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α-PVP; α-Pyrrolidinopentiophenone
2342
Variant: α R2 R3 R4 skeleton isomers all
Analogues: 3 1 2 16 116 2 140

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

Formula: C15H21NO Molecular weight: 231.33334 g/mol InChI Key: YDIIDRWHPFMLGR-UHFFFAOYSA-N

InChI=1S/C15H21NO/c1-2-8-14(16-11-6-7-12-16)15(17)13-9-4-3-5-10-13/h3-5,9-10,14H,2,6-8,11-12H2,1H3

PubChem CID: 11148955; ChemSpider: 9324063; Wikipedia: Alpha-Pyrrolidinopentiophenone

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

Iversen, LL. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010.

Casale, JF; Hays, PA. The characterization of α-pyrrolidinopentiophenone. Microgram J., 1 Jan 2012, 9 (1), 33–38. 1194 kB.

Three α analogues:
2114
Analogue 1: Substituting Methyl for Propyl at α

α-PPP
PPP
α-Pyrrolidinopropiophenone

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

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

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

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

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

Maurer, HH; Kraemer, T; Springer, D; Staack, RF. Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (Ecstasy), piperazine, and pyrrolidinophenone types. A synopsis. Ther. Drug Monit., 1 Apr 2004, 26 (2), 127–131. 121 kB.

Iversen, LL. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010.

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

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

Rösner, P; Junge, T; Fritschi, G; Klein, B; Thielert, K; Kozlowski, M. Neue synthetische Drogen: Piperazin-, propicyclidin- und α-aminopropiophenonderivate. Toxichem Krimtech, 1999, 66 (2), 81–90. 1202 kB.

2341
Analogue 2: Substituting Ethyl for Propyl at α

α-PBP
α-Pyrrolidinobutrophenone

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

Formula: C14H19NO Molecular weight: 217.30676 g/mol InChI Key: GSESDIFGJCCBHN-UHFFFAOYSA-N

InChI=1S/C14H19NO/c1-2-13(15-10-6-7-11-15)14(16)12-8-4-3-5-9-12/h3-5,8-9,13H,2,6-7,10-11H2,1H3

PubChem CID: 23199082; Wikipedia: Alpha-Pyrrolidinobutiophenone

Iversen, LL. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010.

1098
Analogue 3: Substituting Pentyl for Propyl at α

PV8

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

Formula: C17H25NO Molecular weight: 259.3865 g/mol InChI Key: DLRWKNLMJAIFQB-UHFFFAOYSA-N

InChI=1S/C17H25NO/c1-2-3-5-12-16(18-13-8-9-14-18)17(19)15-10-6-4-7-11-15/h4,6-7,10-11,16H,2-3,5,8-9,12-14H2,1H3

One R2 analogue:
1413
Analogue 1: Adding Methyl at R2

O-2479

IUPAC: 1-(2-Methylphenyl)-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C16H23NO Molecular weight: 245.35992 g/mol InChI Key: VVIVTDYOMWHKAE-UHFFFAOYSA-N

InChI=1S/C16H23NO/c1-3-8-15(17-11-6-7-12-17)16(18)14-10-5-4-9-13(14)2/h4-5,9-10,15H,3,6-8,11-12H2,1-2H3

PubChem CID: 11311147; ChemSpider: 9486115

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

Two R3 analogues:
1404
Analogue 1: Adding Iodo at R3

O-2495

IUPAC: 1-(3-Iodophenyl)-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C15H20INO Molecular weight: 357.22987 g/mol InChI Key: NYDUTEZMPZHSRY-UHFFFAOYSA-N

InChI=1S/C15H20INO/c1-2-6-14(17-9-3-4-10-17)15(18)12-7-5-8-13(16)11-12/h5,7-8,11,14H,2-4,6,9-10H2,1H3

PubChem CID: 11210506; ChemSpider: 9385568

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1414
Analogue 2: Adding Methyl at R3

O-2480

IUPAC: 1-(3-Methylphenyl)-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C16H23NO Molecular weight: 245.35992 g/mol InChI Key: HHSYAWUBPBEDMP-UHFFFAOYSA-N

InChI=1S/C16H23NO/c1-3-7-15(17-10-4-5-11-17)16(18)14-9-6-8-13(2)12-14/h6,8-9,12,15H,3-5,7,10-11H2,1-2H3

PubChem CID: 11470616; ChemSpider: 9645446

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

16 R4 analogues:
2117
Analogue 1: Adding Methyl at R4

Pyrovalerone
PVP
4′-Methyl-α-pyrrolidinovalerophenone
4′-Methyl-α-pyrrolidinopentanophenone

IUPAC: 1-(4-Methylphenyl)-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C16H23NO Molecular weight: 245.35992 g/mol InChI Key: SWUVZKWCOBGPTH-UHFFFAOYSA-N

InChI=1S/C16H23NO/c1-3-6-15(17-11-4-5-12-17)16(18)14-9-7-13(2)8-10-14/h7-10,15H,3-6,11-12H2,1-2H3

PubChem CID: 14373; ChemSpider: 13733; Wikipedia: Pyrovalerone

Iversen, LL. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010.

Gorceix, A; Jacquemin, C. Intérêt du pyrovalérone dans le traitement ambulatoire des états de fatigue (French). Ann. Méd.-Psychol., 1970, 1970 (2), 624–632. 8223 kB.

Deniker, P; Lôo, H; Cuche, H; Houx, JM. Utilisation abusive par les toxicomanes d’un psycho-stimulant, la pyrovalérone (French). Ann. Méd.-Psychol., 27 Oct 1975, 2 (4), 745–748. 5196 kB.

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

Lancelot, JC; Robba, M; Bonnet, JJ; Vaugeois, JM; Costentin, J. Synthesis and preliminary study of the activity of thiophene analogues of pyrovalerone on the neuronal uptake of the monoamines. Eur. J. Med. Chem., 1 Apr 1992, 27 (3), 297–200. 305 kB. doi:10.1016/0223-5234(92)90015-S

Prosser, JM; Nelson, LS. The toxicology of bath salts: a review of synthetic cathinones. J. Med. Toxicol., 1 Nov 2011, 8 (1), 33–22. 267 kB. doi:10.1007/s13181-011-0193-z

1401
Analogue 2: Adding Fluoro at R4

4F-PVP
O-2370

IUPAC: 1-(4-Fluorophenyl)-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C15H20FNO Molecular weight: 249.3238032 g/mol InChI Key: BQLSUBYYRRZHRK-UHFFFAOYSA-N

InChI=1S/C15H20FNO/c1-2-5-14(17-10-3-4-11-17)15(18)12-6-8-13(16)9-7-12/h6-9,14H,2-5,10-11H2,1H3

PubChem CID: 11322641; ChemSpider: 9497595

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1402
Analogue 3: Adding Bromo at R4

O-2419

IUPAC: 1-(4-Bromophenyl)-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C15H20BrNO Molecular weight: 310.2294 g/mol InChI Key: RAHKQMUBMIJUFG-UHFFFAOYSA-N

InChI=1S/C15H20BrNO/c1-2-5-14(17-10-3-4-11-17)15(18)12-6-8-13(16)9-7-12/h6-9,14H,2-5,10-11H2,1H3

PubChem CID: 11220599; ChemSpider: 9395653

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1403
Analogue 4: Adding Iodo at R4

O-2493

IUPAC: 1-(4-Iodophenyl)-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C15H20INO Molecular weight: 357.22987 g/mol InChI Key: QXBWECFEEZMKTN-UHFFFAOYSA-N

InChI=1S/C15H20INO/c1-2-5-14(17-10-3-4-11-17)15(18)12-6-8-13(16)9-7-12/h6-9,14H,2-5,10-11H2,1H3

PubChem CID: 11152502; ChemSpider: 9327610

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1405
Analogue 5: Adding Cyano at R4

O-2475

IUPAC: 4-[2-(Pyrrolidin-1-yl)pentanoyl]benzonitrile

Formula: C16H20N2O Molecular weight: 256.3428 g/mol InChI Key: AQQRGNNYEPRIIF-UHFFFAOYSA-N

InChI=1S/C16H20N2O/c1-2-5-15(18-10-3-4-11-18)16(19)14-8-6-13(12-17)7-9-14/h6-9,15H,2-5,10-11H2,1H3

PubChem CID: 11550626; ChemSpider: 9725404

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1406
Analogue 6: Adding Hydroxymethyl at R4

O-2577

IUPAC: 1-[4-(Hydroxymethyl)phenyl]-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C16H23NO2 Molecular weight: 261.35932 g/mol InChI Key: FDCLNKXJEZCPEW-UHFFFAOYSA-N

InChI=1S/C16H23NO2/c1-2-5-15(17-10-3-4-11-17)16(19)14-8-6-13(12-18)7-9-14/h6-9,15,18H,2-5,10-12H2,1H3

PubChem CID: 11459667; ChemSpider: 9634508

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1407
Analogue 7: Adding Nitro at R4

O-2443

IUPAC: 1-(4-Nitrophenyl)-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C15H20N2O3 Molecular weight: 276.3309 g/mol InChI Key: NAHZCGQMXZCULW-UHFFFAOYSA-N

InChI=1S/C15H20N2O3/c1-2-5-14(16-10-3-4-11-16)15(18)12-6-8-13(9-7-12)17(19)20/h6-9,14H,2-5,10-11H2,1H3

PubChem CID: 11357862; ChemSpider: 9532789

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1408
Analogue 8: Adding Methoxy at R4

4-MeO-α-PVP
O-2417

IUPAC: 1-(4-Methoxyphenyl)-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C16H23NO2 Molecular weight: 261.35932 g/mol InChI Key: HWYVHRCKBXGZLV-UHFFFAOYSA-N

InChI=1S/C16H23NO2/c1-3-6-15(17-11-4-5-12-17)16(18)13-7-9-14(19-2)10-8-13/h7-10,15H,3-6,11-12H2,1-2H3

PubChem CID: 11299968; ChemSpider: 9474945

Uchiyama, N; Matsuda, S; Kawamura, M; Kikura-Hanajiri, R; Goda, Y. Identification of two new-type designer drugs, piperazine derivative MT-45 (I-C6) and synthetic peptide Noopept (GVS-111), with synthetic cannabinoid A-834735, cathinone derivative 4-methoxy-α-PVP, and phenethylamine derivative 4-methylbuphedrine from illegal products. Forensic Toxicol., 1 Jan 2014, 32 (1), 9–18. 678 kB. doi:10.1007/s11419-013-0194-5

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1409
Analogue 9: Adding Methoxycarbonyl at R4

O-2558

IUPAC: Methyl 4-[2-(pyrrolidin-1-yl)pentanoyl]benzoate

Formula: C17H23NO3 Molecular weight: 289.36942 g/mol InChI Key: RUCXEVOCSDADAL-UHFFFAOYSA-N

InChI=1S/C17H23NO3/c1-3-6-15(18-11-4-5-12-18)16(19)13-7-9-14(10-8-13)17(20)21-2/h7-10,15H,3-6,11-12H2,1-2H3

PubChem CID: 11415039; ChemSpider: 9589926

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1410
Analogue 10: Adding Acetylamino at R4

