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2-MA; 2-Methoxyamphetamine
267
Variant: N α R2 R3 R4 R5 R6 skeleton isomers all
Analogues: 11 2 11 4 7 3 1 7 28 74

IUPAC: 1-(2-Methoxyphenyl)propan-2-amine

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

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

PubChem CID: 159755; ChemSpider: 140465

Shulgin Index: #74 2-MA; Table: 3 Page: 320 Row: 1

See also PiHKAL: #97 4-MA    

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Geertsen, S; Foster, BC; Cyr, DLWTD; Casley, W. Metabolism of methoxyphenamine and 2-methoxyamphetamine inP4502D6-transfected cells and cell preparations. Xenobiotica, 1995, 25 (9), 895–906. 731 kB. doi:10.3109/00498259509046661

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

Katagi, M; Tsuchihashi, H. Update on clandestine amphetamines and their analogues recently seen in Japan. J. Health Sci., 2002, 48 (1), 14–21. 181 kB. doi:10.1248/jhs.48.14

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

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; 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

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

Dal Cason, TA. A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone. Forensic Sci. Int., 1 Jan 2001, 119 (3), 168–194. 678 kB. doi:10.1016/S0379-0738(00)00425-4

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Bailey, K; Beckstead, HD; Legault, D; Verner, D. Identification of 2-, 3-, and 4-methoxyamphetamines and 2-, 3-, and 4-methylamphetamines. J. Assoc. Off. Anal. Chem., 1974, 57 (5), 1134–1143. 1143 kB.

11 N analogues:
269
Analogue 1: Adding Methyl at N

2-MMA
OMMA
Orthoxine
Methoxyphenamine
N-Methyl-2-methoxyamphetamine

IUPAC: 1-(2-Methoxyphenyl)-N-methylpropan-2-amine

Formula: C11H17NO Molecular weight: 179.25878 g/mol InChI Key: OEHAYUOVELTAPG-UHFFFAOYSA-N

InChI=1S/C11H17NO/c1-9(12-2)8-10-6-4-5-7-11(10)13-3/h4-7,9,12H,8H2,1-3H3

PubChem CID: 4117; ChemSpider: 3974; Wikipedia: Methoxyphenamine

Shulgin Index: Table: 3 Page: 320 Row: 3

See also PiHKAL: #97 4-MA #126 METHYL-DMA  

Dal Cason, TA. A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone. Forensic Sci. Int., 1 Jan 2001, 119 (3), 168–194. 678 kB. doi:10.1016/S0379-0738(00)00425-4

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

Geertsen, S; Foster, BC; Cyr, DLWTD; Casley, W. Metabolism of methoxyphenamine and 2-methoxyamphetamine inP4502D6-transfected cells and cell preparations. Xenobiotica, 1995, 25 (9), 895–906. 731 kB. doi:10.3109/00498259509046661

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.

Bailey, K; By, AW; Legault, D; Verner, D. Identification of the N-methylated analogs of the hallucinogenic amphetamines and some isomers. J. Assoc. Off. Anal. Chem., 1975, 58 (1), 62–69. 1987 kB.

Katagi, M; Tsuchihashi, H. Update on clandestine amphetamines and their analogues recently seen in Japan. J. Health Sci., 2002, 48 (1), 14–21. 181 kB. doi:10.1248/jhs.48.14

Clark, CC. The identification of methoxy-N-methylamphetamines. J. Forensic Sci., 1 Oct 1984, 29 (4), 1056–1071. 423 kB. doi:10.1520/JFS11772J

296
Analogue 2: Adding Dimethyl at N

N,N-Me-2-MA
2-MNNA
2-Methoxy-N,N-dimethylamphetamine

IUPAC: 1-(2-Methoxyphenyl)-N,N-dimethylpropan-2-amine

Formula: C12H19NO Molecular weight: 193.28536 g/mol InChI Key: MKVBOOXXOLQOHN-UHFFFAOYSA-N

InChI=1S/C12H19NO/c1-10(13(2)3)9-11-7-5-6-8-12(11)14-4/h5-8,10H,9H2,1-4H3

PubChem CID: 3054974; ChemSpider: 2316550

Shulgin Index: See #74 2-MA; Table: 3 Page: 320 Row: 5

See also PiHKAL: #130 METHYL-MA    

Zaitsu, K; Miyagawa, H; Sakamoto, Y; Matsuta, S; Tsuboi, K; Nishioka, H; Katagi, M; Sato, T; Tatsuno, M; Tsuchihashi, H; Suzuki, K; Ishii, A. Mass spectrometric differentiation of the isomers of mono-methoxyethylamphetamines and mono-methoxydimethylamphetamines by GC-EI-MS-MS. Forensic Toxicol., 1 Jul 2013, 31 (2), 292–300. 344 kB. doi:10.1007/s11419-013-0193-6

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

Katagi, M; Tsuchihashi, H. Update on clandestine amphetamines and their analogues recently seen in Japan. J. Health Sci., 2002, 48 (1), 14–21. 181 kB. doi:10.1248/jhs.48.14

Al-Hossaini, AM. GC-MS and GC-IRD studies on ethoxyphenethylamines related to MDEA, MDMMA and MBDB. Ph. D. Thesis, Auburn University, Auburn, AL, USA, 18 Dec 2009. 1195 kB.

6106
Analogue 3: Adding Ethyl at N

N-Et-2-MA
N-Ethyl-2-methoxyamphetamine

IUPAC: N-Ethyl-1-(2-methoxyphenyl)propan-2-amine

Formula: C12H19NO Molecular weight: 193.28536 g/mol InChI Key: BQCBZRLRSYDWAC-UHFFFAOYSA-N

InChI=1S/C12H19NO/c1-4-13-10(2)9-11-7-5-6-8-12(11)14-3/h5-8,10,13H,4,9H2,1-3H3

PubChem CID: 21433829

Shulgin Index: See #74 2-MA; Table: 3 Page: 320 Row: 6

Zaitsu, K; Miyagawa, H; Sakamoto, Y; Matsuta, S; Tsuboi, K; Nishioka, H; Katagi, M; Sato, T; Tatsuno, M; Tsuchihashi, H; Suzuki, K; Ishii, A. Mass spectrometric differentiation of the isomers of mono-methoxyethylamphetamines and mono-methoxydimethylamphetamines by GC-EI-MS-MS. Forensic Toxicol., 1 Jul 2013, 31 (2), 292–300. 344 kB. doi:10.1007/s11419-013-0193-6

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

Al-Hossaini, AM. GC-MS and GC-IRD studies on ethoxyphenethylamines related to MDEA, MDMMA and MBDB. Ph. D. Thesis, Auburn University, Auburn, AL, USA, 18 Dec 2009. 1195 kB.

