Exploring 5-MeO-DMT. To explore a different substance…

Names:
5-MeO-DMT · N,N,O-TMS · OMB · Bufotenine methyl ether · Tryptamine, 5-methoxy-N,N-dimethyl · N,N,O-Trimethylserotonin · Indole, 5-methoxy-3-[2-(dimethylamino)ethyl] · 5-Methoxy-N,N-dimethyltryptamine · O-Methylbufotenine · 5-Methoxy-3-[2-(dimethylamino)ethyl]indole
IUPAC name:
2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine
ID: 5038 · Formula: C13H18N2O · Molecular weight: 218.295
InChI: 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

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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. http://dx.doi.org/10.1007/s00213-011-2616-6

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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. http://dx.doi.org/10.1039/b413014f

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Glennon, RA; Titeler, M; McKenney, JD. Evidence for 5-HT2 involvement in the mechanism of action of hallucinogenic agents. Life Sci., 17 Dec 1984, 35 (25), 2505–2511. 332 kB. http://dx.doi.org/10.1016/0024-3205(84)90436-3

Schmid, CL; Bohn, LM. Serotonin, but not N-methyltryptamines, activates the serotonin 2A receptor via a β-arrestin2/Src/Akt signaling complex in vivo. J. Neurosci., 6 Oct 2010, 30 (40), 13513–13524. 1.5 MB. http://dx.doi.org/10.1523/JNEUROSCI.1665-10.2010

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. http://dx.doi.org/10.1016/0014-2999(81)90106-0

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, 1 Oct 2014, 231 (21), 4135-4144. 298 kB. http://dx.doi.org/10.1007/s00213-014-3557-7

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. http://dx.doi.org/10.1021/jo01106a046

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.

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., 1 Dec 2013, 27 (12), 1690-1700. 929 kB. http://dx.doi.org/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. http://dx.doi.org/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. 1.0 MB. http://dx.doi.org/10.1002/bmc.1551

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. 12.2 MB.

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. http://dx.doi.org/10.1124/mol.107.039255

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. http://dx.doi.org/10.1002/jlcr.1557

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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1016/0024-3205(68)90200-2

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. http://dx.doi.org/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. http://dx.doi.org/10.1016/j.neuropharm.2011.01.017

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

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

Callaway, J; 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. http://dx.doi.org/10.1093/jat/30.6.406

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB.

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. http://dx.doi.org/10.1016/0024-3205(91)90582-V

Winter, J; Filipink, R; Timineri, D; Helsley, S; Rabin, R. 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. http://dx.doi.org/10.1016/S0091-3057(99)00178-1

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

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. http://dx.doi.org/10.1016/S0376-8716(99)00148-9

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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. http://dx.doi.org/10.1039/b504001a