O-2439

IUPAC: N-{4-[2-(Pyrrolidin-1-yl)pentanoyl]phenyl}acetamide

Formula: C17H24N2O2 Molecular weight: 288.38466 g/mol InChI Key: DSIUMNNVBQZCEG-UHFFFAOYSA-N

InChI=1S/C17H24N2O2/c1-3-6-16(19-11-4-5-12-19)17(21)14-7-9-15(10-8-14)18-13(2)20/h7-10,16H,3-6,11-12H2,1-2H3,(H,18,20)

PubChem CID: 11277680; ChemSpider: 9452680

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1411
Analogue 11: Adding Trifluoromethyl at R4

O-2451

IUPAC: 2-(Pyrrolidin-1-yl)-1-[4-(trifluoromethyl)phenyl]pentan-1-one

Formula: C16H20F3NO Molecular weight: 299.3313096 g/mol InChI Key: OIZUHURZTLEFGZ-UHFFFAOYSA-N

InChI=1S/C16H20F3NO/c1-2-5-14(20-10-3-4-11-20)15(21)12-6-8-13(9-7-12)16(17,18)19/h6-9,14H,2-5,10-11H2,1H3

PubChem CID: 11530118; ChemSpider: 9704901

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1412
Analogue 12: Adding Prop-1-ynyl at R4

O-2537

IUPAC: 1-[4-(Prop-1-yn-1-yl)phenyl]-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C18H23NO Molecular weight: 269.38132 g/mol InChI Key: FCINLQHPPAWABH-UHFFFAOYSA-N

InChI=1S/C18H23NO/c1-3-7-15-9-11-16(12-10-15)18(20)17(8-4-2)19-13-5-6-14-19/h9-12,17H,4-6,8,13-14H2,1-2H3

PubChem CID: 11594677; ChemSpider: 9769437

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1415
Analogue 13: Adding Hydroxy at R4

O-2418

IUPAC: 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C15H21NO2 Molecular weight: 247.33274 g/mol InChI Key: XCHIECWEKDGHNL-UHFFFAOYSA-N

InChI=1S/C15H21NO2/c1-2-5-14(16-10-3-4-11-16)15(18)12-6-8-13(17)9-7-12/h6-9,14,17H,2-5,10-11H2,1H3

PubChem CID: 11311204; ChemSpider: 9486172

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1419
Analogue 14: Adding Furan-2-yl at R4

O-2441

IUPAC: 1-[4-(Furan-2-yl)phenyl]-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C19H23NO2 Molecular weight: 297.39142 g/mol InChI Key: ULUHBYVKNOUSDX-UHFFFAOYSA-N

InChI=1S/C19H23NO2/c1-2-6-17(20-12-3-4-13-20)19(21)16-10-8-15(9-11-16)18-7-5-14-22-18/h5,7-11,14,17H,2-4,6,12-13H2,1H3

PubChem CID: 11197267; ChemSpider: 9372336

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1420
Analogue 15: Adding Thiophen-2-yl at R4

O-2438

IUPAC: 2-(Pyrrolidin-1-yl)-1-[4-(thiophen-2-yl)phenyl]pentan-1-one

Formula: C19H23NOS Molecular weight: 313.45702 g/mol InChI Key: HEFDYDISPNHKAM-UHFFFAOYSA-N

InChI=1S/C19H23NOS/c1-2-6-17(20-12-3-4-13-20)19(21)16-10-8-15(9-11-16)18-7-5-14-22-18/h5,7-11,14,17H,2-4,6,12-13H2,1H3

PubChem CID: 11209208; ChemSpider: 9384270

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

1421
Analogue 16: Adding 1-Methylpyrrol-2-yl at R4

O-2446

IUPAC: 1-[4-(1-Methyl-1H-pyrrol-2-yl)phenyl]-2-(pyrrolidin-1-yl)pentan-1-one

Formula: C20H26N2O Molecular weight: 310.43324 g/mol InChI Key: ROXOOMBIDGERBZ-UHFFFAOYSA-N

InChI=1S/C20H26N2O/c1-3-7-19(22-14-4-5-15-22)20(23)17-11-9-16(10-12-17)18-8-6-13-21(18)2/h6,8-13,19H,3-5,7,14-15H2,1-2H3

PubChem CID: 44407714; ChemSpider: 23266369

Meltzer, PC; Butler, D; Deschamps, JR; Madras, BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors. J. Med. Chem., 23 Feb 2006, 49 (4), 1420–1432. 179 kB. doi:10.1021/jm050797a

116 skeleton analogues:
142
Analogue 1: With 2-Phenylethan-1-amine skeleton

PEA
β-PEA
2-PEA
β-Phenethylamine
Phenethylamine

IUPAC: 2-Phenylethan-1-amine

Formula: C8H11N Molecular weight: 121.17964 g/mol InChI Key: BHHGXPLMPWCGHP-UHFFFAOYSA-N

InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2

PubChem CID: 1001; ChemSpider: 13856352; Wikipedia: Phenethylamine

Shulgin Index: #107 PEA; Table: 2 Page: 318 Row: 1

See also TiHKAL: #2 DBT
#5 α,O-DMS
#8 α,N-DMT
#11 α-ET
#30 4,5-MDO-DMT
#32 5,6-MDO-MIPT
#37 5-MeO-DIPT
#46 5-MeS-DMT
#53 T
#55 α,N,O-TMS

Suter, CM; Weston, AW. Some fluorinated amines of the pressor type. J. Am. Chem. Soc., 1 Feb 1941, 63 (2), 602–605. 444 kB. doi:10.1021/ja01847a069

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

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

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

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.

Baker, GB; Coutts, RT; Rao, TS. Neuropharmacological and neurochemical properties of N- (2-cyanoethyl)-2-phenylethylamine, a prodrug of 2-phenylethylamine. Br. J. Pharmacol., 1 Oct 1987, 92 (2), 243–255. 1932 kB. doi:10.1111/j.1476-5381.1987.tb11318.x

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

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

Repke, DB; Ferguson, WJ; Bates, DK. Synthesis of secondary methylalkylamines. Tetrahedron Lett., 1979, 20 (43), 4183–4184. 149 kB. doi:10.1016/S0040-4039(01)86538-2

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

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

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

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.

2121
Analogue 2: With Phenylethyl-cyclic-amine skeleton

Prolintane
1-(1-Benzylbutyl)pyrrolidine

IUPAC: 1-(1-Phenylpentan-2-yl)pyrrolidine

Formula: C15H23N Molecular weight: 217.34982 g/mol InChI Key: OJCPSBCUMRIPFL-UHFFFAOYSA-N

InChI=1S/C15H23N/c1-2-8-15(16-11-6-7-12-16)13-14-9-4-3-5-10-14/h3-5,9-10,15H,2,6-8,11-13H2,1H3

PubChem CID: 14592; ChemSpider: 13930; Wikipedia: Prolintane

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

2357
Analogue 3: With 2,3-Dihydro-1H-inden-2-amine skeleton

2-AI
2-Aminoindane

IUPAC: 2,3-Dihydro-1H-inden-2-amine

Formula: C9H11N Molecular weight: 133.19034 g/mol InChI Key: LMHHFZAXSANGGM-UHFFFAOYSA-N

InChI=1S/C9H11N/c10-9-5-7-3-1-2-4-8(7)6-9/h1-4,9H,5-6,10H2

PubChem CID: 76310; ChemSpider: 68787; Erowid: 2-Aminoindan; Wikipedia: 2-Aminoindane

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

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

400
Analogue 4: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

2-AT
2-Aminotetralin

IUPAC: 1,2,3,4-Tetrahydronaphthalen-2-amine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: LCGFVWKNXLRFIF-UHFFFAOYSA-N

InChI=1S/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2

PubChem CID: 34677; ChemSpider: 31912; Wikipedia: 2-Aminotetralin

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 α-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

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

Nichols, DE; Pfister, WR; Yim, GKW; Cosgrove, RJ. A new view of the structural relationship between LSD and mescaline. Brain Res. Bull., 1 May 1977, 2 (3), 169–171. 338 kB. doi:10.1016/0361-9230(77)90034-X

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

Barfknecht, CF; Nichols, DE; Rusterholz, DB; Long, JP; Engelbrecht, JA; Beaton, JM; Bradley, RJ; Dyer, DC. Potential psychotomimetics. 2-Amino-1,2,3,4-tetrahydronaphthalene analogs. J. Med. Chem., 1 Jan 1973, 16, (7), 804–808. 614 kB. doi:10.1021/jm00265a013

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

2371
Analogue 5: With 2-Phenylethan-1-amine skeleton

N-MePEA
N-Methylphenethylamine

IUPAC: N-Methyl-2-phenylethan-1-amine

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

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

PubChem CID: 11503; ChemSpider: 11019; Wikipedia: Methylphenethylamine

Shulgin Index: #89 N-MePEA; Table: 2 Page: 318 Row: 2

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

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

Suter, CM; Weston, AW. Some fluorinated amines of the pressor type. J. Am. Chem. Soc., 1 Feb 1941, 63 (2), 602–605. 444 kB. doi:10.1021/ja01847a069

5554
Analogue 6: With 2-Phenylethan-1-amine skeleton

β-Me-PEA
β-Methylphenethylamine

IUPAC: 2-Phenylpropan-1-amine

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

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

PubChem CID: 11398; ChemSpider: 10920; Wikipedia: Beta-Methylphenethylamine

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

2378
Analogue 7: With 2-Phenylethan-1-amine skeleton

Phenibut

IUPAC: 4-Amino-3-phenylbutanoic acid

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

InChI=1S/C10H13NO2/c11-7-9(6-10(12)13)8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)

PubChem CID: 14113; ChemSpider: 13491; Erowid: Phenibut; Wikipedia: Phenibut

801
Analogue 8: With 1-Phenylpiperazine skeleton

PP

IUPAC: 1-Phenylpiperazine

Formula: C10H14N2 Molecular weight: 162.23156 g/mol InChI Key: YZTJYBJCZXZGCT-UHFFFAOYSA-N

InChI=1S/C10H14N2/c1-2-4-10(5-3-1)12-8-6-11-7-9-12/h1-5,11H,6-9H2

PubChem CID: 7096; ChemSpider: 6829; Wikipedia: Phenylpiperazine

Shulgin Index: See #24 oCPP; Table: 8 Page: 357 Row: 1

Schoenwald, RD; Gadiraju, RR; Barfknecht, CF. Serotonin antagonists for use as antiglaucoma agents and their ocular penetration. Eur. J. Pharm. Biopharm., 1 Jun 1997, 43 (3), 273–281. 688 kB. doi:10.1016/S0939-6411(97)00055-6

904
Analogue 9: With 1-Benzylpiperazine skeleton

MBZP

IUPAC: 1-Benzyl-4-methylpiperazine

Formula: C12H18N2 Molecular weight: 190.28472 g/mol InChI Key: MLJOKPBESJWYGL-UHFFFAOYSA-N

InChI=1S/C12H18N2/c1-13-7-9-14(10-8-13)11-12-5-3-2-4-6-12/h2-6H,7-11H2,1H3

PubChem CID: 763557; ChemSpider: 667589; Wikipedia: Methylbenzylpiperazine

Shulgin Index: Table: 9 Page: 357 Row: 20

Zuba, D; Byrska, B. Prevalence and co-existence of active components of ‘legal highs’ Drug Test. Anal., 1 Jun 2013, 5 (6), 420–429. 1294 kB. doi:10.1002/dta.1365

903
Analogue 10: With 1-Benzylpiperazine skeleton

BZP

IUPAC: 1-Benzylpiperazine

Formula: C11H16N2 Molecular weight: 176.25814 g/mol InChI Key: IQXXEPZFOOTTBA-UHFFFAOYSA-N

InChI=1S/C11H16N2/c1-2-4-11(5-3-1)10-13-8-6-12-7-9-13/h1-5,12H,6-10H2

PubChem CID: 75994; ChemSpider: 68493; Wikipedia: Benzylpiperazine

Shulgin Index: Table: 9 Page: 357 Row: 19

Rösner, P; Junge, T; Fritschi, G; Klein, B; Thielert, K; Kozlowski, M. Neue synthetische Drogen: Piperazin-, propicyclidin- und α-aminopropiophenonderivate. Toxichem Krimtech, 1999, 66 (2), 81–90. 1202 kB.

