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TiHKAL#36 5-MeO-DPT
5059
Variant: N R2 R5 skeleton isomers all
Analogues: 84 1 3 4 11 103

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-propylpropan-1-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: PNHPVNBKLQWBKH-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-4-9-19(10-5-2)11-8-14-13-18-17-7-6-15(20-3)12-16(14)17/h6-7,12-13,18H,4-5,8-11H2,1-3H3

PubChem CID: 14011047; ChemSpider: 14106484; Wikipedia: 5-MeO-DPT

See also Chemistry notes VIII: p. 105, 5-MeO-DPT: Synthesis

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Glennon, RA; Titeler, M; Lyon, RA; Slusher, RM. N,N-Di-n-propylserotonin: Binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin. J. Med. Chem., 1 Jan 1988, 31 (4), 867–870. 600 kB. doi:10.1021/jm00399a031

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

84 N analogues:
5035
Analogue 1: Substituting Acetyl for Dipropyl at N

Melatonin
Regulin
Tryptamine, N-acetyl-5-methoxy
Indole, 3-(2-acetamidoethyl)-5-methoxy
Serotonin, N-acetyl-O-methyl
Acetamide, N-[2-(5-methoxyindol-3-yl)ethyl]
N-Acetyl-5-methoxytryptamine
3-(2-Acetamidoethyl)-5-methoxyindole
N-Acetyl-O-methylserotonin
N-[2-(5-Methoxyindol-3-yl)ethyl]acetamide

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide

Formula: C13H16N2O2 Molecular weight: 232.27834 g/mol InChI Key: DRLFMBDRBRZALE-UHFFFAOYSA-N

InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)

PubChem CID: 896; ChemSpider: 872; Wikipedia: Melatonin

See also TiHKAL: #37 5-MeO-DIPT
#38 5-MeO-DMT
#44 6-MeO-THH
#48 α-MT
See also Chemistry notes VIII: p. 184, Melatonin: Synthesis

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

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

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 2013. 929 kB. doi:10.1002/bmc.2981

5036
Analogue 2: Substituting Diethyl for Dipropyl at N

5-MeO-DET
Tryptamine, N,N-diethyl-5-methoxy
Indole, 3-[2-(diethylamino)ethyl]-5-methoxy
N,N-Diethyl-5-methoxytryptamine
3-[2-(Diethylamino)ethyl]-5-methoxyindole

IUPAC: N,N-Diethyl-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

Formula: C15H22N2O Molecular weight: 246.34798 g/mol InChI Key: KGDVJQQWCDDEPP-UHFFFAOYSA-N

InChI=1S/C15H22N2O/c1-4-17(5-2)9-8-12-11-16-15-7-6-13(18-3)10-14(12)15/h6-7,10-11,16H,4-5,8-9H2,1-3H3

PubChem CID: 417608; ChemSpider: 369669; Wikipedia: 5-MeO-DET

See also TiHKAL: #10 EIPT  
See also Chemistry notes VIII: p. 94, 5-MeO-DET: Synthesis
p. 95, 5-MeO-DET: GC-MS

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

Gatch, MB; Forster, MJ; Janowsky, A; Eshleman, AJ. Abuse liability profile of three substituted tryptamines. J. Pharmacol. Exp. Ther., 1 Jul 2011, 338 (1), 280–289. 1188 kB. doi:10.1124/jpet.111.179705

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

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

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. doi:10.1016/0024-3205(68)90200-2

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

5037
Analogue 3: Substituting Diisopropyl for Dipropyl at N

5-MeO-DIPT
Tryptamine, N,N-diisopropyl-5-methoxy
Indole, 3-[2-(diisopropylamino)ethyl]-5-methoxy
N,N-Diisopropyl-5-methoxytryptamine
3-[2-(Diisopropylamino)ethyl]-5-methoxyindole

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: DNBPMBJFRRVTSJ-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-12(2)19(13(3)4)9-8-14-11-18-17-7-6-15(20-5)10-16(14)17/h6-7,10-13,18H,8-9H2,1-5H3

PubChem CID: 151182; ChemSpider: 133247; Drugs Forum: 5-MeO-DIPT; Erowid: 5-MeO-DIPT; Wikipedia: 5-Methoxy-diisopropyltryptamine

See also TiHKAL: #17 4-HO-DIPT
#36 5-MeO-DET
#40 5-MeO-MIPT
See also Pharmacology notes I: p. 176, 5-MeO-DIPT: Trials
p. 191, Chronology on 5-Methoxy-N,N-diisopropyltryptamine
See also Chemistry notes VIII: p. 87, 5-MeO-DIPT: Synthesis
p. 88, 5-MeO-DIPT: Synthesis
p. 90, 5-MeO-DIPT: Synthesis
p. 91, 5-MeO-DIPT: GC-MS
p. 92, 5-MeO-DIPT: Synthesis
p. 93, 5-MeO-DIPT: GC-MS
p. 98, 5-MeO-DIPT: GC-MS
p. 108, 5-MeO-DIPT:
p. 109, 5-MeO-DIPT: Synthesis
p. 121, 5-MeO-DIPT: Synthesis
p. 167, 5-MeO-DIPT: Synthesis

Rodriguez-Cruz, SE. Analysis and characterization of designer tryptamines using electrospray ionization mass spectrometry (ESI-MS). Microgram J., 1 Jul 2005, 3 (3–4), 107–129. 1577 kB.

Spratley, TK; Hays, PA; Geer, LC; Cooper, SD; McKibben, TD. Analytical profiles for five “designer” tryptamines. Microgram J., 1 Jan 2005, 3 (1–2), 54–68. 473 kB.

Meatherall, R; Sharma, P. Foxy, a designer tryptamine hallucinogen. J. Anal. Toxicol., 1 Jul 2003, 27 (5), 313–317. 988 kB. doi:10.1093/jat/27.5.313

Kamata, T; Katagi, M; Kamata, HT; Miki, A; Shima, N; Zaitsu, K; Nishikawa, M; tanaka, E; Honda, K; Tsuchihashi, H. Metabolism of the psychotomimetic tryptamine derivative 5-methoxy-N,N-diisopropyltryptamine in humans: Identification and quantification of its urinary metabolites. Drug Metab. Dispos., 1 Feb 2006, 34 (2), 281–287. 427 kB. doi:10.1124/dmd.105.005835.

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

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part I. Characterisation of the Speeter and Anthony synthetic route to 5-methoxy-N,N-diisopropyltryptamine using ESI-MS-MS and ESI-TOF-MS. Analyst, 2004, 129 (11), 1047–1057. 420 kB. doi:10.1039/b407239c

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Shulgin, AT; Carter, MF. N,N-diisopropyltryptamine (DIPT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT). Two orally active tryptamine analogs with CNS activity. Commun. Psychopharmacol., 1 Jan 1981, 4 (5), 363–369. 1166 kB.

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Shulgin, AT. 5-Methoxy-N-ethyl-N-isopropyltryptamine, 5-MeO-MIPT, 5-MeO-DIPT, 5-MeO-EIPT. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 27 Feb 2002.

Tanaka, E; Kamata, T; Katagi, M; Tsuchihashi, H; Honda, K. A fatal poisoning with 5-methoxy-N,N-diisopropyltryptamine, Foxy. Forensic Sci. Int., 1 Jan 2006, 163 (1), 152–154. 105 kB. doi:10.1016/j.forsciint.2005.11.026

Wilson, JM; McGeorge, F; Smolinske, S; Meatherall, R. A foxy intoxication. Forensic Sci. Int., 1 Jan 2005, 148 (1), 31–36. 160 kB. doi:10.1016/j.forsciint.2004.04.017

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

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

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. doi:10.1016/j.talanta.2007.06.012

5038
Analogue 4: Substituting Dimethyl for Dipropyl at N

5-MeO-DMT
N,N,O-TMS
OMB
Tryptamine, 5-methoxy-N,N-dimethyl
Indole, 5-methoxy-3-[2-(dimethylamino)ethyl]
5-Methoxy-N,N-dimethyltryptamine
5-Methoxy-3-[2-(dimethylamino)ethyl]indole
N,N,O-Trimethylserotonin
Bufotenine methyl ether
O-Methylbufotenine

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: ZSTKHSQDNIGFLM-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3

PubChem CID: 1832; ChemSpider: 1766; Erowid: 5-MeO-DMT; Wikipedia: 5-MeO-DMT

See also TiHKAL: #6 DMT
#7 2,α-DMT
#10 EIPT
#13 Harmaline
#19 5-HO-DMT
#31 5,6-MDO-DMT
#35 Melatonin
#36 5-MeO-DET
#39 4-MeO-MIPT
#40 5-MeO-MIPT
#42 5-MeO-NMT
#43 5-MeO-pyr-T
#45 5-MeO-TMT
#46 5-MeS-DMT
#50 NMT
See also Pharmacology notes I: p. 194, 5-MeO-DMT
p. 195, 5-MeO-DMT
See also Pharmacology notes II: app. 4, Experiment for Death Valley
p. 298, 5-MeO-DMT

Ciprian-Ollivier, J; Cetkovich-Bakmas, MG. Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr. Res., 19 Dec 1997, 28 (2–3), 257–265. 722 kB. doi:10.1039/S0920-9964(97)00116-3

Benington, F; Morin, RD; Clark, LC. Synthesis of O- and N-methylated derivatives of 5-hydroxytryptamine. J. Org. Chem., 1 Dec 1958, 23 (12), 1977–1979. 401 kB. doi:10.1021/jo01106a046

Glennon, RA; Lee, M; Rangisetty, JB; Dukat, M; Roth, BL; Savage, JE; McBridge, A; Rauser, L; Hufeisen, SJ; Lee, DKH. 2-Substituted tryptamines: Agents with selectivity for 5-HT6 serotonin receptors. J. Med. Chem., 9 Mar 2000, 43 (5), 1011–1018. 137 kB. doi:10.1021/jm990550b

Shen, H; Jiang, X; Winter, JC; Yu, A. Psychedelic 5-methoxy-N,N-dimethyltryptamine: Metabolism, pharmacokinetics, drug interactions, and pharmacological actions. Curr. Drug Metab., 1 Oct 2010, 11 (8), 659–666. 589 kB. doi:10.2174/138920010794233495

Glennon, RA; Hong, S; Bondarev, M; Law, H; Dukat, M; Rakhit, S; Power, P; Fan, E; Kinneau, D; Kamboj, R; Teitler, M; Herrick-Davis, K; Smith, C. Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors. J. Med. Chem., 5 Jan 1996, 39 (1), 314–322. 193 kB. doi:10.1021/jm950498t

Glennon, RA; Titeler, M; Lyon, RA; Slusher, RM. N,N-Di-n-propylserotonin: Binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin. J. Med. Chem., 1 Jan 1988, 31 (4), 867–870. 600 kB. doi:10.1021/jm00399a031

Kline, TB; Benington, F; Morin, RD; Beaton, JM; Glennon, RA; Domelsmith, LN; Houk, KN; Rozeboom, MD. Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives. J. Med. Chem., 1 Jan 1982, 25 (11), 1381–1383. 378 kB. doi:10.1021/jm00353a021

Kline, TB; Benington, F; Morin, RD; Beaton, JM. Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety. J. Med. Chem., 1 Jan 1982, 25 (8), 908–913. 845 kB. doi:10.1021/jm00350a005

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Callaway, JC; Grob, CS; McKenna, DJ; Nichols, DE; Shulgin, AT; Tupper, KW; Sklerov, JH; Levine, B; Moore, KA. A demand for clarity regarding a case report on the ingestion of 5-methoxy-N, N-Dimethyltryptamine (5-MeO-DMT) in an Ayahuasca preparation. J. Anal. Toxicol., 1 Jul 2006, 30 (6), 406–407. 53 kB. doi:10.1093/jat/30.6.406

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

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Analysis of phenethylamines and tryptamines in designer drugs using gas chromatography-mass spectrometry. J. Health Sci., 2008, 54 (1), 89–96. 1882 kB. doi:10.1248/jhs.54.89

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Spratley, TK; Hays, PA; Geer, LC; Cooper, SD; McKibben, TD. Analytical profiles for five “designer” tryptamines. Microgram J., 1 Jan 2005, 3 (1–2), 54–68. 473 kB.

