Literature DB >> 33936768

'Foxtrot' fumarate: a water-soluble salt of N,N-di-allyl-5-methoxytryptamine (5-MeO-DALT).

Duyen N K Pham1, Vamshikrishna Reddy Sammeta1, Andrew R Chadeayne2, James A Golen1, David R Manke1.   

Abstract

The title compound, bis-(N,N-diallyl-5-meth-oxy-tryptammonium) (5-MeO-DALT) fumarate (systematic name: bis-{N-[2-(5-meth-oxy-1H-indol-3-yl)eth-yl]- N-(prop-2-en-1-yl)prop-2-en-1-aminium} (E)-but-2-enedioate), 2C17H23N2O+·C4H2O4 2-, has a single tryptammonium cation and half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by a series of N-H⋯O hydrogen bonds. These chains are combinations of R 4 4(22) rings, and C 2 2(14) and C 4 4(28) parallel chains along [111]. © Pham et al. 2021.

Entities:  

Keywords:  crystal structure; hydrogen bonding; indoles; tryptamines

Year:  2021        PMID: 33936768      PMCID: PMC8025863          DOI: 10.1107/S2056989021002838

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


  8 in total

1.  The epidemiology of 5-methoxy- N, N-dimethyltryptamine (5-MeO-DMT) use: Benefits, consequences, patterns of use, subjective effects, and reasons for consumption.

Authors:  Alan K Davis; Joseph P Barsuglia; Rafael Lancelotta; Robert M Grant; Elise Renn
Journal:  J Psychopharmacol       Date:  2018-04-30       Impact factor: 4.153

2.  Graph-set analysis of hydrogen-bond patterns in organic crystals.

Authors:  M C Etter; J C MacDonald; J Bernstein
Journal:  Acta Crystallogr B       Date:  1990-04-01

Review 3.  The recreational tryptamine 5-MeO-DALT (N,N-diallyl-5-methoxytryptamine): a brief review.

Authors:  John M Corkery; Emma Durkin; Simon Elliott; Fabrizio Schifano; A Hamid Ghodse
Journal:  Prog Neuropsychopharmacol Biol Psychiatry       Date:  2012-06-07       Impact factor: 5.067

Review 4.  Bufo alvarius: a potent hallucinogen of animal origin.

Authors:  A T Weil; W Davis
Journal:  J Ethnopharmacol       Date:  1994-01       Impact factor: 4.360

5.  Receptor binding profiles and quantitative structure-affinity relationships of some 5-substituted-N,N-diallyltryptamines.

Authors:  Nicholas V Cozzi; Paul F Daley
Journal:  Bioorg Med Chem Lett       Date:  2015-12-18       Impact factor: 2.823

6.  SHELXT - integrated space-group and crystal-structure determination.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A Found Adv       Date:  2015-01-01       Impact factor: 2.290

7.  Crystal structure refinement with SHELXL.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr C Struct Chem       Date:  2015-01-01       Impact factor: 1.172

8.  Synthesis and Characterization of 5-MeO-DMT Succinate for Clinical Use.

Authors:  Alexander M Sherwood; Romain Claveau; Rafael Lancelotta; Kristi W Kaylo; Kelsey Lenoch
Journal:  ACS Omega       Date:  2020-12-02
  8 in total

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