Zuba, D; Byrska, B. Prevalence and co-existence of active components of ‘legal highs’ Drug Test. Anal., 1 Jun 2013, 5 (6), 420–429. 1294 kB. doi:10.1002/dta.1365

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.

Maurer, HH. Mass spectra of select benzyl- and phenyl- piperazine designer drugs. Microgram J., 1 Jan 2004, 2 (1–4), 22–26. 326 kB.

Wood, DM; Button, J; Lidder, S; Ramsey, J; Holt, DW; Dargan, PI. Dissociative and sympathomimetic toxicity associated with recreational use of 1-(3-trifluoromethylphenyl)piperazine (TFMPP) and 1-benzylpiperzine (BZP). J. Med. Toxicol., 1 Dec 2008, 4 (4), 254–257. 334 kB. doi:10.1007/BF03161209

Byrska, B; Zuba, D; Stanaszek, R. Determination of piperazine derivatives in “legal highs” Probl. Forensic Sci., 2010, 81, 101–113. 852 kB.

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

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

Schep, LJ; Slaughter, RJ; Temple, WA; Gee, P. Comments on BZP and New Zealand’s alternative approach to prohibition. Drug Test. Anal., 1 Jan 2012, 4 (1), 57. 47 kB. doi:10.1002/dta.356

Anon. Report on the risk assessment of BZP, European Monitoring Centre for Drugs and Drug Addiction, Feb 2009.

Elie, L; Baron, M; Croxton, R; Elie, M. Microcrystalline identification of selected designer drugs. Forensic Sci. Int., 10 Jan 2012, 214 (1–3),. 1364 kB. doi:10.1016/j.forsciint.2011.08.005

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

Baumann, MH; Clark, RD; Budzynski, AG; Partilla, JS; Blough, BE; Rothman, RB. N-Substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or ‘Ecstasy’). Neuropsychopharmacology, 1 Mar 2005, 30 (3), 550–560. 184 kB. doi:10.1038/sj.npp.1300585

901
Analogue 11: With Phenylmethanamine skeleton

Benzylamine

IUPAC: 1-Phenylmethanamine

Formula: C7H9N Molecular weight: 107.15306 g/mol InChI Key: WGQKYBSKWIADBV-UHFFFAOYSA-N

InChI=1S/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2

PubChem CID: 7504; ChemSpider: 7223; Wikipedia: Benzylamine

Shulgin Index: See #107 PEA; Table: 9 Page: 357 Row: 17

602
Analogue 12: With 3-Phenylpropan-1-amine skeleton

homo-β,N-MePEA

IUPAC: N,2-Dimethyl-3-phenylpropan-1-amine

Formula: C11H17N Molecular weight: 163.25938 g/mol InChI Key: QAWKZRYBSNVOAF-UHFFFAOYSA-N

InChI=1S/C11H17N/c1-10(9-12-2)8-11-6-4-3-5-7-11/h3-7,10,12H,8-9H2,1-2H3

PubChem CID: 21714712

Shulgin Index: See #107 PEA; Table: 10 Page: 358 Row: 9

601
Analogue 13: With 3-Phenylpropan-1-amine skeleton

homo-PEA

IUPAC: 3-Phenylpropan-1-amine

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

InChI=1S/C9H13N/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8,10H2

PubChem CID: 16259; ChemSpider: 15427

Shulgin Index: See #107 PEA; Table: 10 Page: 358 Row: 8

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

2434
Analogue 14: With 2-Amino-1-phenylethanone skeleton

Pentedrone

IUPAC: 2-(Methylamino)-1-phenylpentan-1-one

Formula: C12H17NO Molecular weight: 191.26948 g/mol InChI Key: WLIWIUNEJRETFX-UHFFFAOYSA-N

InChI=1S/C12H17NO/c1-3-7-11(13-2)12(14)10-8-5-4-6-9-10/h4-6,8-9,11,13H,3,7H2,1-2H3

PubChem CID: 57501499; ChemSpider: 26286729

Maheux, CR; Copeland, CR. Chemical analysis of two new designer drugs: Buphedrone and pentedrone. Drug Test. Anal., 1 Jan 2012, 4 (1), 17–23. 314 kB. doi:10.1002/dta.385

Westphal, F; Junge, T; Girreser, U; Greibl, W; Doering, C. Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 157–167. 853 kB. doi:10.1016/j.forsciint.2011.10.045

Zuba, D. Identification of cathinones and other active components of ‘legal highs’ by mass spectrometric methods. Trends Anal. Chem., 1 Feb 2012, 32, 15–30. 576 kB. doi:10.1016/j.trac.2011.09.009

Zuba, D; Byrska, B. Prevalence and co-existence of active components of ‘legal highs’ Drug Test. Anal., 1 Jun 2013, 5 (6), 420–429. 1294 kB. doi:10.1002/dta.1365

6003
Analogue 15: With 2-Phenylethan-1-amine skeleton

N,N-MePEA
DM-PEA

IUPAC: N,N-Dimethyl-2-phenylethan-1-amine

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

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

PubChem CID: 25125; ChemSpider: 23470

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 3

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

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

6004
Analogue 16: With 2-Phenylethan-1-amine skeleton

N-EtPEA

IUPAC: N-Ethyl-2-phenylethan-1-amine

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

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

PubChem CID: 547324; ChemSpider: 476381

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 4

6005
Analogue 17: With 2-Phenylethan-1-amine skeleton

N-PrPEA

IUPAC: N-(2-Phenylethyl)propan-1-amine

Formula: C11H17N Molecular weight: 163.25938 g/mol InChI Key: IIIRPZWDICEMGU-UHFFFAOYSA-N

InChI=1S/C11H17N/c1-2-9-12-10-8-11-6-4-3-5-7-11/h3-7,12H,2,8-10H2,1H3

PubChem CID: 3142088; ChemSpider: 2394524

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 5

6006
Analogue 18: With 2-Phenylethan-1-amine skeleton

N-iPrPEA

IUPAC: N-(2-Phenylethyl)propan-2-amine

Formula: C11H17N Molecular weight: 163.25938 g/mol InChI Key: HNPAEWJKFXEUDW-UHFFFAOYSA-N

InChI=1S/C11H17N/c1-10(2)12-9-8-11-6-4-3-5-7-11/h3-7,10,12H,8-9H2,1-2H3

PubChem CID: 10154198; ChemSpider: 8329706

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 6

6007
Analogue 19: With Phenylethyl-cyclic-amine skeleton

pip-PEA

IUPAC: 1-(2-Phenylethyl)piperidine

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

InChI=1S/C13H19N/c1-3-7-13(8-4-1)9-12-14-10-5-2-6-11-14/h1,3-4,7-8H,2,5-6,9-12H2

PubChem CID: 9513; ChemSpider: 9141

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 7

6008
Analogue 20: With 2-Phenylethan-1-amine skeleton

β,N-MePEA

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

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

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

PubChem CID: 22276; ChemSpider: 21277725

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 8

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

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.

6009
Analogue 21: With 2-Phenylethan-1-amine skeleton

β-Me-N-Et-PEA

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

Formula: C11H17N Molecular weight: 163.25938 g/mol InChI Key: YRJYTEMOKSUBHJ-UHFFFAOYSA-N

InChI=1S/C11H17N/c1-3-12-9-10(2)11-7-5-4-6-8-11/h4-8,10,12H,3,9H2,1-2H3

PubChem CID: 15788198; ChemSpider: 10617484

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 9

6010
Analogue 22: With 2-Phenylethan-1-amine skeleton

β-HO-PEA

IUPAC: 2-Amino-1-phenylethanol

Formula: C8H11NO Molecular weight: 137.17904 g/mol InChI Key: ULSIYEODSMZIPX-UHFFFAOYSA-N

InChI=1S/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2

PubChem CID: 1000; ChemSpider: 975

Shulgin Index: See #107 PEA; Table: 2 Page: 318 Row: 10

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

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

6011
Analogue 23: With 2-Phenylethan-1-amine skeleton

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

6012
Analogue 24: With 2-Amino-1-phenylethanone skeleton

AA

IUPAC: 2-Amino-1-phenylethanone

Formula: C8H9NO Molecular weight: 135.16316 g/mol InChI Key: HEQOJEGTZCTHCF-UHFFFAOYSA-N

InChI=1S/C8H9NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6,9H2

PubChem CID: 11952; ChemSpider: 11458

Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 12

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

6013
Analogue 25: With 2-Amino-1-phenylethanone skeleton

MAA

IUPAC: 2-(Methylamino)-1-phenylethanone

Formula: C9H11NO Molecular weight: 149.18974 g/mol InChI Key: VVFCJVLORNFVHI-UHFFFAOYSA-N

InChI=1S/C9H11NO/c1-10-7-9(11)8-5-3-2-4-6-8/h2-6,10H,7H2,1H3

PubChem CID: 416157; ChemSpider: 368424

Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 13

6014
Analogue 26: With 2-Amino-1-phenylethanone skeleton

DMAA

IUPAC: 2-(Dimethylamino)-1-phenylethanone

Formula: C10H13NO Molecular weight: 163.21632 g/mol InChI Key: UMLWXYJZDNNBTD-UHFFFAOYSA-N

InChI=1S/C10H13NO/c1-11(2)8-10(12)9-6-4-3-5-7-9/h3-7H,8H2,1-2H3

PubChem CID: 137890; ChemSpider: 121539

Shulgin Index: See #40 DMAP; Table: 2 Page: 318 Row: 14

6028
Analogue 27: With Phenyl-cyclic-amine skeleton

Phenmetrazine

IUPAC: 3-Methyl-2-phenylmorpholine

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

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

PubChem CID: 4762; ChemSpider: 4598

Shulgin Index: Table: 2 Page: 318 Row: 28

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

Banks, ML; Blough, BE; Fennell, TR; Snyder, RW; Negus, SS. Role of phenmetrazine as an active metabolite of phendimetrazine: Evidence from studies of drug discrimination and pharmacokinetics in rhesus monkeys. Drug Alcohol Depend., 1 Jun 2013, 130 (1–3), 158–166. 520 kB. doi:10.1016/j.drugalcdep.2012.10.026

