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You are currently exploring AA.
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6012
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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 |
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Two N analogues:
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6013
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Analogue 1: Adding Methyl at N
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6014
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Analogue 2: Adding Dimethyl at N
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One α analogue:
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2004
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Analogue 1: Adding Methyl at α
Cathinone IUPAC: 2-Amino-1-phenylpropan-1-one Formula: C9H11NO Molecular weight: 149.18974 g/mol InChI Key: PUAQLLVFLMYYJJ-UHFFFAOYSA-N InChI=1S/C9H11NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,10H2,1H3 PubChem CID: 107786; ChemSpider: 96940; Erowid: Cathinone & Methcathinone; Wikipedia: Cathinone Shulgin Index: Table: 2 Page: 318 Row: 29
Glennon, RA; Young, R; Martin, BR; Dal Cason, TA. Methcathinone (“Cat”): An enantiomeric potency comparison. Pharmacol. Biochem. Behav., 1 Jan 1995, 50 (4) 601–606. 709 kB. doi:10.1016/0091-3057(94)00348-3 Dal Cason, TA; Young, R; Glennon, RA. Cathinone: An investigation of several N-alkyl and methylenedioxy-substituted analogs. Pharmacol. Biochem. Behav., 1 Jan 1997, 58 (4), 1109–1116. 97 kB. doi:10.1016/S0091-3057(97)00323-7 Archer, RP. Fluoromethcathinone, a new substance of abuse. Forensic Sci. Int., 1 Jan 2009, 185 (1–3), 10–20. 1355 kB. doi:10.1016/j.forsciint.2008.11.013 Gambaro, V; Arnoldi, S; Colombo, ML; Dell’Acqua, L; Guerrini, K; Roda, G. Determination of the active principles of Catha Edulis: Quali-quantitative analysis of cathinone, cathine, and phenylpropanolamine. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 87–92. 479 kB. doi:10.1016/j.forsciint.2011.09.028 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 Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017 Glennon, RA; 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 Rothman, RB; Vu, N; Partilla, JS; Roth, BL; Hufeisen, SJ; Compton-Toth, BA; Birkes, J; Young, R; Glennon, RA. In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J. Pharmacol. Exp. Ther., 1 Oct 2003, 307 (1), 138–145. 516 kB. doi:10.1124/jpet.103.053975 Iversen, L. Consideration of the cathinones, Advisory Council on the Misuse of Drugs, 31 Mar 2010. Toole, KE; Fu, S; Shimmon, RG; Kraymen, M; Taflaga, S. Color tests for the preliminary identification of methcathinone and analogues of methcathinone. Microgram J., 2012, 9 (1), 27–32. 496 kB. Shulgin, AT. Cathinone. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 3 Jun 2004. |
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One R2 analogue:
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6068
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Analogue 1: Adding Amino at R2
2-APEA-βk IUPAC: 2-Amino-1-(2-aminophenyl)ethanone Formula: C8H10N2O Molecular weight: 150.1778 g/mol InChI Key: ACTLYQCWIWMUSY-UHFFFAOYSA-N InChI=1S/C8H10N2O/c9-5-8(11)6-3-1-2-4-7(6)10/h1-4H,5,9-10H2 PubChem CID: 12290895 Shulgin Index: See #100 2-MPEA; Table: 3 Page: 319 Row: 18 |
40 skeleton analogues:
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142
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Analogue 1: With 2-Phenylethan-1-amine skeleton
PEA IUPAC: 2-Phenylethanamine 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
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 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 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 Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017 Glennon, RA; 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 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 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 Meyers-Riggs, B. Phenethylamine and amphetamine. countyourculture: rational exploration of the underground, 2 Nov 2010. |
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2357
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Analogue 2: With 2,3-Dihydro-1H-inden-2-amine skeleton
2-AI 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 |
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400
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Analogue 3: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton
2-AT 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 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 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 |
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5554
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Analogue 4: With 2-Phenylethan-1-amine skeleton
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 |
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2378
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Analogue 5: With 2-Phenylethan-1-amine skeleton
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801
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Analogue 6: 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 |
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903
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Analogue 7: 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 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 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 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 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 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 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 Anon. Report on the risk assessment of BZP in the framework of the Council decision on new psychoactive substances, European Monitoring Centre for Drugs and Drug Addiction, 2009. doi:10.2810/44197 |
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901
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Analogue 8: 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 |
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601
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Analogue 9: 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 |
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6007
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Analogue 10: 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 |
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6010
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Analogue 11: 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 |
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6028
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Analogue 12: 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 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 |
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6055
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Analogue 13: 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 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 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 |
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2462
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Analogue 14: 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 |
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2463
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Analogue 15: 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 |
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2465
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Analogue 16: 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 |
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544
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Analogue 17: 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 |
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557
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Analogue 18: With Benzyl-cyclic-amine skeleton
Desoxypipradrol 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 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 |
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558
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Analogue 19: With Benzyl-cyclic-amine skeleton
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559
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Analogue 20: With Benzyl-cyclic-amine skeleton
Desoxy-D2PM 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 |
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560
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Analogue 21: With Benzyl-cyclic-amine skeleton
D2PM 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 |
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561
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Analogue 22: With Phenyl-cyclic-amine skeleton
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562
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Analogue 23: With Phenyl-cyclic-amine skeleton
4-MAR 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 |
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565
|
Analogue 24: 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 |
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566
|
Analogue 25: 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. |
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1235
|
Analogue 26: With Phenyl-cyclic-amine skeleton
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1141
|
Analogue 27: 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 |
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![6,7,8,9-Tetrahydro-5H-benzo[7]annulen-6-amine](C/pk1307.png "Explore the structure and analogues of 6,7,8,9-Tetrahydro-5H-benzo[7]annulen-6-amine")
1307
|
Analogue 28: 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 |
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1339
|
Analogue 29: 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 |
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1511
|
Analogue 30: With 1-Benzylcyclopropan-1-amine skeleton
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1502
|
Analogue 31: 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 |
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1500
|
Analogue 32: 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 |
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1499
|
Analogue 33: 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 |
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1498
|
Analogue 34: 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 |
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1497
|
Analogue 35: 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 |
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1471
|
Analogue 36: 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 |
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1438
|
Analogue 37: 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 |
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1437
|
Analogue 38: With Phenyl-cyclic-amine skeleton
|
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1435
|
Analogue 39: 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 |
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1434
|
Analogue 40: 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 |
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