Go to PiHKAL • info home
Browse the short index of PiHKAL phenethylamines. Read book II of PiHKAL
Search for phenethylamines and related structures Beyond PiHKAL—Selected writings by Sasha and others. Explore phenethylamine structures and analogues
The essential oils and their amphetamine analogues How PiHKAL • info differs from the printed version
Go to TiHKAL • info home
You are currently exploring 6-EAPB.
To explore a different substance, type its name: Help
6-EAPB; 1-(1-Benzofuran-6-yl)-N-ethylpropan-2-amine
1290
Variant: N R3,4 isomers all
Analogues: 2 8 2 12

IUPAC: 1-(1-Benzofuran-6-yl)-N-ethylpropan-2-amine

Formula: C13H17NO Molecular weight: 203.28018 g/mol InChI Key: MIRNYUKRRZFBOI-UHFFFAOYSA-N

InChI=1S/C13H17NO/c1-3-14-10(2)8-11-4-5-12-6-7-15-13(12)9-11/h4-7,9-10,14H,3,8H2,1-2H3

Two N analogues:
2358
Analogue 1: Removing Ethyl at N

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

1288
Analogue 2: Substituting Methyl for Ethyl at N

6-MAPB

IUPAC: 1-(1-Benzofuran-6-yl)-N-methylpropan-2-amine

Formula: C12H15NO Molecular weight: 189.2536 g/mol InChI Key: QLAAURQYEAEHBO-UHFFFAOYSA-N

InChI=1S/C12H15NO/c1-9(13-2)7-10-3-4-11-5-6-14-12(11)8-10/h3-6,8-9,13H,7H2,1-2H3

Wikipedia: 6-MAPB

Eight R3,4 analogues:
106
Analogue 1: Substituting Methylenedioxy for Furo[d] at R3,4

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.

2316
Analogue 2: Substituting 1,1-Difluoromethylenedioxy for Furo[d] at R3,4

F2-MDE
3,4-(1,1-Difluoromethylenedioxy)-N-ethylamphetamine

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

Formula: C12H15F2NO2 Molecular weight: 243.2498064 g/mol InChI Key: IHRWBIUQOLBKKG-UHFFFAOYSA-N

InChI=1S/C12H15F2NO2/c1-3-15-8(2)6-9-4-5-10-11(7-9)17-12(13,14)16-10/h4-5,7-8,15H,3,6H2,1-2H3

Shulgin Index: See #81 MDE; Table: 4 Page: 333 Row: 28

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

6534
Analogue 3: Substituting Dihydroxy for Furo[d] at R3,4

DHEA

IUPAC: 4-[2-(Ethylamino)propyl]benzene-1,2-diol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: CKUGRMSDBDIJRN-UHFFFAOYSA-N

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

PubChem CID: 130357; ChemSpider: 115342

Shulgin Index: See #33 DHA; Table: 4 Page: 328 Row: 34

6622
Analogue 4: Substituting Dimethoxy for Furo[d] at R3,4

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

Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: ZRXZDUBEZXLNLM-UHFFFAOYSA-N

InChI=1S/C13H21NO2/c1-5-14-10(2)8-11-6-7-12(15-3)13(9-11)16-4/h6-7,9-10,14H,5,8H2,1-4H3

PubChem CID: 22061570; ChemSpider: 10814149

6803
Analogue 5: Substituting Ethylenedioxy for Furo[d] at R3,4

EDEA

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

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

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

ChemSpider: 26679362

Shulgin Index: See #65 EDA; Table: 4 Page: 334 Row: 3

1291
Analogue 6: Substituting Furo[b] for Furo[d] at R3,4

5-EAPB

IUPAC: 1-(1-Benzofuran-5-yl)-N-ethylpropan-2-amine

Formula: C13H17NO Molecular weight: 203.28018 g/mol InChI Key: ZBZDDOARNPAMSP-UHFFFAOYSA-N

InChI=1S/C13H17NO/c1-3-14-10(2)8-11-4-5-13-12(9-11)6-7-15-13/h4-7,9-10,14H,3,8H2,1-2H3

Wikipedia: 5-EAPB

1430
Analogue 7: Substituting 2,3-Dihydrofuro[d] for Furo[d] at R3,4

6-EAPDB

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

Formula: C13H19NO Molecular weight: 205.29606 g/mol InChI Key: JHDSHYDQQUHNQA-UHFFFAOYSA-N

InChI=1S/C13H19NO/c1-3-14-10(2)8-11-4-5-12-6-7-15-13(12)9-11/h4-5,9-10,14H,3,6-8H2,1-2H3

1431
Analogue 8: Substituting 2,3-Dihydrofuro[b] for Furo[d] at R3,4

5-EAPDB

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

Formula: C13H19NO Molecular weight: 205.29606 g/mol InChI Key: DIUULXJKNRMJEH-UHFFFAOYSA-N

InChI=1S/C13H19NO/c1-3-14-10(2)8-11-4-5-13-12(9-11)6-7-15-13/h4-5,9-10,14H,3,6-8H2,1-2H3

Two isomers:
2114
Isomer 1

α-PPP
PPP
α-Pyrrolidinopropiophenone

IUPAC: 1-Phenyl-2-(pyrrolidin-1-yl)propan-1-one

Formula: C13H17NO Molecular weight: 203.28018 g/mol InChI Key: KPUJAQRFIJAORQ-UHFFFAOYSA-N

InChI=1S/C13H17NO/c1-11(14-9-5-6-10-14)13(15)12-7-3-2-4-8-12/h2-4,7-8,11H,5-6,9-10H2,1H3

PubChem CID: 209045; ChemSpider: 181124; Wikipedia: Alpha-Pyrrolidinopropiophenone

Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 30

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

Reitzel, LA; Dalsgaard, PW; Müller, IB; Cornett, C. Identification of ten new designer drugs by GC-MS, UPLC-QTOF-MS, and NMR as part of a police investigation of a Danish Internet company. Drug Test. Anal., 1 May 2012, 4 (5), 342–354. 538 kB. doi:10.1002/dta.358

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.

1291
Isomer 2

5-EAPB

IUPAC: 1-(1-Benzofuran-5-yl)-N-ethylpropan-2-amine

Formula: C13H17NO Molecular weight: 203.28018 g/mol InChI Key: ZBZDDOARNPAMSP-UHFFFAOYSA-N

InChI=1S/C13H17NO/c1-3-14-10(2)8-11-4-5-13-12(9-11)6-7-15-13/h4-7,9-10,14H,3,8H2,1-2H3

Wikipedia: 5-EAPB

Show all 12 analogues and isomers Show only the two N analogues Show only the eight R3,4 analogues
Page updated 21 November 2014 · This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License ·