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ONE; 3,4-Methylenedioxycathinone
2122
Variant: N α R3,4 skeleton isomers all
Analogues: 13 1 1 25 1 41

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.

13 N analogues:
2041
Analogue 1: Adding Methyl at N

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.

2123
Analogue 2: Adding Diethyl at N

DEONE
N,N-Diethyl MDCATH
N,N-Diethyl-3,4-methylenedioxycathinone
N,N-Diethyl-β-keto-3,4-methylenedioxyamphetamine

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

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

InChI=1S/C14H19NO3/c1-4-15(5-2)10(3)14(16)11-6-7-12-13(8-11)18-9-17-12/h6-8,10H,4-5,9H2,1-3H3

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 18

See also Chemistry notes VIII: p. 12, DEONE: GC-MS
p. 13, DEONE: GC-MS

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

2124
Analogue 3: Adding Dimethyl at N

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

2344
Analogue 4: Adding Ethyl at N

EtONE
bk-MDEA
Ethylone
3,4-Methylenedioxyethcathinone

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

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

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

PubChem CID: 57252245; ChemSpider: 21106271; Wikipedia: Ethylone

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 17

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

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

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

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.

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.

6719
Analogue 5: Adding Propyl at N

PrONE

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

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

InChI=1S/C13H17NO3/c1-3-6-14-9(2)13(15)10-4-5-11-12(7-10)17-8-16-11/h4-5,7,9,14H,3,6,8H2,1-2H3

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 19

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.

6720
Analogue 6: Adding Isopropyl at N

iPrONE

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

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

InChI=1S/C13H17NO3/c1-8(2)14-9(3)13(15)10-4-5-11-12(6-10)17-7-16-11/h4-6,8-9,14H,7H2,1-3H3

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 20

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.

6721
Analogue 7: Adding Cyclopropyl at N

cPrONE

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

Formula: C13H15NO3 Molecular weight: 233.2631 g/mol InChI Key: RBWFEKNDTXYOQB-UHFFFAOYSA-N

InChI=1S/C13H15NO3/c1-8(14-10-3-4-10)13(15)9-2-5-11-12(6-9)17-7-16-11/h2,5-6,8,10,14H,3-4,7H2,1H3

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 21

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.

6722
Analogue 8: Adding Allyl at N

ALONE

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

Formula: C13H15NO3 Molecular weight: 233.2631 g/mol InChI Key: NTECKPYFFUUNLP-UHFFFAOYSA-N

InChI=1S/C13H15NO3/c1-3-6-14-9(2)13(15)10-4-5-11-12(7-10)17-8-16-11/h3-5,7,9,14H,1,6,8H2,2H3

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 22

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.

6723
Analogue 9: Adding Prop-1-ynyl at N

PRONE

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

Formula: C13H13NO3 Molecular weight: 231.24722 g/mol InChI Key: LJBKRPYZOMUJGH-UHFFFAOYSA-N

InChI=1S/C13H13NO3/c1-3-6-14-9(2)13(15)10-4-5-11-12(7-10)17-8-16-11/h4-5,7,9,14H,8H2,1-2H3

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 23

6724
Analogue 10: Adding Butyl at N

BuONE

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

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

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

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 24

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.

6725
Analogue 11: Adding Isobutyl at N

iBuONE

IUPAC: 1-(1,3-Benzodioxol-5-yl)-2-[(2-methylpropyl)amino]propan-1-one

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

InChI=1S/C14H19NO3/c1-9(2)7-15-10(3)14(16)11-4-5-12-13(6-11)18-8-17-12/h4-6,9-10,15H,7-8H2,1-3H3

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 25

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.

6726
Analogue 12: Adding sec-Butyl at N

sBuONE

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

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

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

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 26

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.

6727
Analogue 13: Adding tert-Butyl at N

tBuONE

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

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

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

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 27

See also Chemistry notes VIII: p. 14, tBuONE: GC-MS
p. 15, tBuONE: GC-MS

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.

One α analogue:
2532
Analogue 1: Substituting Ethyl for Methyl at α

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

One R3,4 analogue:
2460
Analogue 1: Substituting Dimethoxy for Methylenedioxy at R3,4

3,4-Dimethoxycathinone

IUPAC: 2-Amino-1-(3,4-dimethoxyphenyl)propan-1-one

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

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

PubChem CID: 4656485; ChemSpider: 3845721

Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012

25 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

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

MDA
EA-1298
Amphedoxamine
3,4-Methylenedioxyamphetamine

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB.

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

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

Pentney, AR. An exploration of the history and controversies surrounding MDMA and MDA. J. Psychoactive Drugs, 1 Jul 2001, 33 (3), 213–221. 871 kB. doi:10.1080/02791072.2001.10400568

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

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.

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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

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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

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

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.

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Glennon, RA; Young, R. MDA: An agent that produces stimulus effects similar to those of 3,4-DMA, LSD and cocaine. Eur. J. Pharmacol., 23 Mar 1984, 99 (2–3), 249–250. 139 kB. doi:10.1016/0014-2999(84)90250-4

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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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

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

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

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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

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

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

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

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115
Analogue 3: 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

230
Analogue 4: 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
272
Analogue 5: 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 6: 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 7: 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 8: 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

2125
Analogue 9: 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 10: 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

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

913
Analogue 12: 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

910
Analogue 13: 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.

610
Analogue 14: 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

6667
Analogue 15: 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

6713
Analogue 16: With 2-Phenylethan-1-amine skeleton

β-HO-MDA

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

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

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

PubChem CID: 12348291

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 13

6729
Analogue 17: 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 18: 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 19: 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 20: 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 21: 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

2563
Analogue 22: 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 23: 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

2569
Analogue 24: With 3-Phenylpropan-1-amine skeleton

MMDPPA

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

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

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

PubChem CID: 21125447; ChemSpider: 19992311

Dal Cason, TA; Corbett, CA; Poole, PK; Haseth, JA; Gouldthorpe, DK. An unusual clandestine laboratory synthesis of 3,4-methylenedioxyamphetamine (MDA). Forensic Sci. Int., 30 Nov 2012, 223 (1–3), 279–291. 898 kB. doi:10.1016/j.forsciint.2012.10.002

1049
Analogue 25: 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:
2273
Isomer 1

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
Show all 41 analogues and isomers Show only the 13 N analogues Show only the one α analogues Show only the one R3,4 analogues Show only the 25 skeleton analogues
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