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MDMVP; Pentylone
2346
Variant: N α skeleton isomers all
Analogues: 7 2 27 11 47

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

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

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

PubChem CID: 60208608; Wikipedia: Pentylone

Shulgin Index: See #93 Methylone; Table: 4 Page: 333 Row: 11

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

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

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.

Seven N analogues:
6762
Analogue 1: Substituting Dimethyl for Methyl at N

MDDMVP

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

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

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

Shulgin Index: See #93 Methylone; Table: 4 Page: 333 Row: 12

6764
Analogue 2: Substituting Ethyl for Methyl at N

MDEVP

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

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

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

PubChem CID: 57359308; ChemSpider: 26949655

Shulgin Index: See #93 Methylone; Table: 4 Page: 333 Row: 14

6765
Analogue 3: Substituting Diethyl for Methyl at N

MDDEVP

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

Formula: C16H23NO3 Molecular weight: 277.35872 g/mol InChI Key: CUPSLSIMIHCVIA-UHFFFAOYSA-N

InChI=1S/C16H23NO3/c1-4-7-13(17(5-2)6-3)16(18)12-8-9-14-15(10-12)20-11-19-14/h8-10,13H,4-7,11H2,1-3H3

Shulgin Index: See #93 Methylone; Table: 4 Page: 333 Row: 15

6766
Analogue 4: Substituting Propyl for Methyl at N

MDPVP

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

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

InChI=1S/C15H21NO3/c1-3-5-12(16-8-4-2)15(17)11-6-7-13-14(9-11)19-10-18-13/h6-7,9,12,16H,3-5,8,10H2,1-2H3

Shulgin Index: See #93 Methylone; Table: 4 Page: 333 Row: 16

6767
Analogue 5: Substituting Isopropyl for Methyl at N

MDIPVP

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

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

InChI=1S/C15H21NO3/c1-4-5-12(16-10(2)3)15(17)11-6-7-13-14(8-11)19-9-18-13/h6-8,10,12,16H,4-5,9H2,1-3H3

Shulgin Index: See #93 Methylone; Table: 4 Page: 333 Row: 17

6768
Analogue 6: Substituting Butyl for Methyl at N

MDBVP

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

Formula: C16H23NO3 Molecular weight: 277.35872 g/mol InChI Key: SEIQPCGGBMTHCB-UHFFFAOYSA-N

InChI=1S/C16H23NO3/c1-3-5-9-17-13(6-4-2)16(18)12-7-8-14-15(10-12)20-11-19-14/h7-8,10,13,17H,3-6,9,11H2,1-2H3

Shulgin Index: See #93 Methylone; Table: 4 Page: 333 Row: 18

6769
Analogue 7: Substituting sec-Butyl for Methyl at N

MDSBVP

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

Formula: C16H23NO3 Molecular weight: 277.35872 g/mol InChI Key: BKWYAZGGZTXSSF-UHFFFAOYSA-N

InChI=1S/C16H23NO3/c1-4-6-13(17-11(3)5-2)16(18)12-7-8-14-15(9-12)20-10-19-14/h7-9,11,13,17H,4-6,10H2,1-3H3

Shulgin Index: See #93 Methylone; Table: 4 Page: 333 Row: 19

Two α analogues:
2041
Analogue 1: Substituting Methyl for Propyl at α

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

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

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

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

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.

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.

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.

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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

2042
Analogue 2: Substituting Ethyl for Propyl at α

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

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.

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.

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.

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

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

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

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

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

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

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

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

27 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  

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

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

115
Analogue 2: 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 Chemistry notes VIII: p. 186, MDPEA: Synthesis
p. 187, MDPEA: Synthesis
p. 188, MDPEA: Synthesis
p. 189, MDPEA: Synthesis
p. 190, MDPEA: Synthesis
p. 192, MDPEA: GC-MS
p. 193, MDPEA: GC-MS
p. 208, MDPEA: Synthesis

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

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

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

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

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

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

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

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

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

129
Analogue 3: With 2-Phenylethan-1-amine skeleton

METHYL-K
2-Methylamino-1-(3,4-methylenedioxyphenyl)pentane
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-pentylamine
N-Methyl-α-propyl-3,4-methylenedioxyphenethylamine

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

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

InChI=1S/C13H19NO2/c1-3-4-11(14-2)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: 17757316; ChemSpider: 21106348; Wikipedia: Methylbenzodioxolylpentanamine

Shulgin Index: See #77 MDA; Table: 4 Page: 333 Row: 10

See also PiHKAL: #78 ETHYL-K      

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

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 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      
285
Analogue 6: 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.

