PiHKAL • info | explore | PiHKAL#100 MDA; SI#77 MDA

29 N analogues:

FLEA

Analogue 1: Adding Hydroxy and Methyl at N

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

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

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

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

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

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

See also PiHKAL:	#114 MDOH

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

MDAL

101

Analogue 2: Adding Allyl at N

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

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

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

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

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

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

See also Pharmacology notes II:	p. 255, MDAL

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

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

MDBU

102

Analogue 3: Adding n-Butyl at N

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

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

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

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

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

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

See also PiHKAL:	#103 MDBZ	#112 MDMEOET

See also Pharmacology notes II:	p. 262, MDBU

MDBZ

103

Analogue 4: Adding Benzyl at N

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

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

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

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

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

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

See also PiHKAL:	#102 MDBU	#106 MDE

See also Pharmacology notes II:	p. 308, MDBZ

MDCPM

104

Analogue 5: Adding Cyclopropylmethyl at N

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

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

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

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

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

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

See also Pharmacology notes II:	p. 272, MDCPM

MDDM

105

Analogue 6: Adding Dimethyl at N

MDDM
MDDMA
N,N-Dimethyl-MDA
N,N-Dimethyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N,N-dimethylamphetamine

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

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

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

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

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

See also PiHKAL:	#103 MDBZ

See also Pharmacology notes II:	p. 244, MDDM

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

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

MDE

106

Analogue 7: Adding Ethyl at N

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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

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

MDHOET

107

Analogue 8: Adding 2-Hydroxyethyl at N

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

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

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

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

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

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

See also Pharmacology notes II:	p. 250, MDHOET

MDIP

108

Analogue 9: Adding Isopropyl at N

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

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

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

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

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

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

See also Pharmacology notes II:	p. 237, MDIP

MDMA

109

Analogue 10: Adding Methyl at N

MDMA
XTC
X
MDM
ADAM
Ecstasy
N-Methyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N-methylamphetamine

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

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

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

PubChem CID: 1615; ChemSpider: 1556; Drugs Forum: MDMA; Erowid: MDMA; Wikipedia: MDMA

Shulgin Index: #82 MDMA; Table: 4 Page: 331 Row: 21

See also PiHKAL:	#14 BOD #20 2C-B #34 2C-N #39 2C-T #40 2C-T-2 #43 2C-T-7 #58 DMMDA #67 DOI #77 ETHYL-J #81 FLEA #94 J #96 M #98 MADAM-6	#100 MDA #101 MDAL #102 MDBU #103 MDBZ #104 MDCPM #105 MDDM #106 MDE #107 MDHOET #108 MDIP #110 MDMC #111 MDMEO #112 MDMEOET #113 MDMP	#114 MDOH #116 MDPH #117 MDPL #118 MDPR #119 ME #122 MEM #126 METHYL-DMA #127 METHYL-DOB #128 METHYL-J #130 METHYL-MA #132 MMDA #133 MMDA-2 #142 PEA
See also TiHKAL:	#1 AL-LAD #4 DIPT #5 α,O-DMS #8 α,N-DMT #11 α-ET	#13 Harmaline #17 4-HO-DIPT #18 4-HO-DMT #22 4-HO-MIPT #31 5,6-MDO-DMT	#38 5-MeO-DMT #51 PRO-LAD #55 α,N,O-TMS

See also Pharmacology notes II:

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Shulgin, AT. What is MDMA?. PharmChem Newsletter, 1 Jan 1985, 14 (3), 3–11. 952 kB.

Trudeau, GB. Ecstasy: Whither the future?. In Doonesbury Deluxe; , Henry Holt and Company, 19 Aug 1985; . 3328 kB.

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

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

Meyers-Riggs, B. The mirrored magic of MDMA. countyourculture: rational exploration of the underground, 23 May 2011.

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

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. doi:10.1016/j.talanta.2007.06.012

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

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

Torre, R; Farré, M. Neurotoxicity of MDMA (ecstasy): the limitations of scaling from animals to humans. Trends Pharmacol. Sci., 1 Oct 2004, 25 (10), 505–508. 104 kB. doi:10.1016/j.tips.2004.08.001

Sprague, JE; Nichols, DE. Neurotoxicity of MDMA (ecstasy): beyond metabolism. Trends Pharmacol. Sci., 1 Feb 2005, 26 (2), 59–60. 60 kB. doi:10.1016/j.tips.2004.12.001

Torre, R; Farré, M; Monks, TJ; Jones, D. Response to Sprague and Nichols: Contribution of metabolic activation to MDMA neurotoxicity. Trends Pharmacol. Sci., 1 Feb 2005, 26 (2), 60–61. 60 kB. doi:10.1016/j.tips.2004.12.004

Lieberman, JA; Mailman, RB; Duncan, G; Sikich, L; Chakos, M; Nichols, DE; Kraus, JE. Serotonergic basis of antipsychotic drug effects in schizophrenia. Biol. Psychiat., 1 Dec 1998, 44 (11), 1099–1117. 154 kB. doi:10.1016/S0006-3223(98)00187-5

Baumann, MH; Clark, RD; Budzynski, AG; Partilla, JS; Blough, BE; Rothman, RB. N-Substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or ‘Ecstasy’). Neuropsychopharmacology, 1 Mar 2005, 30 (3), 550–560. 184 kB. doi:10.1038/sj.npp.1300585

Puerta, E; Aguirre, N. Methylenedioxymethamphetamine (MDMA, ‘Ecstasy’): Neurodegeneration versus neuromodulation. Pharmaceuticals, 5 Jul 2011, 4 (7), 992–1018. 411 kB. doi:10.3390/ph4070992

Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. doi:10.1016/j.pbb.2007.06.001

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

Anderson, GM; Braun, G; Braun, U; Nichols, DE; Shulgin, AT. Absolute configuration and psychotomimetic activity. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 8–15. 457 kB.