Clarke, FH. cis- and trans-3-methyl-2-phenylmorpholine. J. Org. Chem., 1 Sep 1962, 27 (9), 3251–3253. 409 kB. doi:10.1021/jo01056a063

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

6055
Analogue 28: With 2-Phenylcyclopropan-1-amine skeleton

cPr-PEA

IUPAC: 2-Phenylcyclopropanamine

Formula: C9H11N Molecular weight: 133.19034 g/mol InChI Key: AELCINSCMGFISI-UHFFFAOYSA-N

InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2

PubChem CID: 5530; ChemSpider: 5329

Shulgin Index: See #107 PEA; Table: 2 Page: 319 Row: 5

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

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

Arvidsson, L; Johansson, AM; Hacksell, U; Nilsson, JLG; Svensson, K; Hjorth, S; Magnusson, T; Carlsson, A; Lindberg, P; Andersson, B; Sanchez, D; Wikström, H; Sundell, S. N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: Novel central 5-hydroxytryptamine receptor agonists. J. Med. Chem., 1 Jan 1988, 31 (1), 92–99. 1162 kB. doi:10.1021/jm00396a014

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

Walters, GC; Cooper, PD. Alicyclic analogue of mescaline. Nature, 20 Apr 1968, 218 (5138), 298–300. 3141 kB. doi:10.1038/218298a0

2462
Analogue 29: With 2-Amino-3,4-dihydronaphthalen-1(2H)-one skeleton

bk-2-AT

IUPAC: 2-Amino-3,4-dihydronaphthalen-1(2H)-one

Formula: C10H11NO Molecular weight: 161.20044 g/mol InChI Key: MUGWUYGVUZLWRB-UHFFFAOYSA-N

InChI=1S/C10H11NO/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-4,9H,5-6,11H2

PubChem CID: 412890; ChemSpider: 365595

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

2463
Analogue 30: With 1-(3,4-Dihydronaphthalen-1-yl)methanamine skeleton

IUPAC: 1-(3,4-Dihydronaphthalen-1-yl)methanamine

Formula: C11H13N Molecular weight: 159.22762 g/mol InChI Key: WNFNQSTXHLQIED-UHFFFAOYSA-N

InChI=1S/C11H13N/c12-8-10-6-3-5-9-4-1-2-7-11(9)10/h1-2,4,6-7H,3,5,8,12H2

PubChem CID: 12914860; ChemSpider: 14442059

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

2465
Analogue 31: With 1-(2H-Chromen-4-yl)methanamine skeleton

IUPAC: 1-(2H-Chromen-4-yl)methanamine

Formula: C10H11NO Molecular weight: 161.20044 g/mol InChI Key: WRQGQTBQEWMFLP-UHFFFAOYSA-N

InChI=1S/C10H11NO/c11-7-8-5-6-12-10-4-2-1-3-9(8)10/h1-5H,6-7,11H2

PubChem CID: 12914869

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

524
Analogue 32: With 2-Phenylethan-1-amine skeleton

Coryphanthine

IUPAC: 2-Methoxy-N,N,N-trimethyl-2-phenylethanaminium

Formula: C12H20NO Molecular weight: 194.2933 g/mol InChI Key: GQINVYXEQWNVSG-UHFFFAOYSA-N

InChI=1S/C12H20NO/c1-13(2,3)10-12(14-4)11-8-6-5-7-9-11/h5-9,12H,10H2,1-4H3/q+1

PubChem CID: 159221; ChemSpider: 140038

Meyer, BN; Helfrich, JS; Nichols, DE; McLaughlin, JL; Davis, DV; Cooks, RG. Cactus alkaloids. LIII. Coryphanthine and O-methyl-candicine, two new quaternary alkaloids from Coryphantha greenwoodii. J. Nat. Prod., 1 Jan 1983, 45 (5), 688–639. 442 kB. doi:10.1021/np50029a017

544
Analogue 33: With 1,2-Dihydronaphthalen-2-amine skeleton

2-ADN

IUPAC: 1,2-Dihydronaphthalen-2-amine

Formula: C10H11N Molecular weight: 145.20104 g/mol InChI Key: SHLZSYAMFQNEOF-UHFFFAOYSA-N

InChI=1S/C10H11N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-6,10H,7,11H2

PubChem CID: 133605; ChemSpider: 117856; Wikipedia: 2-Amino-1,2-dihydronaphthalene

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

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

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 α-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

557
Analogue 34: With Benzyl-cyclic-amine skeleton

Desoxypipradrol
2-DPMP
2-Diphenylmethylpiperidine;

IUPAC: 2-(Diphenylmethyl)piperidine

Formula: C18H21N Molecular weight: 251.36604 g/mol InChI Key: RWTNXJXZVGHMGI-UHFFFAOYSA-N

InChI=1S/C18H21N/c1-3-9-15(10-4-1)18(16-11-5-2-6-12-16)17-13-7-8-14-19-17/h1-6,9-12,17-19H,7-8,13-14H2

PubChem CID: 160506; ChemSpider: 141045

Iversen, L; Gibbons, S; Treble, R; Setola, V; Huang, X; Roth, BL. Neurochemical profiles of some novel psychoactive substances. Eur. J. Pharmacol., 30 Jan 2013, 700 (1–3), 147–151. 490 kB. doi:10.1016/j.ejphar.2012.12.006

Corkery, JM; Elliott, S; Schifano, F; Corazza, O; Ghodse, AH. 2-DPMP (desoxypipradrol, 2-benzhydrylpiperidine, 2-phenylmethylpiperidine) and D2PM (diphenyl-2-pyrrolidin-2-yl-methanol, diphenylprolinol): A preliminary review. Prog. Neuro-Psychopharmacol. Biol. Psych., 3 Dec 2012, 39 (2), 253–258. 347 kB. doi:10.1016/j.pnpbp.2012.05.021

Wood, DM; Dargan, PI. Use and acute toxicity associated with the novel psychoactive substances diphenylprolinol (D2PM) and desoxypipradrol (2-DPMP). Clin. Toxicol., 1 Sep 2012, 50 (8), 727–732. 117 kB. doi:10.3109/15563650.2012.716158

Iversen, LL. Consideration of desoxypipradrol (2-DPMP) and related pipradrol compounds, Advisory Council on the Misuse of Drugs, 13 Sep 2011.

558
Analogue 35: With Benzyl-cyclic-amine skeleton

Pipradrol

IUPAC: Diphenyl(piperidin-2-yl)methanol

Formula: C18H21NO Molecular weight: 267.36544 g/mol InChI Key: XSWHNYGMWWVAIE-UHFFFAOYSA-N

InChI=1S/C18H21NO/c20-18(15-9-3-1-4-10-15,16-11-5-2-6-12-16)17-13-7-8-14-19-17/h1-6,9-12,17,19-20H,7-8,13-14H2

PubChem CID: 10083; ChemSpider: 9681

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

559
Analogue 36: With Benzyl-cyclic-amine skeleton

Desoxy-D2PM
2-Diphenylmethylpyrrolidine

IUPAC: 2-(Diphenylmethyl)pyrrolidine

Formula: C17H19N Molecular weight: 237.33946 g/mol InChI Key: OXOBKZZXZVFOBB-UHFFFAOYSA-N

InChI=1S/C17H19N/c1-3-8-14(9-4-1)17(16-12-7-13-18-16)15-10-5-2-6-11-15/h1-6,8-11,16-18H,7,12-13H2

PubChem CID: 1295; ChemSpider: 1256

Paoli, GD; Brandt, SD; Pounder, DJ. Analytical characterization and rapid determination of 2-(diphenylmethyl)pyrrolidine in blood and application to an internet product. J. Chromatogr. B, 1 Dec 2011, 879 (31), 3771–3774. 353 kB. doi:10.1016/j.jchromb.2011.10.014

560
Analogue 37: With Benzyl-cyclic-amine skeleton

D2PM
Diphenylprolinol

IUPAC: Diphenyl(pyrrolidin-2-yl)methanol

Formula: C17H19NO Molecular weight: 253.33886 g/mol InChI Key: OGCGXUGBDJGFFY-UHFFFAOYSA-N

InChI=1S/C17H19NO/c19-17(16-12-7-13-18-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,18-19H,7,12-13H2

PubChem CID: 204386; ChemSpider: 177034

Corkery, JM; Elliott, S; Schifano, F; Corazza, O; Ghodse, AH. 2-DPMP (desoxypipradrol, 2-benzhydrylpiperidine, 2-phenylmethylpiperidine) and D2PM (diphenyl-2-pyrrolidin-2-yl-methanol, diphenylprolinol): A preliminary review. Prog. Neuro-Psychopharmacol. Biol. Psych., 3 Dec 2012, 39 (2), 253–258. 347 kB. doi:10.1016/j.pnpbp.2012.05.021

Lidder, S; Dargan, PI; Sexton, M; Button, J; Ramsey, J; Holt, DW; Wood, DM. Cardiovascular toxicity associated with recreational use of diphenylprolinol (diphenyl-2-pyrrolidinemethanol [D2PM]). J. Med. Toxicol., 1 Sep 2008, 4 (3), 167–169. 164 kB. doi:10.1007/BF03161195

Wood, DM; Dargan, PI. Use and acute toxicity associated with the novel psychoactive substances diphenylprolinol (D2PM) and desoxypipradrol (2-DPMP). Clin. Toxicol., 1 Sep 2012, 50 (8), 727–732. 117 kB. doi:10.3109/15563650.2012.716158

Zuba, D; Byrska, B. Prevalence and co-existence of active components of ‘legal highs’ Drug Test. Anal., 1 Jun 2013, 5 (6), 420–429. 1294 kB. doi:10.1002/dta.1365

561
Analogue 38: With Phenyl-cyclic-amine skeleton

Aminorex

IUPAC: 5-Phenyl-4,5-dihydro-1,3-oxazol-2-amine

Formula: C9H10N2O Molecular weight: 162.1885 g/mol InChI Key: SYAKTDIEAPMBAL-UHFFFAOYSA-N

InChI=1S/C9H10N2O/c10-9-11-6-8(12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H2,10,11)

PubChem CID: 16630; Wikipedia: Aminorex

Hess, C; Ritke, N; Sydow, K; Mehling, L; Ruehs, H; Madea, B; Musshoff, F. Determination of levamisole, aminorex, and pemoline in plasma by means of liquid chromatography-mass spectrometry and application to a pharmacokinetic study of levamisole. Drug Test. Anal., 20 Feb 2014. 451 kB. doi:10.1002/dta.1619

Brandt, SD; Baumann, MH; Partilla, JS; Kavanagh, PV; Power, JD; Talbot, B; Twamley, B; Mahony, O; O’Brien, J; Elliott, SP; Archer, RP; Patrick, J; Singh, K; Dempster, NM; Cosbey, SH. Characterization of a novel and potentially lethal designer drug (±)-cis-para-methyl-4-methylaminorex (4,4′-DMAR, or ‘Serotoni’). Drug Test. Anal., 2014. 1068 kB. doi:10.1002/dta.1668

Young, R; Glennon, RA. Cocaine-stimulus generalization to two new designer drugs: Methcathinone and 4-methylaminorex. Pharmacol. Biochem. Behav., 1 May 1993, 45 (1), 209–214. 224 kB. doi:10.1016/0091-3057(93)90110-F

Woolverton, WL; Massey, BW; Winger, G; Patrick, GA; Harris, LS. Evaluation of the abuse liability of aminorex. Drug Alcohol Depend., 1 Dec 1994, 36 (3), 187–192. 711 kB. doi:10.1016/0376-8716(94)90144-9

562
Analogue 39: With Phenyl-cyclic-amine skeleton

4-MAR
4-Methylaminorex

IUPAC: 4-Methyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine

Formula: C10H12N2O Molecular weight: 176.21508 g/mol InChI Key: LJQBMYDFWFGESC-UHFFFAOYSA-N

InChI=1S/C10H12N2O/c1-7-9(13-10(11)12-7)8-5-3-2-4-6-8/h2-7,9H,1H3,(H2,11,12)

PubChem CID: 92196; ChemSpider: 83237; Wikipedia: 4-Methylaminorex

Brandt, SD; Baumann, MH; Partilla, JS; Kavanagh, PV; Power, JD; Talbot, B; Twamley, B; Mahony, O; O’Brien, J; Elliott, SP; Archer, RP; Patrick, J; Singh, K; Dempster, NM; Cosbey, SH. Characterization of a novel and potentially lethal designer drug (±)-cis-para-methyl-4-methylaminorex (4,4′-DMAR, or ‘Serotoni’). Drug Test. Anal., 2014. 1068 kB. doi:10.1002/dta.1668

Rodriguez, WR; Allred, RA. Synthesis of trans-4-methylaminorex from norephedrine and potassium cyanate. Microgram J., 1 Jul 2005, 3 (3–4), 154–165. 559 kB.

