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PiHKAL#100 MDA; SI#77 MDA
100
Variant: N α β R2 R3,4 skeleton isomers all
Analogues: 29 7 1 4 22 18 16 97

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

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

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

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

Nichols, DE; Oberlender, R; Burris, K; Hoffman, AJ; Johnson, MP. Studies of dioxole ring substituted 3,4-methylenedioxyamphetamine (MDA) analogues. Pharmacol. Biochem. Behav., 1 Jan 1989, 34 (3), 571–576. 680 kB. doi:10.1016/0091-3057(89)90560-1

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

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

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

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

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

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

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

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.

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

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

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

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

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

Ho, B; McIsaac, WM; An, R; Tansey, LW; Walker, KE; Englert, LF; Noel, MB. Analogs of α-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs. J. Med. Chem., 1 Jan 1970, 13 (1), 26–30. 601 kB. doi:10.1021/jm00295a007

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

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

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

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

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

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

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

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

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

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

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

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

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.

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

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

Naranjo, C; Shulgin, AT; Sargent, T. Evaluation of 3,4-methylenedioxyamphetamine (MDA) as an adjunct to psychotherapy. Med. Pharmacol. Exp., 1 Jan 1967, 17 (4), 359–364. 694 kB. doi:10.1159/000137100

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

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

McKenna, DJ; Guan, AM; Shulgin, AT. 3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 505–12. 783 kB. doi:10.1016/0091-3057(91)90005-M

Nichols, DE; Hoffman, AJ; Oberlender, RA; Jacob, P; Shulgin, AT. Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: Representatives of a novel therapeutic class. J. Med. Chem., 1 Jan 1986, 29 (10), 2009–2015. 1024 kB. doi:10.1021/jm00160a035

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

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

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

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.

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.

White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. doi:10.1016/0027-5107(77)90210-X

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.

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; 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.

29 N analogues:
81
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

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 Transcripts: 2.255

See also Pharmacology notes II: p. 255, MDAL

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

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

102
Analogue 3: Adding 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 Transcripts: 2.262

See also Pharmacology notes II: p. 262, MDBU

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

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

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

103
Analogue 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 Transcripts: 2.308

See also Pharmacology notes II: p. 308, MDBZ

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

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

104
Analogue 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 Transcripts: 2.272

See also Pharmacology notes II: p. 272, MDCPM

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

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

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

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 Transcripts: 2.244

See also Pharmacology notes II: p. 244, MDDM

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

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

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

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

Thigpen, AL; Awad, T; DeRuiter, J; Clark, CR. GC-MS studies on the regioisomeric methoxy-methyl-phenethylamines related to MDEA, MDMMA, and MBDB. J. Chromatogr. Sci., 1 Nov 2008, 46 (10), 900–206. 448 kB. doi:10.1093/chromsci/46.10.900

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

Thigpen, AL; DeRuiter, J; Clark, CR. GC-MS studies on the regioisomeric 2,3- and 3,4-methylenedioxyphenethylamines related to MDEA, MDMMA, and MBDB. J. Chromatogr. Sci., 1 May 2007, 45 (5), 229–235. 332 kB. doi:10.1093/chromsci/45.5.229

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

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

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

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

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

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

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

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

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

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

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

Thigpen, AL; DeRuiter, J; Clark, CR. GC-MS studies on the regioisomeric 2,3- and 3,4-methylenedioxyphenethylamines related to MDEA, MDMMA, and MBDB. J. Chromatogr. Sci., 1 May 2007, 45 (5), 229–235. 332 kB. doi:10.1093/chromsci/45.5.229

Thigpen, AL; Awad, T; DeRuiter, J; Clark, CR. GC-MS studies on the regioisomeric methoxy-methyl-phenethylamines related to MDEA, MDMMA, and MBDB. J. Chromatogr. Sci., 1 Nov 2008, 46 (10), 900–206. 448 kB. doi:10.1093/chromsci/46.10.900

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

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

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

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

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

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

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

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

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

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

McKenna, DJ; Guan, AM; Shulgin, AT. 3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 505–12. 783 kB. doi:10.1016/0091-3057(91)90005-M