291
Analogue 7: With 2-Phenylethan-1-amine skeleton

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

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

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

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

PubChem CID: 22007048; ChemSpider: 13616549

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

See also PiHKAL: #100 MDA #128 METHYL-J #129 METHYL-K  
1031
Analogue 8: With Prop-2-en-1-ylbenzene skeleton

Safrole
3,4-Methylenedioxyphenylprop-2-ene

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

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

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

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

See also PiHKAL: #100 MDA #157 TMA    

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

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

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

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

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

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

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

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

1032
Analogue 9: 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 10: 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

2143
Analogue 11: With 2-Cyclic-amine-1-phenylethanone skeleton

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

2149
Analogue 12: With 2,3-Dihydro-1H-inden-2-amine skeleton

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

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

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

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

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

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

See also PiHKAL: #100 MDA      

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

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

Nichols, DE; Brewster, WK; Johnson, MP; Oberlender, R; Riggs, RM. Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA). J. Med. Chem., 1 Jan 1990, 33 (2), 703–710. 1078 kB. doi:10.1021/jm00164a037

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

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

Elie, L; Baron, M; Croxton, R; Elie, M. Microcrystalline identification of selected designer drugs. Forensic Sci. Int., 10 Jan 2012, 214 (1–3),. 1364 kB. doi:10.1016/j.forsciint.2011.08.005

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

Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 581–586. 586 kB. doi:10.1016/0091-3057(91)90017-V

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

2151
Analogue 13: With 2,3-Dihydro-1H-inden-2-amine skeleton

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

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

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

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

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

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

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

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

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

402
Analogue 14: 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

415
Analogue 15: 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

911
Analogue 16: 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 17: 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.

6667
Analogue 18: 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 19: 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 20: 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 21: 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 22: 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 23: 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 24: 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

2565
Analogue 25: With 2-Cyclic-amine-1-phenylethanone skeleton

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

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

InChI=1S/C17H23NO3/c1-2-6-14(18-9-4-3-5-10-18)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

2568
Analogue 26: With 2-Cyclic-amine-1-phenylethanone skeleton

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

Formula: C18H25NO3 Molecular weight: 303.396 g/mol InChI Key: SXETTXLNCVUJHJ-UHFFFAOYSA-N

InChI=1S/C18H25NO3/c1-2-7-15(19-10-5-3-4-6-11-19)18(20)14-8-9-16-17(12-14)22-13-21-16/h8-9,12,15H,2-7,10-11,13H2,1H3

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

1049
Analogue 27: 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.

11 isomers:
143
Isomer 1

PROPYNYL
4-Propynyloxy-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-(2-propynyloxy)phenethylamine

IUPAC: 2-[3,5-Dimethoxy-4-(prop-2-yn-1-yloxy)phenyl]ethan-1-amine

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

InChI=1S/C13H17NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h1,8-9H,5-7,14H2,2-3H3

PubChem CID: 44719613; ChemSpider: 21106371; Wikipedia: Propynyl (psychedelic)

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 17

See also PiHKAL: #99 MAL      
2029
Isomer 2

MeTriox

IUPAC: 1-(4-Methyl-6,7-dihydrofuro[2,3-f][1,3]benzodioxol-8-yl)propan-2-amine

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

InChI=1S/C13H17NO3/c1-7(14)5-10-9-3-4-15-11(9)8(2)12-13(10)17-6-16-12/h7H,3-6,14H2,1-2H3

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

2350
Isomer 3

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

2376
Isomer 4

2-Methylbutylone

IUPAC: 2-(Methylamino)-1-(4-methyl-1,3-benzodioxol-5-yl)butan-1-one

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

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

2377
Isomer 5

5-Methylbutylone

IUPAC: 2-(Methylamino)-1-(7-methyl-1,3-benzodioxol-5-yl)butan-1-one

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

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

2039
Isomer 6

MeO-2C-2,6-IFLY
Mescaline-FLY
M-FLY

IUPAC: 2-(8-Methoxy-2,3,5,6-tetrahydrobenzo[1,2-b:5,4-b′]difuran-4-yl)ethan-1-amine

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

InChI=1S/C13H17NO3/c1-15-13-11-9(3-6-16-11)8(2-5-14)10-4-7-17-12(10)13/h2-7,14H2,1H3

PubChem CID: 10609802; ChemSpider: 8785169

Shulgin Index: See #68 FLY; Table: 7 Page: 356 Row: 16

Monte, AP; Waldman, SR; Marona-Lewicka, D; Wainscott, DB; Nelson, DL; Sanders-Bush, E; Nichols, DE. Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives. J. Med. Chem., 1 Jan 1997, 40 (19), 2997–3008. 367 kB. doi:10.1021/jm970219x

2380
Isomer 7

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

6719
Isomer 8

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
Isomer 9

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.

2528
Isomer 10

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

1085
Isomer 11

IUPAC: 4-[2-(Acetylamino)propyl]phenyl acetate

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

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

PubChem CID: 520328; ChemSpider: 453870

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

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