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DHA; 4-(2-Aminopropyl)benzene-1,2-diol
447
Variant: N α β R3 R4 R5 R3,4 skeleton isomers all
Analogues: 5 3 1 4 3 1 21 5 20 63

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

Five N analogues:
6527
Analogue 1: Adding Hydroxy at N

DHAOH

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

Formula: C9H13NO3 Molecular weight: 183.20442 g/mol InChI Key: IKBIYXACJDZMFU-UHFFFAOYSA-N

InChI=1S/C9H13NO3/c1-6(10-13)4-7-2-3-8(11)9(12)5-7/h2-3,5-6,10-13H,4H2,1H3

PubChem CID: 11298338; ChemSpider: 9473316

Shulgin Index: See #33 DHA; Table: 4 Page: 328 Row: 27

6528
Analogue 2: Adding Methyl at N

DHMA

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

Formula: C10H15NO2 Molecular weight: 181.2316 g/mol InChI Key: NTCPGTZTPGFNOM-UHFFFAOYSA-N

InChI=1S/C10H15NO2/c1-7(11-2)5-8-3-4-9(12)10(13)6-8/h3-4,6-7,11-13H,5H2,1-2H3

PubChem CID: 161126; ChemSpider: 141547

Shulgin Index: See #33 DHA; Table: 4 Page: 328 Row: 28

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

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

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

Felim, A; Herrera, G; Neudörffer, A; Blanco, M; O’Connor, J; Largeron, M. Synthesis and in vitro cytotoxicity profile of the R-enantiomer of 3,4-dihydroxymethamphetamine (R-(-)-HHMA): Comparison with related catecholamines. Chem. Res. Toxicol., 2010, 23 (1), 211–219. 349 kB. doi:10.1021/tx9003374

6529
Analogue 3: Adding Methyl and Hydroxy at N

DHMAOH

IUPAC: 4-{2-[Hydroxy(methyl)amino]propyl}benzene-1,2-diol

Formula: C10H15NO3 Molecular weight: 197.231 g/mol InChI Key: GOQYYVGPQUFNCY-UHFFFAOYSA-N

InChI=1S/C10H15NO3/c1-7(11(2)14)5-8-3-4-9(12)10(13)6-8/h3-4,6-7,12-14H,5H2,1-2H3

PubChem CID: 11816442; ChemSpider: 9991097

Shulgin Index: See #33 DHA; Table: 4 Page: 328 Row: 29

6530
Analogue 4: Adding Dimethyl at N

N,N-Me-DHA

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

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

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

PubChem CID: 21151685

Shulgin Index: See #33 DHA; Table: 4 Page: 328 Row: 30

6534
Analogue 5: Adding Ethyl at N

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

Three α analogues:
2012
Analogue 1: Removing Methyl at α

Dopamine
3,4-Dihydroxyphenethylamine

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

Formula: C8H11NO2 Molecular weight: 153.17844 g/mol InChI Key: VYFYYTLLBUKUHU-UHFFFAOYSA-N Properties: Neurotransmitter and Peyote alkaloid

InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2

PubChem CID: 681; ChemSpider: 661; Wikipedia: Dopamine

Shulgin Index: Table: 4 Page: 328 Row: 9

See also PiHKAL: #14 BOD #55 3,4-DMA #60 DMPEA #115 MDPEA

Short, JH; Dunnigan, DA; Ours, CW. Synthesis of phenethylamines from phenylacetonitriles obtained by alkylation of cyanide ion with Mannich bases from phenols and other benzylamines. Tetrahedron, 1973, 29 (14), 1931–1939. 791 kB. doi:10.1016/0040-4020(73)80127-9

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

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

Horn, AS. Structure-activity relations for the inhibition of catecholamine uptake into synaptosomes from noradrenaline and dopaminergic neurones in rat brain homogenates. Br. J. Pharmacol., 1 Feb 1973, 47 (2), 332–338. 903 kB. doi:10.1111/j.1476-5381.1973.tb08331.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

Chemel, BR; Bonner, LA; Watts, VJ; Nichols, DE. Ligand-specific roles for transmembrane 5 serine residues in the binding and efficacy of dopamine D1 receptor catechol agonists. Mol. Pharmacol., 1 May 2012, 81 (5), 729–738. 1213 kB. doi:10.1124/mol.111.077339

Chemel, BR. Exploring the molecular determinants of binding selectivity and efficacy for D1 dopamine receptor agonists. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 May 2010. 1919 kB.

