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MDPBP; 3′,4′-Methylenedioxy-α-pyrrolidinobutiophenone
2345
Variant: Nc α skeleton isomers all
Analogues: 2 3 49 1 55

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

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

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

PubChem CID: 71300672; Wikipedia: 3',4'-Methylenedioxy-α-pyrrolidinobutiophenone

Shulgin Index: See #93 Methylone; Table: 4 Page: 333 Row: 5

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

Brandt, SD; Freeman, S; Sumnall, HR; Measham, F; Cole, JC. Analysis of NRG ‘legal highs’ in the UK: Identification and formation of novel cathinones. Drug Test. Anal., 1 Sep 2011, 3 (9), 569–575. 176 kB. doi:10.1002/dta.204

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

Zuba, D. Identification of cathinones and other active components of ‘legal highs’ by mass spectrometric methods. Trends Anal. Chem., 1 Feb 2012, 32, 15–30. 576 kB. doi:10.1016/j.trac.2011.09.009

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

Two Nc analogues:
2564
Analogue 1: Substituting Piperidine for Pyrrolidine at Nc

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

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

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

2567
Analogue 2: Substituting Azepane for Pyrrolidine at Nc

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

Formula: C17H23NO3 Molecular weight: 289.36942 g/mol InChI Key: DPMDXDRLNBPDTG-UHFFFAOYSA-N

InChI=1S/C17H23NO3/c1-2-14(18-9-5-3-4-6-10-18)17(19)13-7-8-15-16(11-13)21-12-20-15/h7-8,11,14H,2-6,9-10,12H2,1H3

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

Three α analogues:
2125
Analogue 1: Substituting Methyl for Ethyl at α

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.

2143
Analogue 2: Substituting Propyl for Ethyl at α

MDPV
MDPK
Methylenedioxypyrovalerone

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

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

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

PubChem CID: 20111961; ChemSpider: 16788110; Drugs Forum: MDPV; Erowid: MDPV; Wikipedia: Methylenedioxypyrovalerone

Anon. Report on the risk assessment of 1-(1,3-benzodioxol-5-yl)-2-(pyrrolidin-1-yl)pentan-1-one (MDPV), European Monitoring Centre for Drugs and Drug Addiction, May 2014.

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

Cameron, K; Kolanos, R; Vekariya, R; Felice, LD; Glennon, RA. Mephedrone and methylenedioxypyrovalerone (MDPV), major constituents of “bath salts,” produce opposite effects at the human dopamine transporter. Psychopharmacology, 1 Jun 2013, 227 (3), 493–499. 190 kB. doi:10.1007/s00213-013-2967-2

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

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

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

Prosser, JM; Nelson, LS. The toxicology of bath salts: a review of synthetic cathinones. J. Med. Toxicol., 1 Nov 2011, 8 (1), 33–22. 267 kB. doi:10.1007/s13181-011-0193-z

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

Ross, EA; Reisfield, GM; Watson, MC; Chronister, CW; Goldberger, BA. Psychoactive “bath salts” intoxication with methylenedioxypyrovalerone. Sep 2012. 248 kB. doi:10.1016/j.amjmed.2012.02.019

Zuba, D. Identification of cathinones and other active components of ‘legal highs’ by mass spectrometric methods. Trends Anal. Chem., 1 Feb 2012, 32, 15–30. 576 kB. doi:10.1016/j.trac.2011.09.009

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

Brandt, SD; Freeman, S; Sumnall, HR; Measham, F; Cole, JC. Analysis of NRG ‘legal highs’ in the UK: Identification and formation of novel cathinones. Drug Test. Anal., 1 Sep 2011, 3 (9), 569–575. 176 kB. doi:10.1002/dta.204

Brandt, SD; Sumnall, HR; Measham, F; Cole, JC. Analyses of second-generation ‘legal highs’ in the UK: Initial findings. Drug Test. Anal., 1 Aug 2010, 2 (8), 377–382. 317 kB. doi:10.1002/dta.155

