|
 
|
|||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
|
|
|||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
You are currently exploring 6-APDB.
To explore a different substance, type its name: 
|
|||||||||
2351
|
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. |
||||||||
22 R3,4 analogues:
|
||||||||
55
|
Analogue 1: Substituting Dimethoxy for 2,3-Dihydrofuro[d] at R3,4
3,4-DMA 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
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 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 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 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 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 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 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 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 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 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. 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!. |
|||||||
100
|
Analogue 2: Substituting Methylenedioxy for 2,3-Dihydrofuro[d] at R3,4
MDA 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
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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009 Nichols, DE; 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 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 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 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 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 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 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 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 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 Ray, TS. Psychedelics and the human receptorome. PLoS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019 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 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 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 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; 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. 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. 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; 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. 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. Oberlender, R; Nichols, DE. (+)-N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a discriminative stimulus in studies of 3,4-methylenedioxymethamphetamine-like behavioral activity. J. Pharmacol. Exp. Ther., 1 Dec 1990, 255 (3), 1098–1106. 1876 kB. Nichols, DE. 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. 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. 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. Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB. Shulgin, AT. Making MDA, MDEA, MDMA. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 15 Mar 2001. |
|||||||
273
|
Analogue 3: Substituting Ethylidenedioxy for 2,3-Dihydrofuro[d] at R3,4
7-Me-MDA 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
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 4: Substituting Isopropylidinedioxy for 2,3-Dihydrofuro[d] at R3,4
IDA 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
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 5: Substituting Trimethylene for 2,3-Dihydrofuro[d] at R3,4
IAP IUPAC: 1-(2,3-Dihydro-1H-inden-5-yl)propan-2-amine Formula: C12H17N Molecular weight: 175.27008 g/mol InChI Key: QYVNZHBQYJRLEX-UHFFFAOYSA-N InChI=1S/C12H17N/c1-9(13)7-10-5-6-11-3-2-4-12(11)8-10/h5-6,8-9H,2-4,7,13H2,1H3 PubChem CID: 192600; ChemSpider: 167142; Erowid: IAP; Wikipedia: Indanylaminopropane Shulgin Index: See #42 DMeA; Table: 4 Page: 327 Row: 26 Monte, AP; Marona-Lewicka, D; Cozzi, NV; Nichols, DE. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine. J. Med. Chem., 1 Jan 1993, 36 (23), 3700–3706. 1026 kB. doi:10.1021/jm00075a027 Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB. |
|||||||
2314
|