6551
Analogue 2: Substituting Ethyl for Methyl at α

DH-α-Et-PEA

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

Formula: C10H15NO2 Molecular weight: 181.2316 g/mol InChI Key: ZVTVIPHSXNUZQH-UHFFFAOYSA-N

InChI=1S/C10H15NO2/c1-2-8(11)5-7-3-4-9(12)10(13)6-7/h3-4,6,8,12-13H,2,5,11H2,1H3

PubChem CID: 20329954; ChemSpider: 15276107

Shulgin Index: See #33 DHA; Table: 4 Page: 329 Row: 1

540
Analogue 3: Substituting Carboxy for Methyl at α

α-Carboxy-DHA
3-Hydroxytyrosine

IUPAC: 2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid

Formula: C9H11NO4 Molecular weight: 197.18794 g/mol InChI Key: WTDRDQBEARUVNC-UHFFFAOYSA-N

InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)

PubChem CID: 836; ChemSpider: 813

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

One β analogue:
6531
Analogue 1: Adding Hydroxy at β

β-HO-DHA

IUPAC: 4-(2-Amino-1-hydroxypropyl)benzene-1,2-diol

Formula: C9H13NO3 Molecular weight: 183.20442 g/mol InChI Key: GEFQWZLICWMTKF-UHFFFAOYSA-N

InChI=1S/C9H13NO3/c1-5(10)9(13)6-2-3-7(11)8(12)4-6/h2-5,9,11-13H,10H2,1H3

PubChem CID: 3917; ChemSpider: 3780

Shulgin Index: See #33 DHA; Table: 4 Page: 328 Row: 31

Four R3 analogues:
2148
Analogue 1: Removing Hydroxy at R3

PHA
4-OH-A
4-Hydroxyamphetamine

IUPAC: 4-(2-Aminopropyl)phenol

Formula: C9H13NO Molecular weight: 151.20562 g/mol InChI Key: GIKNHHRFLCDOEU-UHFFFAOYSA-N

InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3

PubChem CID: 3651; ChemSpider: 3525; Wikipedia: Norpholedrine

Shulgin Index: #109 PHA; Table: 3 Page: 323 Row: 22

See also PiHKAL: #97 4-MA      

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

Foster, BC; Nantais, LM; Wilson, DL; By, AW; Zamecnik, J; Lodge, BA. Fungal metabolism of 4-substituted amphetamines. Xenobiotica, 1990, 20 (6), 583–590. 510 kB. doi:10.3109/00498259009046873

Buttar, HS; Moffatt, JH; Foster, BC. Developmental toxicity of 4-substituted amphetamines in mice. Reprod. Toxicol., 1 Jul 1996, 10 (4), 301–310. 710 kB. doi:10.1016/0890-6238(96)00059-7

Warren, RJ; Begosh, PP; Zarembo, JE. Identification of amphetamines and related sympathomimetic amines. J. Assoc. Off. Anal. Chem., 1971, 54 (5), 1179–1191. 3851 kB.

Horn, AS. Structure-activity relations for the inhibition of catecholamine uptake into synaptosomes from noradrenaline and dopaminergic neurones in rat brain homogenates. Br. J. Pharmacol., 1 Feb 1973, 47 (2), 332–338. 903 kB. doi:10.1111/j.1476-5381.1973.tb08331.x

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

452
Analogue 2: Substituting Methoxy for Hydroxy at R3

MHA

IUPAC: 4-(2-Aminopropyl)-2-methoxyphenol

Formula: C10H15NO2 Molecular weight: 181.2316 g/mol InChI Key: GPBOYXOSSQEJBH-UHFFFAOYSA-N

InChI=1S/C10H15NO2/c1-7(11)5-8-3-4-9(12)10(6-8)13-2/h3-4,6-7,12H,5,11H2,1-2H3

PubChem CID: 197139; ChemSpider: 170725

Shulgin Index: #94 MHA; Table: 4 Page: 329 Row: 12

Fennoy, LV. Substituted phenylalanines and phenylethylamines. J. Org. Chem., 1 Nov 1961, 26 (11), 4696–4698. 279 kB. doi:10.1021/jo01069a516