6107
Analogue 4: Adding Diethyl at N

N,N-Et-2-MA

IUPAC: N,N-Diethyl-1-(2-methoxyphenyl)propan-2-amine

Formula: C14H23NO Molecular weight: 221.33852 g/mol InChI Key: OOIDQNORPFCTPM-UHFFFAOYSA-N

InChI=1S/C14H23NO/c1-5-15(6-2)12(3)11-13-9-7-8-10-14(13)16-4/h7-10,12H,5-6,11H2,1-4H3

Shulgin Index: See #74 2-MA; Table: 3 Page: 320 Row: 7

6108
Analogue 5: Adding Isopropyl at N

N-iPr-2-MA

IUPAC: 1-(2-Methoxyphenyl)-N-(propan-2-yl)propan-2-amine

Formula: C13H21NO Molecular weight: 207.31194 g/mol InChI Key: VIWVDXYATJDPPN-UHFFFAOYSA-N

InChI=1S/C13H21NO/c1-10(2)14-11(3)9-12-7-5-6-8-13(12)15-4/h5-8,10-11,14H,9H2,1-4H3

PubChem CID: 211122; ChemSpider: 183028

Shulgin Index: See #74 2-MA; Table: 3 Page: 320 Row: 8

6109
Analogue 6: Adding n-Butyl at N

N-Bu-2-MA

IUPAC: N-[1-(2-Methoxyphenyl)propan-2-yl]butan-1-amine

Formula: C14H23NO Molecular weight: 221.33852 g/mol InChI Key: WHNDMDFVNAQKSW-UHFFFAOYSA-N

InChI=1S/C14H23NO/c1-4-5-10-15-12(2)11-13-8-6-7-9-14(13)16-3/h6-9,12,15H,4-5,10-11H2,1-3H3

PubChem CID: 3063468; ChemSpider: 2324023

Shulgin Index: See #74 2-MA; Table: 3 Page: 320 Row: 9

6110
Analogue 7: Adding Isobutyl at N

N-iBu-2-MA

IUPAC: N-[1-(2-Methoxyphenyl)propan-2-yl]-2-methylpropan-1-amine

Formula: C14H23NO Molecular weight: 221.33852 g/mol InChI Key: JCOWNZLWONPHNH-UHFFFAOYSA-N

InChI=1S/C14H23NO/c1-11(2)10-15-12(3)9-13-7-5-6-8-14(13)16-4/h5-8,11-12,15H,9-10H2,1-4H3

PubChem CID: 3064403; ChemSpider: 2324876

Shulgin Index: See #74 2-MA; Table: 3 Page: 320 Row: 10

6111
Analogue 8: Adding n-Hexyl at N

N-He-2-MA

IUPAC: N-[1-(2-Methoxyphenyl)propan-2-yl]hexan-1-amine

Formula: C16H27NO Molecular weight: 249.39168 g/mol InChI Key: RYYURZSIWOPZFB-UHFFFAOYSA-N

InChI=1S/C16H27NO/c1-4-5-6-9-12-17-14(2)13-15-10-7-8-11-16(15)18-3/h7-8,10-11,14,17H,4-6,9,12-13H2,1-3H3

PubChem CID: 3029805; ChemSpider: 2295078

Shulgin Index: See #74 2-MA; Table: 3 Page: 320 Row: 11

6112
Analogue 9: Adding Difuran-2-ylmethyl at N

N-fur-2-MA

IUPAC: N-(Furan-2-ylmethyl)-1-(2-methoxyphenyl)propan-2-amine

Formula: C15H19NO2 Molecular weight: 245.31686 g/mol InChI Key: RNCJWGNMKVTARX-UHFFFAOYSA-N

InChI=1S/C15H19NO2/c1-12(16-11-14-7-5-9-18-14)10-13-6-3-4-8-15(13)17-2/h3-9,12,16H,10-11H2,1-2H3

PubChem CID: 58181; ChemSpider: 52413

Shulgin Index: See #74 2-MA; Table: 3 Page: 320 Row: 12

1533
Analogue 10: Adding Formyl and 1-(2-Methoxyphenyl)propan-2-yl at N

IUPAC: N,N-Bis[1-(2-methoxyphenyl)propan-2-yl]formamide

Formula: C21H27NO3 Molecular weight: 341.44398 g/mol InChI Key: RBAPFAIQNDXASG-UHFFFAOYSA-N

InChI=1S/C21H27NO3/c1-16(13-18-9-5-7-11-20(18)24-3)22(15-23)17(2)14-19-10-6-8-12-21(19)25-4/h5-12,15-17H,13-14H2,1-4H3

Błachut, D; Danikiewicz, W; Wojtasiewicz, K; Olejnik, M; Kalinowska, I; Szawkało, J; Czarnocki, Z. The synthesis, mass spectrometric properties and identification of some N,N-di-(β-arylisopropyl)formamides related to the synthesis of ring-modified amphetamines. Forensic Sci. Int., 20 Mar 2011, 206 (1), 197–206. 760 kB. doi:10.1016/j.forsciint.2010.08.007

1006
Analogue 11: Adding Acetyl at N

IUPAC: N-[1-(2-Methoxyphenyl)propan-2-yl]acetamide

Formula: C12H17NO2 Molecular weight: 207.26888 g/mol InChI Key: KMMMHHCNFVYPIJ-UHFFFAOYSA-N

InChI=1S/C12H17NO2/c1-9(13-10(2)14)8-11-6-4-5-7-12(11)15-3/h4-7,9H,8H2,1-3H3,(H,13,14)

PubChem CID: 541953; ChemSpider: 471935

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

Two α analogues:
2363
Analogue 1: Removing Methyl at α

2-MPEA
2-Methoxyphenethylamine

IUPAC: 2-(2-Methoxyphenyl)ethanamine

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

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

PubChem CID: 74896; ChemSpider: 67459

Shulgin Index: #100 2-MPEA; Table: 3 Page: 319 Row: 28

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

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

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

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

Bailey, K; By, AW. The conformation of β-phenylethylamines in solution. Can. J. Pharm. Sci., 1975, 10 (1), 31–32. 117 kB.

6115
Analogue 2: Substituting Ethyl for Methyl at α

4C-2-MPEA

IUPAC: 1-(2-Methoxyphenyl)butan-2-amine

Formula: C11H17NO Molecular weight: 179.25878 g/mol InChI Key: YTEROTYXILFWNI-UHFFFAOYSA-N

InChI=1S/C11H17NO/c1-3-10(12)8-9-6-4-5-7-11(9)13-2/h4-7,10H,3,8,12H2,1-2H3

PubChem CID: 43566027; ChemSpider: 26539742

Shulgin Index: See #74 2-MA; Table: 3 Page: 320 Row: 15

11 R2 analogues:
219
Analogue 1: Substituting Methyl for Methoxy at R2

2-MeA
2-Methylamphetamine

IUPAC: 1-(2-Methylphenyl)propan-2-amine

Formula: C10H15N Molecular weight: 149.2328 g/mol InChI Key: ZEMQBDFHXOOXLY-UHFFFAOYSA-N

InChI=1S/C10H15N/c1-8-5-3-4-6-10(8)7-9(2)11/h3-6,9H,7,11H2,1-2H3

PubChem CID: 115808; ChemSpider: 103572; Wikipedia: Ortetamine

Shulgin Index: See #111 PMeA; Table: 3 Page: 319 Row: 20

See also PiHKAL: #54 2,5-DMA    

Higgs, RA; Glennon, RA. Stimulus properties of ring-methyl amphetamine analogs. Pharmacol. Biochem. Behav., 1 Dec 1990, 37 (4), 835–837. 238 kB. doi:10.1016/0091-3057(90)90571-X

Bailey, K; Legault, D. Analysis of the 13C-NMR spectra of mono- and dimethylamphetamines. Anal. Chim. Acta., 1 Jan 1981, 123, 75–82. 654 kB. doi:10.1016/S0003-2670(01)83160-3

Davis, S; Blakey, K; Rands-Trevor, K. GC-MS and GC-IRD analysis of 2-, 3- and 4-methylmethamphetamine and 2-, 3- and 4-methylamphetamine. Forensic Sci. Int., 10 Jul 2012, 220 (1–3), 67–73. 1158 kB. doi:10.1016/j.forsciint.2012.01.028

Power, JD; Clarke, K; McDermott, SD; McGlynn, P; Barry, M; White, C; O’Brien, J; Kavanagh, P. The identification of 4-methylamphetamine and its synthesis by-products in forensic samples. Forensic Sci. Int., 10 May 2013, 228 (1–3), 115–131. 1893 kB. doi:10.1016/j.forsciint.2013.02.039

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. 36161 kB. Rhodium.

Bailey, K; Beckstead, HD; Legault, D; Verner, D. Identification of 2-, 3-, and 4-methoxyamphetamines and 2-, 3-, and 4-methylamphetamines. J. Assoc. Off. Anal. Chem., 1974, 57 (5), 1134–1143. 1143 kB.