Analogue 6: Substituting 1,1-Difluoromethylenedioxy for 2,3-Dihydrofuro[d] at R3,4
F2-MDA 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 |
|||||||
2352
|
Analogue 7: Substituting 2,3-Dihydrofuro[b] for 2,3-Dihydrofuro[d] at R3,4
BF5AP 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 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. |
|||||||
2353
|
Analogue 8: Substituting Benzo for 2,3-Dihydrofuro[d] at R3,4
NAP 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 2,3-Dihydrofuro[d] at R3,4
TAP IUPAC: 1-(5,6,7,8-Tetrahydronaphthalen-2-yl)propan-2-amine Formula: C13H19N Molecular weight: 189.29666 g/mol InChI Key: UTVKUFYOPJCDPE-UHFFFAOYSA-N InChI=1S/C13H19N/c1-10(14)8-11-6-7-12-4-2-3-5-13(12)9-11/h6-7,9-10H,2-5,8,14H2,1H3 PubChem CID: 14964398; ChemSpider: 23204045; Wikipedia: Tetralinylaminopropane Shulgin Index: See #42 DMeA; Table: 4 Page: 327 Row: 28 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 2,3-Dihydrofuro[d] at R3,4
6-APB IUPAC: 1-(1-Benzofuran-6-yl)propan-2-amine Formula: C11H13NO Molecular weight: 175.22702 g/mol InChI Key: FQDAMYLMQQKPRX-UHFFFAOYSA-N InChI=1S/C11H13NO/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-5,7-8H,6,12H2,1H3 PubChem CID: 9794343; ChemSpider: 7970110; Drugs Forum: 6-APB; Wikipedia: 6-APB 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. Meyers-Riggs, B. AIRCR jumps the shark. countyourculture: rational exploration of the underground, 30 Dec 2010. |
|||||||
2359
|
Analogue 11: Substituting Furo[b] for 2,3-Dihydrofuro[d] at R3,4
5-APB 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. |
|||||||
5534
|
Analogue 12: Substituting Pyrrolo[b] for 2,3-Dihydrofuro[d] at R3,4
5-API 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
|
|||||||
447
|
Analogue 13: Substituting Dihydroxy for 2,3-Dihydrofuro[d] 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 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 Capela, JP; Macedo, C; Branco, PS; Ferreira, LM; Lobo, AM; Fernandes, E; Remião, F; Bastos, ML; Dirnagl, U; Meisel, A; Carvalho, F. Neurotoxicity mechanisms of thioether Ecstasy metabolites. Neuroscience, 1 Jan 2007, 146, 1743–1757. 995 kB. doi:10.1016/j.neuroscience.2007.03.028 |
|||||||
6480
|
Analogue 14: Substituting 2,5-Dihydrofuro[c] for 2,3-Dihydrofuro[d] 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 2,3-Dihydrofuro[d] at R3,4
|
|||||||
2466
|
Analogue 16: Substituting 4-Methoxybenzo for 2,3-Dihydrofuro[d] 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 2,3-Dihydrofuro[d] 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 2,3-Dihydrofuro[d] 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 2,3-Dihydrofuro[d] 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 |
|||||||
![6-BnO-NAP; 1-[6-(Benzyloxy)naphthalen-2-yl]propan-2-amine](C/pk2470.png "Explore the structure and analogues of 6-BnO-NAP; 1-[6-(Benzyloxy)naphthalen-2-yl]propan-2-amine")
2470
|
Analogue 20: Substituting 4-Benzyloxybenzo for 2,3-Dihydrofuro[d] 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 |
|||||||
![6-MeS-NAP; 1-[6-(Methylsulfanyl)naphthalen-2-yl]propan-2-amine](C/pk2471.png "Explore the structure and analogues of 6-MeS-NAP; 1-[6-(Methylsulfanyl)naphthalen-2-yl]propan-2-amine")
2471
|
Analogue 21: Substituting 4-Methylthiobenzo for 2,3-Dihydrofuro[d] 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 2,3-Dihydrofuro[d] at R3,4
|
|||||||
17 isomers:
|
|
2018
|
Isomer 1
4-Me-MCAT IUPAC: 2-(Methylamino)-1-(4-methylphenyl)propan-1-one Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: YELGFTGWJGBAQU-UHFFFAOYSA-N InChI=1S/C11H15NO/c1-8-4-6-10(7-5-8)11(13)9(2)12-3/h4-7,9,12H,1-3H3 PubChem CID: 45266826; ChemSpider: 21485694; Drugs Forum: Mephedrone; Erowid: 4-Methylmethcathinone; Wikipedia: Mephedrone Shulgin Index: See #92 METHCATH; Table: 3 Page: 323 Row: 2 Brandt, SD; Sumnall, HR; Measham, F; Cole, J. Analyses of second-generation ‘legal highs’ in the UK: Initial findings. Drug Test. Anal., 1 Aug 2010, 2 (8), 377–382. 