6505
Analogue 3: Substituting Bromo for Hydroxy at R3

3-Br-PHA

IUPAC: 4-(2-Aminopropyl)-2-bromophenol

Formula: C9H12BrNO Molecular weight: 230.10168 g/mol InChI Key: DIBBHKXBNUUUOA-UHFFFAOYSA-N

InChI=1S/C9H12BrNO/c1-6(11)4-7-2-3-9(12)8(10)5-7/h2-3,5-6,12H,4,11H2,1H3

ChemSpider: 26495118

Shulgin Index: See #38 DMA; Table: 4 Page: 328 Row: 5

6507
Analogue 4: Substituting Chloro for Hydroxy at R3

3-Cl-PHA

IUPAC: 4-(2-Aminopropyl)-2-chlorophenol

Formula: C9H12ClNO Molecular weight: 185.65068 g/mol InChI Key: XAROQDPJMGCSII-UHFFFAOYSA-N

InChI=1S/C9H12ClNO/c1-6(11)4-7-2-3-9(12)8(10)5-7/h2-3,5-6,12H,4,11H2,1H3

PubChem CID: 54459594; ChemSpider: 26495114

Shulgin Index: See #38 DMA; Table: 4 Page: 328 Row: 7

Three R4 analogues:
364
Analogue 1: Removing Hydroxy at R4

3-HA
Gepefrine
3-Hydroxyamphetamine

IUPAC: 3-(2-Aminopropyl)phenol

Formula: C9H13NO Molecular weight: 151.20562 g/mol InChI Key: WTDGMHYYGNJEKQ-UHFFFAOYSA-N

InChI=1S/C9H13NO/c1-7(10)5-8-3-2-4-9(11)6-8/h2-4,6-7,11H,5,10H2,1H3

PubChem CID: 102551; ChemSpider: 92626; Wikipedia: Gepefrine

Shulgin Index: See #75 3-MA; Table: 3 Page: 321 Row: 8

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

6501
Analogue 2: Substituting Methyl for Hydroxy at R4

3,4-HMeA

IUPAC: 5-(2-Aminopropyl)-2-methylphenol

Formula: C10H15NO Molecular weight: 165.2322 g/mol InChI Key: XWLXNPMITZDCHL-UHFFFAOYSA-N

InChI=1S/C10H15NO/c1-7-3-4-9(5-8(2)11)6-10(7)12/h3-4,6,8,12H,5,11H2,1-2H3

PubChem CID: 167995; ChemSpider: 146955

Shulgin Index: See #96 3,4-MMA; Table: 4 Page: 328 Row: 1

6602
Analogue 3: Substituting Methoxy for Hydroxy at R4

HMA

IUPAC: 5-(2-Aminopropyl)-2-methoxyphenol

Formula: C10H15NO2 Molecular weight: 181.2316 g/mol InChI Key: IHPFVQVCJHQPFN-UHFFFAOYSA-N

InChI=1S/C10H15NO2/c1-7(11)5-8-3-4-10(13-2)9(12)6-8/h3-4,6-7,12H,5,11H2,1-2H3

PubChem CID: 12611606; ChemSpider: 16816977

Shulgin Index: See #33 DHA; Table: 4 Page: 330 Row: 2

One R5 analogue:
7552
Analogue 1: Adding Hydroxy at R5

THA

IUPAC: 5-(2-Aminopropyl)benzene-1,2,3-triol

Formula: C9H13NO3 Molecular weight: 183.20442 g/mol InChI Key: GYQMECTUTWANKQ-UHFFFAOYSA-N

InChI=1S/C9H13NO3/c1-5(10)2-6-3-7(11)9(13)8(12)4-6/h3-5,11-13H,2,10H2,1H3

PubChem CID: 55253841; ChemSpider: 26495032

Shulgin Index: See #117 TMA; Table: 5 Page: 349 Row: 2

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

21 R3,4 analogues:
100
Analogue 1: Substituting Methylenedioxy for Dihydroxy at R3,4

MDA
EA-1298
Amphedoxamine
3,4-Methylenedioxyamphetamine

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.