2006
Analogue 2: Removing Methoxy at R2

Amphetamine

IUPAC: 1-Phenylpropan-2-amine

Formula: C9H13N Molecular weight: 135.20622 g/mol InChI Key: KWTSXDURSIMDCE-UHFFFAOYSA-N

InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3

PubChem CID: 3007; ChemSpider: 13852819; Drugs Forum: Amphetamine; Erowid: Amphetamines; Wikipedia: Amphetamine

See also TiHKAL: #5 α,O-DMS
#8 α,N-DMT
#13 Harmaline
#48 α-MT
#55 α,N,O-TMS
See also Pharmacology notes I: p. 133, Amphetamine

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.

Bustamante, D; Diaz-Véliz, G; Paeile, C; Zapata-Torres, G; Cassels, BK. Analgesic and behavioral effects of amphetamine enantiomers, p-methoxyamphetamine and N-alkyl-p-methoxyamphetamine derivatives. Pharmacol. Biochem. Behav., 1 Oct 2004, 79 (2), 199–212. 404 kB. doi:10.1016/j.pbb.2004.06.017

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Bailey, K; Legault, D. Analysis of the 13C-NMR spectra of mono- and dimethylamphetamines. Anal. Chim. Acta., 1 Jan 1981, 123, 75–82. 654 kB. doi:10.1016/S0003-2670(01)83160-3

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

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

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

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

Thunhorst, M; Holzgrabe, U. Utilizing NMR spectroscopy for assessing drug enantiomeric composition. Magn. Reson. Chem., 1 Mar 1998, 36 (3), 211–216. 237 kB. doi:10.1002/(SICI)1097-458X(199803)363211AID-OMR2463.0.CO;2-Y

Ögren, S; Ross, SB. Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones. Acta pharmacol. Et toxicol., 1 Oct 1977, 41 (4), 353–368. 1335 kB. doi:10.1111/j.1600-0773.1977.tb02674.x

Lurie, IS; Bozenko, JS; Li, L; Miller, EE; Greenfield, SJ. Chiral separation of methamphetamine and related compounds using capillary electrophoresis with dynamically coated capillaries. Microgram J., 1 Jan 2011, 8 (1), 24–28. 786 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

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of ?-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-X

Heal, DJ; Smith, SL; Gosden, J; Nutt, DJ. Amphetamine, past and present—a pharmacological and clinical perspective. J. Psychopharmacol., 1 Jun 2013, 27 (6), 479–496. 740 kB. doi:10.1177/0269881113482532

Clarke, EGC. The identification of amphetamine type drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 31–36. 770 kB. doi:10.1016/S0015-7368(67)70368-0

Rasmussen, N. Making the first anti-depressant: Amphetamine in American medicine, 1929-1950. J. Hist. Med. Allied Sci., 1 Jul 2006, 61 (3), 288–323. 175 kB. doi:10.1093/jhmas/jrj039

Worsham, JN. 5-HT3 receptor ligands and their effect on psychomotor stimulants. M. Sc. Thesis, Virginia Commonwealth University, Richmond, VA, USA, 1 May 2008. 956 kB.

Oberlender, R; Nichols, DE. Drug discrimination studies with MDMA and amphetamine. Psychopharmacology, 1 May 1988, 95 (1), 71–26. 674 kB. doi:10.1007/BF00212770

Benington, F; Morin, RD; Clark, LC. Behavioral and neuropharmacological actions of N-aralkylhydroxylamines and their O-methyl ethers. J. Med. Chem., 1 Jan 1965, 8 (1), 100–104. 634 kB. doi:10.1021/jm00325a020

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

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

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.

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

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

Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. doi:10.1016/j.pbb.2007.06.001

McGraw, NP; Callery, PS; Castagnoli, N. In vitro stereoselective metabolism of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane. An apparent enantiomeric interaction. J. Med. Chem., 1 Jan 1977, 20 (2), 185–189. 661 kB. doi:10.1021/jm00212a001

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

Marona-Lewicka, D; Kurrasch-Orbaugh, DM; Selken, JR; Cumbay, MG; Lisnicchia, JG; Nichols, DE. Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioural effects overlap its other properties in rats. Psychopharmacology, 1 Oct 2002, 164 (1), 93–107. 293 kB. doi:10.1007/s00213-002-1141-z

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

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

Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012

Meyers-Riggs, B. Phenethylamine and amphetamine. countyourculture: rational exploration of the underground, 2 Nov 2010.

Glennon, RA; Young, R; Martin, BR; Dal Cason, TA. Methcathinone (“Cat”): An enantiomeric potency comparison. Pharmacol. Biochem. Behav., 1 Jan 1995, 50 (4) 601–606. 709 kB. doi:10.1016/0091-3057(94)00348-3

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.

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

Hathaway, BA; Nichols, DE; Nichols, MB; Yim, GKW. A new, potent, conformationally-restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene. J. Med. Chem., 1 Jan 1982, 25 (5), 535–538. 563 kB. doi:10.1021/jm00347a011

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

Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 581–586. 586 kB. doi:10.1016/0091-3057(91)90017-V

Huang, X; Nichols, DE. 5-HT2 receptor-mediated potentiation of dopamine synthesis and central serotonergic deficits. Eur. J. Pharmacol., 1 Jan 1993, 238 (2–3), 291–296. 553 kB. doi:10.1016/0014-2999(93)90859-G

Woolverton, WL; Shybut, G; Johanson, CE. Structure-activity relationships among some d-N-alkylated amphetamines. Pharmacol. Biochem. Behav., 1 Jan 1980, 13 (6), 869–876. 783 kB. doi:10.1016/0091-3057(80)90221-X

Alles, GA; Feigen, GA. Comparative physiological actions of phenyl-, thienyl- and furylisopropylamines. J. Pharmacol. Exp. Ther., 1 Jul 1941, 72 (3), 265–275. 1459 kB.

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

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

2129
Analogue 3: Substituting Fluoro for Methoxy at R2

2-FA
2-Fluoroamphetamine

IUPAC: 1-(2-Fluorophenyl)propan-2-amine

Formula: C9H12FN Molecular weight: 153.1966832 g/mol InChI Key: GDSXNLDTQFFIEU-UHFFFAOYSA-N

InChI=1S/C9H12FN/c1-7(11)6-8-4-2-3-5-9(8)10/h2-5,7H,6,11H2,1H3

PubChem CID: 121531; ChemSpider: 108441; Drugs Forum: 2-FA; Wikipedia: 2-Fluoroamphetamine

Rösner, P; Quednow, B; Girreser, U; Junge, T. Isomeric fluoro-methoxy-phenylalkylamines: A new series of controlled-substance analogues (designer drugs). Forensic Sci. Int., 1 Jan 2004, 148 (2–3), 143–156. 282 kB. doi:10.1016/j.forsciint.2004.05.003

Westphal, F; Rösner, P; Junge, T. Differentiation of regioisomeric ring-substituted fluorophenethylamines with product ion spectrometry. Forensic Sci. Int., 30 Jan 2010, 194 (1–3), 53–59. 521 kB. doi:10.1016/j.forsciint.2009.10.007

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

6062
Analogue 4: Substituting Chloro for Methoxy at R2

2-CA

IUPAC: 1-(2-Chlorophenyl)propan-2-amine

Formula: C9H12ClN Molecular weight: 169.65128 g/mol InChI Key: IQHHOHJDIZRBGM-UHFFFAOYSA-N

InChI=1S/C9H12ClN/c1-7(11)6-8-4-2-3-5-9(8)10/h2-5,7H,6,11H2,1H3

PubChem CID: 152331; ChemSpider: 134269; Drugs Forum: 2-CA

Shulgin Index: See #74 2-MA; Table: 3 Page: 319 Row: 12

Ögren, S; Ross, SB. Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones. Acta pharmacol. Et toxicol., 1 Oct 1977, 41 (4), 353–368. 1335 kB. doi:10.1111/j.1600-0773.1977.tb02674.x