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

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

Shulgin, AT. The background and chemistry of MDMA. J. Psychoactive Drugs, 1 Jan 1986, 18 (4), 291–304. 13190 kB. doi:10.1080/02791072.1986.10472361

Brown, CR; McKinney, H; Osterloh, JD; Shulgin, AT; Jacob, P; Olson, KR. Severe adverse reaction to 3,4-methylenedioxymethamphetamine (MDMA). Vet. Hum. Toxicol., 1 Oct 1986, 28 (5), 490. 239 kB.

Shulgin, AT. History of MDMA. In Ecstasy: The Clinical, Pharmacological and Neurotoxicological Effects of the Drug MDMA; Peroutka, S, Ed., Kluwer Academic Publishers, Norwell, MA, 1 Jan 1990; pp 1–20. 3840 kB.

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

Nichols, DE; Lloyd, DH; Hoffman, AJ; Nichols, MB; Yim, GKW. Effects of certain hallucinogenic amphetamine analogues on the release of [3H]-serotonin from rat brain synaptosomes. J. Med. Chem., 1 Jan 1982, 25 (5), 530–535. 804 kB. doi:10.1021/jm00347a010

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

Steele, TD; Nichols, DE; Yim, GKW. MDMA transiently alters biogenic amines and metabolites in mouse brain and heart. Pharmacol. Biochem. Behav., 1 Jan 1989, 34 (2), 223–227. 477 kB. doi:10.1016/0091-3057(89)90303-1

Johnson, MP; Nichols, DE. Neurotoxic effects of the alpha-ethyl homologue of MDMA following subacute administration. Pharmacol. Biochem. Behav., 1 Jan 1989, 33 (1), 105–108. 399 kB. doi:10.1016/0091-3057(89)90437-1

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

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

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

Huang, X; Nichols, DE. 5-HT2 receptor-mediated potentiation of dopamine synthesis and central serotonergic deficits. Eur. J. Pharmacol., 1 Jan 1993, 238 (2–3), 291–296. 553 kB. doi:10.1016/0014-2999(93)90859-G

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

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

Callaghan, PD. Comparative neuropharmacology of the substituted amphetamines, p-methoxyamphatamine (PMA) & 3,4-methylenedioxymethamphetamine (MDMA). Ph. D. Thesis, University of Adelaide, Adelaide, Australia, 1 Aug 2008. 1551 kB.

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MDMEO

111

Analogue 11: Adding Methoxy at N

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

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

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

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

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

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

See also Pharmacology notes II:	p. 248, MDMEO

MDMEOET

112

Analogue 12: Adding 2-Methoxyethyl at N

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

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

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

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

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

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

See also Pharmacology notes II:	p. 245, MDMEOET

MDOH

114

Analogue 13: Adding Hydroxy at N

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

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

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

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

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

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

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

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

MDPL

117

Analogue 14: Adding Prop-2-ynyl at N

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

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

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

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

ChemSpider: 21106336; Wikipedia: Methylenedioxypropargylamphetamine

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

See also Pharmacology notes II:	p. 264, MDPL

MDPR

118

Analogue 15: Adding n-Propyl at N

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

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

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

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

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

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

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

See also Pharmacology notes II:	p. 254, MDPR

MDIB

276

Analogue 16: Adding Isobutyl at N

MDIB
3,4-Methylenedioxy-N-isobutylamphetamine

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

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

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

PubChem CID: 3058000; ChemSpider: 2319188

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

See also PiHKAL:	#103 MDBZ

MDTB

277

Analogue 17: Adding tert-Butyl at N

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

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

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

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

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

See also PiHKAL:	#103 MDBZ

MDAM

278

Analogue 18: Adding n-Pentyl at N

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

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

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

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

PubChem CID: 69396692

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

See also PiHKAL:	#103 MDBZ

MDHE

279

Analogue 19: Adding n-Hexyl at N

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

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

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

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

PubChem CID: 69454836

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

See also PiHKAL:	#103 MDBZ

MDOC

280

Analogue 20: Adding n-Octyl at N

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

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

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

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

PubChem CID: 69453458

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

See also PiHKAL:	#103 MDBZ

MDDEA; MDDE

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

281

Analogue 21: Adding Diethyl at N

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

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

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

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

PubChem CID: 69390377

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

See also PiHKAL:	#103 MDBZ

MDCM

282

Analogue 22: Adding Cyanomethyl at N

MDCM
3,4-Methylenedioxy-N-cyanomethylamphetamine

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

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

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

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

See also PiHKAL:	#103 MDBZ

MDBA

283

Analogue 23: Adding tert-Butylamino at N

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

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

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

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

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

See also PiHKAL:	#103 MDBZ

284

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

284

Analogue 24: Adding 2,2,2-Trifluoroethyl at N

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

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

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

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

See also PiHKAL:	#106 MDE

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

MDMEA

6675

Analogue 25: Adding Methyl and Ethyl at N

MDMEA

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

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

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

PubChem CID: 6421392; ChemSpider: 4926929

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

MDMPA

6676

Analogue 26: Adding Methyl and n-Propyl at N

MDMPA

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

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

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

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

MDMIPA

6677

Analogue 27: Adding Methyl and Isopropyl at N

MDMIPA

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

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

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

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

MDSB

6703

Analogue 28: Adding sec-Butyl at N

MDSB

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

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

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

PubChem CID: 3087181; ChemSpider: 2343683

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

N-Formyl-MDMA

2477

Analogue 29: Adding Formyl and Methyl at N

N-Formyl-MDMA

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

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

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

PubChem CID: 559857; ChemSpider: 486685

Seven α analogues:

Analogue 1: Substituting Ethyl for Methyl at α

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

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

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

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

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

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

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

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

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

MDPEA

115

Analogue 2: Removing Methyl at α

MDPEA
EA-1297
Homopiperonylamine
3,4-Methylenedioxyphenethylamine

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

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

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

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

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

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

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

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

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

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

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

MDPH

116

Analogue 3: Substituting Dimethyl for Methyl at α

MDPH
3,4-Methylenedioxyphentermine
α,α-Dimethyl-3,4-methylenedioxyphenethylamine

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

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

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

PubChem CID: 13020598; ChemSpider: 15204207; Wikipedia: Methylenedioxyphentermine

Shulgin Index: See #77 MDA; Table: 4 Page: 332 Row: 30

See also PiHKAL:	#8 ARIADNE	#113 MDMP

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

291

Analogue 4: Substituting n-Propyl for Methyl at α

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

L; 2-Amino-1-(3,4-methylenedioxyphenyl)hexane

292

Analogue 5: Substituting n-Butyl for Methyl at α

L
2-Amino-1-(3,4-methylenedioxyphenyl)hexane

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

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

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

ChemSpider: 26670697

Shulgin Index: See #77 MDA; Table: 4 Page: 333 Row: 21

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

α-Et-MDA

6732

Analogue 6: Substituting Methyl and Ethyl for Methyl at α

α-Et-MDA

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

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

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

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

α-iPr-MDPEA

6770

Analogue 7: Substituting Isopropyl for Methyl at α

α-iPr-MDPEA

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

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

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

ChemSpider: 26670831

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

One β analogue:
β-HO-MDA 6713	Analogue 1: Adding Hydroxy at β 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

Four R2 analogues:

MMDA-3a

134

Analogue 1: Adding Methoxy at R2

MMDA-3a
2-Methoxy-3,4-methylenedioxyamphetamine

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

Formula: C11H15NO3 Molecular weight: 209.2417 g/mol InChI Key: OSJXZWMDUMAITM-UHFFFAOYSA-N Properties: Essential amphetamine

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

PubChem CID: 90967; ChemSpider: 82148; Wikipedia: MMDA (drug)

Shulgin Index: #99 MMDA-3a; Table: 5 Page: 338 Row: 31

See also PiHKAL:	#135 MMDA-3b	#157 TMA

See also Pharmacology notes I:	p. 62.1, MMDA-3a: Subacute evaluation p. 66, MMDA-3a: Subjective response p. 67, MMDA-3a: Subjective response p. 68, MMDA-3a: Subjective response p. 69, MMDA-3a: Subjective response p. 70, MMDA-3a: Subjective response p. 71, MMDA-3a: Subjective response p. 83, Further effects of MMDA-3a
See also Pharmacology notes II:	p. 281, MMDA-3a: Subacute evaluation

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

2T-MMDA-3a

166

Analogue 2: Adding Methylthio at R2

2T-MMDA-3a
2-Methylthio-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-2-methylthioamphetamine

IUPAC: 1-[4-(Methylsulfanyl)-1,3-benzodioxol-5-yl]propan-2-amine

Formula: C11H15NO2S Molecular weight: 225.3073 g/mol InChI Key: NMNCXGKWTVPITN-UHFFFAOYSA-N

InChI=1S/C11H15NO2S/c1-7(12)5-8-3-4-9-10(11(8)15-2)14-6-13-9/h3-4,7H,5-6,12H2,1-2H3

PubChem CID: 44719661; ChemSpider: 23553177; Wikipedia: MMDA (drug)

Shulgin Index: See #99 MMDA-3a; Table: 5 Page: 338 Row: 33

2-Me-MDA; 2-Methyl-MDA

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

2144

Analogue 3: Adding Methyl at R2

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

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

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

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

PubChem CID: 10104064; ChemSpider: 8279591; Wikipedia: 2-Methyl-MDA

Shulgin Index: See #77 MDA; Table: 5 Page: 338 Row: 24

Parker, MA; Marona-Lewicka, D; Kurrasch, D; Shulgin, AT; Nichols, DE. Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA). J. Med. Chem., 1 Jan 1998, 41 (6), 1001–1005. 117 kB. doi:10.1021/jm9705925

Roman, DL; Saldaña, SN; Nichols, DE; Carroll, FI; Barker, EL. Distinct molecular recognition of psychostimulants by human and Drosophila serotonin transporters. J. Pharmacol. Exp. Ther., 1 Jan 2004, 308 (2), 679–687. 519 kB. doi:10.1124/jpet.103.057836

2F-MDA

488

Analogue 4: Adding Fluoro at R2

2F-MDA

IUPAC: 1-(4-Fluoro-1,3-benzodioxol-5-yl)propan-2-amine

Formula: C10H12FNO2 Molecular weight: 197.2061832 g/mol InChI Key: GMJUJRHJNRBOCP-UHFFFAOYSA-N