Jankovics, P; Váradi, A; Tölgyesi, L; Lohner, S; Németh-Palotás, J; Kőszegi-Szalai, H. Identification and characterization of the new designer drug 4′-methylethcathinone (4-MEC) and elaboration of a novel liquid chromatography-tandem mass spectrometry (LC-MS/MS) screening method for seven different methcathinone analogs. Forensic Sci. Int., 15 Jul 2011, 210 (1–3), 213–220. 899 kB. doi:10.1016/j.forsciint.2011.03.019

Coppola, M; Mondola, R. 3,4-Methylenedioxypyrovalerone (MDPV): Chemistry, pharmacology and toxicology of a new designer drug of abuse marketed online. Toxicol. Lett., 5 Jan 2012, 208 (1), 12–25. 138 kB. doi:10.1016/j.toxlet.2011.10.002

Yohannan, JC; Bozenko, JS. The characterization of 3,4-methylenedioxypyrovalerone. Microgram J., 1 Mar 2010, 7 (1), 12–15. 690 kB.

Westphal, F; Junge, T; Rösner, P; Sönnichsen, F; Schuster, F. Mass and NMR spectroscopic characterization of 3,4-methylenedioxypyrovalerone: A designer drug with α-pyrrolidinophenone structure. Forensic Sci. Int., 10 Sep 2009, 190 (1–3), 1–8. 657 kB. doi:10.1016/j.forsciint.2009.05.001

Kriikku, P; Wilhelm, L; Schwarz, O; Rintatalo, J. New designer drug of abuse: 3,4-Methylenedioxypyrovalerone (MDPV). Findings from apprehended drivers in Finland. Forensic Sci. Int., 15 Jul 2011, 210 (1–3), 195–200. 618 kB. doi:10.1016/j.forsciint.2011.03.015

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

2562
Analogue 3: Substituting Isopropyl for Ethyl at α

MDPIV

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

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

InChI=1S/C16H21NO3/c1-11(2)15(17-7-3-4-8-17)16(18)12-5-6-13-14(9-12)20-10-19-13/h5-6,9,11,15H,3-4,7-8,10H2,1-2H3

PubChem CID: 53423539; ChemSpider: 26554179

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

49 skeleton analogues:
15
Analogue 1: With 2-Phenylethan-1-amine skeleton

BOH
β-Methoxy-3,4-methylenedioxyphenethylamine

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

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

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

PubChem CID: 44719487; ChemSpider: 21106264; Wikipedia: BOH (drug)

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 9, #15 BOH; Table: 4 Page: 331 Row: 19

See also PiHKAL: #13 BOB #57 DME #115 MDPEA  

See also Transcripts: 5.652

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

Torres, MA; Cassels, BK; Rezende, MC. The preparation of potentially psychoactive β-alkoxyphenethylamines. Synth. Commun., 1 Jan 1995, 25 (8), 1239–1247. 415 kB. doi:10.1080/00397919508012687

77
Analogue 2: With 2-Phenylethan-1-amine skeleton

ETHYL-J
EBDB
2-Ethylamino-1-(3,4-methylenedioxyphenyl)butane
N-Ethyl-1-(1,3-benzodioxol-5-yl)-2-butanamine
N,α-Diethyl-3,4-methylenedioxyphenethylamine

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

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

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

PubChem CID: 10214504; ChemSpider: 8389996; Wikipedia: Ethylbenzodioxolylbutanamine

Shulgin Index: See #77 MDA; Table: 4 Page: 333 Row: 1

See also PiHKAL: #128 METHYL-J      
94
Analogue 3: With 2-Phenylethan-1-amine skeleton

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

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

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

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

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

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

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

See also Transcripts: 4.469, 5.588, 5.631, 5.632

Guy, M; Freeman, S; Alder, JF; Brandt, SD. The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines. Cent. Eur. J. Chem., 1 Dec 2008, 6 (4), 526–534. 982 kB. doi:10.2478/s11532-008-0054-z