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

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

107
Analogue 8: 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 Transcripts: 2.250

See also Pharmacology notes II: p. 250, MDHOET

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

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

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

108
Analogue 9: 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 Transcripts: 2.237

See also Pharmacology notes II: p. 237, MDIP

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

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

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

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

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

109
Analogue 10: 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 Transcripts: 1.139, 1.186, 2.207, 2.210, 2.230, 2.231, 2.232, 2.233, 2.234, 2.235, 2.241, 2.242, 2.243, 2.261, 2.271, 2.275, 2.284, 2.289, 2.290, 2.295, 2.299, 2.304, 2.306, 2.307, 2.311, 2.314, 2.320, 3.328, 3.331, 3.333, 3.336, 3.340, 3.350, 3.360, 3.362, 3.366, 3.374, 3.375, 3.376, 3.378, 3.379, 3.382, 3.384, 3.385, 3.386, 3.387, 3.388, 3.391, 3.392, 3.393, 3.398, 3.399, 3.403, 3.404, 3.405, 3.408, 3.410, 3.414, 3.415, 3.420, 3.421, 3.423, 3.425, 3.427, 3.435, 3.441, 3.442, 3.444, 4.456, 4.457, 4.458, 4.463, 4.467, 4.467.2, 4.469, 4.473, 4.488, 4.492, 4.493, 4.494, 4.496, 4.503, 4.504, 4.505, 4.506, 4.507, 4.510, 4.520, 5.568, 5.570, 5.572, 5.583, 5.584, 5.594, 5.600, 5.601, 5.608, 5.609, 5.610, 5.611, 5.612, 5.613, 5.614, 5.621, 5.622, 5.623, 5.624, 5.629, 5.630, 5.632, 5.635, 5.636, 5.637, 5.638, 5.640, 5.641, 5.642, 5.643, 5.653, 5.654, 5.655, 5.656, 5.657, 5.658, 5.659, 5.660, 5.663, 5.664

See also Pharmacology notes I: p. 139, The Pseunut Cocktail
p. 186, MDMA
See also Pharmacology notes II: p. 207, MDMA
p. 210, MDMA
p. 230, MDMA
p. 231, MDMA
p. 232, MDMA
p. 233, MDMA: Saturation experiments
p. 234, MDMA: Saturation experiments
p. 235, MDMA
p. 241, MDMA
p. 242, MDMA
p. 243, MDMA
p. 261, MDMA
p. 271, MDMA
p. 275, MDMA: Report of results
p. 284, MDMA: Report of experience
p. 289, MDMA: Report of experience
p. 290, MDMA
p. 295, MDMA: Report of experience
p. 299, MDMA: Report of experience
p. 304, MDMA: Report of experience
p. 306, MDMA: Report of experiment
p. 307, MDMA: Report of experiment
p. 311, MDMA: Report of experience
p. 314, MDMA: Report of experience
p. 320, MDMA: Report of experience

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

McKenna, DJ; Guan, AM; Shulgin, AT. 3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 505–12. 783 kB. doi:10.1016/0091-3057(91)90005-M

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

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

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

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

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

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

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

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

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

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

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

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC–IRD methods for the identification of some tertiary amines related to MDMA. Forensic Sci. Int., 15 Jun 2010, 199 (1–3), 18–28. 877 kB. doi:10.1016/j.forsciint.2010.02.022

Pilgrim, JL; Gerostamoulos, D; Woodford, N; Drummer, OH. Serotonin toxicity involving MDMA (ecstasy) and moclobemide. Forensic Sci. Int., 10 Feb 2012, 215 (1–3), 184–188. 189 kB. doi:10.1016/j.forsciint.2011.04.008

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

Stojanovska, N; Fu, S; Tahtouh, M; Kelly, T; Beavis, A; Kirkbride, KP. A review of impurity profiling and synthetic route of manufacture of methylamphetamine, 3,4-methylenedioxymethylamphetamine, amphetamine, dimethylamphetamine and p-methoxyamphetamine. Forensic Sci. Int., 10 Jan 2013, 224 (1–3), 8–26. 813 kB. doi:10.1016/j.forsciint.2012.10.040

Halpin, LE; Collins, SA; Yamamoto, BK. Neurotoxicity of methamphetamine and 3,4-methylenedioxymethamphetamine. Life Sci., 27 Feb 2014, 97 (1), 37–44. 507 kB. doi:10.1016/j.lfs.2013.07.014