317 kB. doi:10.1002/dta.155 Dargan, PI; Sedefov, R; Gallegos, A; Wood, DM. The pharmacology and toxicology of the synthetic cathinone mephedrone (4-methylmethcathinone). Drug Test. Anal., 1 Jul 2011, 3 (7–8), 454–463. 149 kB. doi:10.1002/dta.312 Morris, K. UK places generic ban on mephedrone drug family. Lancet, 17 Apr 2010, 375 (9723), 1333–1334. 52 kB. doi:10.1016/S0140-6736(10)60559-4 Archer, RP. Fluoromethcathinone, a new substance of abuse. Forensic Sci. Int., 1 Jan 2009, 185 (1–3), 10–20. 1355 kB. doi:10.1016/j.forsciint.2008.11.013 Camilleri, A; Johnston, MR; Brennan, M; Davis, S; Caldicott, DGE. Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine, α-phthalimidopropiophenone and N-ethylcathinone. Forensic Sci. Int., 1 Jan 2010, in press. 736 kB. doi:10.1016/j.forsciint.2009.12.048 Jankovics, P; Váradi, A; Tölgyesi, L; Lohner, S; Németh-Palotás, J; Kőszegi-Szalai, H. Identification and characterization of the new designer drug 4′-methylethcathinone (4-MEC) and elaboration of a novel liquid chromatography-tandem mass spectrometry (LC-MS/MS) screening method for seven different methcathinone analogs. Forensic Sci. Int., 15 Jul 2011, 210 (1–3), 213–220. 899 kB. doi:10.1016/j.forsciint.2011.03.019 Power, JD; McGlynn, P; Clarke, K; McDermott, S; Kavanagh, P; O’Brien, J. The analysis of substituted cathinones. Part 1: Chemical analysis of 2-, 3-, and 4-methylmethcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 6–12. 1032 kB. doi:10.1016/j.forsciint.2011.04.020 McDermott, SD; Power, JD; Kavanagh, P; O’Brien, J. The analysis of substituted cathinones. Part 2: An investigation into the phenylacetone based isomers of 4-methylmethcathinone and N-ethylcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 13–21. 1129 kB. doi:10.1016/j.forsciint.2011.06.030 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 Tsujikawa, K; Mikuma, T; Kuwayama, K; Miyaguchi, H; Kanamori, T; Iwata, YT; Inoue, H. Degradation pathways of 4-methylmethcathinone in alkaline solution and stability of methcathinone analogs in various pH solutions. Forensic Sci. Int., 10 Jul 2012, 220 (1–3), 103–110. 671 kB. doi:10.1016/j.forsciint.2012.02.005 Santali, EY; Cadogan, A; Daeid, NN; Savage, KA; Sutcliffe, OB. Synthesis, full chemical characterisation and development of validated methods for the quantification of (±)-4′-methylmethcathinone (mephedrone): a new “legal high”. J. Pharmaceut. Biomed. Anal., 10 Sep 2011, 56 (2), 246–255. 705 kB. doi:10.1016/j.jpba.2011.05.022 Khreit, OIG; Grant, MH; Zhang, T; Henderson, C; Watson, DG; Sutcliffe, OB. Elucidation of the Phase I and Phase II metabolic pathways of (±)-4′-methylmethcathinone (4-MMC) and (±)-4′-(trifluoromethyl)methcathinone (4-TFMMC) in rat liver hepatocytes using LC–MS and LC–MS2. J. Pharm. Biomed. Anal., 18 Jan 2013, 72, 177–185. 800 kB. doi:10.1016/j.jpba.2012.08.015 Wood, DM; Dargan, PI. Mephedrone (4-methylmethcathinone): What is new in our understanding of its use and toxicity. Prog. Neuro-Psychopharmacol. Biol. Psychiatry, . 251 kB. doi:10.1016/j.pnpbp.2012.04.020 Zuba, D. Identification of cathinones and other active components of ‘legal highs’ by mass spectrometric methods. Trends Anal. Chem., 1 Feb 2012, 32, 15–30. 576 kB. doi:10.1016/j.trac.2011.09.009 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 Angoa-Pérez, M; Kane, MJ; Francescutti, DM; Sykes, KE; Shah, MM; Mohammed, AM; Thomas, DM; Kuhn, DM. Mephedrone, an abused psychoactive component of ‘bath salts’ and methamphetamine congener, does not cause neurotoxicity to dopamine nerve endings of the striatum. J. Neurochem., 1 Mar 2012, 120 (6), 1097–1107. 777 kB. doi:10.1111/j.1471-4159.2011.07632.x 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 Iversen, L. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010. Maheux, CR; Copeland, CR; Pollard, MM. Characterization of three methcathinone analogs: 4-methylmethcathinone, methylone, and bk-MBDB. Microgram J., 1 Dec 2010, 7 (2), 43–49. 765 kB. Toole, KE; Fu, S; Shimmon, RG; Kraymen, M; Taflaga, S. Color tests for the preliminary identification of methcathinone and analogues of methcathinone. Microgram J., 2012, 9 (1), 27–32. 496 kB. Meyers-Riggs, B. AIRCR jumps the shark. countyourculture: rational exploration of the underground, 30 Dec 2010. |