565
Analogue 40: With Benzyl-cyclic-amine skeleton

Methylphenidate

IUPAC: Methyl phenyl(piperidin-2-yl)acetate

Formula: C14H19NO2 Molecular weight: 233.30616 g/mol InChI Key: DUGOZIWVEXMGBE-UHFFFAOYSA-N

InChI=1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3

PubChem CID: 4158; ChemSpider: 4015

Griffiths, RR; Richards, WA; McCann, U; Jesse, R. Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance. Psychopharmacology, 1 Aug 2006, 187 (3), 268–283. 342 kB. doi:10.1007/s00213-006-0457-5

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

566
Analogue 41: With Benzyl-cyclic-amine skeleton

Ethylphenidate

IUPAC: Ethyl phenyl(piperidin-2-yl)acetate

Formula: C15H21NO2 Molecular weight: 247.33274 g/mol InChI Key: AIVSIRYZIBXTMM-UHFFFAOYSA-N

InChI=1S/C15H21NO2/c1-2-18-15(17)14(12-8-4-3-5-9-12)13-10-6-7-11-16-13/h3-5,8-9,13-14,16H,2,6-7,10-11H2,1H3

PubChem CID: 3080846; ChemSpider: 2338571

Casale, JF; Hays, PA. Ethylphenidate: An analytical profile. Microgram J., 2011, 8 (2), 58–61. 906 kB.

1235
Analogue 42: With Phenyl-cyclic-amine skeleton

Phendimetrazine

IUPAC: 3,4-Dimethyl-2-phenylmorpholine

Formula: C12H17NO Molecular weight: 191.26948 g/mol InChI Key: MFOCDFTXLCYLKU-UHFFFAOYSA-N

InChI=1S/C12H17NO/c1-10-12(14-9-8-13(10)2)11-6-4-3-5-7-11/h3-7,10,12H,8-9H2,1-2H3

PubChem CID: 12460; ChemSpider: 11950

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

Banks, ML; Blough, BE; Fennell, TR; Snyder, RW; Negus, SS. Role of phenmetrazine as an active metabolite of phendimetrazine: Evidence from studies of drug discrimination and pharmacokinetics in rhesus monkeys. Drug Alcohol Depend., 1 Jun 2013, 130 (1–3), 158–166. 520 kB. doi:10.1016/j.drugalcdep.2012.10.026

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

1141
Analogue 43: With Prop-2-en-1-ylbenzene skeleton

IUPAC: Prop-2-en-1-ylbenzene

Formula: C9H10 Molecular weight: 118.1757 g/mol InChI Key: HJWLCRVIBGQPNF-UHFFFAOYSA-N

InChI=1S/C9H10/c1-2-6-9-7-4-3-5-8-9/h2-5,7-8H,1,6H2

PubChem CID: 9309; ChemSpider: 8950

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

1285
Analogue 44: With Phenylmethanamine skeleton

Pargyline

IUPAC: N-Benzyl-N-methylprop-2-yn-1-amine

Formula: C11H13N Molecular weight: 159.22762 g/mol InChI Key: DPWPWRLQFGFJFI-UHFFFAOYSA-N

InChI=1S/C11H13N/c1-3-9-12(2)10-11-7-5-4-6-8-11/h1,4-8H,9-10H2,2H3

PubChem CID: 4688; ChemSpider: 4526; Wikipedia: Pargyline

1307
Analogue 45: 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

1308
Analogue 46: With 6,7,8,9-Tetrahydro-5H-benzo[7]annulen-6-amine skeleton

IUPAC: N-(Propan-2-yl)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-amine

Formula: C14H21N Molecular weight: 203.32324 g/mol InChI Key: XJQDBYSBWJWTFU-UHFFFAOYSA-N

InChI=1S/C14H21N/c1-11(2)15-14-9-5-8-12-6-3-4-7-13(12)10-14/h3-4,6-7,11,14-15H,5,8-10H2,1-2H3

PubChem CID: 44377151; ChemSpider: 25041321

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

1309
Analogue 47: With 6,7,8,9-Tetrahydro-5H-benzo[7]annulen-6-amine skeleton

IUPAC: N,N-Dimethyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-amine

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

InChI=1S/C13H19N/c1-14(2)13-9-5-8-11-6-3-4-7-12(11)10-13/h3-4,6-7,13H,5,8-10H2,1-2H3

PubChem CID: 41900; ChemSpider: 38232

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

1317
Analogue 48: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

N-Methyl-2-aminotetralin

IUPAC: N-Methyl-1,2,3,4-tetrahydronaphthalen-2-amine

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

InChI=1S/C11H15N/c1-12-11-7-6-9-4-2-3-5-10(9)8-11/h2-5,11-12H,6-8H2,1H3

PubChem CID: 13579644; ChemSpider: 10437468

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

1318
Analogue 49: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

N-Ethyl-2-aminotetralin

IUPAC: N-Ethyl-1,2,3,4-tetrahydronaphthalen-2-amine

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

InChI=1S/C12H17N/c1-2-13-12-8-7-10-5-3-4-6-11(10)9-12/h3-6,12-13H,2,7-9H2,1H3

PubChem CID: 12843074; ChemSpider: 12956378

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

1319
Analogue 50: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

N-Propyl-2-aminotetralin

IUPAC: N-Propyl-1,2,3,4-tetrahydronaphthalen-2-amine

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

InChI=1S/C13H19N/c1-2-9-14-13-8-7-11-5-3-4-6-12(11)10-13/h3-6,13-14H,2,7-10H2,1H3

PubChem CID: 18331743; ChemSpider: 11512479

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

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

1320
Analogue 51: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

N-Isopropyl-2-aminotetralin

IUPAC: N-(Propan-2-yl)-1,2,3,4-tetrahydronaphthalen-2-amine

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

InChI=1S/C13H19N/c1-10(2)14-13-8-7-11-5-3-4-6-12(11)9-13/h3-6,10,13-14H,7-9H2,1-2H3

PubChem CID: 43222610; ChemSpider: 25039841

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

1321
Analogue 52: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

N-Butyl-2-aminotetralin

IUPAC: N-Butyl-1,2,3,4-tetrahydronaphthalen-2-amine

Formula: C14H21N Molecular weight: 203.32324 g/mol InChI Key: FSXXDNPGFQZQSR-UHFFFAOYSA-N

InChI=1S/C14H21N/c1-2-3-10-15-14-9-8-12-6-4-5-7-13(12)11-14/h4-7,14-15H,2-3,8-11H2,1H3

PubChem CID: 43222712; ChemSpider: 25037440

1322
Analogue 53: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

N,N-Dimethyl-2-aminotetralin

IUPAC: N,N-Dimethyl-1,2,3,4-tetrahydronaphthalen-2-amine

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

InChI=1S/C12H17N/c1-13(2)12-8-7-10-5-3-4-6-11(10)9-12/h3-6,12H,7-9H2,1-2H3

PubChem CID: 242461; ChemSpider: 211952

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

1323
Analogue 54: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

N,N-Diethyl-2-aminotetralin

IUPAC: N,N-Diethyl-1,2,3,4-tetrahydronaphthalen-2-amine

Formula: C14H21N Molecular weight: 203.32324 g/mol InChI Key: HKKFAEDOOMPSFN-UHFFFAOYSA-N

InChI=1S/C14H21N/c1-3-15(4-2)14-10-9-12-7-5-6-8-13(12)11-14/h5-8,14H,3-4,9-11H2,1-2H3

PubChem CID: 12381622; ChemSpider: 25047384

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

1324
Analogue 55: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

N,N-DIpropyl-2-aminotetralin

IUPAC: N,N-Dipropyl-1,2,3,4-tetrahydronaphthalen-2-amine

Formula: C16H25N Molecular weight: 231.3764 g/mol InChI Key: IMMAROBNUIRASX-UHFFFAOYSA-N

InChI=1S/C16H25N/c1-3-11-17(12-4-2)16-10-9-14-7-5-6-8-15(14)13-16/h5-8,16H,3-4,9-13H2,1-2H3

PubChem CID: 90285; ChemSpider: 81510

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

1325
Analogue 56: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

N,N-Dibutyl-2-aminotetralin

IUPAC: N,N-Dibutyl-1,2,3,4-tetrahydronaphthalen-2-amine

Formula: C18H29N Molecular weight: 259.42956 g/mol InChI Key: DSCIKHHYTOXYKT-UHFFFAOYSA-N

InChI=1S/C18H29N/c1-3-5-13-19(14-6-4-2)18-12-11-16-9-7-8-10-17(16)15-18/h7-10,18H,3-6,11-15H2,1-2H3

PubChem CID: 12381625; ChemSpider: 25039032

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

1326
Analogue 57: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

N-Isopropyl-N-methyl-2-aminotetralin

IUPAC: N-Methyl-N-(propan-2-yl)-1,2,3,4-tetrahydronaphthalen-2-amine

Formula: C14H21N Molecular weight: 203.32324 g/mol InChI Key: IVDMGOWPNCJYBO-UHFFFAOYSA-N

InChI=1S/C14H21N/c1-11(2)15(3)14-9-8-12-6-4-5-7-13(12)10-14/h4-7,11,14H,8-10H2,1-3H3

PubChem CID: 44377344; ChemSpider: 25040855

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

1327
Analogue 58: With 2,3-Dihydro-1H-inden-2-amine skeleton

NM-2-AI
N-Methyl-2-aminoindane

IUPAC: N-Methyl-2,3-dihydro-1H-inden-2-amine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: SXWZQUCTTOBHJT-UHFFFAOYSA-N