Angoa-Pérez, M; Kane, MJ; Herrera-Mundo, N; Francescutti, DM; Kuhn, DM. Effects of combined treatment with mephedrone and methamphetamine or 3,4-methylenedioxymethamphetamine on serotonin nerve endings of the hippocampus. Life Sci., 27 Feb 2014, 97 (1), 31–36. 888 kB. doi:10.1016/j.lfs.2013.07.015

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

Passie, T; Hartmann, U; Schneider, U; Emrich, HM; Krüger, THC. Ecstasy (MDMA) mimics the post-orgasmic state: Impairment of sexual drive and function during acute MDMA-effects may be due to increased prolactin secretion. Med. Hypotheses, 2005, 64 (5), 899–903. 110 kB. doi:10.1016/j.mehy.2004.11.044

Capela, JP; Macedo, C; Branco, PS; Ferreira, LM; Lobo, AM; Fernandes, E; Remião, F; Bastos, ML; Dirnagl, U; Meisel, A; Carvalho, FG. Neurotoxicity mechanisms of thioether Ecstasy metabolites. Neuroscience, 1 Jan 2007, 146, 1743–1757. 995 kB. doi:10.1016/j.neuroscience.2007.03.028

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

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

Mohamed, WMY; Hamida, SB; Cassel, J; Vasconcelos, AP; Jones, BC. MDMA: Interactions with other psychoactive drugs. Pharmacol. Biochem. Behav., 1 Oct 2011, 99 (4), 759–774. 396 kB. doi:10.1016/j.pbb.2011.06.032

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

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

Nichols, DE; Hoffman, AJ; Oberlender, RA; Jacob, P; Shulgin, AT. Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: Representatives of a novel therapeutic class. J. Med. Chem., 1 Jan 1986, 29 (10), 2009–2015. 1024 kB. doi:10.1021/jm00160a035

Nichols, DE; 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

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

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

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

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

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

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

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

Moonzwe, LS; Schensul, JJ; Kostick, KM. The role of MDMA (Ecstasy) in coping with negative life situations among urban young adults. J. Psychoactive Drugs, 29 Aug 2011, 43 (3), 199–210. 137 kB. doi:10.1080/02791072.2011.605671

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

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

Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. doi:10.1124/jpet.106.103622

Green, AR; Mechan, AO; Elliott, JM; O’Shea, E; Colado, MI. The pharmacology and clinical pharmacology of 3,4-methylenedioxymethamphetamine (MDMA, “Ecstasy”). Pharmacol. Rev., 1 Jan 2003, 55 (3), 463–508. 544 kB. doi:10.1124/pr.55.3.3

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’.

Griffin, OH. Is the government keeping the peace or acting like our parents? Rationales for the legal prohibitions of GHB and MDMA. J. Drug Issues, 1 Jul 2012, 42 (3), 247–262. 703 kB. doi:10.1177/0022042612456014

Sessa, B; Nutt, DJ. MDMA, politics and medical research: Have we thrown the baby out with the bathwater? J. Psychopharmacol., 1 Nov 2007, 21 (8), 787–791. 178 kB. doi:10.1177/0269881107084738

Brunt, TM; Poortman, A; Niesink, RJM; Brink, W. Instability of the ecstasy market and a new kid on the block: mephedrone. J. Psychopharmacol., 1 Nov 2011, 25 (11), 1543–1547. 238 kB. doi:10.1177/0269881110378370

Armenian, P; Mamantov, TM; Tsutaoka, BT; Gerona, RRL; Silman, EF; Wu, AHB; Olson, KR. Multiple MDMA (ecstasy) overdoses at a rave event: A case series. J. Intensive Care, 2012. 130 kB. doi:10.1177/0885066612445982

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

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

Fromberg, E. Ecstasy: the Dutch story. J. Subst. Use, 1998, 3 (2), 89–94. 709 kB. doi:10.3109/14659899809053479

Grob, CS. Deconstructing ecstasy: The politics of MDMA research. Addict. Res. Theory, 2000, 8 (6), 549–588. 2361 kB. doi:10.3109/16066350008998989

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

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.