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

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

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

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

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

115
Analogue 4: With 2-Phenylethan-1-amine skeleton

MDPEA
EA-1297
Homopiperonylamine
3,4-Methylenedioxyphenethylamine

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

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

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

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

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

See also PiHKAL: #10 B
#15 BOH
#16 BOHD
#57 DME
#100 MDA
#128 METHYL-J
 

See also Transcripts: 3.364

See also Chemistry notes VIII: p. 186, MDPEA: Synthesis
p. 187, MDPEA: Synthesis
p. 188, MDPEA: Synthesis
p. 189, MDPEA: Synthesis
p. 190, MDPEA: Synthesis
p. 192, MDPEA: GC-MS
p. 193, MDPEA: GC-MS
p. 208, MDPEA: Synthesis

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

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

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

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

Bruhn, JG; EI-Seedi, HR; Stephanson, N; Beck, O; Shulgin, AT. Ecstasy analogues found in cacti. J. Psychoactive Drugs, 1 Jun 2008, 40 (2), 219–222. 884 kB. doi:10.1080/02791072.2008.10400635

Glennon, RA; Yousif, M; Patrick, G. Stimulus properties of 1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDA) analogs. Pharmacol. Biochem. Behav., 1 Mar 1988, 29 (3), 443–449. 551 kB. doi:10.1016/0091-3057(88)90001-9

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

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.

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

128
Analogue 5: With 2-Phenylethan-1-amine skeleton

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

230
Analogue 6: With 2-Phenylethan-1-amine skeleton

BOHH
3,4-Methylenedioxy-β-hydroxyphenethylamine

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

Formula: C9H11NO3 Molecular weight: 181.18854 g/mol InChI Key: NFDJYUZZSPJWLV-UHFFFAOYSA-N

InChI=1S/C9H11NO3/c10-4-7(11)6-1-2-8-9(3-6)13-5-12-8/h1-3,7,11H,4-5,10H2

PubChem CID: 343688; ChemSpider: 304688

See also PiHKAL: #15 BOH #57 DME #115 MDPEA  

See also Transcripts: 1.149

See also Pharmacology notes I: p. 149, 2-OH-MDA [sic]; MDE; MethyleneDioxyEthanolamine
270
Analogue 7: With Phenylmethanamine skeleton

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

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

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

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

PubChem CID: 14647596; ChemSpider: 11853242

See also PiHKAL: #100 MDA      

King, LA; Meer, AJP; Huizer, H. 1-Phenylethylamines: a new series of illicit drugs? Forensic Sci. Int., 9 Feb 1996, 77 (3), 141–149. 491 kB. doi:10.1016/0379-0738(95)01852-2

271
Analogue 8: With Phenylmethanamine skeleton

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

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

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

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

PubChem CID: 14647597

See also PiHKAL: #100 MDA      
272
Analogue 9: 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      
285
Analogue 10: With 2-Phenylethan-1-amine skeleton

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

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

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

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

PubChem CID: 10776; ChemSpider: 10321

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

See also PiHKAL: #115 MDPEA      

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

326
Analogue 11: With 2-Phenylethan-1-amine skeleton

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

1031
Analogue 12: 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 13: 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 14: 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

2042
Analogue 15: With 2-Amino-1-phenylethanone skeleton

MDMBP
bk-MBDB
Butylone

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

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

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

PubChem CID: 56843046; ChemSpider: 21106270; Drugs Forum: Butylone; Erowid: bk-MBDB; Wikipedia: Butylone

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 35

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

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.

Kanu, AB; Brandt, SD; Williams, MD; Zhang, N; Hill, HH. Analysis of psychoactive cathinones and tryptamines by electrospray ionization atmospheric pressure ion mobility time-of-flight mass spectrometry. Anal. Chem., 17 Sep 2013, 85 (18), 8535–8542. 1636 kB. doi:10.1021/ac401951a

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

Prosser, JM; Nelson, LS. The toxicology of bath salts: a review of synthetic cathinones. J. Med. Toxicol., 1 Nov 2011, 8 (1), 33–22. 267 kB. doi:10.1007/s13181-011-0193-z

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

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

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.

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

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

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

Brandt, SD; Sumnall, HR; Measham, F; Cole, JC. Analyses of second-generation ‘legal highs’ in the UK: Initial findings. Drug Test. Anal., 1 Aug 2010, 2 (8), 377–382. 317 kB. doi:10.1002/dta.155

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.