InChI=1S/C10H13N/c1-11-10-6-8-4-2-3-5-9(8)7-10/h2-5,10-11H,6-7H2,1H3

PubChem CID: 15023225; ChemSpider: 13566342

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

1328
Analogue 59: With 2,3-Dihydro-1H-inden-2-amine skeleton

NE-2-AI
N-Ethyl-2-aminoindane

IUPAC: N-Ethyl-2,3-dihydro-1H-inden-2-amine

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

InChI=1S/C11H15N/c1-2-12-11-7-9-5-3-4-6-10(9)8-11/h3-6,11-12H,2,7-8H2,1H3

PubChem CID: 12452138; ChemSpider: 10635088

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

1329
Analogue 60: With 2,3-Dihydro-1H-inden-2-amine skeleton

NP-2-AI
N-Propyl-2-aminoindane

IUPAC: N-Propyl-2,3-dihydro-1H-inden-2-amine

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

InChI=1S/C12H17N/c1-2-7-13-12-8-10-5-3-4-6-11(10)9-12/h3-6,12-13H,2,7-9H2,1H3

PubChem CID: 17221237; ChemSpider: 13775926

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

1330
Analogue 61: With 2,3-Dihydro-1H-inden-2-amine skeleton

NIP-2-AI
N-Isopropyl-2-aminoindane

IUPAC: N-(Propan-2-yl)-2,3-dihydro-1H-inden-2-amine

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

InChI=1S/C12H17N/c1-9(2)13-12-7-10-5-3-4-6-11(10)8-12/h3-6,9,12-13H,7-8H2,1-2H3

PubChem CID: 18790309; ChemSpider: 19330265

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

1331
Analogue 62: With 2,3-Dihydro-1H-inden-2-amine skeleton

NB-2-AI
N-Butyl-2-aminoindane

IUPAC: N-Butyl-2,3-dihydro-1H-inden-2-amine

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

InChI=1S/C13H19N/c1-2-3-8-14-13-9-11-6-4-5-7-12(11)10-13/h4-7,13-14H,2-3,8-10H2,1H3

PubChem CID: 43512786; ChemSpider: 25045448

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

1332
Analogue 63: With 2,3-Dihydro-1H-inden-2-amine skeleton

DM-2-AI
N,N-Dimethyl-2-aminoindane

IUPAC: N,N-Dimethyl-2,3-dihydro-1H-inden-2-amine

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

InChI=1S/C11H15N/c1-12(2)11-7-9-5-3-4-6-10(9)8-11/h3-6,11H,7-8H2,1-2H3

PubChem CID: 3016704; ChemSpider: 2284609

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

1333
Analogue 64: With 2,3-Dihydro-1H-inden-2-amine skeleton

DE-2-AI
N,N-Diethyl-2-aminoindane

IUPAC: N,N-Diethyl-2,3-dihydro-1H-inden-2-amine

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

InChI=1S/C13H19N/c1-3-14(4-2)13-9-11-7-5-6-8-12(11)10-13/h5-8,13H,3-4,9-10H2,1-2H3

PubChem CID: 44377347; ChemSpider: 25059704

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

1334
Analogue 65: With 2,3-Dihydro-1H-inden-2-amine skeleton

DP-2-AI
N,N-Dipropyl-2-aminoindane

IUPAC: N,N-Dipropyl-2,3-dihydro-1H-inden-2-amine

Formula: C15H23N Molecular weight: 217.34982 g/mol InChI Key: LEACNHXRZNVYRP-UHFFFAOYSA-N

InChI=1S/C15H23N/c1-3-9-16(10-4-2)15-11-13-7-5-6-8-14(13)12-15/h5-8,15H,3-4,9-12H2,1-2H3

PubChem CID: 130402; ChemSpider: 115377

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

1335
Analogue 66: With 2,3-Dihydro-1H-inden-2-amine skeleton

DB-2-AI
N,N-Dibutyl-2-aminoindane

IUPAC: N,N-Dibutyl-2,3-dihydro-1H-inden-2-amine

Formula: C17H27N Molecular weight: 245.40298 g/mol InChI Key: KPEQEOIOBDNTTE-UHFFFAOYSA-N

InChI=1S/C17H27N/c1-3-5-11-18(12-6-4-2)17-13-15-9-7-8-10-16(15)14-17/h7-10,17H,3-6,11-14H2,1-2H3

PubChem CID: 44377160; ChemSpider: 25047505

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

1336
Analogue 67: With 2,3-Dihydro-1H-inden-2-amine skeleton

MIP-2-AI
N-Isopropyl-N-methyl-2-aminoindane

IUPAC: N-Methyl-N-(propan-2-yl)-2,3-dihydro-1H-inden-2-amine

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

InChI=1S/C13H19N/c1-10(2)14(3)13-8-11-6-4-5-7-12(11)9-13/h4-7,10,13H,8-9H2,1-3H3

PubChem CID: 44377147; ChemSpider: 25056058

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

1339
Analogue 68: With 2-Phenylethanol skeleton

1-Phenyl-2-propanol

IUPAC: 1-Phenylpropan-2-ol

Formula: C9H12O Molecular weight: 136.19098 g/mol InChI Key: WYTRYIUQUDTGSX-UHFFFAOYSA-N

InChI=1S/C9H12O/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8,10H,7H2,1H3

PubChem CID: 94185; ChemSpider: 84999

Barfknecht, CF; Smith, RV; Nichols, DE; Leseney, JL; Long, JP; Engelbrecht, JA. Chemistry and pharmacological evaluation of 1-phenyl-2-propanols and 1-phenyl-2-propanones. J. Pharm. Sci., 1 May 1971, 60 (5), 799–801. 352 kB. doi:10.1002/jps.2600600533

1345
Analogue 69: With 2-Phenylethan-1-amine skeleton

IUPAC: N,N-Bis(2-phenylethyl)butan-1-amine

Formula: C20H27N Molecular weight: 281.43508 g/mol InChI Key: AWWNNIPXRFZEHF-UHFFFAOYSA-N

InChI=1S/C20H27N/c1-2-3-16-21(17-14-19-10-6-4-7-11-19)18-15-20-12-8-5-9-13-20/h4-13H,2-3,14-18H2,1H3

PubChem CID: 69944478

Spetea, M; Berzetei-Gurske, IP; Guerrieri, E; Schmidhammer, H. Discovery and pharmacological evaluation of a diphenethylamine derivative (HS665), a highly potent and selective K opioid receptor agonist. J. Med. Chem., 26 Nov 2012, 55 (22), 10302–10306. 409 kB. doi:10.1021/jm301258w

1344
Analogue 70: With 2-Phenylethan-1-amine skeleton

RU24213

IUPAC: N,N-Bis(2-phenylethyl)propan-1-amine

Formula: C19H25N Molecular weight: 267.4085 g/mol InChI Key: RPEJSKBNTPQAFK-UHFFFAOYSA-N

InChI=1S/C19H25N/c1-2-15-20(16-13-18-9-5-3-6-10-18)17-14-19-11-7-4-8-12-19/h3-12H,2,13-17H2,1H3

PubChem CID: 12488258

Spetea, M; Berzetei-Gurske, IP; Guerrieri, E; Schmidhammer, H. Discovery and pharmacological evaluation of a diphenethylamine derivative (HS665), a highly potent and selective K opioid receptor agonist. J. Med. Chem., 26 Nov 2012, 55 (22), 10302–10306. 409 kB. doi:10.1021/jm301258w

1346
Analogue 71: With 2-Phenylethan-1-amine skeleton

IUPAC: N,N-Bis(2-phenylethyl)pentan-1-amine

Formula: C21H29N Molecular weight: 295.46166 g/mol InChI Key: GEJBOXCILASHSH-UHFFFAOYSA-N

InChI=1S/C21H29N/c1-2-3-10-17-22(18-15-20-11-6-4-7-12-20)19-16-21-13-8-5-9-14-21/h4-9,11-14H,2-3,10,15-19H2,1H3

Spetea, M; Berzetei-Gurske, IP; Guerrieri, E; Schmidhammer, H. Discovery and pharmacological evaluation of a diphenethylamine derivative (HS665), a highly potent and selective K opioid receptor agonist. J. Med. Chem., 26 Nov 2012, 55 (22), 10302–10306. 409 kB. doi:10.1021/jm301258w

1347
Analogue 72: With 2-Phenylethan-1-amine skeleton

IUPAC: N,N-Bis(2-phenylethyl)hexan-1-amine

Formula: C22H31N Molecular weight: 309.48824 g/mol InChI Key: KXMITIRIRBGKCJ-UHFFFAOYSA-N

InChI=1S/C22H31N/c1-2-3-4-11-18-23(19-16-21-12-7-5-8-13-21)20-17-22-14-9-6-10-15-22/h5-10,12-15H,2-4,11,16-20H2,1H3

Spetea, M; Berzetei-Gurske, IP; Guerrieri, E; Schmidhammer, H. Discovery and pharmacological evaluation of a diphenethylamine derivative (HS665), a highly potent and selective K opioid receptor agonist. J. Med. Chem., 26 Nov 2012, 55 (22), 10302–10306. 409 kB. doi:10.1021/jm301258w

1348
Analogue 73: With 2-Phenylethan-1-amine skeleton

IUPAC: N-(Cyclopropylmethyl)-2-phenyl-N-(2-phenylethyl)ethan-1-amine

Formula: C20H25N Molecular weight: 279.4192 g/mol InChI Key: RSWVQPPLNYBDAN-UHFFFAOYSA-N

InChI=1S/C20H25N/c1-3-7-18(8-4-1)13-15-21(17-20-11-12-20)16-14-19-9-5-2-6-10-19/h1-10,20H,11-17H2

Spetea, M; Berzetei-Gurske, IP; Guerrieri, E; Schmidhammer, H. Discovery and pharmacological evaluation of a diphenethylamine derivative (HS665), a highly potent and selective K opioid receptor agonist. J. Med. Chem., 26 Nov 2012, 55 (22), 10302–10306. 409 kB. doi:10.1021/jm301258w

1349
Analogue 74: With 2-Phenylethan-1-amine skeleton

HS665

IUPAC: N-(Cyclobutylmethyl)-2-phenyl-N-(2-phenylethyl)ethan-1-amine

Formula: C21H27N Molecular weight: 293.44578 g/mol InChI Key: UVVSMIXHWCSTBL-UHFFFAOYSA-N

InChI=1S/C21H27N/c1-3-8-19(9-4-1)14-16-22(18-21-12-7-13-21)17-15-20-10-5-2-6-11-20/h1-6,8-11,21H,7,12-18H2

1434
Analogue 75: With Phenyl-cyclic-amine skeleton

Cyclazodone

IUPAC: 2-(Cyclopropylamino)-5-phenyl-1,3-oxazol-4(5H)-one

Formula: C12H12N2O2 Molecular weight: 216.23588 g/mol InChI Key: DNRKTAYPGADPGW-UHFFFAOYSA-N

InChI=1S/C12H12N2O2/c15-11-10(8-4-2-1-3-5-8)16-12(14-11)13-9-6-7-9/h1-5,9-10H,6-7H2,(H,13,14,15)