273
Analogue 2: Substituting Ethylidenedioxy for Dihydroxy 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 Dihydroxy 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 Dihydroxy 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 Dihydroxy 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 Dihydroxy 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 Dihydroxy 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 Dihydroxy 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 Dihydroxy 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 Dihydroxy 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 Dihydroxy 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 Dihydroxy 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.

6480
Analogue 13: Substituting 2,5-Dihydrofuro[c] for Dihydroxy 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 14: Substituting Ethylenedioxy for Dihydroxy 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 15: Substituting 4-Methoxybenzo for Dihydroxy 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 16: Substituting 4-Ethoxybenzo for Dihydroxy 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 17: Substituting 4-n-Propoxybenzo for Dihydroxy 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 18: Substituting 4-n-Butoxybenzo for Dihydroxy 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 19: Substituting 4-Benzyloxybenzo for Dihydroxy 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 20: Substituting 4-Methylthiobenzo for Dihydroxy 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 21: Substituting Pyrrolo[d] for Dihydroxy 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

Five skeleton analogues:
909
Analogue 1: With Phenylmethanamine skeleton

DHBA

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

Formula: C7H9NO2 Molecular weight: 139.15186 g/mol InChI Key: YFMPSMITLLBENU-UHFFFAOYSA-N

InChI=1S/C7H9NO2/c8-4-5-1-2-6(9)7(10)3-5/h1-3,9-10H,4,8H2

PubChem CID: 91623; ChemSpider: 82729

Shulgin Index: See #49 DMPEA; Table: 9 Page: 357 Row: 25

607
Analogue 2: With 3-Phenylpropan-1-amine skeleton

homo-Dopamine

IUPAC: 4-(3-Aminopropyl)benzene-1,2-diol

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

InChI=1S/C9H13NO2/c10-5-1-2-7-3-4-8(11)9(12)6-7/h3-4,6,11-12H,1-2,5,10H2

PubChem CID: 521660; ChemSpider: 455047

Shulgin Index: See #38 DMA; Table: 10 Page: 358 Row: 14

6523
Analogue 3: With 2-Amino-1-phenylethanone skeleton

DHPEA-βk

IUPAC: 2-Amino-1-(3,4-dihydroxyphenyl)ethanone

Formula: C8H9NO3 Molecular weight: 167.16196 g/mol InChI Key: CNFQARFTXUBHJY-UHFFFAOYSA-N

InChI=1S/C8H9NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,10-11H,4,9H2

PubChem CID: 10359; ChemSpider: 9932

Shulgin Index: See #49 DMPEA; Table: 4 Page: 328 Row: 23

506
Analogue 4: With 2-Phenylcyclopropan-1-amine skeleton

3,4-DHO-CPA

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

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

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

PubChem CID: 21156001

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

1260
Analogue 5: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

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

20 isomers:
2206
Isomer 1

N-Me-DHPEA
Epinine
3,4-Dihydroxy-N-methylphenethylamine

IUPAC: 4-[2-(Methylamino)ethyl]benzene-1,2-diol

Formula: C9H13NO2 Molecular weight: 167.20502 g/mol InChI Key: NGKZFDYBISXGGS-UHFFFAOYSA-N Properties: Peyote alkaloid

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

PubChem CID: 4382; ChemSpider: 4229; Wikipedia: Deoxyepinephrine

Shulgin Index: See #49 DMPEA; Table: 4 Page: 328 Row: 10

2207
Isomer 2

GEA
Homovanilylamine
4-Hydroxy-3-methoxyphenethylamine

IUPAC: 4-(2-Aminoethyl)-2-methoxyphenol

Formula: C9H13NO2 Molecular weight: 167.20502 g/mol InChI Key: DIVQKHQLANKJQO-UHFFFAOYSA-N Properties: Peyote alkaloid

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

PubChem CID: 1669; ChemSpider: 1606

Shulgin Index: #69 GEA; Table: 4 Page: 329 Row: 3

Short, JH; Dunnigan, DA; Ours, CW. Synthesis of phenethylamines from phenylacetonitriles obtained by alkylation of cyanide ion with Mannich bases from phenols and other benzylamines. Tetrahedron, 1973, 29 (14), 1931–1939. 791 kB. doi:10.1016/0040-4020(73)80127-9

