3,4-DMA
DMA
3,4-Dimethoxyamphetamine

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

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: KAZPHAGSWZTKDW-UHFFFAOYSA-N Properties: Essential amphetamine

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

PubChem CID: 8423; ChemSpider: 8116; Wikipedia: Dimethoxyamphetamine

Shulgin Index: #38 DMA; Table: 4 Page: 330 Row: 17

See also PiHKAL:	#53 2,4-DMA	#124 META-DOB	#157 TMA

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

Butterick, JR; Unrau, AM. Studies on theoretical psychotogens. Synthesis of O-methylated analogs of catecholamine neurotransmitters and metabolic precursors. Can. J. Chem., 1 Jan 1974, 52 (16), 2873–2879. 305 kB. doi:10.1139/v74-418

Barfknecht, CF; Nichols, DE. Effects of S-(+)- and R-(-)-3,4,dimethoxyphenylisopropylamines in the rat. J. Med. Chem., 1 Jan 1972, 15 (1), 109–110. 295 kB. doi:10.1021/jm00271a037

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

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

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

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; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. doi:10.1021/jm00263a013

Butterick, JR. Synthesis of O-transmethylated catecholamines and psychodysleptic β-phenylisopropylamines. Ph. D. Thesis, Simon Faser University, Burnaby, BC, Canada, 11 Mar 1975. 6069 kB. External examiner: A. T. Shulgin!.

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; 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

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

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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

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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

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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

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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.

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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.

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.

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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.

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

DHA

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

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

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

PubChem CID: 17005; ChemSpider: 16110

Shulgin Index: #33 DHA; Table: 4 Page: 328 Row: 26

Torre, R; Farré, M. Neurotoxicity of MDMA (ecstasy): the limitations of scaling from animals to humans. Trends Pharmacol. Sci., 1 Oct 2004, 25 (10), 505–508. 104 kB. doi:10.1016/j.tips.2004.08.001

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

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

IUPAC: 2-(Naphthalen-1-yl)cyclopropanamine

Formula: C13H13N Molecular weight: 183.24902 g/mol InChI Key: QSBCZQISIPLNNT-UHFFFAOYSA-N

InChI=1S/C13H13N/c14-13-8-12(13)11-7-3-5-9-4-1-2-6-10(9)11/h1-7,12-13H,8,14H2

PubChem CID: 43810345; ChemSpider: 25871166

Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018

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

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

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

PubChem CID: 413939; ChemSpider: 366505

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