InChI=1S/C10H12FNO2/c1-6(12)4-7-2-3-8-10(9(7)11)14-5-13-8/h2-3,6H,4-5,12H2,1H3

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

22 R3,4 analogues:

3,4-DMA

Analogue 1: Substituting Dimethoxy for Methylenedioxy at R3,4

3,4-DMA
DMA
3,4-Dimethoxyamphetamine

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

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: KAZPHAGSWZTKDW-UHFFFAOYSA-N Properties: Essential amphetamine

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

PubChem CID: 8423; ChemSpider: 8116; Wikipedia: Dimethoxyamphetamine

Shulgin Index: #38 DMA; Table: 4 Page: 330 Row: 17

See also PiHKAL:	#53 2,4-DMA	#124 META-DOB	#157 TMA

See also Pharmacology notes I:	p. 143, 3,4-DMA

Butterick, JR; Unrau, AM. Studies on theoretical psychotogens. Synthesis of O-methylated analogs of catecholamine neurotransmitters and metabolic precursors. Can. J. Chem., 1 Jan 1974, 52 (16), 2873–2879. 305 kB. doi:10.1139/v74-418

Barfknecht, CF; Nichols, DE. Effects of S-(+)- and R-(-)-3,4,dimethoxyphenylisopropylamines in the rat. J. Med. Chem., 1 Jan 1972, 15 (1), 109–110. 295 kB. doi:10.1021/jm00271a037

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. doi:10.1021/jm00263a013

Butterick, JR. Synthesis of O-transmethylated catecholamines and psychodysleptic β-phenylisopropylamines. Ph. D. Thesis, Simon Faser University, Burnaby, BC, Canada, 11 Mar 1975. 6069 kB. External examiner: A. T. Shulgin!.

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

7-Me-MDA; EDA

7-Me-MDA; 3,4-Ethylidenedioxyamphetamine

273

Analogue 2: Substituting Ethylidenedioxy for Methylenedioxy at R3,4

7-Me-MDA
EDA
3,4-Ethylidenedioxyamphetamine

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

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

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

PubChem CID: 130542; ChemSpider: 115478

Shulgin Index: See #77 MDA; Table: 4 Page: 333 Row: 31, #65 EDA; Table: 4 Page: 333 Row: 37

See also PiHKAL:	#100 MDA	#120 MEDA

Nichols, DE; Kostuba, LJ. Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring. J. Med. Chem., 1 Jan 1979, 22 (10), 1264–1267. 606 kB. doi:10.1021/jm00196a022

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

IDA

274

Analogue 3: Substituting Isopropylidinedioxy for Methylenedioxy at R3,4

IDA
3,4-Isopropylidenedioxyamphetamine

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

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

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

PubChem CID: 130544; ChemSpider: 115480

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

See also PiHKAL:	#100 MDA	#120 MEDA

IAP

2043

Analogue 4: Substituting Trimethylene for Methylenedioxy at R3,4

IAP
Indanylaminopropane

IUPAC: 1-(2,3-Dihydro-1H-inden-5-yl)propan-2-amine

Formula: C12H17N Molecular weight: 175.27008 g/mol InChI Key: QYVNZHBQYJRLEX-UHFFFAOYSA-N

InChI=1S/C12H17N/c1-9(13)7-10-5-6-11-3-2-4-12(11)8-10/h5-6,8-9H,2-4,7,13H2,1H3

PubChem CID: 192600; ChemSpider: 167142; Erowid: IAP; Wikipedia: Indanylaminopropane

Shulgin Index: See #42 DMeA; Table: 4 Page: 327 Row: 26

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

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

F2-MDA

2314

Analogue 5: Substituting 1,1-Difluoromethylenedioxy for Methylenedioxy at R3,4

F2-MDA
DFMDA
Difluoro-MDA
3,4-(1,1-Difluoromethylenedioxy)amphetamine
3,4-Difluoromethylenedioxyamphetamine

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

Formula: C10H11F2NO2 Molecular weight: 215.1966464 g/mol InChI Key: BHDXKBALNFHXDV-UHFFFAOYSA-N

InChI=1S/C10H11F2NO2/c1-6(13)4-7-2-3-8-9(5-7)15-10(11,12)14-8/h2-3,5-6H,4,13H2,1H3

PubChem CID: 57467735; ChemSpider: 26495356

Shulgin Index: See #77 MDA; Table: 4 Page: 333 Row: 26

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

BF6AP; 6-APDB

BF6AP; 1-(2,3-Dihydro-1-benzofuran-6-yl)propan-2-amine

2351

Analogue 6: Substituting 2,3-Dihydrofuro[d] for Methylenedioxy at R3,4

BF6AP
6-APDB
4-Desoxy-MDA

IUPAC: 1-(2,3-Dihydro-1-benzofuran-6-yl)propan-2-amine

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: VRNGXHJGMCJRSQ-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-3,7-8H,4-6,12H2,1H3

PubChem CID: 192599; ChemSpider: 167141; Wikipedia: 6-APDB

Shulgin Index: See #77 MDA; Table: 4 Page: 327 Row: 29, See #77 MDA; Table: 4 Page: 331 Row: 9

Casale, JF; Hays, PA. The characterization of 5- and 6-(2-aminopropyl)-2,3-dihydrobenzofuran. Microgram J., 2011, 8 (2), 62–74. 1031 kB.