Fennoy, LV. Substituted phenylalanines and phenylethylamines. J. Org. Chem., 1 Nov 1961, 26 (11), 4696–4698. 279 kB. doi:10.1021/jo01069a516

5547
Isomer 3

β-HO-N-Me-HPEA
Synephrine
β,4-Dihydroxy-N-methylphenethylamine

IUPAC: 4-[1-Hydroxy-2-(methylamino)ethyl]phenol

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

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

PubChem CID: 7172; ChemSpider: 6904; Wikipedia: Synephrine

Shulgin Index: See #71 Hordenine; Table: 3 Page: 323 Row: 19

Horn, AS. Structure-activity relations for the inhibition of catecholamine uptake into synaptosomes from noradrenaline and dopaminergic neurones in rat brain homogenates. Br. J. Pharmacol., 1 Feb 1973, 47 (2), 332–338. 903 kB. doi:10.1111/j.1476-5381.1973.tb08331.x

5548
Isomer 4

Phenylephrine
β,2-Dihydroxy-N-methylphenethylamine

IUPAC: 2-[1-Hydroxy-2-(methylamino)ethyl]phenol

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

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

PubChem CID: 159187; ChemSpider: 140010; Wikipedia: Phenylephrine

Rusterholz, DB; Dryer, SE; Long, JP; Barfknecht, CF; Mott, J. Sedative and analgesic actions of methoxylated 2-aminotetralins; involvement of α1- and α2-adrenoreceptors. Eur. J. Pharmacol., 25 Jul 1980, 65 (2–3), 201–211. 870 kB. doi:10.1016/0014-2999(80)90393-3

607
Isomer 5

homo-Dopamine

IUPAC: 4-(3-Aminopropyl)benzene-1,2-diol

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

InChI=1S/C9H13NO2/c10-5-1-2-7-3-4-8(11)9(12)6-7/h3-4,6,11-12H,1-2,5,10H2

PubChem CID: 521660; ChemSpider: 455047

Shulgin Index: See #38 DMA; Table: 10 Page: 358 Row: 14

6157
Isomer 6

β-HO-N-Me-3-HPEA

IUPAC: 3-[1-Hydroxy-2-(methylamino)ethyl]phenol

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

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

PubChem CID: 4782; ChemSpider: 4618

Shulgin Index: See #71 Hordenine; Table: 3 Page: 321 Row: 7

6160
Isomer 7

β-HO-3-HA

IUPAC: 3-(2-Amino-1-hydroxypropyl)phenol

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

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

PubChem CID: 4087; ChemSpider: 3945

Shulgin Index: See #75 3-MA; Table: 3 Page: 321 Row: 10

6275
Isomer 8

β-HO-PHA

IUPAC: 4-(2-Amino-1-hydroxypropyl)phenol

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

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

PubChem CID: 11099; ChemSpider: 10628

Shulgin Index: See #109 PHA; Table: 3 Page: 323 Row: 25

Warren, RJ; Begosh, PP; Zarembo, JE. Identification of amphetamines and related sympathomimetic amines. J. Assoc. Off. Anal. Chem., 1971, 54 (5), 1179–1191. 3851 kB.

6285
Isomer 9

β-HO-4-MPEA

IUPAC: 2-Amino-1-(4-methoxyphenyl)ethanol

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

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

PubChem CID: 3016949; ChemSpider: 2284793

Shulgin Index: See #102 4-MPEA; Table: 3 Page: 323 Row: 35

6376
Isomer 10

2,3-HMPEA

IUPAC: 2-(2-Aminoethyl)-6-methoxyphenol

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

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

PubChem CID: 20118748; ChemSpider: 16821708

Shulgin Index: See #34 2,3-DMA; Table: 4 Page: 325 Row: 26

Short, JH; Dunnigan, DA; Ours, CW. Synthesis of phenethylamines from phenylacetonitriles obtained by alkylation of cyanide ion with Mannich bases from phenols and other benzylamines. Tetrahedron, 1973, 29 (14), 1931–1939. 791 kB. doi:10.1016/0040-4020(73)80127-9