6066
Analogue 5: Substituting Bromo for Methoxy at R2

2-BA

IUPAC: 1-(2-Bromophenyl)propan-2-amine

Formula: C9H12BrN Molecular weight: 214.10228 g/mol InChI Key: VGJBPBDFJNFFRO-UHFFFAOYSA-N

InChI=1S/C9H12BrN/c1-7(11)6-8-4-2-3-5-9(8)10/h2-5,7H,6,11H2,1H3

PubChem CID: 22026326; ChemSpider: 10763853; Drugs Forum: 2-BA

Shulgin Index: See #74 2-MA; Table: 3 Page: 319 Row: 16

6071
Analogue 6: Substituting Trifluoromethyl for Methoxy at R2

2-TFMA

IUPAC: 1-[2-(Trifluoromethyl)phenyl]propan-2-amine

Formula: C10H12F3N Molecular weight: 203.2041896 g/mol InChI Key: MBSQCJRYAIIWCP-UHFFFAOYSA-N

InChI=1S/C10H12F3N/c1-7(14)6-8-4-2-3-5-9(8)10(11,12)13/h2-5,7H,6,14H2,1H3

PubChem CID: 120763; ChemSpider: 107801

Shulgin Index: See #63 DOTFM; Table: 3 Page: 319 Row: 21

6076
Analogue 7: Substituting Hydroxy for Methoxy at R2

2-HA

IUPAC: 2-(2-Aminopropyl)phenol

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

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

PubChem CID: 541960; ChemSpider: 471942

Shulgin Index: See #74 2-MA; Table: 3 Page: 319 Row: 26

6118
Analogue 8: Substituting Ethoxy for Methoxy at R2

2-EA

IUPAC: 1-(2-Ethoxyphenyl)propan-2-amine

Formula: C11H17NO Molecular weight: 179.25878 g/mol InChI Key: BTRNIAUTIJBXFZ-UHFFFAOYSA-N

InChI=1S/C11H17NO/c1-3-13-11-7-5-4-6-10(11)8-9(2)12/h4-7,9H,3,8,12H2,1-2H3

PubChem CID: 541929; ChemSpider: 471913

Shulgin Index: See #74 2-MA; Table: 3 Page: 320 Row: 18

6120
Analogue 9: Substituting Methylthio for Methoxy at R2

2-MTA

IUPAC: 1-[2-(Methylsulfanyl)phenyl]propan-2-amine

Formula: C10H15NS Molecular weight: 181.2978 g/mol InChI Key: VGKAKJXMHGNTFY-UHFFFAOYSA-N

InChI=1S/C10H15NS/c1-8(11)7-9-5-3-4-6-10(9)12-2/h3-6,8H,7,11H2,1-2H3

PubChem CID: 63819037; ChemSpider: 26495787

Shulgin Index: See #103 MTA; Table: 3 Page: 320 Row: 20

2440
Analogue 10: Substituting Iodo for Methoxy at R2

2-IA

IUPAC: 1-(2-Iodophenyl)propan-2-amine

Formula: C9H12IN Molecular weight: 261.10275 g/mol InChI Key: WSTDXRKNIDTRHW-UHFFFAOYSA-N

InChI=1S/C9H12IN/c1-7(11)6-8-4-2-3-5-9(8)10/h2-5,7H,6,11H2,1H3

PubChem CID: 13367854; ChemSpider: 11500661

2761
Analogue 11: Substituting Hydroxy for Methoxy at R2

IUPAC: 2-(2-Aminopropyl)phenol

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

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

PubChem CID: 541960; ChemSpider: 471942

Geertsen, S; Foster, BC; Cyr, DLWTD; Casley, W. Metabolism of methoxyphenamine and 2-methoxyamphetamine inP4502D6-transfected cells and cell preparations. Xenobiotica, 1995, 25 (9), 895–906. 731 kB. doi:10.3109/00498259509046661

Four R3 analogues:
2162
Analogue 1: Adding Methoxy at R3

2,3-DMA
2,3-Dimethoxyamphetamine

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

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

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

PubChem CID: 91255; ChemSpider: 82404

Shulgin Index: #34 2,3-DMA; Table: 4 Page: 325 Row: 30

See also PiHKAL: #55 3,4-DMA #124 META-DOB  

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

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

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

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

6369
Analogue 2: Adding Methyl at R3

2,3-MMeA

IUPAC: 1-(2-Methoxy-3-methylphenyl)propan-2-amine

Formula: C11H17NO Molecular weight: 179.25878 g/mol InChI Key: WWGNFBZBLDQURC-UHFFFAOYSA-N

InChI=1S/C11H17NO/c1-8-5-4-6-10(7-9(2)12)11(8)13-3/h4-6,9H,7,12H2,1-3H3

PubChem CID: 3029797; ChemSpider: 2295070

Shulgin Index: See #34 2,3-DMA; Table: 4 Page: 325 Row: 19

2762
Analogue 3: Adding Hydroxy at R3

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

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

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

Geertsen, S; Foster, BC; Cyr, DLWTD; Casley, W. Metabolism of methoxyphenamine and 2-methoxyamphetamine inP4502D6-transfected cells and cell preparations. Xenobiotica, 1995, 25 (9), 895–906. 731 kB. doi:10.3109/00498259509046661

2760
Analogue 4: Adding Hydroxy at R3

IUPAC: 2-Methoxy-3-[2-(methylamino)propyl]phenol

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

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

Geertsen, S; Foster, BC; Cyr, DLWTD; Casley, W. Metabolism of methoxyphenamine and 2-methoxyamphetamine inP4502D6-transfected cells and cell preparations. Xenobiotica, 1995, 25 (9), 895–906. 731 kB. doi:10.3109/00498259509046661

Seven R4 analogues:
53
Analogue 1: Adding Methoxy at R4

2,4-DMA
2,4-Dimethoxyamphetamine

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

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

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

PubChem CID: 417604; ChemSpider: 124411; Wikipedia: Dimethoxyamphetamine

Shulgin Index: #35 2,4-DMA; Table: 4 Page: 327 Row: 11

See also PiHKAL: #55 3,4-DMA #124 META-DOB #157 TMA
See also Pharmacology notes I: p. 144, 2,4-DMA

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

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. 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. 36161 kB. Rhodium.

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

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

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; 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

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

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

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

5502
Analogue 2: Adding Methyl at R4

2,4-MMA
5-H-DOM
2-Methoxy-4-methylamphetamine

IUPAC: 1-(2-Methoxy-4-methylphenyl)propan-2-amine

Formula: C11H17NO Molecular weight: 179.25878 g/mol InChI Key: GCODSUWFMIHFEM-UHFFFAOYSA-N

InChI=1S/C11H17NO/c1-8-4-5-10(7-9(2)12)11(6-8)13-3/h4-6,9H,7,12H2,1-3H3

PubChem CID: 91245; ChemSpider: 82395

Shulgin Index: See #35 2,4-DMA; Table: 4 Page: 327 Row: 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

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1175 kB. doi:10.1021/jm00256a016

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

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. doi:10.1124/mol.107.039255

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

2332
Analogue 3: Adding Phenylpropyl at R4

2-Methoxy-4-phenylpropylamphetamine

IUPAC: 1-[2-Methoxy-4-(3-phenylpropyl)phenyl]propan-2-amine

Formula: C19H25NO Molecular weight: 283.4079 g/mol InChI Key: ZGGKVIHEOVKYJK-UHFFFAOYSA-N

InChI=1S/C19H25NO/c1-15(20)13-18-12-11-17(14-19(18)21-2)10-6-9-16-7-4-3-5-8-16/h3-5,7-8,11-12,14-15H,6,9-10,13,20H2,1-2H3