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

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Macor, JE; Fox, CB; Johnson, C; Koe, BK; Lebel, LA; Zorn, SH. 1-(2-Aminoethyl)-3-methyl-8,9-dihydropyrano[3,2-e]indole: A rotationally restricted phenolic analog of the neurotransmitter serotonin and agonist selective for serotonin (5-HT2-type) receptors. J. Med. Chem., 1 Jan 1992, 35 (20), 3625–3632. 1944 kB. doi:10.1021/jm00098a005

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Halberstadt, AL; Nichols, DE; Geyer, MA. Behavioral effects of α,α,β,β-tetradeutero-5-MeO-DMT in rats: comparison with 5-MeO-DMT administered in combination with a monoamine oxidase inhibitor. Psychopharmacology, 1 Jun 2012, 221 (4), 709–218. 296 kB. doi:10.1007/s00213-011-2616-6

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Barker, SA; McIlhenny, EH; Strassman, R. A critical review of reports of endogenous psychedelic N,N-dimethyltryptamines in humans: 1955–2010. Drug Test. Anal., 2012. 270 kB. doi:10.1002/dta.422

Brandt, SD; Tearavarich, R; Dempster, N; Cozzi, NV; Daley, PF. Synthesis and characterization of 5-methoxy-2-methyl-N,N-dialkylated tryptamines. Drug Test. Anal., 1 Jan 2012, 4 (1), 24–32. 506 kB. doi:10.1002/dta.398

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 2013. 929 kB. doi:10.1002/bmc.2981

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for determining major constituents of ayahuasca and their metabolites in blood. Biomed. Chromatogr., 1 Mar 2012, 26 (3), 301–313. 557 kB. doi:10.1002/bmc.1657

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for and the determination of the major constituents and metabolites of the Amazonian botanical medicine ayahuasca in human urine. Biomed. Chromatogr., 1 Sep 2011, 25 (9), 970–984. 1030 kB. doi:10.1002/bmc.1551

Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of α-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. doi:10.1016/0006-2952(83)90281-2

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

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

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. doi:10.1016/j.talanta.2007.06.012

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

McIlhenny, EH; Pipkin, KE; Standish, LJ; Wechkin, HA; Strassman, R; Barker, SA. Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography–electrospray ionization-tandem mass spectrometry. J. Chromatogr. A, 18 Dec 2009, 1216 (51), 8960–8968. 450 kB. doi:10.1016/j.chroma.2009.10.088

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

Winter, JC; Filipink, RA; Timineri, D; Helsley, SE; Rabin, RA. The paradox of 5-methoxy-N,N-dimethyltryptamine: an indoleamine hallucinogen that induces stimulus control via 5-HT1A receptors. Pharmacol. Biochem. Behav., 1 Jan 2000, 65 (1), 75–82. 157 kB. doi:10.1016/S0091-3057(99)00178-1

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. doi:10.1016/0024-3205(91)90582-V

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. doi:10.1016/0024-3205(68)90200-2

5040
Analogue 5: Substituting Methyl and Isopropyl for Dipropyl at N

5-MeO-MIPT
Tryptamine, N-isopropyl-5-methoxy-N-methyl
Indole, 3-[2-(isopropylmethylamino)ethyl]-5-methoxy
N-Isopropyl-5-methoxy-N-methyltryptamine
3-[2-(Isopropylmethylamino)ethyl]-5-methoxyindole

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methylpropan-2-amine

Formula: C15H22N2O Molecular weight: 246.34798 g/mol InChI Key: HEDOODBJFVUQMS-UHFFFAOYSA-N

InChI=1S/C15H22N2O/c1-11(2)17(3)8-7-12-10-16-15-6-5-13(18-4)9-14(12)15/h5-6,9-11,16H,7-8H2,1-4H3

PubChem CID: 2763156; ChemSpider: 2043845; Drugs Forum: 5-MeO-MIPT; Erowid: 5-MeO-MIPT; Wikipedia: 5-MeO-MiPT

See also TiHKAL: #36 5-MeO-DET #39 4-MeO-MIPT

Repke, DB; Grotjahn, DB; Shulgin, AT. Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents. J. Med. Chem., 1 Jan 1985, 28 (7), 892–896. 711 kB. doi:10.1021/jm00145a007

Rodriguez-Cruz, SE. Analysis and characterization of designer tryptamines using electrospray ionization mass spectrometry (ESI-MS). Microgram J., 1 Jul 2005, 3 (3–4), 107–129. 1577 kB.

Spratley, TK; Hays, PA; Geer, LC; Cooper, SD; McKibben, TD. Analytical profiles for five “designer” tryptamines. Microgram J., 1 Jan 2005, 3 (1–2), 54–68. 473 kB.

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Analysis of phenethylamines and tryptamines in designer drugs using gas chromatography-mass spectrometry. J. Health Sci., 2008, 54 (1), 89–96. 1882 kB. doi:10.1248/jhs.54.89

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. doi:10.1016/0024-3205(91)90582-V

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Shulgin, AT. 5-Methoxy-N-ethyl-N-isopropyltryptamine, 5-MeO-MIPT, 5-MeO-DIPT, 5-MeO-EIPT. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 27 Feb 2002.

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

5042
Analogue 6: Substituting Methyl for Dipropyl at N

5-MeO-NMT
N,O-DMS
nor-5-MeO-DMT
Tryptamine, 5-methoxy-N-methyl
Indole, 5-methoxy-3-[2-(methylamino)ethyl]
Serotonin, N,O-dimethyl
5-Methoxy-N-methyltryptamine
5-Methoxy-3-[2-(methylamino)ethyl]indole
N,O-Dimethylserotonin

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-methylethan-1-amine

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

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

PubChem CID: 16184; ChemSpider: 15360; Wikipedia: 5-MeO-NMT

See also TiHKAL: #6 DMT
#36 5-MeO-DET
#38 5-MeO-DMT
#40 5-MeO-MIPT

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5109
Analogue 7: Substituting Cyclopropyl for Dipropyl at N

5-MeO-NCPT
N-Cyclopropyl-5-methoxytryptamine

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]cyclopropanamine

Formula: C14H18N2O Molecular weight: 230.30552 g/mol InChI Key: IXNIHMCRVXSNBT-UHFFFAOYSA-N

InChI=1S/C14H18N2O/c1-17-12-4-5-14-13(8-12)10(9-16-14)6-7-15-11-2-3-11/h4-5,8-9,11,15-16H,2-3,6-7H2,1H3

PubChem CID: 41423; ChemSpider: 37796

See also TiHKAL: #6 DMT  
5143
Analogue 8: Removing Dipropyl at N

5-MeO-T
Mexamine
5-Methoxytryptamine

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)ethan-1-amine

Formula: C11H14N2O Molecular weight: 190.24166 g/mol InChI Key: JTEJPPKMYBDEMY-UHFFFAOYSA-N

InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3

PubChem CID: 1833; ChemSpider: 1767; Wikipedia: 5-Methoxytryptamine

See also TiHKAL: #35 Melatonin
#36 5-MeO-DET
#38 5-MeO-DMT
#42 5-MeO-NMT

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

Wiseman-Distler, MH; Sourkes, TL. The effect of 4-hydroxyindoles on the metabolism of 5-hydroxytryptamine (serotonin). Ann. N.Y. Acad. Sci., 1 Jan 1962, 96, 142–151. 458 kB. doi:10.1111/j.1749-6632.1962.tb50109.x

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 2013. 929 kB. doi:10.1002/bmc.2981

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

Glennon, RA; Hong, S; Bondarev, M; Law, H; Dukat, M; Rakhit, S; Power, P; Fan, E; Kinneau, D; Kamboj, R; Teitler, M; Herrick-Davis, K; Smith, C. Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors. J. Med. Chem., 5 Jan 1996, 39 (1), 314–322. 193 kB. doi:10.1021/jm950498t

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Nichols, DE; Lloyd, DH; Johnson, MP; Hoffman, AJ. Synthesis and serotonin receptor affinities of a series of enantiomers of α-methyltryptamines: Evidence for the binding conformation of tryptamines at serotonin 5-HT1B receptors. J. Med. Chem., 1 Jan 1988, 31 (7), 1406–1412. 1085 kB. doi:10.1021/jm00402a026

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

Glennon, RA; Titeler, M; Lyon, RA; Slusher, RM. N,N-Di-n-propylserotonin: Binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin. J. Med. Chem., 1 Jan 1988, 31 (4), 867–870. 600 kB. doi:10.1021/jm00399a031

Glennon, RA; Chaurasia, C; Titeler, M. Binding of indolylalkylamines at 5-HT2 serotonin receptors: Examination of a hydrophobic binding region. J. Med. Chem., 1 Jan 1990, 33 (10), 2777–2784. 1248 kB. doi:10.1021/jm00172a016

Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of α-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. doi:10.1016/0006-2952(83)90281-2

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

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

5144
Analogue 9: Substituting Hexanoyl for Dipropyl at N

N-Hexanoyl-5-MeO-T
N-Hexanoyl-5-methoxytryptamine

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]hexanamide

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

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

PubChem CID: 10356776; ChemSpider: 8532228

See also TiHKAL: #35 Melatonin  
5145
Analogue 10: Substituting Octanoyl for Dipropyl at N

N-Octanoyl-5-MeO-T
5-Methoxy-N-octanoyltryptamine

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]octanamide

Formula: C19H28N2O2 Molecular weight: 316.43782 g/mol InChI Key: MBOMFXMUMIKGBV-UHFFFAOYSA-N