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Melatonin
5-MeO-DET
5-MeO-DIPT
5-MeO-MIPT
5-MeO-NMT
5-MeO-DPT
5-MeO-NCPT
5-MeO-T
N-Hexanoyl-5-MeO-T
N-Octanoyl-5-MeO-T
N-Heptafluorobutyroyl-5-MeO-T
5-MeO-DALT
5MT-NBOMe · 5MT-NB2OMe
5-MeO-EIPT
5-MeO-NALT
5-MeO-DPRT
5-MeO-MET
5MT-NB
5MT-NBOH
5MT-NB2OTFM
5MT-NB4OMe
5MT-NB4NO2
5MT-NB4NH2
5MT-NB4Me
5MT-NB4I
5-MeO-NBpBrT · 5MT-NB4B
5MT-NB4Cl
5MT-NB4F
5-MeO-NET
428
427
5-MeO-NIPT
5-MeO-MPT
5-MeO-EPT
5-MeO-DIBT
5-MeO-DBT
5-MeO-MIBT
5655
5657
5658
5659
5660
5661
5662
5663
5664
5665
5666
5667
5668
5669
5670
5671
5672
5673
5674
5675
5676
5677
5678
5679
5680
5681
5682
5683
5684
5685
5686
5687
5688
5689
5690
5691
5692
5694
5-MeO-MALT
5696
5697
5698
Methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylglycinate
tert-Butyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylglycinate
N2-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N2-methylglycinamide
5712
5713
5MT-NB3TFM
5MT-NB3Me
5MT-NB3I
5MT-NB3Cl
5MT-NB3F
5MT-NB3B
5MT-NB2B · 5MT-NBBr
5MT-NB3OMe
5MT-NB3SMe
5-MeO-DMT N-oxide
α,N,N,O-Tetramethylserotonin
1-iPr-5-MeO-DMT
5-MeO-1-Me-DMT
1-Et-5-MeO-DMT
5-MeO-1-Pr-DMT
5-MeO-2-Me-DMT · 5-MeO-TMT
EMDT
PMDT
5-MeO-2-Pr-DMT
4-HO-5-MeO-DMT
DMT
5-HO-DMT
5-MeS-DMT
5-Br-DMT
Bufoviridine
5-EtO-DMT
5-AcO-DMT
5,N,N-TMT
Sumatriptan
5-F-DMT
5-Et-DMT
5-Chloro-DMT
5-TMS-DMT
5-Ac-DMT
5-Cam-DMT
6-HO-5-MeO-DMT
5,6-MeO-DMT
5,6-MeOM-DMT
6-F-5-MeO-DMT
7-Me-5-MeO-DMT
5,7-MeO-DMT
5-MeO-pyr-T
5-MeO-mor-T
5-MeO-pip-T
5-MeO-MPMI
5-MeO-BFE · Dimemebfe
5-MeO-ICPA
5-MeO-N-Me-IPYR
5768
4-HO-MET
α,N,O-TMS
1-MeO-DMT · Lespedamine
CMY · 1-Methylpsilocin
5-MeO-α-ET
4-MeO-DMT
6-MeO-DMT
7-MeO-DMT
5-HTQ · Bufotenidine
5-MeO-NET
2-Methylpsilocin
α-Methylpsilocin
4-HO-DMHT
1-Methylbufotenine
5859
5852
5851
Melatonin
5-MeO-DET
5-MeO-DIPT
5-MeO-MIPT
5-MeO-NMT
5-MeO-DPT
5-MeO-NCPT
5-MeO-T
N-Hexanoyl-5-MeO-T
N-Octanoyl-5-MeO-T
N-Heptafluorobutyroyl-5-MeO-T
5-MeO-DALT
5MT-NBOMe · 5MT-NB2OMe
5-MeO-EIPT
5-MeO-NALT
5-MeO-DPRT
5-MeO-MET
5MT-NB
5MT-NBOH
5MT-NB2OTFM
5MT-NB4OMe
5MT-NB4NO2
5MT-NB4NH2
5MT-NB4Me
5MT-NB4I
5-MeO-NBpBrT · 5MT-NB4B
5MT-NB4Cl
5MT-NB4F
5-MeO-NET
428
427
5-MeO-NIPT
5-MeO-MPT
5-MeO-EPT
5-MeO-DIBT
5-MeO-DBT
5-MeO-MIBT
5655
5657
5658
5659
5660
5661
5662
5663
5664
5665
5666
5667
5668
5669
5670
5671
5672
5673
5674
5675
5676
5677
5678
5679
5680
5681
5682
5683
5684
5685
5686
5687
5688
5689
5690
5691
5692
5694
5-MeO-MALT
5696
5697
5698
Methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylglycinate
tert-Butyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylglycinate
N2-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N2-methylglycinamide
5712
5713
5MT-NB3TFM
5MT-NB3Me
5MT-NB3I
5MT-NB3Cl
5MT-NB3F
5MT-NB3B
5MT-NB2B · 5MT-NBBr
5MT-NB3OMe
5MT-NB3SMe
5-MeO-DMT N-oxide
α,N,N,O-Tetramethylserotonin
1-iPr-5-MeO-DMT
5-MeO-1-Me-DMT
1-Et-5-MeO-DMT
5-MeO-1-Pr-DMT
5-MeO-2-Me-DMT · 5-MeO-TMT
EMDT
PMDT
5-MeO-2-Pr-DMT
4-HO-5-MeO-DMT
DMT
5-HO-DMT
5-MeS-DMT
5-Br-DMT
Bufoviridine
5-EtO-DMT
5-AcO-DMT
5,N,N-TMT
Sumatriptan
5-F-DMT
5-Et-DMT
5-Chloro-DMT
5-TMS-DMT
5-Ac-DMT
5-Cam-DMT
6-HO-5-MeO-DMT
5,6-MeO-DMT
5,6-MeOM-DMT
6-F-5-MeO-DMT
7-Me-5-MeO-DMT
5,7-MeO-DMT
5-MeO-pyr-T
5-MeO-mor-T
5-MeO-pip-T
5-MeO-MPMI
5-MeO-BFE · Dimemebfe
5-MeO-ICPA
5-MeO-N-Me-IPYR
5768
4-HO-MET
α,N,O-TMS
1-MeO-DMT · Lespedamine
CMY · 1-Methylpsilocin
5-MeO-α-ET
4-MeO-DMT
6-MeO-DMT
7-MeO-DMT
5-HTQ · Bufotenidine
5-MeO-NET
2-Methylpsilocin
α-Methylpsilocin
4-HO-DMHT
1-Methylbufotenine
5859
5852
5851
22 June 2017 · Creative Commons BY-NC-SA ·