PubChem CID: 10802941; ChemSpider: 8978247

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

Dowd, CS; Herrick-Davis, K; Egan, C; DuPre, A; Smith, C; Teitler, M; Glennon, RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A partial agonists. J. Med. Chem., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. doi:10.1021/jm9906062

357
Analogue 4: Adding Chloro at R4

4-Cl-2-MA
4-Chloro-2-methoxyamphetamine

IUPAC: 1-(4-Chloro-2-methoxyphenyl)propan-2-amine

Formula: C10H14ClNO Molecular weight: 199.67726 g/mol InChI Key: IOZPIOSCQZHUHR-UHFFFAOYSA-N

InChI=1S/C10H14ClNO/c1-7(12)5-8-3-4-9(11)6-10(8)13-2/h3-4,6-7H,5,12H2,1-2H3

Shulgin Index: See #35 2,4-DMA; Table: 4 Page: 326 Row: 27

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1175 kB. doi:10.1021/jm00256a016

6429
Analogue 5: Adding Bromo at R4

4-Br-2-MA

IUPAC: 1-(4-Bromo-2-methoxyphenyl)propan-2-amine

Formula: C10H14BrNO Molecular weight: 244.12826 g/mol InChI Key: YWONMRKCBJPFCM-UHFFFAOYSA-N

InChI=1S/C10H14BrNO/c1-7(12)5-8-3-4-9(11)6-10(8)13-2/h3-4,6-7H,5,12H2,1-2H3

PubChem CID: 13547422; ChemSpider: 23153503

Shulgin Index: See #35 2,4-DMA; Table: 4 Page: 326 Row: 29

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

6431
Analogue 6: Adding Iodo at R4

4-I-2-MA

IUPAC: 1-(4-Iodo-2-methoxyphenyl)propan-2-amine

Formula: C10H14INO Molecular weight: 291.12873 g/mol InChI Key: WPUXCVOFWTUZTP-UHFFFAOYSA-N

InChI=1S/C10H14INO/c1-7(12)5-8-3-4-9(11)6-10(8)13-2/h3-4,6-7H,5,12H2,1-2H3

PubChem CID: 15128241; ChemSpider: 23233632

Shulgin Index: See #35 2,4-DMA; Table: 4 Page: 326 Row: 31

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

6432
Analogue 7: Adding Trifluoromethyl at R4

2-MTFMA

IUPAC: 1-[2-Methoxy-4-(trifluoromethyl)phenyl]propan-2-amine

Formula: C11H14F3NO Molecular weight: 233.2301696 g/mol InChI Key: YORMNJGJJYAYTR-UHFFFAOYSA-N

InChI=1S/C11H14F3NO/c1-7(15)5-8-3-4-9(11(12,13)14)6-10(8)16-2/h3-4,6-7H,5,15H2,1-2H3

ChemSpider: 26472575

Shulgin Index: See #63 DOTFM; Table: 4 Page: 326 Row: 32

Three R5 analogues:
54
Analogue 1: Adding Methoxy at R5

2,5-DMA
DMA
DOH
2,5-Dimethoxyamphetamine

IUPAC: 1-(2,5-Dimethoxyphenyl)propan-2-amine

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

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

PubChem CID: 62787; ChemSpider: 56526; Wikipedia: Dimethoxyamphetamine

Shulgin Index: #38 DMA; Table: 4 Page: 330 Row: 17, #36 2,5-DMA; Table: 4 Page: 335 Row: 22

See also PiHKAL: #55 3,4-DMA
#62 DOB
#64 DOC
#67 DOI
#90 IDNNA
#124 META-DOB
#126 METHYL-DMA
See also Pharmacology notes I: p. 57, 2,5-DMA: Subacute evaluation
p. 58, 2,5-DMA: Subjective response
See also Pharmacology notes II: p. 276, 2,5-DMA

Fenderson5555. Shulgin’s syntheses of 2,5-DMA, DOB and DOEF. 5 Dec 2011.

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

Shulgin, AT; Dyer, DC. Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines. J. Med. Chem., 1 Jan 1975, 18 (12), 1201–1204. 534 kB. doi:10.1021/jm00246a006

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1175 kB. doi:10.1021/jm00256a016

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

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; Bondarev, ML; Khorana, N; Young, R. β-Oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 2004, 47 (24), 6034–6041. 146 kB. doi:10.1021/jm040082s

Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

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

Acuña-Castillo, C; Villalobos, C; Moya, PR; Sáez, P; Cassels, BK; Huidobro-Toro, JP. Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT2A and 5-HT2C receptors. Br. J. Pharmacol., 1 Jun 2002, 136 (4), 510–519. 232 kB. doi:10.1038/sj.bjp.0704747

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. doi:10.1124/jpet.106.117507

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. doi:10.1124/mol.107.039255

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

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1992, 22 (12), 1383–1394. 765 kB. doi:10.3109/00498259209056689

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. 36161 kB. Rhodium.

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.

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

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; Snyder, SE; Oberlender, R; Johnson, MP; Huang, X. 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines. J. Med. Chem., 1 Jan 1991, 34 (1), 276–281. 833 kB. doi:10.1021/jm00105a043

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Kanai, K; Takekawa, K; Kumamoto, T; Ishikawa, T; Ohmori, T. Simultaneous analysis of six phenethylamine-type designer drugs by TLC, LC-MS, and GC-MS. Forensic Toxicol., 1 Nov 2008, 26 (2), 6–12. 406 kB. doi:10.1007/s11419-008-0041-2

Dyer, DC; Nichols, DE; Rusterholz, DB; Barfknecht, CF. Comparative effects of stereoisomers of psychotomimetic phenylisopropylamines. Life Sci., 1 Oct 1973, 13 (7), 885–896. 398 kB. doi:10.1016/0024-3205(73)90079-9

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. doi:10.1016/0024-3205(77)90099-6

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; Young, R; Rosecrans, JA. A comparison of the behavioral effects of DOM homologs. Pharmacol. Biochem. Behav., 1 Apr 1982, 16 (4), 557–559. 256 kB. doi:10.1016/0091-3057(82)90414-2

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

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

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

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

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

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. doi:10.1016/j.bmc.2008.02.033

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; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

2134
Analogue 2: Adding Fluoro at R5

5-Fluoro-2-methoxyamphetamine

IUPAC: 1-(5-Fluoro-2-methoxyphenyl)propan-2-amine

Formula: C10H14FNO Molecular weight: 183.2226632 g/mol InChI Key: CUFIONJZZIARKQ-UHFFFAOYSA-N

InChI=1S/C10H14FNO/c1-7(12)5-8-6-9(11)3-4-10(8)13-2/h3-4,6-7H,5,12H2,1-2H3

PubChem CID: 55253736; ChemSpider: 26495210

Rösner, P; Quednow, B; Girreser, U; Junge, T. Isomeric fluoro-methoxy-phenylalkylamines: A new series of controlled-substance analogues (designer drugs). Forensic Sci. Int., 1 Jan 2004, 148 (2–3), 143–156. 282 kB. doi:10.1016/j.forsciint.2004.05.003

6807
Analogue 3: Adding Iodo at R5

5-I-2-MA

IUPAC: 1-(5-Iodo-2-methoxyphenyl)propan-2-amine

Formula: C10H14INO Molecular weight: 291.12873 g/mol InChI Key: JJRFSTFKKLFEGO-UHFFFAOYSA-N

InChI=1S/C10H14INO/c1-7(12)5-8-6-9(11)3-4-10(8)13-2/h3-4,6-7H,5,12H2,1-2H3

PubChem CID: 21632695; ChemSpider: 10263770

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 334 Row: 7

Dawson, BA; Black, DB; Sy, W; Graham, K. 13C NMR of some iodinated methoxy-amphetamines. Magn. Reson. Chem., 1 Sep 1994, 32 (9), 557–558. 171 kB. doi:10.1002/mrc.1260320913