2019
|
Isomer 2
EAP IUPAC: 2-(Ethylamino)-1-phenylpropan-1-one Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: LYMHIBZGTAPASQ-UHFFFAOYSA-N InChI=1S/C11H15NO/c1-3-12-9(2)11(13)10-7-5-4-6-8-10/h4-9,12H,3H2,1-2H3 PubChem CID: 458519; ChemSpider: 403504; Erowid: Ethylcathinone; Wikipedia: Ethcathinone Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 35 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 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 McDermott, SD; Power, JD; Kavanagh, P; O’Brien, J. The analysis of substituted cathinones. Part 2: An investigation into the phenylacetone based isomers of 4-methylmethcathinone and N-ethylcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 13–21. 1129 kB. doi:10.1016/j.forsciint.2011.06.030 Tsujikawa, K; Mikuma, T; Kuwayama, K; Miyaguchi, H; Kanamori, T; Iwata, YT; Inoue, H. Degradation pathways of 4-methylmethcathinone in alkaline solution and stability of methcathinone analogs in various pH solutions. Forensic Sci. Int., 10 Jul 2012, 220 (1–3), 103–110. 671 kB. doi:10.1016/j.forsciint.2012.02.005 Zuba, D. Identification of cathinones and other active components of ‘legal highs’ by mass spectrometric methods. Trends Anal. Chem., 1 Feb 2012, 32, 15–30. 576 kB. doi:10.1016/j.trac.2011.09.009 Iversen, L. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010. |
2110
|
Isomer 3
DMAP IUPAC: 2-(Dimethylamino)-1-phenylpropan-1-one Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: KBHMHROOFHVLBA-UHFFFAOYSA-N InChI=1S/C11H15NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9H,1-3H3 PubChem CID: 71872; ChemSpider: 64889; Wikipedia: Metamfepramone Shulgin Index: #40 DMAP; Table: 2 Page: 318 Row: 34 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 Iversen, L. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010. Tsujikawa, K; Mikuma, T; Kuwayama, K; Miyaguchi, H; Kanamori, T; Iwata, YT; Inoue, H. Degradation pathways of 4-methylmethcathinone in alkaline solution and stability of methcathinone analogs in various pH solutions. Forensic Sci. Int., 10 Jul 2012, 220 (1–3), 103–110. 671 kB. doi:10.1016/j.forsciint.2012.02.005 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. |
2150
|
Isomer 4
MMAI IUPAC: 5-Methoxy-6-methyl-2,3-dihydro-1H-inden-2-amine Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: JLESVLCTIOAHPT-UHFFFAOYSA-N InChI=1S/C11H15NO/c1-7-3-8-4-10(12)5-9(8)6-11(7)13-2/h3,6,10H,4-5,12H2,1-2H3 PubChem CID: 131575; ChemSpider: 116274; Wikipedia: MMAI Shulgin Index: See #96 3,4-MMA; Table: 5 Page: 342 Row: 6 Marona-Lewicka, D; Kurrasch-Orbaugh, DM; Selken, JR; Cumbay, MG; Lisnicchia, JG; Nichols, DE. Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioural effects overlap its other properties in rats. Psychopharmacology, 1 Oct 2002, 164 (1), 93–107. 293 kB. doi:10.1007/s00213-002-1141-z 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 Huang, X; Nichols, DE. 5-HT2 receptor-mediated potentiation of dopamine synthesis and central serotonergic deficits. Eur. J. Pharmacol., 1 Jan 1993, 238 (2–3), 291–296. 553 kB. doi:10.1016/0014-2999(93)90859-G Marona-Lewicka, D; Nichols, DE. Behavioral effects of the highly selective serotonin releasing agent 5-methoxy-6-methyl-2-aminoindan. Eur. J. Pharmacol., 1 Jan 1994, 258 (1–2), 1–13. 1252 kB. doi:10.1016/0014-2999(94)90051-5 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 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 Rodríguez, GJ; Roman, DL; White, KJ; Nichols, DE; Barker, EL. Distinct recognition of substrates by the human and Drosophila serotonin transporters. J. Pharmacol. Exp. Ther., 1 Jan 2004, 306 (1), 338–346. 452 kB. doi:10.1124/jpet.103.048751 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 |
2340
|
Isomer 5
