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

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, F. Neurotoxicity mechanisms of thioether Ecstasy metabolites. Neuroscience, 1 Jan 2007, 146, 1743–1757. 995 kB. doi:10.1016/j.neuroscience.2007.03.028

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

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

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

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

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

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

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

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

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

PHA
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

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

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

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

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

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

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

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, F. Neurotoxicity mechanisms of thioether Ecstasy metabolites. Neuroscience, 1 Jan 2007, 146, 1743–1757. 995 kB. doi:10.1016/j.neuroscience.2007.03.028

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 Pharmacology notes I:	p. 37, MDA: Subacute evaluation p. 123, MDA: Subjective response p. 139, The Pseunut Cocktail
See also Pharmacology notes II:	app. 3, MDA: Record p. 202, MDA: Subjective response p. 203, MDA: Subjective response p. 246, MDA: Subjective response p. 278, MDA: Subjective response

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.

7-Me-MDA
EDA
3,4-Ethylidenedioxyamphetamine

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

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

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

PubChem CID: 130542; ChemSpider: 115478

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

See also PiHKAL:	#100 MDA	#120 MEDA

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

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

IDA
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

IAP
Indanylaminopropane

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

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

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

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

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

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

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

F2-MDA
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

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.

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

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.

NAP
PAL-287
Naphthylaminopropane

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

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

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

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

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

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

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

TAP
Tetralinylaminopropane

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

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

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

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

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

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.

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

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

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

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

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

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.

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.

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

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

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

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

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

PubChem CID: 5017291; ChemSpider: 4196440

6-MeO-NAP

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

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

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

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

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

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

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

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

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

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

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

ADTN

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

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

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

PubChem CID: 3153; ChemSpider: 3041

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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