Sy, W. Iodination of methoxyamphetamines with iodine and silver sulphate. Tetrahedron Lett., 24 Sep 1993, 34 (39), 6223–6224. 133 kB. doi:10.1016/S0040-4039(00)73715-4

One R6 analogue:
2163
Analogue 1: Adding Methoxy at R6

2,6-DMA
2,6-Dimethoxyamphetamine

IUPAC: 1-(2,6-Dimethoxyphenyl)propan-2-amine

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

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

PubChem CID: 141048; ChemSpider: 124412

Shulgin Index: #37 2,6-DMA; Table: 4 Page: 337 Row: 23

See also PiHKAL: #55 3,4-DMA #124 META-DOB  

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

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

Seven skeleton analogues:
811
Analogue 1: With 1-Phenylpiperazine skeleton

2-MeOPP

IUPAC: 1-(2-Methoxyphenyl)piperazine

Formula: C11H16N2O Molecular weight: 192.25754 g/mol InChI Key: VNZLQLYBRIOLFZ-UHFFFAOYSA-N

InChI=1S/C11H16N2O/c1-14-11-5-3-2-4-10(11)13-8-6-12-7-9-13/h2-5,12H,6-9H2,1H3

PubChem CID: 1346; ChemSpider: 1306

Shulgin Index: See #88 MeOPP; Table: 8 Page: 357 Row: 11

6113
Analogue 2: With Phenylethyl-cyclic-amine skeleton

N-mor-2-MA

IUPAC: 4-[1-(2-Methoxyphenyl)propan-2-yl]morpholine

Formula: C14H21NO2 Molecular weight: 235.32204 g/mol InChI Key: FBHHJANCRCAJCC-UHFFFAOYSA-N

InChI=1S/C14H21NO2/c1-12(15-7-9-17-10-8-15)11-13-5-3-4-6-14(13)16-2/h3-6,12H,7-11H2,1-2H3

PubChem CID: 3021973; ChemSpider: 2288564

Shulgin Index: See #74 2-MA; Table: 3 Page: 320 Row: 13

6114
Analogue 3: With Phenylethyl-cyclic-amine skeleton

N-pip-2-MA

IUPAC: 1-[1-(2-Methoxyphenyl)propan-2-yl]piperidine

Formula: C15H23NO Molecular weight: 233.34922 g/mol InChI Key: URCPTLOZDHGEKH-UHFFFAOYSA-N

InChI=1S/C15H23NO/c1-13(16-10-6-3-7-11-16)12-14-8-4-5-9-15(14)17-2/h4-5,8-9,13H,3,6-7,10-12H2,1-2H3

PubChem CID: 3024317; ChemSpider: 2290275

Shulgin Index: See #74 2-MA; Table: 3 Page: 320 Row: 14

2455
Analogue 4: With 2-Amino-1-phenylethanone skeleton

2-Methoxycathinone

IUPAC: 2-Amino-1-(2-methoxyphenyl)propan-1-one

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

InChI=1S/C10H13NO2/c1-7(11)10(12)8-5-3-4-6-9(8)13-2/h3-7H,11H2,1-2H3

PubChem CID: 12914879; ChemSpider: 23208219

Glennon, RA; Liebowitz, SM. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem., 1 Jan 1982, 25 (4), 393–397. 665 kB. doi:10.1021/jm00346a012

1142
Analogue 5: With Prop-2-en-1-ylbenzene skeleton

IUPAC: 1-Methoxy-2-(prop-2-en-1-yl)benzene

Formula: C10H12O Molecular weight: 148.20168 g/mol InChI Key: BCINBJDCXBFCDT-UHFFFAOYSA-N

InChI=1S/C10H12O/c1-3-6-9-7-4-5-8-10(9)11-2/h3-5,7-8H,1,6H2,2H3

PubChem CID: 97101; ChemSpider: 87650

Nichols, DE; Mason, DL; Jacobsen, LB. Allylbenzene analogs of Δ9-tetrahydrocannabinol as tumor growth inhibitors. Life Sci., 1 Nov 1977, 21 (9), 1245–1247. 150 kB. doi:10.1016/0024-3205(77)90004-2

1307
Analogue 6: With 6,7,8,9-Tetrahydro-5H-benzo[7]annulen-6-amine skeleton

IUPAC: 6,7,8,9-Tetrahydro-5H-benzo[7]annulen-6-amine

Formula: C11H15N Molecular weight: 161.2435 g/mol InChI Key: MDVRGZASGHPBAG-UHFFFAOYSA-N

InChI=1S/C11H15N/c12-11-7-3-6-9-4-1-2-5-10(9)8-11/h1-2,4-5,11H,3,6-8,12H2

PubChem CID: 41896; ChemSpider: 38228

Cannon, JG; Perez, JA; Pease, JP; Long, JP; Flynn, JR; Rusterholz, DB; Dryer., SE. Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene. J. Med. Chem., 1 Jan 1980, 23 (7), 745–749. 731 kB. doi:10.1021/jm00181a009

1443
Analogue 7: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

IUPAC: 8-Methoxy-1,2,3,4-tetrahydronaphthalen-2-amine

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: RVKOHSCTEHZRRT-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-13-11-4-2-3-8-5-6-9(12)7-10(8)11/h2-4,9H,5-7,12H2,1H3

PubChem CID: 10197933; ChemSpider: 8373433

Naiman, N; Lyon, RA; Bullock, AE; Rydelek, LT; Teitler, M; Glennon, RA. 2-(Alkylamino)tetralin derivatives: interaction with 5-HT1A serotonin binding sites. J. Med. Chem., 1 Jan 1989, 32 (1), 253–256. 597 kB. doi:10.1021/jm00121a045

28 isomers:
97
Isomer 1

PMA
4-MA
4-Methoxyamphetamine

IUPAC: 1-(4-Methoxyphenyl)propan-2-amine

Formula: C10H15NO Molecular weight: 165.2322 g/mol InChI Key: NEGYEDYHPHMHGK-UHFFFAOYSA-N Properties: Essential amphetamine

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

PubChem CID: 31721; ChemSpider: 29417; Erowid: PMA; Wikipedia: PMA

Shulgin Index: #110 PMA; Table: 3 Page: 324 Row: 4

See also PiHKAL: #126 METHYL-DMA
#130 METHYL-MA
#142 PEA
#157 TMA
 
See also Pharmacology notes I: p. 141, 4-MA

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

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

Katagi, M; Tsuchihashi, H. Update on clandestine amphetamines and their analogues recently seen in Japan. J. Health Sci., 2002, 48 (1), 14–21. 181 kB. doi:10.1248/jhs.48.14

Staack, RF; Maurer, HH. Metabolism of designer drugs of abuse. Curr. Drug Metab., 1 Jun 2005, 6 (3), 259–274. 104 kB. doi:10.2174/1389200054021825

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

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

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. 36161 kB. Rhodium.

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.

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.

Bailey, K; Beckstead, HD; Legault, D; Verner, D. Identification of 2-, 3-, and 4-methoxyamphetamines and 2-, 3-, and 4-methylamphetamines. J. Assoc. Off. Anal. Chem., 1974, 57 (5), 1134–1143. 1143 kB.

Waumans, D; Bruneel, N; Hermans, B; Tytgat, J. A rapid and simple GC/MS screening method for 4-methoxyphenol in illicitly prepared 4-methoxyamphetamine (PMA). Microgram J., 1 Jul 2003, 1 (3–4), 184–189. 231 kB.

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.

Callaghan, PD. Comparative neuropharmacology of the substituted amphetamines, p-methoxyamphatamine (PMA) & 3,4-methylenedioxymethamphetamine (MDMA). Ph. D. Thesis, University of Adelaide, Adelaide, Australia, 1 Aug 2008. 1551 kB.

Shulgin, AT. TMA, PMA, PMMA, and MDMA effects. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 27 Mar 2003.