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.

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; 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.

Kalant, H. The pharmacology and toxicology of “Ecstasy” (MDMA) and related drugs. CMAJ, 1 Jan 2001, 165 (7), 917–928. 253 kB.

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

Fenderson5555. Mechanisms in MDMA synthesis. 5 Jan 2011. 4446 kB.

Vollenweider, FX; Geyer, M; Greer, G. Acute psychological and neurophysiological effects of MDMA in humans. In Heffter Review; Nichols, DE, Ed., Heffter Research Institute, Santa Fe, NM, 2001; Vol. 2, pp 53–63. 338 kB.

Bailey, K; By, AW; Legault, D; Verner, D. Identification of the N-methylated analogs of the hallucinogenic amphetamines and some isomers. J. Assoc. Off. Anal. Chem., 1975, 58 (1), 62–69. 1987 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.

Shulgin, AT; Shulgin, LA; Jacob, P. A protocol for the evaluation of new psychoactive drugs. Meth. Find. Exp. Clin. Pharmacol., 1 May 1986, 8 (5), 313. 7938 kB.

Makino, Y; Kurobane, S; Miyasaka, K. Profiling of ecstasy tablets seized in Japan. Microgram J., 1 Jul 2003, 1 (3–4), 169–176. 614 kB.

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

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.

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

Mumane, KS. Neuropharmacology of 3,4-methylenedioxymethamphetamine (MDMA, “ecstasy”) and its stereoisomers. Ph. D. Thesis, Emory University, Atlanta, GA, USA, 2010. 4307 kB.

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.

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.

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.

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

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

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

Shulgin, AT. MDMA isomers. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 27 Aug 2001.

Shulgin, AT. Making MDA, MDEA, MDMA. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 15 Mar 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. Roadblocks to entheogen research. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 12 Sep 2001.

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

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

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

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 Transcripts: 2.248

See also Pharmacology notes II: p. 248, MDMEO

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

112
Analogue 12: 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 Transcripts: 2.245

See also Pharmacology notes II: p. 245, MDMEOET

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

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

114
Analogue 13: 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 Transcripts: 2.263, 2.322, 3.324, 3.325, 3.332, 3.422

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

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

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

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

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

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

117
Analogue 14: 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 Transcripts: 2.264

See also Pharmacology notes II: p. 264, MDPL

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

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

118
Analogue 15: Adding Propyl at N

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

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

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

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

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

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

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

See also Transcripts: 2.254, 3.336

See also Pharmacology notes II: p. 254, MDPR

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

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

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

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

276
Analogue 16: 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    

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

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

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

277
Analogue 17: 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    
278
Analogue 18: Adding 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    

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

279
Analogue 19: Adding 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    

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

280
Analogue 20: Adding 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    

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

281
Analogue 21: 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    

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

282
Analogue 22: 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    

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

283
Analogue 23: 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    

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

284
Analogue 24: Adding 2,2,2-Trifluoroethyl at N

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

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

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

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

See also PiHKAL: #106 MDE    

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

6675
Analogue 25: 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

6676
Analogue 26: Adding Methyl and 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

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

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

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

2477
Analogue 29: 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

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

Seven α analogues:
94
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
 

See also Transcripts: 4.469, 5.588, 5.631, 5.632

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

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

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

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

Nichols, DE; Hoffman, AJ; Oberlender, RA; Jacob, P; Shulgin, AT. Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: Representatives of a novel therapeutic class. J. Med. Chem., 1 Jan 1986, 29 (10), 2009–2015. 1024 kB. doi:10.1021/jm00160a035

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

115
Analogue 2: Removing Methyl at α

MDPEA
EA-1297
Homopiperonylamine
3,4-Methylenedioxyphenethylamine

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

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

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

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

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

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

See also Transcripts: 3.364

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

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

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

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

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

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

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

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

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

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

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  

See also Transcripts: 3.361

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

291
Analogue 4: Substituting 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
292
Analogue 5: Substituting 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
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

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:
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:
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 Transcripts: 1.62, 1.62.2, 1.66, 1.67, 1.68, 1.69, 1.70, 1.71, 1.83, 2.281

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

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

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.

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

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.