InChI=1S/C19H28N2O2/c1-3-4-5-6-7-8-19(22)20-12-11-15-14-21-18-10-9-16(23-2)13-17(15)18/h9-10,13-14,21H,3-8,11-12H2,1-2H3,(H,20,22)

PubChem CID: 10425918; ChemSpider: 8601346

See also TiHKAL: #35 Melatonin  
5146
Analogue 11: Substituting Heptafluoro-n-butyroyl for Dipropyl at N

N-Heptafluorobutyroyl-5-MeO-T
N-Heptafluoro-n-butyroyl-5-methoxytryptamine

IUPAC: 2,2,3,3,4,4,4-Heptafluoro-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]butanamide

Formula: C15H13F7N2O2 Molecular weight: 386.2647424 g/mol InChI Key: UHFBWAPTPPYJJS-UHFFFAOYSA-N

InChI=1S/C15H13F7N2O2/c1-26-9-2-3-11-10(6-9)8(7-24-11)4-5-23-12(25)13(16,17)14(18,19)15(20,21)22/h2-3,6-7,24H,4-5H2,1H3,(H,23,25)

See also TiHKAL: #35 Melatonin  
5371
Analogue 12: Substituting Diallyl for Dipropyl at N

5-MeO-DALT
5-Methoxy-DALT
Tryptamine, N,N-diallyl-5-methoxy
N,N-Diallyl-5-methoxytryptamine
Indole, 3-[2-(diallylamino)ethyl]-5-methoxy
3-[2-(Diallylamino)ethyl]-5-methoxyindole

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-(prop-2-en-1-yl)prop-2-en-1-amine

Formula: C17H22N2O Molecular weight: 270.36938 g/mol InChI Key: HGRHWEAUHXYNNP-UHFFFAOYSA-N

InChI=1S/C17H22N2O/c1-4-9-19(10-5-2)11-8-14-13-18-17-7-6-15(20-3)12-16(14)17/h4-7,12-13,18H,1-2,8-11H2,3H3

PubChem CID: 50878551; ChemSpider: 21106245; Drugs Forum: 5-MeO-DALT; Erowid: 5-MeO-DALT; Wikipedia: 5-MeO-DALT

See also TiHKAL: #56 5-MeO-DALT  

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Corkery, JM; Durkin, E; Elliott, S; Scchifano, F; Ghodse, AH. The recreational tryptamine 5-MeO-DALT (N,N-diallyl-5-methoxytryptamine): A brief review. Prog. Neuro-Psychopharmacol. Biol. Psych., 1 Dec 2012, 39 (1), 259—262. 307 kB. doi:10.1016/j.pnpbp.2012.05.022

5505
Analogue 13: Substituting 2-Methoxybenzyl for Dipropyl at N

5-MeO-NBOMe
5-MeO-NBMeO
5-Methoxy-N-(2-methoxybenzyl)tryptamine

IUPAC: N-(2-Methoxybenzyl)-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

Formula: C19H22N2O2 Molecular weight: 310.39018 g/mol InChI Key: OROYLKZKNDLGIQ-UHFFFAOYSA-N

InChI=1S/C19H22N2O2/c1-22-16-7-8-18-17(11-16)14(13-21-18)9-10-20-12-15-5-3-4-6-19(15)23-2/h3-8,11,13,20-21H,9-10,12H2,1-2H3

ChemSpider: 26599679

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

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

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

5525
Analogue 14: Substituting Ethyl and Isopropyl for Dipropyl at N

5-MeO-EIPT
5-Methoxy-N-ethyl-N-isopropyltryptamine

IUPAC: N-Ethyl-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]propan-2-amine

Formula: C16H24N2O Molecular weight: 260.37456 g/mol InChI Key: VVEQXDHSGNBFLZ-UHFFFAOYSA-N

InChI=1S/C16H24N2O/c1-5-18(12(2)3)9-8-13-11-17-16-7-6-14(19-4)10-15(13)16/h6-7,10-12,17H,5,8-9H2,1-4H3

PubChem CID: 53485366

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Shulgin, AT. 5-Methoxy-N-ethyl-N-isopropyltryptamine, 5-MeO-MIPT, 5-MeO-DIPT, 5-MeO-EIPT. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 27 Feb 2002.

5528
Analogue 15: Substituting Allyl for Dipropyl at N

5-MeO-NALT
N-Allyl-5-methoxytryptamine

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]prop-2-en-1-amine

Formula: C14H18N2O Molecular weight: 230.30552 g/mol InChI Key: GTUMVYJHXMIYKV-UHFFFAOYSA-N

InChI=1S/C14H18N2O/c1-3-7-15-8-6-11-10-16-14-5-4-12(17-2)9-13(11)14/h3-5,9-10,15-16H,1,6-8H2,2H3

See also TiHKAL: #56 5-MeO-DALT  
5529
Analogue 16: Substituting Diprop-2-ynyl for Dipropyl at N

5-MeO-DPRT
5-Methoxy-N,N-dipropargyltryptamine

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-(prop-2-yn-1-yl)prop-2-yn-1-amine

Formula: C17H18N2O Molecular weight: 266.33762 g/mol InChI Key: UFAVVTIYVKRGRD-UHFFFAOYSA-N

InChI=1S/C17H18N2O/c1-4-9-19(10-5-2)11-8-14-13-18-17-7-6-15(20-3)12-16(14)17/h1-2,6-7,12-13,18H,8-11H2,3H3

See also TiHKAL: #56 5-MeO-DALT  
5201
Analogue 17: Substituting Methyl and Ethyl for Dipropyl at N

5-MeO-MET
N-Ethyl-5-methoxy-N-methyltryptamine

IUPAC: N-Ethyl-2-(5-methoxy-1H-indol-3-yl)-N-methylethan-1-amine

Formula: C14H20N2O Molecular weight: 232.3214 g/mol InChI Key: AVECDEWGCOLCPZ-UHFFFAOYSA-N

InChI=1S/C14H20N2O/c1-4-16(2)8-7-11-10-15-14-6-5-12(17-3)9-13(11)14/h5-6,9-10,15H,4,7-8H2,1-3H3

PubChem CID: 6619012; ChemSpider: 5051184

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. doi:10.1016/0024-3205(68)90200-2

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

5560
Analogue 18: Substituting Benzyl for Dipropyl at N

N-Benzyl-5-methoxytryptamine

IUPAC: N-Benzyl-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

Formula: C18H20N2O Molecular weight: 280.3642 g/mol InChI Key: FQRAHCLOFRBKKA-UHFFFAOYSA-N

InChI=1S/C18H20N2O/c1-21-16-7-8-18-17(11-16)15(13-20-18)9-10-19-12-14-5-3-2-4-6-14/h2-8,11,13,19-20H,9-10,12H2,1H3

PubChem CID: 134909; ChemSpider: 118888

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

5561
Analogue 19: Substituting 2-Hydroxybenzyl for Dipropyl at N

5-Methoxy-N-(2-methylbenzyl)tryptamine
N-(2-Hydroxybenzyl)-5-methoxytryptamine

IUPAC: 2-({[2-(5-Methoxy-1H-indol-3-yl)ethyl]amino}methyl)phenol

Formula: C18H20N2O2 Molecular weight: 296.3636 g/mol InChI Key: NRIZFLCDOCBOGZ-UHFFFAOYSA-N

InChI=1S/C18H20N2O2/c1-22-15-6-7-17-16(10-15)13(12-20-17)8-9-19-11-14-4-2-3-5-18(14)21/h2-7,10,12,19-21H,8-9,11H2,1H3

ChemSpider: 26599678

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

5563
Analogue 20: Substituting 2-(Trifluoromethyl)benzyl for Dipropyl at N

5-Methoxy-N-[2-(trifluoromethyl)benzyl]tryptamine

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-[2-(trifluoromethoxy)benzyl]ethan-1-amine

Formula: C19H19F3N2O2 Molecular weight: 364.3615696 g/mol InChI Key: SWZKTMCOFOPNJG-UHFFFAOYSA-N

InChI=1S/C19H19F3N2O2/c1-25-15-6-7-17-16(10-15)13(12-24-17)8-9-23-11-14-4-2-3-5-18(14)26-19(20,21)22/h2-7,10,12,23-24H,8-9,11H2,1H3

ChemSpider: 26599680

Heim, R; Pertz, HH; Elz, S. Partial 5-HT2A-receptor agonists of the phenylethanamine series: Effect of a trifluoromethyl substituent. Arch. Pharm. Pharm. Med. Chem., 3 May 2000, 333 (Suppl. 2), 45. 542 kB. Poster abstract

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

437
Analogue 21: Substituting 4-Methoxybenzyl for Dipropyl at N

IUPAC: N-(4-Methoxybenzyl)-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

Formula: C19H22N2O2 Molecular weight: 310.39018 g/mol InChI Key: XOPDXWXKMSAABA-UHFFFAOYSA-N

InChI=1S/C19H22N2O2/c1-22-16-5-3-14(4-6-16)12-20-10-9-15-13-21-19-8-7-17(23-2)11-18(15)19/h3-8,11,13,20-21H,9-10,12H2,1-2H3

PubChem CID: 2989597; ChemSpider: 2261450

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

436
Analogue 22: Substituting 4-Nitrobenzyl for Dipropyl at N

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-(4-nitrobenzyl)ethan-1-amine

Formula: C18H19N3O3 Molecular weight: 325.36176 g/mol InChI Key: RNBLGGTZIQMPGY-UHFFFAOYSA-N

InChI=1S/C18H19N3O3/c1-24-16-6-7-18-17(10-16)14(12-20-18)8-9-19-11-13-2-4-15(5-3-13)21(22)23/h2-7,10,12,19-20H,8-9,11H2,1H3

PubChem CID: 10358955; ChemSpider: 8534404

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

435
Analogue 23: Substituting 4-Aminobenzyl for Dipropyl at N

IUPAC: 4-({[2-(5-Methoxy-1H-indol-3-yl)ethyl]amino}methyl)aniline

Formula: C18H21N3O Molecular weight: 295.37884 g/mol InChI Key: IFVUNWPYBPIEIO-UHFFFAOYSA-N

InChI=1S/C18H21N3O/c1-22-16-6-7-18-17(10-16)14(12-21-18)8-9-20-11-13-2-4-15(19)5-3-13/h2-7,10,12,20-21H,8-9,11,19H2,1H3

PubChem CID: 10357163; ChemSpider: 8532612

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

434
Analogue 24: Substituting 4-Methylbenzyl for Dipropyl at N

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-(4-methylbenzyl)ethan-1-amine

Formula: C19H22N2O Molecular weight: 294.39078 g/mol InChI Key: LDYFCKSKNXVVIZ-UHFFFAOYSA-N