Shulgin, AT. PMA. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 20 Feb 2001.

Shulgin, AT. Making MDMA (II): “Ecstasy”, MDMA, & Safrole. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 1 May 2002.

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

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

Benington, F; Morin, RD; Clark, LC. Behavioral and neuropharmacological actions of N-aralkylhydroxylamines and their O-methyl ethers. J. Med. Chem., 1 Jan 1965, 8 (1), 100–104. 634 kB. doi:10.1021/jm00325a020

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of ?-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-X

Dyer, DC; Nichols, DE; Rusterholz, DB; Barfknecht, CF. Comparative effects of stereoisomers of psychotomimetic phenylisopropylamines. Life Sci., 1 Oct 1973, 13 (7), 885–896. 398 kB. doi:10.1016/0024-3205(73)90079-9

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. doi:10.1016/0024-3205(77)90099-6

Corrigall, WA; Robertson, JM; Coen, KM; Lodge, BA. The reinforcing and discriminative stimulus properties of para-ethoxy- and para-methoxyamphetamine. Pharmacol. Biochem. Behav., 1 Jan 1992, 41 (1), 165–169. 538 kB. doi:10.1016/0091-3057(92)90077-S

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

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

Dal Cason, TA. A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone. Forensic Sci. Int., 1 Jan 2001, 119 (3), 168–194. 678 kB. doi:10.1016/S0379-0738(00)00425-4

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

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

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

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

Bustamante, D; Diaz-Véliz, G; Paeile, C; Zapata-Torres, G; Cassels, BK. Analgesic and behavioral effects of amphetamine enantiomers, p-methoxyamphetamine and N-alkyl-p-methoxyamphetamine derivatives. Pharmacol. Biochem. Behav., 1 Oct 2004, 79 (2), 199–212. 404 kB. doi:10.1016/j.pbb.2004.06.017

Cimbura, G. PMA deaths in Ontario. Can. Med. Assoc. J., 8 Jun 1974, 110 (8), 1263–1267.

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

Błachut, D; Wojtasiewicz, K; Czarnocki, Z; Szukalski, B. The analytical profile of some 4-methylthioamphetamine (4-MTA) homologues. Forensic Sci. Int., 20 Nov 2009, 192 (1–3) 98–114. 683 kB. doi:10.1016/j.forsciint.2009.08.009

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

268
Isomer 2

3-MA
MMA (3-MA)
3-Methoxyamphetamine

IUPAC: 1-(3-Methoxyphenyl)propan-2-amine

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

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

PubChem CID: 152234; ChemSpider: 134180; Wikipedia: 3-Methoxyamphetamine

Shulgin Index: #75 3-MA; Table: 3 Page: 321 Row: 26

See also PiHKAL: #97 4-MA    

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Bailey, K; Beckstead, HD; Legault, D; Verner, D. Identification of 2-, 3-, and 4-methoxyamphetamines and 2-, 3-, and 4-methylamphetamines. J. Assoc. Off. Anal. Chem., 1974, 57 (5), 1134–1143. 1143 kB.

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.

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

Katagi, M; Tsuchihashi, H. Update on clandestine amphetamines and their analogues recently seen in Japan. J. Health Sci., 2002, 48 (1), 14–21. 181 kB. doi:10.1248/jhs.48.14

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

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

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

Dal Cason, TA. A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone. Forensic Sci. Int., 1 Jan 2001, 119 (3), 168–194. 678 kB. doi:10.1016/S0379-0738(00)00425-4

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

2000
Isomer 3

Ephedrine
(1R,2S)-2-Methylamino-1-phenylpropan-1-ol

IUPAC: (1R,2S)-2-(Methylamino)-1-phenylpropan-1-ol

Formula: C10H15NO Molecular weight: 165.2322 g/mol InChI Key: KWGRBVOPPLSCSI-WPRPVWTQSA-N

InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1

PubChem CID: 9294; ChemSpider: 8935; Erowid: Ephedrine; Wikipedia: Ephedrine

Shulgin Index: Table: 2 Page: 318 Row: 25

See also PiHKAL: #42 Ψ-2C-T-4 #142 PEA  
See also TiHKAL: #8 α,N-DMT    

Glennon, RA; Young, R; Martin, BR; Dal Cason, TA. Methcathinone (“Cat”): An enantiomeric potency comparison. Pharmacol. Biochem. Behav., 1 Jan 1995, 50 (4) 601–606. 709 kB. doi:10.1016/0091-3057(94)00348-3

LeBelle, MJ; Savard, C; Dawson, BA; Black, DB; Katyal, LK; Zrcek, F; By, AW. Chiral identification and determination of ephedrine, pseudoephedrine, methamphetamine and metecathinone by gas chromatography and nuclear magnetic resonance. Forensic Sci. Int., 28 Feb 1995, 71 (3), 215–223. 405 kB. doi:10.1016/0379-0738(94)01669-0

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

Rothman, RB; Vu, N; Partilla, JS; Roth, BL; Hufeisen, SJ; Compton-Toth, BA; Birkes, J; Young, R; Glennon, RA. In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J. Pharmacol. Exp. Ther., 1 Oct 2003, 307 (1), 138–145. 516 kB. doi:10.1124/jpet.103.053975

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.

Lurie, IS; Bozenko, JS; Li, L; Miller, EE; Greenfield, SJ. Chiral separation of methamphetamine and related compounds using capillary electrophoresis with dynamically coated capillaries. Microgram J., 1 Jan 2011, 8 (1), 24–28. 786 kB.

2001
Isomer 4

Pseudoephedrine
(1S,2S)-2-Methylamino-1-phenylpropan-1-ol

IUPAC: (1S,2S)-2-(Methylamino)-1-phenylpropan-1-ol

Formula: C10H15NO Molecular weight: 165.2322 g/mol InChI Key: KWGRBVOPPLSCSI-PEHGTWAWSA-N

InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10?/m0/s1

PubChem CID: 7028; ChemSpider: 6761; Wikipedia: Pseudoephedrine

Shulgin Index: Table: 2 Page: 318 Row: 26

See also PiHKAL: #42 Ψ-2C-T-4    

Glennon, RA; Young, R; Martin, BR; Dal Cason, TA. Methcathinone (“Cat”): An enantiomeric potency comparison. Pharmacol. Biochem. Behav., 1 Jan 1995, 50 (4) 601–606. 709 kB. doi:10.1016/0091-3057(94)00348-3

LeBelle, MJ; Savard, C; Dawson, BA; Black, DB; Katyal, LK; Zrcek, F; By, AW. Chiral identification and determination of ephedrine, pseudoephedrine, methamphetamine and metecathinone by gas chromatography and nuclear magnetic resonance. Forensic Sci. Int., 28 Feb 1995, 71 (3), 215–223. 405 kB. doi:10.1016/0379-0738(94)01669-0

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

Rothman, RB; Vu, N; Partilla, JS; Roth, BL; Hufeisen, SJ; Compton-Toth, BA; Birkes, J; Young, R; Glennon, RA. In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J. Pharmacol. Exp. Ther., 1 Oct 2003, 307 (1), 138–145. 516 kB. doi:10.1124/jpet.103.053975

Bianchi, RP; Shah, MN; Rogers, DH; Mrazik, TJ. Laboratory analysis of the conversion of pseudoephedrine to methamphetamine from over-the-counter products. Microgram J., 1 Jan 2005, 3 (1–2), 11–15. 32 kB.

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.

Lurie, IS; Bozenko, JS; Li, L; Miller, EE; Greenfield, SJ. Chiral separation of methamphetamine and related compounds using capillary electrophoresis with dynamically coated capillaries. Microgram J., 1 Jan 2011, 8 (1), 24–28. 786 kB.

