Glycinamide

Glycinamide
Names
	Preferred IUPAC name 2-Aminoacetamide
Identifiers
CAS Number	598-41-4 ; 1668-10-6 (HCl);
3D model (JSmol)	Interactive image ;
Beilstein Reference	635783
ChEBI	CHEBI:42843 ;
ChEMBL	ChEMBL86954 ;
ChemSpider	62242 ;
DrugBank	DB03636 ;
ECHA InfoCard	100.009.031
EC Number	209-932-4;
PubChem CID	69020 ;
UNII	4JDT453NWO ;
CompTox Dashboard (EPA)	DTXSID1060508 ;
	InChI InChI=1S/C2H6N2O/c3-1-2(4)5/h1,3H2,(H2,4,5) Key: BEBCJVAWIBVWNZ-UHFFFAOYSA-N;
	SMILES C(C(=O)N)N;
Properties
Chemical formula	C2H6N2O
Molar mass	74.083 g·mol−1
Appearance	white solid
Melting point	65–67 °C (149–153 °F; 338–340 K)
Boiling point	decomposes
Solubility in water	good
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Last updated August 28, 2025

Glycinamide is an organic compound with the molecular formula H₂NCH₂C(O)NH₂. It is the amide derivative of the amino acid glycine. It is a water-soluble, white solid. Amino acid amides, such as glycinamide are prepared by treating the amino acid ester with ammonia.^[1]

It is a ligand for transition metals, related to amino acid complexes. As a neutral ligand, it binds through the amine. In some complexes, it binds through the amine and the carbonyl oxygen, forming a five-membered chelate ring.^[2]

The hydrochloride salt of glycinamide, glycinamide hydrochloride, is one of Good's buffers with a pH in the physiological range. Glycinamide hydrochloride has a pKa near the physiological pH (8.20 at 20°C), making it useful in cell culture work. Its ΔpKa/°C is -0.029 and it has a solubility in water at 0 °C of 6.4 M.

Glycinamide is a reagent used in the synthesis of glycineamide ribonucleotide (an intermediate in de novo purine biosynthesis).^[3]

References

↑ Yang, Peter S.; Rising, Mary M. (1931). "A Simplified Method of Preparation of Alpha Amino Acid Amides". Journal of the American Chemical Society. 53 (8): 3183–3184. Bibcode:1931JAChS..53.3183Y. doi:10.1021/ja01359a505.
↑ Appleton, Trevor G. (1997). "Donor Atom Preferences in Complexes of Platinum and Palladium with Amino Acids and Related Molecules". Coordination Chemistry Reviews. 166: 313–359. doi:10.1016/S0010-8545(97)00047-7.
↑ "Glycinamide hydrochloride". Gold Biotechnology. Archived from the original on 2017-12-15. Retrieved 2017-07-23.

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[1] Yang, Peter S.; Rising, Mary M. (1931). "A Simplified Method of Preparation of Alpha Amino Acid Amides". Journal of the American Chemical Society. 53 (8): 3183–3184. Bibcode:1931JAChS..53.3183Y. doi:10.1021/ja01359a505.

[2] Appleton, Trevor G. (1997). "Donor Atom Preferences in Complexes of Platinum and Palladium with Amino Acids and Related Molecules". Coordination Chemistry Reviews. 166: 313–359. doi:10.1016/S0010-8545(97)00047-7.

[3] "Glycinamide hydrochloride". Gold Biotechnology. Archived from the original on 2017-12-15. Retrieved 2017-07-23.

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[2]

[3]

Names

Preferred IUPAC name 2-Aminoacetamide
Identifiers
CAS Number	598-41-4 ^Y 1668-10-6 (HCl)
3D model (JSmol)	Interactive image
Beilstein Reference	635783
ChEBI	CHEBI:42843
ChEMBL	ChEMBL86954
ChemSpider	62242
DrugBank	DB03636
ECHA InfoCard	100.009.031
EC Number	209-932-4
PubChem CID	69020
UNII	4JDT453NWO ^Y
CompTox Dashboard (EPA)	DTXSID1060508
InChI InChI=1S/C2H6N2O/c3-1-2(4)5/h1,3H2,(H2,4,5) Key: BEBCJVAWIBVWNZ-UHFFFAOYSA-N
SMILES C(C(=O)N)N
Properties
Chemical formula	C₂H₆N₂O
Molar mass	74.083 g·mol⁻¹
Appearance	white solid
Melting point	65–67 °C (149–153 °F; 338–340 K)
Boiling point	decomposes
Solubility in water	good
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references