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

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

2149
Analogue 16: 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 17: 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.

2350
Analogue 18: With 2-Amino-1-phenylethanone skeleton

MDEBP
bk-EBDB
Eutylone
β-Keto-ethylbenzodioxolylbutanamine

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

Formula: C13H17NO3 Molecular weight: 235.27898 g/mol InChI Key: YERSNXHEOIYEGX-UHFFFAOYSA-N

InChI=1S/C13H17NO3/c1-3-10(14-4-2)13(15)9-5-6-11-12(7-9)17-8-16-11/h5-7,10,14H,3-4,8H2,1-2H3

PubChem CID: 57360686; ChemSpider: 26716427; Wikipedia: Eutylone

Shulgin Index: See #93 Methylone; Table: 4 Page: 333 Row: 2

402
Analogue 19: 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 20: 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

2380
Analogue 21: With 2-Amino-1-phenylethanone skeleton

bk-DMBDB
MDDMBP
Dibutylone

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

Formula: C13H17NO3 Molecular weight: 235.27898 g/mol InChI Key: USEBIPUIVPERGC-UHFFFAOYSA-N

InChI=1S/C13H17NO3/c1-4-10(14(2)3)13(15)9-5-6-11-12(7-9)17-8-16-11/h5-7,10H,4,8H2,1-3H3

Wikipedia: Dibutylone

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 37

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

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.

912
Analogue 22: 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 23: 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 24: 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.

6663
Analogue 25: With 2-Phenylethan-1-amine skeleton

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

6664
Analogue 26: With 2-Phenylethan-1-amine skeleton

N-Et-MDPEA

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

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

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

PubChem CID: 19894326

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

6665
Analogue 27: With 2-Phenylethan-1-amine skeleton

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
Analogue 28: With 2-Phenylethan-1-amine skeleton

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

6667
Analogue 29: With 2-Phenylethan-1-amine skeleton

β-Me-MDPEA

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

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

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

PubChem CID: 15764472; ChemSpider: 15383063

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

6668
Analogue 30: With 2-Phenylethan-1-amine skeleton

β,N-Me-MDPEA

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

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

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

PubChem CID: 62088; ChemSpider: 55925

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

6729
Analogue 31: 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

6736
Analogue 32: With 2-Phenylethan-1-amine skeleton

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

6753
Analogue 33: With 2-Amino-1-phenylethanone skeleton

MDDEBP

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

Formula: C15H21NO3 Molecular weight: 263.33214 g/mol InChI Key: OXRVDMCYCGNZKX-UHFFFAOYSA-N

InChI=1S/C15H21NO3/c1-4-12(16(5-2)6-3)15(17)11-7-8-13-14(9-11)19-10-18-13/h7-9,12H,4-6,10H2,1-3H3

Shulgin Index: See #93 Methylone; Table: 4 Page: 333 Row: 3

6754
Analogue 34: With 2-Phenylethan-1-amine skeleton

PBDB

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

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

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

PubChem CID: 56628250

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

6755
Analogue 35: With 2-Amino-1-phenylethanone skeleton

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

Formula: C14H19NO3 Molecular weight: 249.30556 g/mol InChI Key: NRIHOTHAMAUSRO-UHFFFAOYSA-N

InChI=1S/C14H19NO3/c1-3-7-15-11(4-2)14(16)10-5-6-12-13(8-10)18-9-17-12/h5-6,8,11,15H,3-4,7,9H2,1-2H3

6756
Analogue 36: With 2-Phenylethan-1-amine skeleton

IPBDB

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

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

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

PubChem CID: 56608795

Shulgin Index: See #77 MDA; Table: 4 Page: 333 Row: 6

6757
Analogue 37: With 2-Amino-1-phenylethanone skeleton

MDIPBP

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

Formula: C14H19NO3 Molecular weight: 249.30556 g/mol InChI Key: YLUWYCAYKBCHRS-UHFFFAOYSA-N

InChI=1S/C14H19NO3/c1-4-11(15-9(2)3)14(16)10-5-6-12-13(7-10)18-8-17-12/h5-7,9,11,15H,4,8H2,1-3H3