2203
Isomer 5

Hordenine
4-Hydroxy-N,N-dimethylphenethylamine

IUPAC: 4-[2-(Dimethylamino)ethyl]phenol

Formula: C10H15NO Molecular weight: 165.2322 g/mol InChI Key: KUBCEEMXQZUPDQ-UHFFFAOYSA-N Properties: Peyote alkaloid

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

PubChem CID: 68313; ChemSpider: 61609; Wikipedia: Hordenine

Shulgin Index: #71 Hordenine; Table: 3 Page: 323 Row: 15

Ghosal, S; Srivastava, RS. β-Phenethylamine, tetrahydroisoquinoline and indole alkaloids of Desmodium tiliaefolium. Phytochemistry, 1 Jan 1973, 12 (1), 193–197. 552 kB. doi:10.1016/S0031-9422(00)84646-4

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

Fontanilla, D; Johannessen, M; Hajipour, AR; Cozzi, NV; Jackson, MB; Ruoho, AE. The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator. Science, 13 Feb 2009, 323 (5916):,934–937. 529 kB. doi:10.1126/science.1166127

2405
Isomer 6

β-Methoxyamphetamine

IUPAC: 1-Methoxy-1-phenylpropan-2-amine

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

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

PubChem CID: 12843489; ChemSpider: 28169264

2404
Isomer 7

4-Methylnorephedrine

IUPAC: 2-Amino-1-(4-methylphenyl)propan-1-ol

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

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

PubChem CID: 37044; ChemSpider: 33992

6011
Isomer 8

β-HO-N,N-Me-PEA

IUPAC: 2-(Dimethylamino)-1-phenylethanol

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

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

PubChem CID: 120846; ChemSpider: 107874

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 11

6074
Isomer 9

N,N-Me-2-HPEA

IUPAC: 2-[2-(Dimethylamino)ethyl]phenol

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

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

PubChem CID: 23423072; ChemSpider: 10467022

Shulgin Index: See #71 Hordenine; Table: 3 Page: 319 Row: 24

6077
Isomer 10

2-HMA

IUPAC: 2-[2-(Methylamino)propyl]phenol

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

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

PubChem CID: 11405; ChemSpider: 10927

Shulgin Index: See #74 2-MA; Table: 3 Page: 319 Row: 27

Geertsen, S; Foster, BC; Cyr, DLWTD; Casley, W. Metabolism of methoxyphenamine and 2-methoxyamphetamine inP4502D6-transfected cells and cell preparations. Xenobiotica, 1995, 25 (9), 895–906. 731 kB. doi:10.3109/00498259509046661

6079
Isomer 11

N-Me-2-MPEA

IUPAC: 2-(2-Methoxyphenyl)-N-methylethanamine

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

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

PubChem CID: 13092505; ChemSpider: 10634978

Shulgin Index: See #100 2-MPEA; Table: 3 Page: 319 Row: 29

6081
Isomer 12

β-Me-2-MPEA

IUPAC: 2-(2-Methoxyphenyl)propan-1-amine

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

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

PubChem CID: 408060; ChemSpider: 361051

Shulgin Index: See #100 2-MPEA; Table: 3 Page: 319 Row: 31

6154
Isomer 13

N,N-Me-3-HPEA

IUPAC: 3-[2-(Dimethylamino)ethyl]phenol

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

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

PubChem CID: 3029884; ChemSpider: 2295140

Shulgin Index: See #71 Hordenine; Table: 3 Page: 321 Row: 4

6162
Isomer 14

N-Me-3-MPEA

IUPAC: 2-(3-Methoxyphenyl)-N-methylethanamine

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

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

PubChem CID: 118500; ChemSpider: 105913

Shulgin Index: See #101 3-MPEA; Table: 3 Page: 321 Row: 12

6166
Isomer 15

β-Me-3-MPEA

IUPAC: 2-(3-Methoxyphenyl)propan-1-amine

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

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

PubChem CID: 202627; ChemSpider: 175454

Shulgin Index: See #101 3-MPEA; Table: 3 Page: 321 Row: 16

6273
Isomer 16

Pholedrine

IUPAC: 4-[2-(Methylamino)propyl]phenol

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

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

PubChem CID: 4655; ChemSpider: 4494

Shulgin Index: See #109 PHA; Table: 3 Page: 323 Row: 23

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

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.

6279
Isomer 17

α-Et-4-HPEA

IUPAC: 4-(2-Aminobutyl)phenol

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

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

PubChem CID: 43566042; ChemSpider: 28148634

Shulgin Index: See #110 PMA; Table: 3 Page: 323 Row: 29

6283
Isomer 18

N-Me-4-MPEA

IUPAC: 2-(4-Methoxyphenyl)-N-methylethanamine

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

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

PubChem CID: 104735; ChemSpider: 94550

Shulgin Index: See #102 4-MPEA; Table: 3 Page: 323 Row: 33

6286
Isomer 19

β-Me-4-MPEA

IUPAC: 2-(4-Methoxyphenyl)propan-1-amine

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

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

PubChem CID: 202625; ChemSpider: 175452

Shulgin Index: See #102 4-MPEA; Table: 3 Page: 323 Row: 36

6319
Isomer 20

4-EPEA

IUPAC: 2-(4-Ethoxyphenyl)ethanamine

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

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

PubChem CID: 143354; ChemSpider: 126469

Shulgin Index: See #102 4-MPEA; Table: 3 Page: 324 Row: 19

6364
Isomer 21

2,3-HMeMPEA

IUPAC: 2-Methyl-6-[2-(methylamino)ethyl]phenol

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

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

ChemSpider: 27019897

Shulgin Index: See #34 2,3-DMA; Table: 4 Page: 325 Row: 14

6366
Isomer 22

2,3-HMeA

IUPAC: 2-(2-Aminopropyl)-6-methylphenol

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

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

PubChem CID: 14265622; ChemSpider: 26495759

Shulgin Index: See #34 2,3-DMA; Table: 4 Page: 325 Row: 16

6435
Isomer 23

2,4-MMPEA

IUPAC: 2-(2-Methoxy-4-methylphenyl)ethanamine

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

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

PubChem CID: 15128233; ChemSpider: 23233672

Shulgin Index: See #47 2,4-DMPEA; Table: 4 Page: 326 Row: 35

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

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

6483
Isomer 24

β-HO-3,4-MePEA

IUPAC: 2-Amino-1-(3,4-dimethylphenyl)ethanol

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

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

PubChem CID: 43752583; ChemSpider: 25642914

Shulgin Index: See #43 DMePEA; Table: 4 Page: 327 Row: 33

6501
Isomer 25

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

1018
Isomer 26

Phenylpropanolmethylamine

IUPAC: 2-(Methylamino)-1-phenylpropan-1-ol

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

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

PubChem CID: 5032; ChemSpider: 4856

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.

1087
Isomer 27

N-MeO-A
N-Methoxyamphetamine

IUPAC: N-Methoxy-1-phenylpropan-2-amine

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

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

Benington, F; Morin, RD; Clark, LC. Behavioral and neuropharmacological actions of N-aralkylhydroxylamines and their O-methyl ethers. J. Med. Chem., 1 Jan 1965, 8 (1), 100–104. 634 kB. doi:10.1021/jm00325a020

1080
Isomer 28

4-Me-HOT-A
N-Hydroxy-4-methylamphetamine

IUPAC: N-Hydroxy-1-(4-methylphenyl)propan-2-amine

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

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

Benington, F; Morin, RD; Clark, LC. Behavioral and neuropharmacological actions of N-aralkylhydroxylamines and their O-methyl ethers. J. Med. Chem., 1 Jan 1965, 8 (1), 100–104. 634 kB. doi:10.1021/jm00325a020

Show all 74 analogues and isomers Show only the 11 N analogues Show only the two α analogues Show only the 11 R2 analogues Show only the four R3 analogues Show only the seven R4 analogues Show only the three R5 analogues Show only the one R6 analogues Show only the seven skeleton analogues
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