Ethylenediaminetetraacetic Acid → N-Acetyltryptamine

Participants

Role	Name	HCID	Charge
Reactant	Ethylenediaminetetraacetic Acid	HCID 6049	—
Reactant	5,5'-Dithiobis(2-nitrobenzoic Acid)	HCID 6254	—
Reactant	Acetic Anhydride	HCID 7918	—
Reactant	Tryptophol	HCID 10685	—
Reactant	Trisodium Phosphate	HCID 24243	—
Reactant	Tryptamine hydrochloride	HCID 67652	—
Reactant	Adenosine 5'-(trihydrogen diphosphate), 3'-(dihydrogen phosphate), P'-((3R)-4-((3-(ethylamino)-3-oxopropyl)amino)-3-hydroxy-2,2-dimethyl-4-oxobutyl) ester	HCID 165363	—
Reactant	acetyl CoA	HCID 444493	—
Reactant	D-1,4-Dithiothreitol	HCID 446094	—
Reactant	[14C]acetylCoA	HCID 73755097	—
Solvent	Triethylamine	HCID 8471	—
Product	N-Acetyltryptamine	HCID 70547	88%

Reaction Steps

The following were purchased: acetyl-CoA (Pharmacia Biotech Inc.); tryptamine-HCl, desulfo-CoA, glutathione-agarose, DTNB (Sigma); sodium phosphate, dithiothreitol, guanidinium-HCl, EDTA (Fisher Scientific); tryptophol (Aldrich); and [14C]acetyl-CoA (60 Ci/mol) (NEN Life Science Products). N-acetyltryptamine was synthesized by reacting tryptamine-HCl (500 mg, 2.5 mmol) with acetic anhydride (260 mg, 2.5 mmol) in the presence of excess triethylamine (1.75 ml). After vigorous stirring at room temperature for 50 min, the mixture was partitioned between ethyl acetate (80 ml) and water (70 ml). The organic phase was washed with saturated aqueous NaHCO3 (50 ml), 0.1 M HCl (50 ml), Na2SO4 (anhydride), and the resultant was concentrated in vacuo to afford N-acetyltryptamine as off-white crystals (88% yield). Purity (>95%) was established by TLC and 1H NMR.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05990094
Source dataset	uspto-grants-1999_11
ORD ID	ord-00039a8ac5c842b9bf35fb31b52ea998
Source note	uspto-grants-1999_11