Casale, JF. Letter to the editor regarding: Abbreviations for 5- and 6-(2-aminopropyl)-2,3-dihydrobenzofuran vs. 5- and 6-(2-aminopropyl)benzofuran: A clarification of “APB” and “APDB”. Microgram J., 2012, 9 (1), 46. 220 kB.

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

BF5AP; 5-APDB

BF5AP; 5-(2-Aminopropyl)-2,3-dihydrobenzofuran

2352

Analogue 7: Substituting 2,3-Dihydrofuro[b] for Methylenedioxy at R3,4

BF5AP
5-APDB
3-Desoxy-MDA
5-(2-Aminopropyl)-2,3-dihydrobenzofuran

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

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: PZTJXZKNTPCPJL-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11/h2-3,7-8H,4-6,12H2,1H3

PubChem CID: 192601; ChemSpider: 167143; Wikipedia: 5-APDB

Casale, JF; Hays, PA. The characterization of 5- and 6-(2-aminopropyl)-2,3-dihydrobenzofuran. Microgram J., 2011, 8 (2), 62–74. 1031 kB.

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

NAP; Naphthylaminopropane

2353

Analogue 8: Substituting Benzo for Methylenedioxy at R3,4

NAP
PAL-287
Naphthylaminopropane

IUPAC: 1-(Naphthalen-2-yl)propan-2-amine

Formula: C13H15N Molecular weight: 185.2649 g/mol InChI Key: UPQSZFKXKRKCGZ-UHFFFAOYSA-N

InChI=1S/C13H15N/c1-10(14)8-11-6-7-12-4-2-3-5-13(12)9-11/h2-7,9-10H,8,14H2,1H3

PubChem CID: 10219723; ChemSpider: 8395215; Wikipedia: Napthylaminopropane

Vilches-Herrera, M; Miranda-Sepúlveda, J; Rebolledo-Fuentes, M; Fierro, A; Lühr, S; Iturriaga-Vasquez, P; Cassels, BK; Reyes-Parada, M. Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors. Bioorg. Med. Chem., 15 Mar 2009, 17 (6), 2452–2460. 509 kB. doi:10.1016/j.bmc.2009.01.074

Rothman, RB; Blough, BE; Baumann, MH. Dual dopamine-5-HT releasers: potential treatment agents for cocaine addiction. Trends Pharmacol. Sci., 1 Dec 2006, 27 (12), 612–618. 519 kB. doi:10.1016/j.tips.2006.10.006

Rothman, RB; Blough, BE; Baumann, MH. Dual dopamine/serotonin releasers as potential medications for stimulant and alcohol addictions. AAPS J., 2007, 9 (1), E1–E10. 999 kB. doi:10.1208/aapsj0901001

TAP

2354

Analogue 9: Substituting Tetramethylene for Methylenedioxy at R3,4

TAP
Tetralinylaminopropane

IUPAC: 1-(5,6,7,8-Tetrahydronaphthalen-2-yl)propan-2-amine

Formula: C13H19N Molecular weight: 189.29666 g/mol InChI Key: UTVKUFYOPJCDPE-UHFFFAOYSA-N

InChI=1S/C13H19N/c1-10(14)8-11-6-7-12-4-2-3-5-13(12)9-11/h6-7,9-10H,2-5,8,14H2,1H3

PubChem CID: 14964398; ChemSpider: 23204045; Wikipedia: Tetralinylaminopropane

Shulgin Index: See #42 DMeA; Table: 4 Page: 327 Row: 28

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

6-APB

2358

Analogue 10: Substituting Furo[d] for Methylenedioxy at R3,4

6-APB
BenzoFury
6-(2-Aminopropyl)benzofuran

IUPAC: 1-(1-Benzofuran-6-yl)propan-2-amine

Formula: C11H13NO Molecular weight: 175.22702 g/mol InChI Key: FQDAMYLMQQKPRX-UHFFFAOYSA-N

InChI=1S/C11H13NO/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-5,7-8H,6,12H2,1H3

PubChem CID: 9794343; ChemSpider: 7970110; Drugs Forum: 6-APB; Wikipedia: 6-APB

Meyers-Riggs, B. AIRCR jumps the shark. countyourculture: rational exploration of the underground, 30 Dec 2010.

5-APB

2359

Analogue 11: Substituting Furo[b] for Methylenedioxy at R3,4

5-APB
5-(2-Aminopropyl)benzofuran

IUPAC: 1-(1-Benzofuran-5-yl)propan-2-amine

Formula: C11H13NO Molecular weight: 175.22702 g/mol InChI Key: VKUMKUZDZWHMQU-UHFFFAOYSA-N

InChI=1S/C11H13NO/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11/h2-5,7-8H,6,12H2,1H3

PubChem CID: 9837232; ChemSpider: 8012953; Wikipedia: 5-APB

5-API; 5-IT

5534

Analogue 12: Substituting Pyrrolo[b] for Methylenedioxy at R3,4

5-API
5-IT
5-(2-Aminopropyl)indole
3,4-Pyrrolo[b]amphetamine

IUPAC: 1-(1H-Indol-5-yl)propan-2-amine

Formula: C11H14N2 Molecular weight: 174.24226 g/mol InChI Key: AULGMISRJWGTBA-UHFFFAOYSA-N

InChI=1S/C11H14N2/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11/h2-5,7-8,13H,6,12H2,1H3

PubChem CID: 55253543; ChemSpider: 25991467; Erowid: 5-IT; Wikipedia: 5-(2-Aminopropyl)indole