InChI=1S/C19H22N2O/c1-14-3-5-15(6-4-14)12-20-10-9-16-13-21-19-8-7-17(22-2)11-18(16)19/h3-8,11,13,20-21H,9-10,12H2,1-2H3

PubChem CID: 10469723; ChemSpider: 8645134

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

433
Analogue 25: Substituting 4-Iodobenzyl for Dipropyl at N

IUPAC: N-(4-Iodobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

Formula: C18H19IN2O Molecular weight: 406.26073 g/mol InChI Key: VZBJDERSSBSPTG-UHFFFAOYSA-N

InChI=1S/C18H19IN2O/c1-22-16-6-7-18-17(10-16)14(12-21-18)8-9-20-11-13-2-4-15(19)5-3-13/h2-7,10,12,20-21H,8-9,11H2,1H3

PubChem CID: 10250754; ChemSpider: 8426240

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

432
Analogue 26: Substituting 4-Bromobenzyl for Dipropyl at N

IUPAC: N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

Formula: C18H19BrN2O Molecular weight: 359.26026 g/mol InChI Key: XHLOUFPZLUULGI-UHFFFAOYSA-N

InChI=1S/C18H19BrN2O/c1-22-16-6-7-18-17(10-16)14(12-21-18)8-9-20-11-13-2-4-15(19)5-3-13/h2-7,10,12,20-21H,8-9,11H2,1H3

PubChem CID: 5124753; ChemSpider: 4299315

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

431
Analogue 27: Substituting 4-Chlorobenzyl for Dipropyl at N

IUPAC: N-(4-Chlorobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

Formula: C18H19ClN2O Molecular weight: 314.80926 g/mol InChI Key: OMHWFERWNDTMJH-UHFFFAOYSA-N

InChI=1S/C18H19ClN2O/c1-22-16-6-7-18-17(10-16)14(12-21-18)8-9-20-11-13-2-4-15(19)5-3-13/h2-7,10,12,20-21H,8-9,11H2,1H3

PubChem CID: 5200316; ChemSpider: 4371664

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

430
Analogue 28: Substituting 4-Fluorobenzyl for Dipropyl at N

IUPAC: N-(4-Fluorobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

Formula: C18H19FN2O Molecular weight: 298.3546632 g/mol InChI Key: VLTHPWFQXNRMNW-UHFFFAOYSA-N

InChI=1S/C18H19FN2O/c1-22-16-6-7-18-17(10-16)14(12-21-18)8-9-20-11-13-2-4-15(19)5-3-13/h2-7,10,12,20-21H,8-9,11H2,1H3

PubChem CID: 10424771; ChemSpider: 8600199

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

429
Analogue 29: Substituting Ethyl for Dipropyl at N

5-MeO-NET

IUPAC: N-Ethyl-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: UNPLGMNGAFLKSH-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-3-14-7-6-10-9-15-13-5-4-11(16-2)8-12(10)13/h4-5,8-9,14-15H,3,6-7H2,1-2H3

PubChem CID: 23009084; ChemSpider: 12955759

See also Chemistry notes VIII: p. 101, 5-MeO-NET: Synthesis

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

428
Analogue 30: Substituting Phenylbutyl for Dipropyl at N

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-4-phenylbutan-1-amine

Formula: C21H26N2O Molecular weight: 322.44394 g/mol InChI Key: KFIJSLAJJSSAOJ-UHFFFAOYSA-N

InChI=1S/C21H26N2O/c1-24-19-10-11-21-20(15-19)18(16-23-21)12-14-22-13-6-5-9-17-7-3-2-4-8-17/h2-4,7-8,10-11,15-16,22-23H,5-6,9,12-14H2,1H3

PubChem CID: 9973432; ChemSpider: 8149024

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

427
Analogue 31: Substituting Phenylpropyl for Dipropyl at N

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-3-phenylpropan-1-amine

Formula: C20H24N2O Molecular weight: 308.41736 g/mol InChI Key: IGHQELRITYFNIG-UHFFFAOYSA-N

InChI=1S/C20H24N2O/c1-23-18-9-10-20-19(14-18)17(15-22-20)11-13-21-12-5-8-16-6-3-2-4-7-16/h2-4,6-7,9-10,14-15,21-22H,5,8,11-13H2,1H3

PubChem CID: 10267283; ChemSpider: 8442762

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

5088
Analogue 32: Substituting Isopropyl and Methyl for Dipropyl at N

5-MeO-NIPT
N-Isopropyl-5-methoxytryptamine

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]propan-2-amine

Formula: C14H20N2O Molecular weight: 232.3214 g/mol InChI Key: QQZJNZJNPDORBO-UHFFFAOYSA-N

InChI=1S/C14H20N2O/c1-10(2)15-7-6-11-9-16-14-5-4-12(17-3)8-13(11)14/h4-5,8-10,15-16H,6-7H2,1-3H3

PubChem CID: 707167; ChemSpider: 616592

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. doi:10.1016/0024-3205(91)90582-V

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Kamata, T; Katagi, M; Kamata, HT; Miki, A; Shima, N; Zaitsu, K; Nishikawa, M; tanaka, E; Honda, K; Tsuchihashi, H. Metabolism of the psychotomimetic tryptamine derivative 5-methoxy-N,N-diisopropyltryptamine in humans: Identification and quantification of its urinary metabolites. Drug Metab. Dispos., 1 Feb 2006, 34 (2), 281–287. 427 kB. doi:10.1124/dmd.105.005835.

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

5093
Analogue 33: Substituting Propyl and Methyl for Dipropyl at N

5-MeO-MPT
5-Methoxy-N-methyl-N-propyltryptamine

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methylpropan-1-amine

Formula: C15H22N2O Molecular weight: 246.34798 g/mol InChI Key: YQHARYRPMKOJND-UHFFFAOYSA-N

InChI=1S/C15H22N2O/c1-4-8-17(2)9-7-12-11-16-15-6-5-13(18-3)10-14(12)15/h5-6,10-11,16H,4,7-9H2,1-3H3

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

5094
Analogue 34: Substituting Propyl and Ethyl for Dipropyl at N

5-MeO-EPT
N-Ethyl-5-methoxy-N-propyltryptamine

IUPAC: N-Ethyl-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]propan-1-amine

Formula: C16H24N2O Molecular weight: 260.37456 g/mol InChI Key: OQHFIOKNGNJPPF-UHFFFAOYSA-N

InChI=1S/C16H24N2O/c1-4-9-18(5-2)10-8-13-12-17-16-7-6-14(19-3)11-15(13)16/h6-7,11-12,17H,4-5,8-10H2,1-3H3

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

5095
Analogue 35: Substituting Diisobutyl for Dipropyl at N

5-MeO-DIBT
N,N-Diisobutyl-5-methoxytryptamine

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-2-methyl-N-(2-methylpropyl)propan-1-amine

Formula: C19H30N2O Molecular weight: 302.4543 g/mol InChI Key: LAWIFDHBLQDKEA-UHFFFAOYSA-N

InChI=1S/C19H30N2O/c1-14(2)12-21(13-15(3)4)9-8-16-11-20-19-7-6-17(22-5)10-18(16)19/h6-7,10-11,14-15,20H,8-9,12-13H2,1-5H3

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

5462
Analogue 36: Substituting Dibutyl for Dipropyl at N

5-MeO-DBT

IUPAC: N-Butyl-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]butan-1-amine

Formula: C19H30N2O Molecular weight: 302.4543 g/mol InChI Key: WVGCRISHWANOTO-UHFFFAOYSA-N

InChI=1S/C19H30N2O/c1-4-6-11-21(12-7-5-2)13-10-16-15-20-19-9-8-17(22-3)14-18(16)19/h8-9,14-15,20H,4-7,10-13H2,1-3H3

PubChem CID: 53485365

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

5464
Analogue 37: Substituting Isobutyl and Methyl for Dipropyl at N

5-MeO-MIBT

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N,2-dimethylpropan-1-amine

Formula: C16H24N2O Molecular weight: 260.37456 g/mol InChI Key: POLLXYVGPPSRQX-UHFFFAOYSA-N

InChI=1S/C16H24N2O/c1-12(2)11-18(3)8-7-13-10-17-16-6-5-14(19-4)9-15(13)16/h5-6,9-10,12,17H,7-8,11H2,1-4H3

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5655
Analogue 38: Substituting Methyl and 2-{[2-(5-Methoxy-1H-indol-3-yl)ethyl](methyl)amino}ethyl for Dipropyl at N

IUPAC: N,N′-Bis[2-(5-methoxy-1H-indol-3-yl)ethyl]-N,N′-dimethylethane-1,2-diamine

Formula: C26H34N4O2 Molecular weight: 434.57376 g/mol InChI Key: ABCLANHOOVJJDY-UHFFFAOYSA-N

InChI=1S/C26H34N4O2/c1-29(11-9-19-17-27-25-7-5-21(31-3)15-23(19)25)13-14-30(2)12-10-20-18-28-26-8-6-22(32-4)16-24(20)26/h5-8,15-18,27-28H,9-14H2,1-4H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5657
Analogue 39: Substituting Methyl and Benzyl for Dipropyl at N

IUPAC: N-Benzyl-2-(5-methoxy-1H-indol-3-yl)-N-methylethan-1-amine

Formula: C19H22N2O Molecular weight: 294.39078 g/mol InChI Key: IFRNCHRBJMIVBK-UHFFFAOYSA-N

InChI=1S/C19H22N2O/c1-21(14-15-6-4-3-5-7-15)11-10-16-13-20-19-9-8-17(22-2)12-18(16)19/h3-9,12-13,20H,10-11,14H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5658
Analogue 40: Substituting Methyl and 4-Bromobenzyl for Dipropyl at N

IUPAC: N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)-N-methylethan-1-amine

Formula: C19H21BrN2O Molecular weight: 373.28684 g/mol InChI Key: UBDKAWSVGYJQAW-UHFFFAOYSA-N

InChI=1S/C19H21BrN2O/c1-22(13-14-3-5-16(20)6-4-14)10-9-15-12-21-19-8-7-17(23-2)11-18(15)19/h3-8,11-12,21H,9-10,13H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5659
Analogue 41: Substituting Methyl and 2-Phenylethyl for Dipropyl at N

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-methyl-N-(2-phenylethyl)ethan-1-amine

Formula: C20H24N2O Molecular weight: 308.41736 g/mol InChI Key: FJMBRVSUPSRACR-UHFFFAOYSA-N

InChI=1S/C20H24N2O/c1-22(12-10-16-6-4-3-5-7-16)13-11-17-15-21-20-9-8-18(23-2)14-19(17)20/h3-9,14-15,21H,10-13H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5660
Analogue 42: Substituting Methyl and 2-(2-Methylphenyl)ethyl for Dipropyl at N