Shulgin Index: See #93 Methylone; Table: 4 Page: 333 Row: 7

6758
Analogue 38: With 2-Phenylethan-1-amine skeleton

HOBDB

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

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

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

Shulgin Index: See #77 MDA; Table: 4 Page: 333 Row: 8

499
Analogue 39: 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

503
Analogue 40: With Phenylmethanamine skeleton

N-Ethyl-N-methylpiperonylamine

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

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

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

PubChem CID: 584519; ChemSpider: 508078

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

564
Analogue 41: 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.

2273
Analogue 42: With 2-Phenylethan-1-amine skeleton

N-Formyl-MDPEA

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

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

InChI=1S/C10H11NO3/c12-6-11-4-3-8-1-2-9-10(5-8)14-7-13-9/h1-2,5-6H,3-4,7H2,(H,11,12)

PubChem CID: 4159944; ChemSpider: 3371813

See also Chemistry notes VIII: p. 191, N-Formyl MDPEA: Synthesis
2287
Analogue 43: With 2-Phenylethan-1-amine skeleton

N-Acetyl-MDPEA

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

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

InChI=1S/C11H13NO3/c1-8(13)12-5-4-9-2-3-10-11(6-9)15-7-14-10/h2-3,6H,4-5,7H2,1H3,(H,12,13)

PubChem CID: 322384; ChemSpider: 285432

See also Chemistry notes VIII: p. 209, N-Acetyl MDPEA: Synthesis
1588
Analogue 44: With 1,3-Diphenylpropan-2-amine skeleton

IUPAC: N-[1,3-Bis(1,3-benzodioxol-5-yl)propan-2-yl]acetamide

Formula: C19H19NO5 Molecular weight: 341.35786 g/mol InChI Key: OTDCZHSIOIIKOM-UHFFFAOYSA-N

InChI=1S/C19H19NO5/c1-12(21)20-15(6-13-2-4-16-18(8-13)24-10-22-16)7-14-3-5-17-19(9-14)25-11-23-17/h2-5,8-9,15H,6-7,10-11H2,1H3,(H,20,21)

PubChem CID: 53321444; ChemSpider: 26386437

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

1587
Analogue 45: With 1,3-Diphenylpropan-2-amine skeleton

IUPAC: N-[1,3-Bis(1,3-benzodioxol-5-yl)propan-2-yl]formamide

Formula: C18H17NO5 Molecular weight: 327.33128 g/mol InChI Key: HNEITUUMXZICIV-UHFFFAOYSA-N

InChI=1S/C18H17NO5/c20-9-19-14(5-12-1-3-15-17(7-12)23-10-21-15)6-13-2-4-16-18(8-13)24-11-22-16/h1-4,7-9,14H,5-6,10-11H2,(H,19,20)

PubChem CID: 53325404; ChemSpider: 26384499

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

1586
Analogue 46: 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

2528
Analogue 47: With Phenylacetaldehyde skeleton

Isopentylone

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

Formula: C13H17NO3 Molecular weight: 235.27898 g/mol InChI Key: CWGUSBFXPSSPQC-UHFFFAOYSA-N

InChI=1S/C13H17NO3/c1-3-4-10(15)13(14-2)9-5-6-11-12(7-9)17-8-16-11/h5-7,13-14H,3-4,8H2,1-2H3

Westphal, F; Junge, T; Girreser, U; Greibl, W; Doering, C. Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 157–167. 853 kB. doi:10.1016/j.forsciint.2011.10.045

Westphal, F; Junge, T. Ring positional differentiation of isomeric N-alkylated fluorocathinones by gas chromatography/tandem mass spectrometry. Forensic Sci. Int., 30 Nov 2012, 223 (1–3), 97–105. 470 kB. doi:10.1016/j.forsciint.2012.08.011

2532
Analogue 48: With 2-Amino-1-phenylethanone skeleton

bk-BDB

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

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

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

ChemSpider: 26954708

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

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

1049
Analogue 49: 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.

One isomer:
2563
Isomer 1

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

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