PubChem CID: 26701; ChemSpider: 24875; Wikipedia: Cyclazodone

1435
Analogue 76: With Phenyl-cyclic-amine skeleton

Fenozolone

IUPAC: 2-(Ethylamino)-5-phenyl-1,3-oxazol-4(5H)-one

Formula: C11H12N2O2 Molecular weight: 204.22518 g/mol InChI Key: RXOIEVSUURELPG-UHFFFAOYSA-N

InChI=1S/C11H12N2O2/c1-2-12-11-13-10(14)9(15-11)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,12,13,14)

PubChem CID: 71682; ChemSpider: 64736; Wikipedia: Fenozolone

1437
Analogue 77: With Phenyl-cyclic-amine skeleton

Pemoline

IUPAC: 2-Imino-5-phenyl-1,3-oxazolidin-4-one

Formula: C9H8N2O2 Molecular weight: 176.17202 g/mol InChI Key: NRNCYVBFPDDJNE-UHFFFAOYSA-N

InChI=1S/C9H8N2O2/c10-9-11-8(12)7(13-9)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12)

PubChem CID: 4723; ChemSpider: 4561; Wikipedia: Pemoline

Hess, C; Ritke, N; Sydow, K; Mehling, L; Ruehs, H; Madea, B; Musshoff, F. Determination of levamisole, aminorex, and pemoline in plasma by means of liquid chromatography-mass spectrometry and application to a pharmacokinetic study of levamisole. Drug Test. Anal., 20 Feb 2014. 451 kB. doi:10.1002/dta.1619

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

1438
Analogue 78: With Phenyl-cyclic-amine skeleton

Thozalinone

IUPAC: 2-(Dimethylamino)-5-phenyl-1,3-oxazol-4(5H)-one

Formula: C11H12N2O2 Molecular weight: 204.22518 g/mol InChI Key: JJSHYECKYLDYAR-UHFFFAOYSA-N

InChI=1S/C11H12N2O2/c1-13(2)11-12-10(14)9(15-11)8-6-4-3-5-7-8/h3-7,9H,1-2H3

PubChem CID: 12602; ChemSpider: 12082; Wikipedia: Thozalinone

1439
Analogue 79: With 2-Phenoxyethan-1-amine skeleton

Phenoxybenzamine

IUPAC: N-Benzyl-N-(2-chloroethyl)-1-phenoxypropan-2-amine

Formula: C18H22ClNO Molecular weight: 303.82638 g/mol InChI Key: QZVCTJOXCFMACW-UHFFFAOYSA-N

InChI=1S/C18H22ClNO/c1-16(15-21-18-10-6-3-7-11-18)20(13-12-19)14-17-8-4-2-5-9-17/h2-11,16H,12-15H2,1H3

PubChem CID: 4768; ChemSpider: 4604

1451
Analogue 80: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

IUPAC: N-(3-Phenylpropyl)-1,2,3,4-tetrahydronaphthalen-2-amine

Formula: C19H23N Molecular weight: 265.39262 g/mol InChI Key: CEMUKLXXZBFFNQ-UHFFFAOYSA-N

InChI=1S/C19H23N/c1-2-7-16(8-3-1)9-6-14-20-19-13-12-17-10-4-5-11-18(17)15-19/h1-5,7-8,10-11,19-20H,6,9,12-15H2

PubChem CID: 15061906

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

1471
Analogue 81: With 2-Phenylcyclobutan-1-amine skeleton

IUPAC: 2-Phenylcyclobutanamine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: PKMQLQANCCIABY-UHFFFAOYSA-N

InChI=1S/C10H13N/c11-10-7-6-9(10)8-4-2-1-3-5-8/h1-5,9-10H,6-7,11H2

PubChem CID: 19703781

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

1482
Analogue 82: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: N-Methyl-2-phenylcyclopropanamine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: QJNGEXCJXPQCPA-UHFFFAOYSA-N

InChI=1S/C10H13N/c1-11-10-7-9(10)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3

PubChem CID: 12682037

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

1483
Analogue 83: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: N,N-Dimethyl-2-phenylcyclopropanamine

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

InChI=1S/C11H15N/c1-12(2)11-8-10(11)9-6-4-3-5-7-9/h3-7,10-11H,8H2,1-2H3

PubChem CID: 425148; ChemSpider: 376178

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

1484
Analogue 84: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: N-Ethyl-2-phenylcyclopropanamine

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

InChI=1S/C11H15N/c1-2-12-11-8-10(11)9-6-4-3-5-7-9/h3-7,10-12H,2,8H2,1H3

PubChem CID: 61813376; ChemSpider: 28173221

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

1485
Analogue 85: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: N-Benzyl-2-phenylcyclopropanamine

Formula: C16H17N Molecular weight: 223.31288 g/mol InChI Key: MCBSQMCGSGMJHA-UHFFFAOYSA-N

InChI=1S/C16H17N/c1-3-7-13(8-4-1)12-17-16-11-15(16)14-9-5-2-6-10-14/h1-10,15-17H,11-12H2

PubChem CID: 57822468

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

1486
Analogue 86: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 2-Phenyl-N-(1-phenylpropan-2-yl)cyclopropanamine

Formula: C18H21N Molecular weight: 251.36604 g/mol InChI Key: WYMOILKEUATGHW-UHFFFAOYSA-N

InChI=1S/C18H21N/c1-14(12-15-8-4-2-5-9-15)19-18-13-17(18)16-10-6-3-7-11-16/h2-11,14,17-19H,12-13H2,1H3

PubChem CID: 55148982

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

1487
Analogue 87: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: N,N-Dimethyl-N′-(2-phenylcyclopropyl)ethane-1,2-diamine

Formula: C13H20N2 Molecular weight: 204.3113 g/mol InChI Key: NBJLJFJELKATJD-UHFFFAOYSA-N

InChI=1S/C13H20N2/c1-15(2)9-8-14-13-10-12(13)11-6-4-3-5-7-11/h3-7,12-14H,8-10H2,1-2H3

PubChem CID: 61815452

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

1488
Analogue 88: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: N-(2-Phenylcyclopropyl)formamide

Formula: C10H11NO Molecular weight: 161.20044 g/mol InChI Key: CZPSDBJHVTYMBQ-UHFFFAOYSA-N

InChI=1S/C10H11NO/c12-7-11-10-6-9(10)8-4-2-1-3-5-8/h1-5,7,9-10H,6H2,(H,11,12)

PubChem CID: 54139679

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

1489
Analogue 89: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 2,2,2-Trifluoro-N-(2-phenylcyclopropyl)acetamide

Formula: C11H10F3NO Molecular weight: 229.1984096 g/mol InChI Key: ONHHCCWIZDGBTO-UHFFFAOYSA-N

InChI=1S/C11H10F3NO/c12-11(13,14)10(16)15-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6H2,(H,15,16)

PubChem CID: 575751; ChemSpider: 500574

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

1490
Analogue 90: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: N-(2-Phenylcyclopropyl)pyridine-4-carboxamide

Formula: C15H14N2O Molecular weight: 238.28446 g/mol InChI Key: BDQSRRYMMFKOFM-UHFFFAOYSA-N

InChI=1S/C15H14N2O/c18-15(12-6-8-16-9-7-12)17-14-10-13(14)11-4-2-1-3-5-11/h1-9,13-14H,10H2,(H,17,18)

PubChem CID: 47733746

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

1491
Analogue 91: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: Ethyl (2-phenylcyclopropyl)carbamate

Formula: C12H15NO2 Molecular weight: 205.253 g/mol InChI Key: XVOLBJCYNFCTEZ-UHFFFAOYSA-N

InChI=1S/C12H15NO2/c1-2-15-12(14)13-11-8-10(11)9-6-4-3-5-7-9/h3-7,10-11H,2,8H2,1H3,(H,13,14)

PubChem CID: 19426606

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

1492
Analogue 92: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 2,2-Dimethyl-N-(2-phenylcyclopropyl)propanamide

Formula: C14H19NO Molecular weight: 217.30676 g/mol InChI Key: RRIBAPFLLISMJU-UHFFFAOYSA-N

InChI=1S/C14H19NO/c1-14(2,3)13(16)15-12-9-11(12)10-7-5-4-6-8-10/h4-8,11-12H,9H2,1-3H3,(H,15,16)

PubChem CID: 12901547

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

1493
Analogue 93: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: N-(Benzyloxy)-2-phenylcyclopropanamine

Formula: C16H17NO Molecular weight: 239.31228 g/mol InChI Key: KKEPVPXXWMWQTF-UHFFFAOYSA-N

InChI=1S/C16H17NO/c1-3-7-13(8-4-1)12-18-17-16-11-15(16)14-9-5-2-6-10-14/h1-10,15-17H,11-12H2

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

1494
Analogue 94: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 1-(2-Phenylcyclopropyl)urea

Formula: C10H12N2O Molecular weight: 176.21508 g/mol InChI Key: AVVMSHVXSGLTEZ-UHFFFAOYSA-N

InChI=1S/C10H12N2O/c11-10(13)12-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6H2,(H3,11,12,13)

PubChem CID: 272632; ChemSpider: 239866

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

1495
Analogue 95: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 1,1-Dimethyl-3-(2-phenylcyclopropyl)urea

Formula: C12H16N2O Molecular weight: 204.26824 g/mol InChI Key: KBSXVDXSLRFUIN-UHFFFAOYSA-N

InChI=1S/C12H16N2O/c1-14(2)12(15)13-11-8-10(11)9-6-4-3-5-7-9/h3-7,10-11H,8H2,1-2H3,(H,13,15)

PubChem CID: 47743486

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

1496
Analogue 96: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: N-(2-Phenylcyclopropyl)hydrazinecarboxamide

Formula: C10H13N3O Molecular weight: 191.22972 g/mol InChI Key: GTWUYOIWXDNXKF-UHFFFAOYSA-N

InChI=1S/C10H13N3O/c11-13-10(14)12-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,11H2,(H2,12,13,14)

PubChem CID: 61814870

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

1497
Analogue 97: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 2-Methyl-2-phenylcyclopropanamine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: DZOORLACDVEKJC-UHFFFAOYSA-N

InChI=1S/C10H13N/c1-10(7-9(10)11)8-5-3-2-4-6-8/h2-6,9H,7,11H2,1H3

PubChem CID: 54595265; ChemSpider: 27909807

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

1498
Analogue 98: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 1-Methyl-2-phenylcyclopropanamine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: MHQDTOHVMGQLTE-UHFFFAOYSA-N

InChI=1S/C10H13N/c1-10(11)7-9(10)8-5-3-2-4-6-8/h2-6,9H,7,11H2,1H3

PubChem CID: 54072774

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

1499
Analogue 99: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 2,2-Diphenylcyclopropanamine

Formula: C15H15N Molecular weight: 209.2863 g/mol InChI Key: WVRNJJILWVMIRA-UHFFFAOYSA-N

InChI=1S/C15H15N/c16-14-11-15(14,12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H,11,16H2

PubChem CID: 12345941; ChemSpider: 13566302

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

1500
Analogue 100: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 2-Methyl-3-phenylcyclopropanamine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: VYDUHLWMQFOCQJ-UHFFFAOYSA-N