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-methyl-N-[2-(2-methylphenyl)ethyl]ethan-1-amine

Formula: C21H26N2O Molecular weight: 322.44394 g/mol InChI Key: OKJCUAMPOFOLPQ-UHFFFAOYSA-N

InChI=1S/C21H26N2O/c1-16-6-4-5-7-17(16)10-12-23(2)13-11-18-15-22-21-9-8-19(24-3)14-20(18)21/h4-9,14-15,22H,10-13H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5661
Analogue 43: Substituting Methyl and 2-(2-Fluorophenyl)ethyl for Dipropyl at N

IUPAC: 2-(2-Fluorophenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C20H23FN2O Molecular weight: 326.4078232 g/mol InChI Key: VDIBZURTTOJJMB-UHFFFAOYSA-N

InChI=1S/C20H23FN2O/c1-23(11-9-15-5-3-4-6-19(15)21)12-10-16-14-22-20-8-7-17(24-2)13-18(16)20/h3-8,13-14,22H,9-12H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5662
Analogue 44: Substituting Methyl and 2-(2-Chlorophenyl)ethyl for Dipropyl at N

IUPAC: 2-(2-Chlorophenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C20H23ClN2O Molecular weight: 342.86242 g/mol InChI Key: WIBPLSNWQOIFEC-UHFFFAOYSA-N

InChI=1S/C20H23ClN2O/c1-23(11-9-15-5-3-4-6-19(15)21)12-10-16-14-22-20-8-7-17(24-2)13-18(16)20/h3-8,13-14,22H,9-12H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5663
Analogue 45: Substituting Methyl and 2-(2,5-Dimethylphenyl)ethyl for Dipropyl at N

IUPAC: 2-(2,5-Dimethylphenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C22H28N2O Molecular weight: 336.47052 g/mol InChI Key: RUBADSSLLZPSSG-UHFFFAOYSA-N

InChI=1S/C22H28N2O/c1-16-5-6-17(2)18(13-16)9-11-24(3)12-10-19-15-23-22-8-7-20(25-4)14-21(19)22/h5-8,13-15,23H,9-12H2,1-4H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5664
Analogue 46: Substituting Methyl and 2-(2-Methoxyphenyl)ethyl for Dipropyl at N

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-[2-(2-methoxyphenyl)ethyl]-N-methylethan-1-amine

Formula: C21H26N2O2 Molecular weight: 338.44334 g/mol InChI Key: KOAJSCBWXMMBCP-UHFFFAOYSA-N

InChI=1S/C21H26N2O2/c1-23(12-10-16-6-4-5-7-21(16)25-3)13-11-17-15-22-20-9-8-18(24-2)14-19(17)20/h4-9,14-15,22H,10-13H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5665
Analogue 47: Substituting Methyl and 2-(2,5-Dimethoxyphenyl)ethyl for Dipropyl at N

IUPAC: 2-(2,5-Dimethoxyphenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C22H28N2O3 Molecular weight: 368.46932 g/mol InChI Key: QMNJEIDEVWJMPL-UHFFFAOYSA-N

InChI=1S/C22H28N2O3/c1-24(11-9-16-13-18(25-2)6-8-22(16)27-4)12-10-17-15-23-21-7-5-19(26-3)14-20(17)21/h5-8,13-15,23H,9-12H2,1-4H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5666
Analogue 48: Substituting Methyl and 2-(3-Methylphenyl)ethyl for Dipropyl at N

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-methyl-N-[2-(3-methylphenyl)ethyl]ethan-1-amine

Formula: C21H26N2O Molecular weight: 322.44394 g/mol InChI Key: JYMJFHWTGDXUJF-UHFFFAOYSA-N

InChI=1S/C21H26N2O/c1-16-5-4-6-17(13-16)9-11-23(2)12-10-18-15-22-21-8-7-19(24-3)14-20(18)21/h4-8,13-15,22H,9-12H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5667
Analogue 49: Substituting Methyl and 2-(3-Chlorophenyl)ethyl for Dipropyl at N

IUPAC: 2-(3-Chlorophenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C20H23ClN2O Molecular weight: 342.86242 g/mol InChI Key: QNZUZAGZLGVQMB-UHFFFAOYSA-N

InChI=1S/C20H23ClN2O/c1-23(10-8-15-4-3-5-17(21)12-15)11-9-16-14-22-20-7-6-18(24-2)13-19(16)20/h3-7,12-14,22H,8-11H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5668
Analogue 50: Substituting Methyl and 2-(3-Bromophenyl)ethyl for Dipropyl at N

IUPAC: 2-(3-Bromophenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C20H23BrN2O Molecular weight: 387.31342 g/mol InChI Key: RHQYMFRRBGMYFU-UHFFFAOYSA-N

InChI=1S/C20H23BrN2O/c1-23(10-8-15-4-3-5-17(21)12-15)11-9-16-14-22-20-7-6-18(24-2)13-19(16)20/h3-7,12-14,22H,8-11H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5669
Analogue 51: Substituting Methyl and 2-(3,5-Dimethylphenyl)ethyl for Dipropyl at N

IUPAC: 2-(3,5-Dimethylphenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C22H28N2O Molecular weight: 336.47052 g/mol InChI Key: LSVKESAZNYDEER-UHFFFAOYSA-N

InChI=1S/C22H28N2O/c1-16-11-17(2)13-18(12-16)7-9-24(3)10-8-19-15-23-22-6-5-20(25-4)14-21(19)22/h5-6,11-15,23H,7-10H2,1-4H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5670
Analogue 52: Substituting Methyl and 2-(3,4-Dimethoxyphenyl)ethyl for Dipropyl at N

IUPAC: 2-(3,4-Dimethoxyphenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C22H28N2O3 Molecular weight: 368.46932 g/mol InChI Key: BSVINUWKFGTSHL-UHFFFAOYSA-N

InChI=1S/C22H28N2O3/c1-24(11-9-16-5-8-21(26-3)22(13-16)27-4)12-10-17-15-23-20-7-6-18(25-2)14-19(17)20/h5-8,13-15,23H,9-12H2,1-4H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5671
Analogue 53: Substituting Methyl and 2-(3,4-Dichlorophenyl)ethyl for Dipropyl at N

IUPAC: 2-(3,4-Dichlorophenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C20H22Cl2N2O Molecular weight: 377.30748 g/mol InChI Key: ZGCFUDBTSBAIPV-UHFFFAOYSA-N

InChI=1S/C20H22Cl2N2O/c1-24(9-7-14-3-5-18(21)19(22)11-14)10-8-15-13-23-20-6-4-16(25-2)12-17(15)20/h3-6,11-13,23H,7-10H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5672
Analogue 54: Substituting Methyl and 2-(4-Methylphenyl)ethyl for Dipropyl at N

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-methyl-N-[2-(4-methylphenyl)ethyl]ethan-1-amine

Formula: C21H26N2O Molecular weight: 322.44394 g/mol InChI Key: YEMRBWYJVRLSCG-UHFFFAOYSA-N

InChI=1S/C21H26N2O/c1-16-4-6-17(7-5-16)10-12-23(2)13-11-18-15-22-21-9-8-19(24-3)14-20(18)21/h4-9,14-15,22H,10-13H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5673
Analogue 55: Substituting Methyl and 2-(4-Methoxyphenyl)ethyl for Dipropyl at N

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-[2-(4-methoxyphenyl)ethyl]-N-methylethan-1-amine

Formula: C21H26N2O2 Molecular weight: 338.44334 g/mol InChI Key: RZIMDKVMYKNBHW-UHFFFAOYSA-N

InChI=1S/C21H26N2O2/c1-23(12-10-16-4-6-18(24-2)7-5-16)13-11-17-15-22-21-9-8-19(25-3)14-20(17)21/h4-9,14-15,22H,10-13H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5674
Analogue 56: Substituting Methyl and 2-(4-Fluorophenyl)ethyl for Dipropyl at N

IUPAC: 2-(4-Fluorophenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C20H23FN2O Molecular weight: 326.4078232 g/mol InChI Key: LEPALOGRKPLFIY-UHFFFAOYSA-N

InChI=1S/C20H23FN2O/c1-23(11-9-15-3-5-17(21)6-4-15)12-10-16-14-22-20-8-7-18(24-2)13-19(16)20/h3-8,13-14,22H,9-12H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5675
Analogue 57: Substituting Methyl and 2-(4-Bromophenyl)ethyl for Dipropyl at N

IUPAC: 2-(4-Bromophenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C20H23BrN2O Molecular weight: 387.31342 g/mol InChI Key: XOCHXXUBYCPHQM-UHFFFAOYSA-N

InChI=1S/C20H23BrN2O/c1-23(11-9-15-3-5-17(21)6-4-15)12-10-16-14-22-20-8-7-18(24-2)13-19(16)20/h3-8,13-14,22H,9-12H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5676
Analogue 58: Substituting Methyl and 2-(4-Nitrophenyl)ethyl for Dipropyl at N

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-methyl-N-[2-(4-nitrophenyl)ethyl]ethan-1-amine

Formula: C20H23N3O3 Molecular weight: 353.41492 g/mol InChI Key: HZDDMRXRWSPHCA-UHFFFAOYSA-N

InChI=1S/C20H23N3O3/c1-22(11-9-15-3-5-17(6-4-15)23(24)25)12-10-16-14-21-20-8-7-18(26-2)13-19(16)20/h3-8,13-14,21H,9-12H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5677
Analogue 59: Substituting Methyl and 2-(4-Phenylphenyl)ethyl for Dipropyl at N

IUPAC: 2-(Biphenyl-4-yl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C26H28N2O Molecular weight: 384.51332 g/mol InChI Key: SGGRWOCYKAWONG-UHFFFAOYSA-N

InChI=1S/C26H28N2O/c1-28(17-15-23-19-27-26-13-12-24(29-2)18-25(23)26)16-14-20-8-10-22(11-9-20)21-6-4-3-5-7-21/h3-13,18-19,27H,14-17H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5678
Analogue 60: Substituting Methyl and 5-Methoxyindole-3-ylethyl for Dipropyl at N

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C23H27N3O2 Molecular weight: 377.47938 g/mol InChI Key: VJNJLYMIRMVCAQ-UHFFFAOYSA-N

InChI=1S/C23H27N3O2/c1-26(10-8-16-14-24-22-6-4-18(27-2)12-20(16)22)11-9-17-15-25-23-7-5-19(28-3)13-21(17)23/h4-7,12-15,24-25H,8-11H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5679
Analogue 61: Substituting Methyl and Naphthalen-1-ylethyl for Dipropyl at N

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-methyl-N-[2-(naphthalen-1-yl)ethyl]ethan-1-amine

Formula: C24H26N2O Molecular weight: 358.47604 g/mol InChI Key: VHIKBVMETFUAHK-UHFFFAOYSA-N