See also TiHKAL:	#48 α-MT

DHA

447

Analogue 13: Substituting Dihydroxy for Methylenedioxy at R3,4

DHA

IUPAC: 4-(2-Aminopropyl)benzene-1,2-diol

Formula: C9H13NO2 Molecular weight: 167.20502 g/mol InChI Key: KSRGADMGIRTXAF-UHFFFAOYSA-N

InChI=1S/C9H13NO2/c1-6(10)4-7-2-3-8(11)9(12)5-7/h2-3,5-6,11-12H,4,10H2,1H3

PubChem CID: 17005; ChemSpider: 16110

Shulgin Index: #33 DHA; Table: 4 Page: 328 Row: 26

IBF5AP

6480

Analogue 14: Substituting 2,5-Dihydrofuro[c] for Methylenedioxy at R3,4

IBF5AP

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

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: SLAQRQKVPQBGDF-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8(12)4-9-2-3-10-6-13-7-11(10)5-9/h2-3,5,8H,4,6-7,12H2,1H3

Shulgin Index: See #77 MDA; Table: 4 Page: 327 Row: 30

6787

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

6787

Analogue 15: Substituting Ethylenedioxy for Methylenedioxy at R3,4

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

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

InChI=1S/C11H15NO2/c1-8(12)6-9-2-3-10-11(7-9)14-5-4-13-10/h2-3,7-8H,4-6,12H2,1H3

PubChem CID: 5017291; ChemSpider: 4196440

6-MeO-NAP

2466

Analogue 16: Substituting 4-Methoxybenzo for Methylenedioxy at R3,4

6-MeO-NAP

IUPAC: 1-(6-Methoxynaphthalen-2-yl)propan-2-amine

Formula: C14H17NO Molecular weight: 215.29088 g/mol InChI Key: YYZOZFYDYBTLPQ-UHFFFAOYSA-N

InChI=1S/C14H17NO/c1-10(15)7-11-3-4-13-9-14(16-2)6-5-12(13)8-11/h3-6,8-10H,7,15H2,1-2H3

PubChem CID: 18070083; ChemSpider: 16825590

6-EtO-NAP

2467

Analogue 17: Substituting 4-Ethoxybenzo for Methylenedioxy at R3,4

6-EtO-NAP

IUPAC: 1-(6-Ethoxynaphthalen-2-yl)propan-2-amine

Formula: C15H19NO Molecular weight: 229.31746 g/mol InChI Key: RIBPBDJODPIITD-UHFFFAOYSA-N

InChI=1S/C15H19NO/c1-3-17-15-7-6-13-9-12(8-11(2)16)4-5-14(13)10-15/h4-7,9-11H,3,8,16H2,1-2H3

PubChem CID: 44590294; ChemSpider: 24688119

6-PrO-NAP

2468

Analogue 18: Substituting 4-n-Propoxybenzo for Methylenedioxy at R3,4

6-PrO-NAP

IUPAC: 1-(6-Propoxynaphthalen-2-yl)propan-2-amine

Formula: C16H21NO Molecular weight: 243.34404 g/mol InChI Key: CRXAYNAYXGFRGO-UHFFFAOYSA-N

InChI=1S/C16H21NO/c1-3-8-18-16-7-6-14-10-13(9-12(2)17)4-5-15(14)11-16/h4-7,10-12H,3,8-9,17H2,1-2H3

PubChem CID: 44590295; ChemSpider: 24695427

6-BuO-NAP

2469

Analogue 19: Substituting 4-n-Butoxybenzo for Methylenedioxy at R3,4

6-BuO-NAP

IUPAC: 1-(6-Butoxynaphthalen-2-yl)propan-2-amine

Formula: C17H23NO Molecular weight: 257.37062 g/mol InChI Key: HQJXBGMWVQCDJS-UHFFFAOYSA-N

InChI=1S/C17H23NO/c1-3-4-9-19-17-8-7-15-11-14(10-13(2)18)5-6-16(15)12-17/h5-8,11-13H,3-4,9-10,18H2,1-2H3

PubChem CID: 44590779; ChemSpider: 24686962

6-BnO-NAP

2470

Analogue 20: Substituting 4-Benzyloxybenzo for Methylenedioxy at R3,4

6-BnO-NAP

IUPAC: 1-[6-(Benzyloxy)naphthalen-2-yl]propan-2-amine

Formula: C20H21NO Molecular weight: 291.38684 g/mol InChI Key: KDDLNYYBHKHYRE-UHFFFAOYSA-N

InChI=1S/C20H21NO/c1-15(21)11-17-7-8-19-13-20(10-9-18(19)12-17)22-14-16-5-3-2-4-6-16/h2-10,12-13,15H,11,14,21H2,1H3

PubChem CID: 44590780; ChemSpider: 24689854

6-MeS-NAP

2471

Analogue 21: Substituting 4-Methylthiobenzo for Methylenedioxy at R3,4

6-MeS-NAP

IUPAC: 1-[6-(Methylsulfanyl)naphthalen-2-yl]propan-2-amine

Formula: C14H17NS Molecular weight: 231.35648 g/mol InChI Key: YTLQCSVRMANEOQ-UHFFFAOYSA-N

InChI=1S/C14H17NS/c1-10(15)7-11-3-4-13-9-14(16-2)6-5-12(13)8-11/h3-6,8-10H,7,15H2,1-2H3