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

See also Transcripts: 4.466

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

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:
55
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 Transcripts: 1.143

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

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

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.

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Ho, B; McIsaac, WM; An, R; Tansey, LW; Walker, KE; Englert, LF; Noel, MB. Analogs of α-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs. J. Med. Chem., 1 Jan 1970, 13 (1), 26–30. 601 kB. doi:10.1021/jm00295a007

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

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

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

Bailey, K; Legauld, D; Verner, D. Spectroscopic and chromatographic identification of dimethoxyamphetamines. J. Assoc. Anal. Chem., 1974, 57 (1), 70–78. 426 kB.

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!

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

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

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.

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

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

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

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

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

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  

See also Transcripts: 3.349

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

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  

Nichols, DE; Oberlender, R; Burris, K; Hoffman, AJ; Johnson, MP. Studies of dioxole ring substituted 3,4-methylenedioxyamphetamine (MDA) analogues. Pharmacol. Biochem. Behav., 1 Jan 1989, 34 (3), 571–576. 680 kB. doi:10.1016/0091-3057(89)90560-1

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

2043
Analogue 4: Substituting Trimethylene for Methylenedioxy at R3,4

5-APDI
IAP
Indanylaminopropane
5-(2-Aminopropyl)-2,3-dihydro-1H-indene

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: 5-APDI

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

Casale, JF; McKibben, TD; Bozenko, JS; Hays, PA. Characterization of the “Indanylamphetamines” Microgram J., 1 Jan 2005, 3 (1–2), 3–10. 208 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.

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

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

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

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

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.

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

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.

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.

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

2354
Analogue 9: Substituting Tetramethylene for Methylenedioxy at R3,4

6-APT
TAP
Tetralinylaminopropane
6-(2-Aminopropyl)tetralin

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: 6-APT

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

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.

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; Erowid: 6-APB; Wikipedia: 6-APB

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

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.

Casale, JF; Hays, PA. The characterization of 6-(2-aminopropyl)benzofuran and differentiation from its 4-, 5-, and 7-positional analogues. Microgram J., 1 Jan 2012, 9 (2), 61–74. 1652 kB.

Stanczuk, A; Morris, N; Gardner, EA; Kavanagh, PV. Identification of (2-aminopropyl)benzofuran (APB) phenyl ring positional isomers in Internet purchased products. Drug Test. Anal., 1 Apr 2013, 5 (4), 270–276. 1304 kB. doi:10.1002/dta.1451

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

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

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.

Casale, JF; Hays, PA. The characterization of 6-(2-aminopropyl)benzofuran and differentiation from its 4-, 5-, and 7-positional analogues. Microgram J., 1 Jan 2012, 9 (2), 61–74. 1652 kB.

Stanczuk, A; Morris, N; Gardner, EA; Kavanagh, PV. Identification of (2-aminopropyl)benzofuran (APB) phenyl ring positional isomers in Internet purchased products. Drug Test. Anal., 1 Apr 2013, 5 (4), 270–276. 1304 kB. doi:10.1002/dta.1451

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

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    

Elliott, SP; Brandt, SD; Freeman, S; Archer, RP. AMT (3-(2-aminopropyl)indole) and 5-IT (5-(2-aminopropyl)indole): an analytical challenge and implications for forensic analysis. Drug Test. Anal., 1 Mar 2013, 5 (3), 196–202. 794 kB. doi:10.1002/dta.1420

Herraiz, T; Brandt, SD. 5-(2-Aminopropyl)indole (5-IT): a psychoactive substance used for recreational purposes is an inhibitor of human monoamine oxidase (MAO). Drug Test. Anal., 20 Sep 2013. 567 kB. doi:10.1002/dta.1530

Anon. Report on the risk assessment of 5-(2-aminopropyl)indole (5-IT), European Monitoring Centre for Drugs and Drug Addiction, Jan 2014.

