index: See #85 MDPEA; Table: 4 Page: 331 Row: 13

6665
Isomer 30

N-Pr-MDPEA

IUPAC: N-[2-(1,3-Benzodioxol-5-yl)ethyl]propan-1-amine

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

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

PubChem CID: 11183367; ChemSpider: 9358452

Shulgin Index: See #85 MDPEA; Table: 4 Page: 331 Row: 15

6666
Isomer 31

N-iPr-MDPEA

IUPAC: N-[2-(1,3-Benzodioxol-5-yl)ethyl]propan-2-amine

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

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

PubChem CID: 791705; ChemSpider: 692396

Shulgin Index: See #85 MDPEA; Table: 4 Page: 331 Row: 16

6732
Isomer 32

α-Et-MDA

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

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

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

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 32

6770
Isomer 33

α-iPr-MDPEA

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

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

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

ChemSpider: 26670831

Shulgin Index: See #85 MDPEA; Table: 4 Page: 333 Row: 20

6784
Isomer 34

ED-N-DMPEA

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

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

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

Shulgin Index: See #65 EDA; Table: 4 Page: 333 Row: 34

438
Isomer 35

SF
DMA-5-hemiFLY

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

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

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

PubChem CID: 11745828; ChemSpider: 9920532

Shulgin Index: See #17 B-SF; Table: 5 Page: 353 Row: 5

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Nichols, DE; Snyder, SE; Oberlender, R; Johnson, MP; Huang, X. 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines. J. Med. Chem., 1 Jan 1991, 34 (1), 276–281. 833 kB. doi:10.1021/jm00105a043

7820
Isomer 36

G-1

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

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

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

PubChem CID: 69527862

Shulgin Index: See #113 TeMA; Table: 6 Page: 354 Row: 20

502
Isomer 37

M-7

IUPAC: 6-(Dimethylamino)-5,6,7,8-tetrahydronaphthalene-1,2-diol

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

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

PubChem CID: 37033; ChemSpider: 33982

Ilhan, M; Nichols, DE; Long, JP; Cannon, JG. Apomorphine-like effect of an aminotetralin on the linguomandibular reflex of the cat. Eur. J. Pharmacol., 1 Aug 1975, 33 (1), 61–64. 308 kB. doi:10.1016/0014-2999(75)90138-7

1262
Isomer 38

N-Et-ADTN

IUPAC: 6-(Ethylamino)-5,6,7,8-tetrahydronaphthalene-2,3-diol

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

InChI=1S/C12H17NO2/c1-2-13-10-4-3-8-6-11(14)12(15)7-9(8)5-10/h6-7,10,13-15H,2-5H2,1H3

ChemSpider: 24207261

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

2764
Isomer 39

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

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

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

PubChem CID: 541955; ChemSpider: 471937

Foster, BC; Nantais, LM; Wilson, DL; By, AW; Zamecnik, J; Lodge, BA. Fungal metabolism of 4-substituted amphetamines. Xenobiotica, 1990, 20 (6), 583–590. 510 kB. doi:10.3109/00498259009046873

1095
Isomer 40

IUPAC: N-[1-(3-Methoxyphenyl)propan-2-yl]acetamide

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

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

PubChem CID: 541954; ChemSpider: 471936

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

1084
Isomer 41

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

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

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

PubChem CID: 541955; ChemSpider: 471937

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

1006
Isomer 42

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

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

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

PubChem CID: 541953; ChemSpider: 471935

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 104 analogues and isomers Show only the 29 N analogues Show only the two α analogues Show only the three R3,4 analogues Show only the 28 skeleton analogues
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