MABP IUPAC: 2-(Methylamino)-1-phenylbutan-1-one Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: DDPMGIMJSRUULN-UHFFFAOYSA-N InChI=1S/C11H15NO/c1-3-10(12-2)11(13)9-7-5-4-6-8-9/h4-8,10,12H,3H2,1-2H3 PubChem CID: 53249194; ChemSpider: 26286946; Wikipedia: Buphedrone Maheux, CR; Copeland, CR. Chemical analysis of two new designer drugs: Buphedrone and pentedrone. Drug Test. Anal., 1 Jan 2012, 4 (1), 17–23. 314 kB. doi:10.1002/dta.385 Zuba, D. Identification of cathinones and other active components of ‘legal highs’ by mass spectrometric methods. Trends Anal. Chem., 1 Feb 2012, 32, 15–30. 576 kB. doi:10.1016/j.trac.2011.09.009 Iversen, L. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010. |
|
2352
|
Isomer 6
BF5AP 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 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. |
2375
|
Isomer 7
|
408
|
Isomer 8
|
409
|
Isomer 9
|
6028
|
Isomer 10
Phenmetrazine IUPAC: 3-Methyl-2-phenylmorpholine Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: OOBHFESNSZDWIU-UHFFFAOYSA-N InChI=1S/C11H15NO/c1-9-11(13-8-7-12-9)10-5-3-2-4-6-10/h2-6,9,11-12H,7-8H2,1H3 PubChem CID: 4762; ChemSpider: 4598 Shulgin Index: Table: 2 Page: 318 Row: 28 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 |
|
6480
|
Isomer 11
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 |
6955
|
Isomer 12
MHAT IUPAC: 7-(Methylamino)-5,6,7,8-tetrahydronaphthalen-1-ol Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: RKQNQEQRWHOAOX-UHFFFAOYSA-N InChI=1S/C11H15NO/c1-12-9-6-5-8-3-2-4-11(13)10(8)7-9/h2-4,9,12-13H,5-7H2,1H3 PubChem CID: 21689037; ChemSpider: 14106514 Shulgin Index: See #105 PAT; Table: 4 Page: 337 Row: 5 |
![2-HO-CPDMA; 2-[2-(Dimethylamino)cyclopropyl]phenol](C/pk507.png "Explore the structure and analogues of 2-HO-CPDMA; 2-[2-(Dimethylamino)cyclopropyl]phenol")
507
|
Isomer 13
2-HO-CPDMA IUPAC: 2-[2-(Dimethylamino)cyclopropyl]phenol Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: BVUOMRJSZWYZMF-UHFFFAOYSA-N InChI=1S/C11H15NO/c1-12(2)10-7-9(10)8-5-3-4-6-11(8)13/h3-6,9-10,13H,7H2,1-2H3 PubChem CID: 13972218; ChemSpider: 14106507 Arvidsson, L; Johansson, AM; Hacksell, U; Nilsson, JLG; Svensson, K; Hjorth, S; Magnusson, T; Carlsson, A; Lindberg, P; Andersson, B; Sanchez, D; Wikström, H; Sundell, S. N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: Novel central 5-hydroxytryptamine receptor agonists. J. Med. Chem., 1 Jan 1988, 31 (1), 92–99. 1162 kB. doi:10.1021/jm00396a014 |
![3-HO-CPDMA; 3-[2-(Dimethylamino)cyclopropyl]phenol](C/pk513.png "Explore the structure and analogues of 3-HO-CPDMA; 3-[2-(Dimethylamino)cyclopropyl]phenol")
513
|
Isomer 14
3-HO-CPDMA IUPAC: 3-[2-(Dimethylamino)cyclopropyl]phenol Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: LYTWDOIYZATBOZ-UHFFFAOYSA-N InChI=1S/C11H15NO/c1-12(2)11-7-10(11)8-4-3-5-9(13)6-8/h3-6,10-11,13H,7H2,1-2H3 PubChem CID: 13972242; ChemSpider: 14120168 Arvidsson, L; Johansson, AM; Hacksell, U; Nilsson, JLG; Svensson, K; Hjorth, S; Magnusson, T; Carlsson, A; Lindberg, P; Andersson, B; Sanchez, D; Wikström, H; Sundell, S. N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: Novel central 5-hydroxytryptamine receptor agonists. J. Med. Chem., 1 Jan 1988, 31 (1), 92–99. 1162 kB. doi:10.1021/jm00396a014 |
2479
|
Isomer 15
2-Methylmethcathinone IUPAC: 2-(Methylamino)-1-(2-methylphenyl)propan-1-one Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: PRGXFAWAMOFULD-UHFFFAOYSA-N InChI=1S/C11H15NO/c1-8-6-4-5-7-10(8)11(13)9(2)12-3/h4-7,9,12H,1-3H3 PubChem CID: 56603536 Power, JD; McGlynn, P; Clarke, K; McDermott, S; Kavanagh, P; O’Brien, J. The analysis of substituted cathinones. Part 1: Chemical analysis of 2-, 3-, and 4-methylmethcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 6–12. 1032 kB. doi:10.1016/j.forsciint.2011.04.020 |
2480
|
Isomer 16
3-Methylmethcathinone IUPAC: 2-(Methylamino)-1-(3-methylphenyl)propan-1-one Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: QDNXSIYWHYGMCD-UHFFFAOYSA-N InChI=1S/C11H15NO/c1-8-5-4-6-10(7-8)11(13)9(2)12-3/h4-7,9,12H,1-3H3 Power, JD; McGlynn, P; Clarke, K; McDermott, S; Kavanagh, P; O’Brien, J. The analysis of substituted cathinones. Part 1: Chemical analysis of 2-, 3-, and 4-methylmethcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 6–12. 1032 kB. doi:10.1016/j.forsciint.2011.04.020 |
1443
|
Isomer 17
|