InChI=1S/C10H13N/c1-7-9(10(7)11)8-5-3-2-4-6-8/h2-7,9-10H,11H2,1H3

PubChem CID: 55289096

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

1502
Analogue 101: With 2-Phenylcyclopropan-1-amine skeleton

IUPAC: 2,3-Diphenylcyclopropanamine

Formula: C15H15N Molecular weight: 209.2863 g/mol InChI Key: RYTXAPKVNHVKAX-UHFFFAOYSA-N

InChI=1S/C15H15N/c16-15-13(11-7-3-1-4-8-11)14(15)12-9-5-2-6-10-12/h1-10,13-15H,16H2

PubChem CID: 12523667

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

1511
Analogue 102: With 1-Benzylcyclopropan-1-amine skeleton

IUPAC: 1-Benzylcyclopropanamine

Formula: C10H13N Molecular weight: 147.21692 g/mol InChI Key: GEQRCQKFLCJFEC-UHFFFAOYSA-N

InChI=1S/C10H13N/c11-10(6-7-10)8-9-4-2-1-3-5-9/h1-5H,6-8,11H2

PubChem CID: 152923; ChemSpider: 134782

1512
Analogue 103: With 1-Benzylcyclopropan-1-amine skeleton

IUPAC: 1-Benzyl-N-methylcyclopropanamine

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

InChI=1S/C11H15N/c1-12-11(7-8-11)9-10-5-3-2-4-6-10/h2-6,12H,7-9H2,1H3

PubChem CID: 21748398

1559
Analogue 104: With 2-Phenylethan-1-amine skeleton

β,β-Me-PEA

IUPAC: 2-Methyl-2-phenylpropan-1-amine

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

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

PubChem CID: 210602; ChemSpider: 182543

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

1561
Analogue 105: With 2-Phenylethan-1-amine skeleton

β-iPr-PEA

IUPAC: 3-Methyl-2-phenylbutan-1-amine

Formula: C11H17N Molecular weight: 163.25938 g/mol InChI Key: VDMAQVANUGNDOM-UHFFFAOYSA-N

InChI=1S/C11H17N/c1-9(2)11(8-12)10-6-4-3-5-7-10/h3-7,9,11H,8,12H2,1-2H3

PubChem CID: 9880217; ChemSpider: 8055893

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

1562
Analogue 106: With 2-Phenylethan-1-amine skeleton

DPEA

IUPAC: 2,2-Diphenylethan-1-amine

Formula: C14H15N Molecular weight: 197.2756 g/mol InChI Key: RXMTUVIKZRXSSM-UHFFFAOYSA-N

InChI=1S/C14H15N/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H,11,15H2

PubChem CID: 77575; ChemSpider: 69980

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

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

2526
Analogue 107: With Phenylacetaldehyde skeleton

Isoethcathinone

IUPAC: 1-(Ethylamino)-1-phenylpropan-2-one

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

InChI=1S/C11H15NO/c1-3-12-11(9(2)13)10-7-5-4-6-8-10/h4-8,11-12H,3H2,1-2H3

PubChem CID: 12403217

McDermott, SD; Power, JD; Kavanagh, PV; O’Brien, J. The analysis of substituted cathinones. Part 2: An investigation into the phenylacetone based isomers of 4-methylmethcathinone and N-ethylcathinone. Forensic Sci. Int., 10 Oct 2011, 212 (1–3), 13–21. 1129 kB. doi:10.1016/j.forsciint.2011.06.030

2527
Analogue 108: With Phenylacetaldehyde skeleton

Isopentedrone

IUPAC: 1-(Methylamino)-1-phenylpentan-2-one

Formula: C12H17NO Molecular weight: 191.26948 g/mol InChI Key: ILGRTMNCRBDXBI-UHFFFAOYSA-N

InChI=1S/C12H17NO/c1-3-7-11(14)12(13-2)10-8-5-4-6-9-10/h4-6,8-9,12-13H,3,7H2,1-2H3

Westphal, F; Junge, T; Girreser, U; Greibl, W; Doering, C. Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 157–167. 853 kB. doi:10.1016/j.forsciint.2011.10.045

2531
Analogue 109: With 2-Phenylethan-1-amine skeleton

IUPAC: N-(1-Phenylpropan-2-yl)prop-2-yn-1-amine

Formula: C12H15N Molecular weight: 173.2542 g/mol InChI Key: UUFAJPMQSFXDFR-UHFFFAOYSA-N

InChI=1S/C12H15N/c1-3-9-13-11(2)10-12-7-5-4-6-8-12/h1,4-8,11,13H,9-10H2,2H3

PubChem CID: 200718; ChemSpider: 173756

2759
Analogue 110: With Phenylmethanamine skeleton

IUPAC: N′-[4-(Dimethylamino)-2-methoxy-5-nitrobenzyl]-N,N-diethylethane-1,2-diamine

Formula: C16H28N4O3 Molecular weight: 324.41852 g/mol InChI Key: GDOQXLINNITIBE-UHFFFAOYSA-N

InChI=1S/C16H28N4O3/c1-6-19(7-2)9-8-17-12-13-10-15(20(21)22)14(18(3)4)11-16(13)23-5/h10-11,17H,6-9,12H2,1-5H3

Dawson, BA; Black, DB; Cyr, TD; Ethier, J; By, AW; Beckstead, HD; Neville, GA. Structural elucidation of unusual police exhibits. I. Dimethpramide ('Dimetcarb'). Forensic Sci. Int., 28 Feb 1995, 71 (3), 169–179. 1376 kB. doi:10.1016/0379-0738(94)01664-X

1047
Analogue 111: With Phenyl-cyclic-amine skeleton

Levamisole

IUPAC: 6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole

Formula: C11H12N2S Molecular weight: 204.29138 g/mol InChI Key: HLFSDGLLUJUHTE-UHFFFAOYSA-N

InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2

PubChem CID: 3913; ChemSpider: 3776

Hess, C; Ritke, N; Sydow, K; Mehling, L; Ruehs, H; Madea, B; Musshoff, F. Determination of levamisole, aminorex, and pemoline in plasma by means of liquid chromatography-mass spectrometry and application to a pharmacokinetic study of levamisole. Drug Test. Anal., 20 Feb 2014. 451 kB. doi:10.1002/dta.1619

1027
Analogue 112: With Phenylethyl-cyclic-amine skeleton

W-15

IUPAC: 4-Chloro-N-[(2E)-1-(2-phenylethyl)piperidin-2-ylidene]benzenesulfonamide

Formula: C19H21ClN2O2S Molecular weight: 376.90024 g/mol InChI Key: VJHXSSVOCOBVMI-XUTLUUPISA-N

InChI=1S/C19H21ClN2O2S/c20-17-9-11-18(12-10-17)25(23,24)21-19-8-4-5-14-22(19)15-13-16-6-2-1-3-7-16/h1-3,6-7,9-12H,4-5,8,13-15H2/b21-19+

ChemSpider: 10544257

931
Analogue 113: With Phenylmethanamine skeleton

N-Me-Benzylamine
N-Me-Benzylamine

IUPAC: N-Methyl-1-phenylmethanamine

Formula: C8H11N Molecular weight: 121.17964 g/mol InChI Key: RIWRFSMVIUAEBX-UHFFFAOYSA-N

InChI=1S/C8H11N/c1-9-7-8-5-3-2-4-6-8/h2-6,9H,7H2,1H3

PubChem CID: 7669; ChemSpider: 7386

Sanderson, RM. Identification of N-methylbenzylamine hydrochloride, N-ethylbenzylamine hydrochloride, and N-isopropylbenzylamine hydrochloride. Microgram J., 1 Jan 2008, 6 (1–2), 36–45. 495 kB.

930
Analogue 114: With Phenylmethanamine skeleton

N-IPr-Benzylamine
N-iPr-Benzylamine

IUPAC: N-Benzylpropan-2-amine

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

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

PubChem CID: 66024; ChemSpider: 59415

Sanderson, RM. Identification of N-methylbenzylamine hydrochloride, N-ethylbenzylamine hydrochloride, and N-isopropylbenzylamine hydrochloride. Microgram J., 1 Jan 2008, 6 (1–2), 36–45. 495 kB.

929
Analogue 115: With Phenylmethanamine skeleton

N-Et-Benzylamine
N-Et-Benzylamine

IUPAC: N-Benzylethanamine

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

InChI=1S/C9H13N/c1-2-10-8-9-6-4-3-5-7-9/h3-7,10H,2,8H2,1H3

PubChem CID: 84352; ChemSpider: 76094

Sanderson, RM. Identification of N-methylbenzylamine hydrochloride, N-ethylbenzylamine hydrochloride, and N-isopropylbenzylamine hydrochloride. Microgram J., 1 Jan 2008, 6 (1–2), 36–45. 495 kB.

1086
Analogue 116: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

HOT-2-AT

IUPAC: N-Hydroxy-1,2,3,4-tetrahydronaphthalen-2-amine

Formula: C10H13NO Molecular weight: 163.21632 g/mol InChI Key: ZPELESCWLJSVCY-UHFFFAOYSA-N

InChI=1S/C10H13NO/c12-11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10-12H,5-7H2

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

Two isomers:
2118
Isomer 1

MPBP
4′-Methyl-α-pyrrolidinobutanophenone

IUPAC: 1-(4-Methylphenyl)-2-(pyrrolidin-1-yl)butan-1-one

Formula: C15H21NO Molecular weight: 231.33334 g/mol InChI Key: NXNPGAAZKYDOPW-UHFFFAOYSA-N

InChI=1S/C15H21NO/c1-3-14(16-10-4-5-11-16)15(17)13-8-6-12(2)7-9-13/h6-9,14H,3-5,10-11H2,1-2H3

PubChem CID: 129775; Wikipedia: 4'-Methyl-α-pyrrolidinobutiophenone

Westphal, F; Junge, T; Rösner, P; Fritschi, G; Kleinc, B; Girreser, U. Mass spectral and NMR spectral data of two new designer drugs with an α-aminophenone structure: 4′-Methyl-α-pyrrolidinohexanophenone and 4′-methyl-α-pyrrolidinobutyrophenone. Forensic Sci. Int., 1 Jan 2007, 169 (1), 32–42. 1465 kB. doi:10.1016/j.forsciint.2006.07.024

Iversen, LL. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010.

2120
Isomer 2

IUPAC: 2-Methyl-1-(4-methylphenyl)-2-(pyrrolidin-1-yl)propan-1-one

Formula: C15H21NO Molecular weight: 231.33334 g/mol InChI Key: YMGQEFUZLVESMR-UHFFFAOYSA-N

InChI=1S/C15H21NO/c1-12-6-8-13(9-7-12)14(17)15(2,3)16-10-4-5-11-16/h6-9H,4-5,10-11H2,1-3H3

Westphal, F; Junge, T; Rösner, P; Fritschi, G; Kleinc, B; Girreser, U. Mass spectral and NMR spectral data of two new designer drugs with an α-aminophenone structure: 4′-Methyl-α-pyrrolidinohexanophenone and 4′-methyl-α-pyrrolidinobutyrophenone. Forensic Sci. Int., 1 Jan 2007, 169 (1), 32–42. 1465 kB. doi:10.1016/j.forsciint.2006.07.024

Show all 140 analogues and isomers Show only the three α analogues Show only the one R2 analogues Show only the two R3 analogues Show only the 16 R4 analogues Show only the 116 skeleton analogues
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