InChI=1S/C24H26N2O/c1-26(14-12-19-8-5-7-18-6-3-4-9-22(18)19)15-13-20-17-25-24-11-10-21(27-2)16-23(20)24/h3-11,16-17,25H,12-15H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5680
Analogue 62: Substituting Methyl and Naphthalen-2-ylethyl for Dipropyl at N

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-methyl-N-[2-(naphthalen-2-yl)ethyl]ethan-1-amine

Formula: C24H26N2O Molecular weight: 358.47604 g/mol InChI Key: DSERMJXLGOCBSW-UHFFFAOYSA-N

InChI=1S/C24H26N2O/c1-26(13-11-18-7-8-19-5-3-4-6-20(19)15-18)14-12-21-17-25-24-10-9-22(27-2)16-23(21)24/h3-10,15-17,25H,11-14H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5681
Analogue 63: Substituting Methyl and Phenylpropyl for Dipropyl at N

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methyl-3-phenylpropan-1-amine

Formula: C21H26N2O Molecular weight: 322.44394 g/mol InChI Key: AXAUOLBKOXMYBI-UHFFFAOYSA-N

InChI=1S/C21H26N2O/c1-23(13-6-9-17-7-4-3-5-8-17)14-12-18-16-22-21-11-10-19(24-2)15-20(18)21/h3-5,7-8,10-11,15-16,22H,6,9,12-14H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5682
Analogue 64: Substituting Methyl and 3-(3,4,5-Trimethoxyphenyl)propyl for Dipropyl at N

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methyl-3-(3,4,5-trimethoxyphenyl)propan-1-amine

Formula: C24H32N2O4 Molecular weight: 412.52188 g/mol InChI Key: DUBMBXDGBNJWRT-UHFFFAOYSA-N

InChI=1S/C24H32N2O4/c1-26(12-10-18-16-25-21-9-8-19(27-2)15-20(18)21)11-6-7-17-13-22(28-3)24(30-5)23(14-17)29-4/h8-9,13-16,25H,6-7,10-12H2,1-5H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5683
Analogue 65: Substituting Methyl and Phenylbutyl for Dipropyl at N

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methyl-4-phenylbutan-1-amine

Formula: C22H28N2O Molecular weight: 336.47052 g/mol InChI Key: LRWVRZYPLXOCLF-UHFFFAOYSA-N

InChI=1S/C22H28N2O/c1-24(14-7-6-10-18-8-4-3-5-9-18)15-13-19-17-23-22-12-11-20(25-2)16-21(19)22/h3-5,8-9,11-12,16-17,23H,6-7,10,13-15H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5684
Analogue 66: Substituting Methyl and Phenylthiopropyl for Dipropyl at N

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methyl-3-(phenylsulfanyl)propan-1-amine

Formula: C21H26N2OS Molecular weight: 354.50894 g/mol InChI Key: OYYQMBBFQLTAFT-UHFFFAOYSA-N

InChI=1S/C21H26N2OS/c1-23(12-6-14-25-19-7-4-3-5-8-19)13-11-17-16-22-21-10-9-18(24-2)15-20(17)21/h3-5,7-10,15-16,22H,6,11-14H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5685
Analogue 67: Substituting Methyl and Butyl for Dipropyl at N

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methylbutan-1-amine

Formula: C16H24N2O Molecular weight: 260.37456 g/mol InChI Key: LQYCKXWTNNBJGQ-UHFFFAOYSA-N

InChI=1S/C16H24N2O/c1-4-5-9-18(2)10-8-13-12-17-16-7-6-14(19-3)11-15(13)16/h6-7,11-12,17H,4-5,8-10H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5686
Analogue 68: Substituting Methyl and Pentyl for Dipropyl at N

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methylpentan-1-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: YSLSTFPGMGOQRJ-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-4-5-6-10-19(2)11-9-14-13-18-17-8-7-15(20-3)12-16(14)17/h7-8,12-13,18H,4-6,9-11H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5687
Analogue 69: Substituting Methyl and Octyl for Dipropyl at N

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methyloctan-1-amine

Formula: C20H32N2O Molecular weight: 316.48088 g/mol InChI Key: VWFHRTCUXPCGLB-UHFFFAOYSA-N

InChI=1S/C20H32N2O/c1-4-5-6-7-8-9-13-22(2)14-12-17-16-21-20-11-10-18(23-3)15-19(17)20/h10-11,15-16,21H,4-9,12-14H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5688
Analogue 70: Substituting Methyl and Dodecyl for Dipropyl at N

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methyldodecan-1-amine

Formula: C24H40N2O Molecular weight: 372.5872 g/mol InChI Key: GJAJFSJVMSPFRH-UHFFFAOYSA-N

InChI=1S/C24H40N2O/c1-4-5-6-7-8-9-10-11-12-13-17-26(2)18-16-21-20-25-24-15-14-22(27-3)19-23(21)24/h14-15,19-20,25H,4-13,16-18H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5689
Analogue 71: Substituting Methyl and Tetraadecyl for Dipropyl at N

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methyltetradecan-1-amine

Formula: C26H44N2O Molecular weight: 400.64036 g/mol InChI Key: QBYLUOAUPHDICE-UHFFFAOYSA-N

InChI=1S/C26H44N2O/c1-4-5-6-7-8-9-10-11-12-13-14-15-19-28(2)20-18-23-22-27-26-17-16-24(29-3)21-25(23)26/h16-17,21-22,27H,4-15,18-20H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5690
Analogue 72: Substituting Methyl and Octadecyl for Dipropyl at N

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methyloctadecan-1-amine

Formula: C30H52N2O Molecular weight: 456.74668 g/mol InChI Key: MGXRIPNOTPCDJX-UHFFFAOYSA-N

InChI=1S/C30H52N2O/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23-32(2)24-22-27-26-31-30-21-20-28(33-3)25-29(27)30/h20-21,25-26,31H,4-19,22-24H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5691
Analogue 73: Substituting Methyl and Cyclopentylmethyl for Dipropyl at N

IUPAC: N-(Cyclopentylmethyl)-2-(5-methoxy-1H-indol-3-yl)-N-methylethan-1-amine

Formula: C18H26N2O Molecular weight: 286.41184 g/mol InChI Key: IKVVWUPMRVNKPO-UHFFFAOYSA-N

InChI=1S/C18H26N2O/c1-20(13-14-5-3-4-6-14)10-9-15-12-19-18-8-7-16(21-2)11-17(15)18/h7-8,11-12,14,19H,3-6,9-10,13H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5692
Analogue 74: Substituting Methyl and Cyclohexylmethyl for Dipropyl at N

IUPAC: N-(Cyclohexylmethyl)-2-(5-methoxy-1H-indol-3-yl)-N-methylethan-1-amine

Formula: C19H28N2O Molecular weight: 300.43842 g/mol InChI Key: XVKFTQFLQODWAB-UHFFFAOYSA-N

InChI=1S/C19H28N2O/c1-21(14-15-6-4-3-5-7-15)11-10-16-13-20-19-9-8-17(22-2)12-18(16)19/h8-9,12-13,15,20H,3-7,10-11,14H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5694
Analogue 75: Substituting Methyl and Pentan-3-ylmethyl for Dipropyl at N

IUPAC: 2-Ethyl-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylbutan-1-amine

Formula: C18H28N2O Molecular weight: 288.42772 g/mol InChI Key: DRQUADANVCVSNM-UHFFFAOYSA-N

InChI=1S/C18H28N2O/c1-5-14(6-2)13-20(3)10-9-15-12-19-18-8-7-16(21-4)11-17(15)18/h7-8,11-12,14,19H,5-6,9-10,13H2,1-4H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5695
Analogue 76: Substituting Methyl and Allyl for Dipropyl at N

5-MeO-MALT

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine

Formula: C15H20N2O Molecular weight: 244.3321 g/mol InChI Key: AJHGTCBMUIJSQL-UHFFFAOYSA-N

InChI=1S/C15H20N2O/c1-4-8-17(2)9-7-12-11-16-15-6-5-13(18-3)10-14(12)15/h4-6,10-11,16H,1,7-9H2,2-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5696
Analogue 77: Substituting Methyl and Prop-1-ynyl for Dipropyl at N

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methylprop-2-yn-1-amine

Formula: C15H18N2O Molecular weight: 242.31622 g/mol InChI Key: RIRUSTVUQBBBEU-UHFFFAOYSA-N

InChI=1S/C15H18N2O/c1-4-8-17(2)9-7-12-11-16-15-6-5-13(18-3)10-14(12)15/h1,5-6,10-11,16H,7-9H2,2-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5697
Analogue 78: Substituting Methyl and Cyclohexylpropyl for Dipropyl at N

IUPAC: 3-Cyclohexyl-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylpropan-1-amine

Formula: C21H32N2O Molecular weight: 328.49158 g/mol InChI Key: GJFSIPRAXCKQPH-UHFFFAOYSA-N

InChI=1S/C21H32N2O/c1-23(13-6-9-17-7-4-3-5-8-17)14-12-18-16-22-21-11-10-19(24-2)15-20(18)21/h10-11,15-17,22H,3-9,12-14H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5698
Analogue 79: Substituting Methyl and 3-Phenylprop-2-enyl for Dipropyl at N

IUPAC: (2E)-N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methyl-3-phenylprop-2-en-1-amine

Formula: C21H24N2O Molecular weight: 320.42806 g/mol InChI Key: QPIGGIFVKXJSNI-RMKNXTFCSA-N

InChI=1S/C21H24N2O/c1-23(13-6-9-17-7-4-3-5-8-17)14-12-18-16-22-21-11-10-19(24-2)15-20(18)21/h3-11,15-16,22H,12-14H2,1-2H3/b9-6+

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5699
Analogue 80: Substituting Methyl and 2-Methoxy-2-oxoethyl for Dipropyl at N

IUPAC: Methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylglycinate

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

InChI=1S/C15H20N2O3/c1-17(10-15(18)20-3)7-6-11-9-16-14-5-4-12(19-2)8-13(11)14/h4-5,8-9,16H,6-7,10H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5700
Analogue 81: Substituting Methyl and 2-tertButoxy-2-oxoethyl for Dipropyl at N

IUPAC: tert-Butyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylglycinate

Formula: C18H26N2O3 Molecular weight: 318.41064 g/mol InChI Key: IJECVBVPURUOMM-UHFFFAOYSA-N

InChI=1S/C18H26N2O3/c1-18(2,3)23-17(21)12-20(4)9-8-13-11-19-16-7-6-14(22-5)10-15(13)16/h6-7,10-11,19H,8-9,12H2,1-5H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5711
Analogue 82: Substituting Methyl and 2-Amino-2-oxoethyl for Dipropyl at N

IUPAC: N2-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N2-methylglycinamide

Formula: C14H19N3O2 Molecular weight: 261.31956 g/mol InChI Key: BXBCGRNWXCOHPA-UHFFFAOYSA-N