PubChem CID: 44590781; ChemSpider: 24689225

6-IT

1283

Analogue 22: Substituting Pyrrolo[d] for Methylenedioxy at R3,4

6-IT

IUPAC: 1-(1H-Indol-6-yl)propan-2-amine

Formula: C11H14N2 Molecular weight: 174.24226 g/mol InChI Key: QCFIFKAOUKPFPU-UHFFFAOYSA-N

InChI=1S/C11H14N2/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-5,7-8,13H,6,12H2,1H3

PubChem CID: 30999; ChemSpider: 28759

14 skeleton analogues:

homo-MDPEA; GAMMA

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

272

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

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

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

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

InChI=1S/C10H13NO2/c11-5-1-2-8-3-4-9-10(6-8)13-7-12-9/h3-4,6H,1-2,5,7,11H2

PubChem CID: 413015; ChemSpider: 365714

Shulgin Index: See #78 homo-MDA; Table: 10 Page: 358 Row: 16

See also PiHKAL:	#100 MDA

Safrole

1031

Analogue 2: With Prop-2-en-1-ylbenzene skeleton

Safrole
3,4-Methylenedioxyphenylprop-2-ene

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

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

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

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

See also PiHKAL:	#100 MDA	#157 TMA

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

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

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.

α-Isosafrole

1032

Analogue 3: With (1Z)-Prop-1-en-1-ylbenzene skeleton

α-Isosafrole
cis-3,4-Methylenedioxyphenylprop-1-ene

IUPAC: 5-[(1Z)-Prop-1-en-1-yl]-1,3-benzodioxole

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

InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2-

PubChem CID: 1549044; ChemSpider: 1266029

See also PiHKAL:	#100 MDA

β-Isosafrole

1033

Analogue 4: With (1E)-Prop-1-en-1-ylbenzene skeleton

β-Isosafrole
trans-3,4-Methylenedioxyphenylprop-1-ene

IUPAC: 5-[(1E)-Prop-1-en-1-yl]-1,3-benzodioxole

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

InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2+

PubChem CID: 637796; ChemSpider: 21106329

ONE; MDC

2122

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

ONE
MDC
bk-MDA
3,4-Methylenedioxycathinone
β-Keto-3,4-methylenedioxyamphetamine

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

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

InChI=1S/C10H11NO3/c1-6(11)10(12)7-2-3-8-9(4-7)14-5-13-8/h2-4,6H,5,11H2,1H3

PubChem CID: 57465250; ChemSpider: 25524469; Wikipedia: Methylenedioxycathinone

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 14

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

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

MDPPP

2125

Analogue 6: With 2-Cyclic-amine-1-phenylethanone skeleton

MDPPP
3′,4′-Methylenedioxy-α-pyrrolidinopropiophenone

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

Formula: C14H17NO3 Molecular weight: 247.28968 g/mol InChI Key: NIYQOTCYXGXMPI-UHFFFAOYSA-N

InChI=1S/C14H17NO3/c1-10(15-6-2-3-7-15)14(16)11-4-5-12-13(8-11)18-9-17-12/h4-5,8,10H,2-3,6-7,9H2,1H3

PubChem CID: 6430845; ChemSpider: 4936183; Wikipedia: 3',4'-Methylenedioxy-α-pyrrolidinopropiophenone

Shulgin Index: See #93 Methylone; Table: 4 Page: 332 Row: 28

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

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

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

5,6-MDAI

2149

Analogue 7: With 2,3-Dihydro-1H-inden-2-amine skeleton

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

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

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

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

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

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

See also PiHKAL:	#100 MDA

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

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

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

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

6,7-MDAT

402

Analogue 8: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

6,7-MDAT
2-Amino-6,7-methylenedioxytetralin

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

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

InChI=1S/C11H13NO2/c12-9-2-1-7-4-10-11(14-6-13-10)5-8(7)3-9/h4-5,9H,1-3,6,12H2

PubChem CID: 36483; ChemSpider: 33531; Drugs Forum: MDAT; Wikipedia: MDAT

Shulgin Index: See #77 MDA; Table: 5 Page: 347 Row: 26

α-MMDBA

913

Analogue 9: With Phenylmethanamine skeleton

α-MMDBA

IUPAC: 1-(1,3-Benzodioxol-5-yl)ethanamine

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

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

PubChem CID: 129498; ChemSpider: 114677

Shulgin Index: See #45 α,N-DMMDBA; Table: 9 Page: 357 Row: 29

MDBP

910

Analogue 10: 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

homo-MDA

610

Analogue 11: 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

MDCPA

6729

Analogue 12: With 2-Phenylcyclopropan-1-amine skeleton

MDCPA

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

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

InChI=1S/C10H11NO2/c11-8-4-7(8)6-1-2-9-10(3-6)13-5-12-9/h1-3,7-8H,4-5,11H2

PubChem CID: 21190569; ChemSpider: 25467371

Shulgin Index: See #41 DMCPA; Table: 4 Page: 332 Row: 29

Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018

499

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

499

Analogue 13: With Phenyl-cyclic-amine skeleton

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

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

InChI=1S/C12H15NO3/c1-8-12(14-5-4-13-8)9-2-3-10-11(6-9)16-7-15-10/h2-3,6,8,12-13H,4-5,7H2,1H3

ChemSpider: 26709739

3,4-Methylenedioxyaminorex

564

Analogue 14: With Phenyl-cyclic-amine skeleton

3,4-Methylenedioxyaminorex

IUPAC: 5-(1,3-Benzodioxol-5-yl)-4,5-dihydro-1,3-oxazol-2-amine

Formula: C10H10N2O3 Molecular weight: 206.198 g/mol InChI Key: LOFGJCSNVFFVRE-UHFFFAOYSA-N

InChI=1S/C10H10N2O3/c11-10-12-4-9(15-10)6-1-2-7-8(3-6)14-5-13-7/h1-3,9H,4-5H2,(H2,11,12)

Anon. Personal communication of unpublished research. 1 Jun 2012.