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

Capela, JP; Macedo, C; Branco, PS; Ferreira, LM; Lobo, AM; Fernandes, E; Remião, F; Bastos, ML; Dirnagl, U; Meisel, A; Carvalho, FG. Neurotoxicity mechanisms of thioether Ecstasy metabolites. Neuroscience, 1 Jan 2007, 146, 1743–1757. 995 kB. doi:10.1016/j.neuroscience.2007.03.028

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

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
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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

PubChem CID: 413015; ChemSpider: 365714

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

See also PiHKAL: #100 MDA    
1031
Analogue 2: With Prop-2-en-1-ylbenzene skeleton

Safrole
3,4-Methylenedioxyphenylprop-2-ene

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

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

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

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

See also PiHKAL: #100 MDA #157 TMA  

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

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

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

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

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

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

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

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

1032
Analogue 3: With (1Z)-Prop-1-en-1-ylbenzene skeleton

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

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

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

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

PubChem CID: 1549044; ChemSpider: 1266029

See also PiHKAL: #100 MDA    

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

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

1033
Analogue 4: With (1E)-Prop-1-en-1-ylbenzene skeleton

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

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

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

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

PubChem CID: 637796; ChemSpider: 21106329

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

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

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

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

Zaitsu, K; Katagi, M; Tatsuno, M; Sato, T; Tsuchihashi, H; Suzuki, K. Recently abused β-keto derivatives of 3,4-methylenedioxyphenylalkylamines: a review of their metabolisms and toxicological analysis. Forensic Toxicol., 1 Jul 2011, 29 (2), 73–84. 971 kB. doi:10.1007/s11419-011-0111-8

Jacob, P; Shulgin, AT. Preparation of novel N-substituted-2-amino-3′,4′-methylenedioxypropiophenones as anti-depressant and anti-parkinsonism agents. International patent WO 96/39133, 12 Dec 1996. 941 kB.

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

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

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

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

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

Rösner, P; Junge, T; Fritschi, G; Klein, B; Thielert, K; Kozlowski, M. Neue synthetische Drogen: Piperazin-, propicyclidin- und α-aminopropiophenonderivate. Toxichem Krimtech, 1999, 66 (2), 81–90. 1202 kB.

2149
Analogue 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    

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

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

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

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

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

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

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

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

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

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

402
Analogue 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

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

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

913
Analogue 9: With Phenylmethanamine skeleton

α-MMDBA

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

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

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

PubChem CID: 129498; ChemSpider: 114677

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

910
Analogue 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

Maurer, HH. Mass spectra of select benzyl- and phenyl- piperazine designer drugs. Microgram J., 1 Jan 2004, 2 (1–4), 22–26. 326 kB.

610
Analogue 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

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
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

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 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.

1586
Analogue 15: With 1,3-Diphenylpropan-2-amine skeleton

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

Formula: C17H17NO4 Molecular weight: 299.32118 g/mol InChI Key: WGDBJUJJRWABLD-UHFFFAOYSA-N

InChI=1S/C17H17NO4/c18-13(5-11-1-3-14-16(7-11)21-9-19-14)6-12-2-4-15-17(8-12)22-10-20-15/h1-4,7-8,13H,5-6,9-10,18H2

PubChem CID: 24258016; ChemSpider: 23900827

McNamara, YM; Cloonan, SM; Knox, AJS; Keating, JJ; Butler, SG; Peters, GH; Meegan, MJ; Williams, DC. Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents. Bioorg. Med. Chem., 1 Feb 2011, 19 (3), 1328–1348. 3938 kB. doi:10.1016/j.bmc.2010.11.054

2563
Analogue 16: With 2-Cyclic-amine-1-phenylethanone skeleton

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

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

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

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

2566
Analogue 17: With 2-Cyclic-amine-1-phenylethanone skeleton

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

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

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

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

1049
Analogue 18: 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.

16 isomers:
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    

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

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    
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    

See also Transcripts: 4.462

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

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-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.

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

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

917
Isomer 7

α,N-DMMDBA

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

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

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

PubChem CID: 6424509; ChemSpider: 4930000

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

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

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

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

6406
Isomer 10

2,3-MDMPEA

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

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

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

6783
Isomer 12

EDPEA

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

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

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

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

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

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., Jun 1979, 56 (1–2), 39–44. 454 kB. doi:10.1016/0014-2999(79)90430-8

Show all 97 analogues and isomers Show only the 29 N analogues Show only the seven α analogues Show only the one β analogues Show only the four R2 analogues Show only the 22 R3,4 analogues Show only the 18 skeleton analogues
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