InChI=1S/C14H19N3O2/c1-17(9-14(15)18)6-5-10-8-16-13-4-3-11(19-2)7-12(10)13/h3-4,7-8,16H,5-6,9H2,1-2H3,(H2,15,18)

5712
Analogue 83: Substituting Methyl and 2-Cyanoethyl for Dipropyl at N

IUPAC: 3-{[2-(5-Methoxy-1H-indol-3-yl)ethyl](methyl)amino}propanenitrile

Formula: C15H19N3O Molecular weight: 257.33086 g/mol InChI Key: XDRGHVUXWKNFQO-UHFFFAOYSA-N

InChI=1S/C15H19N3O/c1-18(8-3-7-16)9-6-12-11-17-15-5-4-13(19-2)10-14(12)15/h4-5,10-11,17H,3,6,8-9H2,1-2H3

5713
Analogue 84: Substituting Methyl and 3-(Diethylamino)-3-oxopropyl for Dipropyl at N

IUPAC: N,N-Diethyl-N3-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N3-methyl-&be

Formula: C19H29N3O2 Molecular weight: 331.45246 g/mol InChI Key: AFYLHDILMUCAAE-UHFFFAOYSA-N

InChI=1S/C19H29N3O2/c1-5-22(6-2)19(23)10-12-21(3)11-9-15-14-20-18-8-7-16(24-4)13-17(15)18/h7-8,13-14,20H,5-6,9-12H2,1-4H3

One R2 analogue:
5574
Analogue 1: Adding Methyl at R2

5-MeO-2-Me-DPT

IUPAC: N-[2-(5-Methoxy-2-methyl-1H-indol-3-yl)ethyl]-N-propylpropan-1-amine

Formula: C18H28N2O Molecular weight: 288.42772 g/mol InChI Key: KUJSUSZXSLQFQL-UHFFFAOYSA-N

InChI=1S/C18H28N2O/c1-5-10-20(11-6-2)12-9-16-14(3)19-18-8-7-15(21-4)13-17(16)18/h7-8,13,19H,5-6,9-12H2,1-4H3

Brandt, SD; Tearavarich, R; Dempster, N; Cozzi, NV; Daley, PF. Synthesis and characterization of 5-methoxy-2-methyl-N,N-dialkylated tryptamines. Drug Test. Anal., 1 Jan 2012, 4 (1), 24–32. 506 kB. doi:10.1002/dta.398

Three R5 analogues:
5009
Analogue 1: Removing Methoxy at R5

DPT
Tryptamine, N,N-dipropyl
Indole, 3-[2-(dipropylamino)ethyl]
N,N-Dipropyltryptamine
3-[2-(Dipropylamino)ethyl]indole

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-propylpropan-1-amine

Formula: C16H24N2 Molecular weight: 244.37516 g/mol InChI Key: BOOQTIHIKDDPRW-UHFFFAOYSA-N

InChI=1S/C16H24N2/c1-3-10-18(11-4-2)12-9-14-13-17-16-8-6-5-7-15(14)16/h5-8,13,17H,3-4,9-12H2,1-2H3

PubChem CID: 6091; ChemSpider: 5866; Erowid: DPT; Wikipedia: Dipropyltryptamine

See also TiHKAL: #2 DBT
#20 4-HO-DPT
#27 MBT
#49 NET
See also Chemistry notes VIII: p. 63, DPT: GC-MS
p. 83, DPT: Synthesis
p. 84, DPT: GC-MS
p. 85, DPT: GC-MS

Rodriguez-Cruz, SE. Analysis and characterization of designer tryptamines using electrospray ionization mass spectrometry (ESI-MS). Microgram J., 1 Jul 2005, 3 (3–4), 107–129. 1577 kB.

Spratley, TK; Hays, PA; Geer, LC; Cooper, SD; McKibben, TD. Analytical profiles for five “designer” tryptamines. Microgram J., 1 Jan 2005, 3 (1–2), 54–68. 473 kB.

Szara, S; Hearst, E; Putney, F. Metabolism and behavioural action of psychotropic tryptamine homologues. Int. J. Neuropharmacol., 1 Nov 1962, 1 (1–3), 111–117. 1056 kB. doi:10.1016/0028-3908(62)90015-1

Shulgin, AT. Abused substances. Tech. Rev., 1 Jan 2005, August, 80–81. 415 kB.

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. doi:10.1016/j.talanta.2007.06.012

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

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

Faillace, LA; Vourlekis, A; Szara, S. Clinical evaluation of some hallucinogenic tryptamine derivatives. J. Nerv. Ment. Dis., 1 Jan 1967, 145 (4), 306–313. 635 kB.

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Szara, S. DMT (N,N-dimethyltryptamine) and homologues: Clinical and pharmacological considerations. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 275–286. 1897 kB.

Cozzi, NV; Gopalakrishnan, A; Anderson, LL; Feih, JT; Shulgin, AT; Daley, PF; Ruoho, AE. Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter. J. Neural. Transm., 1 Dec 2009, 116 (12), 1591–1599. 420 kB. doi:10.1007/s00702-009-0308-8

Toad. DPT Primer. Erowid, 15 Nov 1998.

Cozzi, NV; Shulgin, AT; Daley, PF; Gopalakrishnan, A; Anderson, LL; Feih, JT; Ruoho, AE. Psychoactive N,N-dialkyltryptamines modulate serotonin transport by at least two mechanisms. Soc. Neurosci. Abs., 1 Jan 2008, 536.17. 52 kB.

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

5586
Analogue 2: Substituting Ethoxy for Methoxy at R5

5-EtO-DPT

IUPAC: N-[2-(5-Ethoxy-1H-indol-3-yl)ethyl]-N-propylpropan-1-amine

Formula: C18H28N2O Molecular weight: 288.42772 g/mol InChI Key: COGBUYYMZBGFLA-UHFFFAOYSA-N

InChI=1S/C18H28N2O/c1-4-10-20(11-5-2)12-9-15-14-19-18-8-7-16(21-6-3)13-17(15)18/h7-8,13-14,19H,4-6,9-12H2,1-3H3

Tearavarich, R; Hahnvajanawong, V; Dempster, N; Daley, PF; Cozzi, NV; Brandt, SD. Microwave-accelerated preparation and analytical characterization of 5-ethoxy-N,N-dialkyl-[α,α,β,β-H4]- and [α,α,β,β-D4]-tryptamines. Drug Test. Anal., 1 Sep 2011, 3 (9), 597–608. 253 kB. doi:10.1002/dta.223

Kanu, AB; Brandt, SD; Williams, MD; Zhang, N; Hill, HH. Analysis of psychoactive cathinones and tryptamines by electrospray ionization atmospheric pressure ion mobility time-of-flight mass spectrometry. Anal. Chem., 17 Sep 2013, 85 (18), 8535–8542. 1636 kB. doi:10.1021/ac401951a

5884
Analogue 3: Substituting Carbamoyl for Methoxy at R5

IUPAC: 3-[2-(Dipropylamino)ethyl]-1H-indole-5-carboxamide

Formula: C17H25N3O Molecular weight: 287.3999 g/mol InChI Key: DPXOFRGRKPFZOD-UHFFFAOYSA-N

InChI=1S/C17H25N3O/c1-3-8-20(9-4-2)10-7-14-12-19-16-6-5-13(17(18)21)11-15(14)16/h5-6,11-12,19H,3-4,7-10H2,1-2H3,(H2,18,21)

Matzdorf, T. 5-Carboxamidotryptamin-derivate als liganden für 5-HT7- und 5-HT2A-rezeptoren: synthese und in-vitro-pharmakologie. Ph. D. Thesis, Universität Regensburg, Berlin, Germany, 23 Jan 2009. 1011 kB.

Four skeleton analogues:
5043
Analogue 1: With Indol-3-ylethyl-cyclic-amine skeleton

5-MeO-pyr-T
Tryptamine, 5-methoxy-N,N-tetramethylene
Indole, 5-methoxy-3-[2-(1-pyrrolidyl)ethyl]
Pyrrolidine, 1-[2-(5-methoxy-1H-indol-3-yl)ethyl]
5-Methoxy-N,N-tetramethylenetryptamine
5-Methoxy-3-[2-(1-pyrrolidyl)ethyl]indole
1-[2-(5-Methoxy-1H-indol-3-yl)ethyl]pyrrolidine
5-Methoxypyrrolidyltryptamine

IUPAC: 5-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole

Formula: C15H20N2O Molecular weight: 244.3321 g/mol InChI Key: KAASYKNZNPWPQG-UHFFFAOYSA-N

InChI=1S/C15H20N2O/c1-18-13-4-5-15-14(10-13)12(11-16-15)6-9-17-7-2-3-8-17/h4-5,10-11,16H,2-3,6-9H2,1H3

PubChem CID: 17053; ChemSpider: 16153; Wikipedia: 5-MeO-pyr-T

See also TiHKAL: #24 4-HO-pyr-T #36 5-MeO-DET
See also Chemistry notes VIII: p. 115, 5-MeO-pyr-T (α,β-keto): Synthesis
p. 117, 5-MeO-pyr-T: Synthesis
p. 119, 5-MeO-pyr-T (α,β-keto): Synthesis
p. 120, 5-MeO-pyr-T: Synthesis

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5169
Analogue 2: With Indol-3-ylethyl-cyclic-amine skeleton

5-MeO-mor-T
N,N-Ethyleneoxyethylene-5-methoxytryptamine

IUPAC: 5-Methoxy-3-[2-(morpholin-4-yl)ethyl]-1H-indole

Formula: C15H20N2O2 Molecular weight: 260.3315 g/mol InChI Key: NKTMQWGDNZZJHQ-UHFFFAOYSA-N

InChI=1S/C15H20N2O2/c1-18-13-2-3-15-14(10-13)12(11-16-15)4-5-17-6-8-19-9-7-17/h2-3,10-11,16H,4-9H2,1H3

PubChem CID: 24839576

See also TiHKAL: #43 5-MeO-pyr-T  
See also Chemistry notes VIII: p. 116, 5-MeO-mor-T (α,β-keto): Synthesis
5170
Analogue 3: With Indol-3-ylethyl-cyclic-amine skeleton

5-MeO-pip-T
5-Methoxy-N,N-pentamethylenetryptamine

IUPAC: 5-Methoxy-3-[2-(piperidin-1-yl)ethyl]-1H-indole

Formula: C16H22N2O Molecular weight: 258.35868 g/mol InChI Key: QVWFRPYLSDUCFB-UHFFFAOYSA-N

InChI=1S/C16H22N2O/c1-19-14-5-6-16-15(11-14)13(12-17-16)7-10-18-8-3-2-4-9-18/h5-6,11-12,17H,2-4,7-10H2,1H3