16 isomers:

ALPHA

270

Isomer 1

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

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

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

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

PubChem CID: 14647596; ChemSpider: 11853242

See also PiHKAL:	#100 MDA

homo-MDPEA; GAMMA

272

Isomer 2

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

2,3-MDA; ORTHO-MDA

275

Isomer 3

2,3-MDA
ORTHO-MDA
2,3-Methylenedioxyamphetamine

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

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

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

PubChem CID: 152655; ChemSpider: 134547; Wikipedia: 2,3-Methylenedioxyamphetamine

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 10

See also PiHKAL:	#100 MDA
See also TiHKAL:	#28 4,5-MDO-DIPT

Casale, JF; Hays, PA; Klein, RFX. Synthesis and characterization of the 2,3-methylenedioxyamphetamines. J. Forensic Sci., 1 May 1995, 40 (3), 391–400. 500 kB. doi:10.1520/JFS13793J

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

N-Me-MDPEA; METHYL-H

N-Me-MDPEA; N-Methyl-3,4-methylenedixoyphenethylamine

285

Isomer 4

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-methylethanamine

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

PMA-βk; 4-Methoxycathinone

2382

Isomer 5

PMA-βk
4-Methoxycathinone

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

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

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

PubChem CID: 12626564; ChemSpider: 23188095

Shulgin Index: See #110 PMA; Table: 3 Page: 324 Row: 12

Osorio-Olivares, M; Rezende, MC; Sepúlveda-Boza, S; Cassels, BK; Fierro, A. MAO inhibition by arylisopropylamines: the effect of oxygen substituents at the β-position. Bioorg. Med. Chem., 1 Jan 2004, 12 (15), 4055–4066. 412 kB. doi:10.1016/j.bmc.2004.05.033

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

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

Phenibut

2378

Isomer 6

Phenibut

IUPAC: 4-Amino-3-phenylbutanoic acid

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

InChI=1S/C10H13NO2/c11-7-9(6-10(12)13)8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)

PubChem CID: 14113; ChemSpider: 13491; Erowid: Phenibut; Wikipedia: Phenibut

α,N-DMMDBA

917

Isomer 7

α,N-DMMDBA

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

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

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

PubChem CID: 6424509; ChemSpider: 4930000

Shulgin Index: #45 α,N-DMMDBA; Table: 9 Page: 358 Row: 2

α,α-DMMDBA

914

Isomer 8

α,α-DMMDBA

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

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

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

PubChem CID: 20811520; ChemSpider: 19649962

Shulgin Index: See #45 α,N-DMMDBA; Table: 9 Page: 357 Row: 30

N,N-DMMDBA

912

Isomer 9

N,N-DMMDBA
N,N-Dimethylpiperonylamine

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

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

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

PubChem CID: 584596; ChemSpider: 508143

Shulgin Index: See #45 α,N-DMMDBA; Table: 9 Page: 357 Row: 28

2,3-MDMPEA

6406

Isomer 10

2,3-MDMPEA

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

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

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

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 6

β-Me-MDPEA

6667

Isomer 11

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

EDPEA

6783

Isomer 12

EDPEA

IUPAC: 2-(2,3-Dihydro-1,4-benzodioxin-6-yl)ethanamine

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

InChI=1S/C10H13NO2/c11-4-3-8-1-2-9-10(7-8)13-6-5-12-9/h1-2,7H,3-6,11H2

PubChem CID: 3747027; ChemSpider: 2976686

Shulgin Index: See #65 EDA; Table: 4 Page: 333 Row: 33

2-HO-5,N-MePEA-βk

6815

Isomer 13

2-HO-5,N-MePEA-βk

IUPAC: 1-(2-Hydroxy-5-methylphenyl)-2-(methylamino)ethanone

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

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

Shulgin Index: See #22 2C-H; Table: 4 Page: 334 Row: 15

2-M-5-MePEA-βk

6822

Isomer 14

2-M-5-MePEA-βk

IUPAC: 2-Amino-1-(2-methoxy-5-methylphenyl)ethanone

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

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

PubChem CID: 24260972; ChemSpider: 23903821

Shulgin Index: See #22 2C-H; Table: 4 Page: 334 Row: 22

2-Methoxycathinone

2455

Isomer 15

2-Methoxycathinone

IUPAC: 2-Amino-1-(2-methoxyphenyl)propan-1-one

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

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

PubChem CID: 12914879; ChemSpider: 23208219

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

ADTN

1260

Isomer 16

ADTN

IUPAC: 6-Amino-5,6,7,8-tetrahydronaphthalene-2,3-diol

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

InChI=1S/C10H13NO2/c11-8-2-1-6-4-9(12)10(13)5-7(6)3-8/h4-5,8,12-13H,1-3,11H2

PubChem CID: 3153; ChemSpider: 3041

Kohli, JD; Goldberg, LI; Nichols, DE. Dopamine vascular actions of N-substituted derivatives of 2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene (ADTN). Eur. J. Pharmacol., , 56 (1–2), 39–44. 454 kB. doi:10.1016/0014-2999(79)90430-8