6456
Isomer 11

2,4-MHPEA

IUPAC: 4-(2-Aminoethyl)-3-methoxyphenol

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

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

PubChem CID: 3015690; ChemSpider: 2283778

Shulgin Index: See #47 2,4-DMPEA; Table: 4 Page: 327 Row: 6

6517
Isomer 12

β-Me-DHPEA

IUPAC: 4-(1-Aminopropan-2-yl)benzene-1,2-diol

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

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

PubChem CID: 3031524; ChemSpider: 2296629

Shulgin Index: See #49 DMPEA; Table: 4 Page: 328 Row: 17

6579
Isomer 13

HMPEA

IUPAC: 5-(2-Aminoethyl)-2-methoxyphenol

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

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

PubChem CID: 1748; ChemSpider: 1685

Shulgin Index: See #49 DMPEA; Table: 4 Page: 329 Row: 29

Fennoy, LV. Substituted phenylalanines and phenylethylamines. J. Org. Chem., 1 Nov 1961, 26 (11), 4696–4698. 279 kB. doi:10.1021/jo01069a516

6812
Isomer 14

β,2-HO-5-MePEA

IUPAC: 2-(2-Amino-1-hydroxyethyl)-4-methylphenol

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

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

Shulgin Index: See #22 2C-H; Table: 4 Page: 334 Row: 12

6829
Isomer 15

2,5-HMPEA

IUPAC: 2-(2-Aminoethyl)-4-methoxyphenol

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

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

PubChem CID: 12611609; ChemSpider: 23241951

Shulgin Index: See #22 2C-H; Table: 4 Page: 334 Row: 29

6921
Isomer 16

3,5-HMPEA

IUPAC: 3-(2-Aminoethyl)-5-methoxyphenol

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

InChI=1S/C9H13NO2/c1-12-9-5-7(2-3-10)4-8(11)6-9/h4-6,11H,2-3,10H2,1H3

PubChem CID: 69019600

Shulgin Index: See #50 3,5-DMPEA; Table: 4 Page: 336 Row: 21

6967
Isomer 17

2,6-HMPEA

IUPAC: 2-(2-Aminoethyl)-3-methoxyphenol

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

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

PubChem CID: 55254219; ChemSpider: 26492225

Shulgin Index: See #48 2,6-DMPEA; Table: 4 Page: 337 Row: 17

2493
Isomer 18

5-HO-2-MPEA
5-HO-2-MPEA

IUPAC: 3-(2-Aminoethyl)-4-methoxyphenol

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

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

PubChem CID: 44340081; ChemSpider: 23196095

Rangisetty, JB; Dukat, M; Dowd, CS; Herrick-Davis, K; DuPre, A; Gadepalli, S; Teitler, M; Kelley, CR; Sharif, NA; Glennon, RA. 1-[2-Methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT2A serotonin receptor affinity and antagonist character. J. Med. Chem., 1 Jan 2001, 44 (20), 3283–3291. 115 kB. doi:10.1021/jm0100739

1456
Isomer 19

2,5-HO-4-MePEA

IUPAC: 2-(2-Aminoethyl)-5-methylbenzene-1,4-diol

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

InChI=1S/C9H13NO2/c1-6-4-9(12)7(2-3-10)5-8(6)11/h4-5,11-12H,2-3,10H2,1H3

PubChem CID: 14004046; ChemSpider: 23221461

Cheng, AC; Castagnoli, N. Synthesis and physicochemical and neurotoxicity studies of 1-(4-substituted-2,5-dihydroxyphenyl)-2-aminoethane analogs of 6-hydroxydopamine. J. Med. Chem., 1 Apr 1984, 27 (4), 513–520. 1214 kB. doi:10.1021/jm00370a014

1009
Isomer 20

Metaraminol

IUPAC: 3-(2-Amino-1-hydroxypropyl)phenol

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

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

PubChem CID: 4087; ChemSpider: 3945

Horn, AS. Structure-activity relations for the inhibition of catecholamine uptake into synaptosomes from noradrenaline and dopaminergic neurones in rat brain homogenates. Br. J. Pharmacol., 1 Feb 1973, 47 (2), 332–338. 903 kB. doi:10.1111/j.1476-5381.1973.tb08331.x

Show all 63 analogues and isomers Show only the five N analogues Show only the three α analogues Show only the one β analogues Show only the four R3 analogues Show only the three R4 analogues Show only the one R5 analogues Show only the 21 R3,4 analogues Show only the five skeleton analogues
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