PubChem CID: 10467710; ChemSpider: 8643121

See also TiHKAL: #43 5-MeO-pyr-T  
See also Chemistry notes VIII: p. 114, 5-MeO-pip-T (α,β-keto): Synthesis

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5469
Analogue 4: With 2-(1H-Indol-3-yl)cyclopropanamine skeleton

5-MeO-ICPA

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)cyclopropanamine

Formula: C12H14N2O Molecular weight: 202.25236 g/mol InChI Key: QAYBFLBZFYNCJH-UHFFFAOYSA-N

InChI=1S/C12H14N2O/c1-15-7-2-3-12-9(4-7)10(6-14-12)8-5-11(8)13/h2-4,6,8,11,14H,5,13H2,1H3

PubChem CID: 44364215; ChemSpider: 23220172

Vangveravong, S; Kanthasamy, A; Lucaites, VL; Nelson, DL; Nichols, DE. Synthesis and serotonin receptor affinities of a series of trans-2-(indol-3-yl)cyclopropylamine derivatives. J. Med. Chem., 1 Jan 1998, 41 (25), 4995–5001. 140 kB. doi:10.1021/jm980318q

11 isomers:
5037
Isomer 1

5-MeO-DIPT
Tryptamine, N,N-diisopropyl-5-methoxy
Indole, 3-[2-(diisopropylamino)ethyl]-5-methoxy
N,N-Diisopropyl-5-methoxytryptamine
3-[2-(Diisopropylamino)ethyl]-5-methoxyindole

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: DNBPMBJFRRVTSJ-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-12(2)19(13(3)4)9-8-14-11-18-17-7-6-15(20-5)10-16(14)17/h6-7,10-13,18H,8-9H2,1-5H3

PubChem CID: 151182; ChemSpider: 133247; Drugs Forum: 5-MeO-DIPT; Erowid: 5-MeO-DIPT; Wikipedia: 5-Methoxy-diisopropyltryptamine

See also TiHKAL: #17 4-HO-DIPT
#36 5-MeO-DET
#40 5-MeO-MIPT
See also Pharmacology notes I: p. 176, 5-MeO-DIPT: Trials
p. 191, Chronology on 5-Methoxy-N,N-diisopropyltryptamine
See also Chemistry notes VIII: p. 87, 5-MeO-DIPT: Synthesis
p. 88, 5-MeO-DIPT: Synthesis
p. 90, 5-MeO-DIPT: Synthesis
p. 91, 5-MeO-DIPT: GC-MS
p. 92, 5-MeO-DIPT: Synthesis
p. 93, 5-MeO-DIPT: GC-MS
p. 98, 5-MeO-DIPT: GC-MS
p. 108, 5-MeO-DIPT:
p. 109, 5-MeO-DIPT: Synthesis
p. 121, 5-MeO-DIPT: Synthesis
p. 167, 5-MeO-DIPT: Synthesis

Rodriguez-Cruz, SE. Analysis and characterization of designer tryptamines using electrospray ionization mass spectrometry (ESI-MS). Microgram J., 1 Jul 2005, 3 (3–4), 107–129. 1577 kB.

Spratley, TK; Hays, PA; Geer, LC; Cooper, SD; McKibben, TD. Analytical profiles for five “designer” tryptamines. Microgram J., 1 Jan 2005, 3 (1–2), 54–68. 473 kB.

Meatherall, R; Sharma, P. Foxy, a designer tryptamine hallucinogen. J. Anal. Toxicol., 1 Jul 2003, 27 (5), 313–317. 988 kB. doi:10.1093/jat/27.5.313

Kamata, T; Katagi, M; Kamata, HT; Miki, A; Shima, N; Zaitsu, K; Nishikawa, M; tanaka, E; Honda, K; Tsuchihashi, H. Metabolism of the psychotomimetic tryptamine derivative 5-methoxy-N,N-diisopropyltryptamine in humans: Identification and quantification of its urinary metabolites. Drug Metab. Dispos., 1 Feb 2006, 34 (2), 281–287. 427 kB. doi:10.1124/dmd.105.005835.

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

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part I. Characterisation of the Speeter and Anthony synthetic route to 5-methoxy-N,N-diisopropyltryptamine using ESI-MS-MS and ESI-TOF-MS. Analyst, 2004, 129 (11), 1047–1057. 420 kB. doi:10.1039/b407239c

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Shulgin, AT; Carter, MF. N,N-diisopropyltryptamine (DIPT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT). Two orally active tryptamine analogs with CNS activity. Commun. Psychopharmacol., 1 Jan 1981, 4 (5), 363–369. 1166 kB.

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Shulgin, AT. 5-Methoxy-N-ethyl-N-isopropyltryptamine, 5-MeO-MIPT, 5-MeO-DIPT, 5-MeO-EIPT. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 27 Feb 2002.

Tanaka, E; Kamata, T; Katagi, M; Tsuchihashi, H; Honda, K. A fatal poisoning with 5-methoxy-N,N-diisopropyltryptamine, Foxy. Forensic Sci. Int., 1 Jan 2006, 163 (1), 152–154. 105 kB. doi:10.1016/j.forsciint.2005.11.026

Wilson, JM; McGeorge, F; Smolinske, S; Meatherall, R. A foxy intoxication. Forensic Sci. Int., 1 Jan 2005, 148 (1), 31–36. 160 kB. doi:10.1016/j.forsciint.2004.04.017

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

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

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. doi:10.1016/j.talanta.2007.06.012

5173
Isomer 2

4-MeO-DIPT
N,N-Diisopropyl-4-methoxytryptamine

IUPAC: N-[2-(4-Methoxy-1H-indol-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: WIVWUNUDMXNQJD-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-12(2)19(13(3)4)10-9-14-11-18-15-7-6-8-16(20-5)17(14)15/h6-8,11-13,18H,9-10H2,1-5H3

PubChem CID: 24802108; ChemSpider: 21436143

See also TiHKAL: #46 5-MeS-DMT  
5202
Isomer 3

7-MeO-DIPT
N,N-Diisopropyl-7-methoxytryptamine

IUPAC: N-[2-(7-Methoxy-1H-indol-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: CYDOUMFFIKOFBJ-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-12(2)19(13(3)4)10-9-14-11-18-17-15(14)7-6-8-16(17)20-5/h6-8,11-13,18H,9-10H2,1-5H3

5595
Isomer 4

5-EtO-MPT

IUPAC: N-[2-(5-Ethoxy-1H-indol-3-yl)ethyl]-N-ethylpropan-1-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: CPUKUBXQOYIGNB-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-4-10-19(5-2)11-9-14-13-18-17-8-7-15(20-6-3)12-16(14)17/h7-8,12-13,18H,4-6,9-11H2,1-3H3

Tearavarich, R; Hahnvajanawong, V; Dempster, N; Daley, PF; Cozzi, NV; Brandt, SD. Microwave-accelerated preparation and analytical characterization of 5-ethoxy-N,N-dialkyl-[α,α,β,β-H4]- and [α,α,β,β-D4]-tryptamines. Drug Test. Anal., 1 Sep 2011, 3 (9), 597–608. 253 kB. doi:10.1002/dta.223

5591
Isomer 5

5-EtO-EIPT

IUPAC: N-[2-(5-Ethoxy-1H-indol-3-yl)ethyl]-N-ethylpropan-2-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: PEACSMHHYVUVNO-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-5-19(13(3)4)10-9-14-12-18-17-8-7-15(20-6-2)11-16(14)17/h7-8,11-13,18H,5-6,9-10H2,1-4H3

Tearavarich, R; Hahnvajanawong, V; Dempster, N; Daley, PF; Cozzi, NV; Brandt, SD. Microwave-accelerated preparation and analytical characterization of 5-ethoxy-N,N-dialkyl-[α,α,β,β-H4]- and [α,α,β,β-D4]-tryptamines. Drug Test. Anal., 1 Sep 2011, 3 (9), 597–608. 253 kB. doi:10.1002/dta.223

5581
Isomer 6

5-MeO-2-Me-EPT

IUPAC: N-Ethyl-N-[2-(5-methoxy-2-methyl-1H-indol-3-yl)ethyl]propan-1-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: VLKQAXHAXKFIGX-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-5-10-19(6-2)11-9-15-13(3)18-17-8-7-14(20-4)12-16(15)17/h7-8,12,18H,5-6,9-11H2,1-4H3

Brandt, SD; Tearavarich, R; Dempster, N; Cozzi, NV; Daley, PF. Synthesis and characterization of 5-methoxy-2-methyl-N,N-dialkylated tryptamines. Drug Test. Anal., 1 Jan 2012, 4 (1), 24–32. 506 kB. doi:10.1002/dta.398

5579
Isomer 7

5-MeO-2-Me-EIPT

IUPAC: N-Ethyl-N-[2-(5-methoxy-2-methyl-1H-indol-3-yl)ethyl]propan-2-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: HNAFTRUGXTWVHI-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-6-19(12(2)3)10-9-15-13(4)18-17-8-7-14(20-5)11-16(15)17/h7-8,11-12,18H,6,9-10H2,1-5H3

Brandt, SD; Tearavarich, R; Dempster, N; Cozzi, NV; Daley, PF. Synthesis and characterization of 5-methoxy-2-methyl-N,N-dialkylated tryptamines. Drug Test. Anal., 1 Jan 2012, 4 (1), 24–32. 506 kB. doi:10.1002/dta.398

5686
Isomer 8

IUPAC: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methylpentan-1-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: YSLSTFPGMGOQRJ-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-4-5-6-10-19(2)11-9-14-13-18-17-8-7-15(20-3)12-16(14)17/h7-8,12-13,18H,4-6,9-11H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5869
Isomer 9

IUPAC: N,N-Diethyl-2-[5-(propan-2-yloxy)-1H-indol-3-yl]ethan-1-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: CFUWVCMXEVUGJW-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-5-19(6-2)10-9-14-12-18-17-8-7-15(11-16(14)17)20-13(3)4/h7-8,11-13,18H,5-6,9-10H2,1-4H3

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5868
Isomer 10

IUPAC: N,N-Diethyl-2-(5-propoxy-1H-indol-3-yl)ethan-1-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: CNCIKGYNYFWJEE-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-4-11-20-15-7-8-17-16(12-15)14(13-18-17)9-10-19(5-2)6-3/h7-8,12-13,18H,4-6,9-11H2,1-3H3

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5863
Isomer 11

IUPAC: 2-[5-(Hexyloxy)-1H-indol-3-yl]-N-methylethan-1-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: YAUPVUHPFUVZMN-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-3-4-5-6-11-20-15-7-8-17-16(12-15)14(13-19-17)9-10-18-2/h7-8,12-13,18-19H,3-6,9-11H2,1-2H3

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

Show all 103 analogues and isomers Show only the 84 N analogues Show only the one R2 analogues Show only the three R5 analogues Show only the four skeleton analogues
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