Hopantenic acid

Hopantenic acid (homopantothenic acid), also known as N-pantoyl-GABA, is a central nervous system depressant. Formulated as the calcium salt, it is used as a pharmaceutical drug in the Russian Federation for a variety of neurological, psychological and psychiatric conditions and sold as Pantogam (Russian: Пантогам).[1] It is not approved for use in Europe or the United States.

Hopantenic acid

Names
IUPAC name 4-{[(2R)-2,4-Dihydroxy-3,3-dimethylbutanoyl]amino}butanoic acid
Identifiers
CAS Number	18679-90-8 17097-76-6 (Calcium salt)
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2110783
ChemSpider	26309
KEGG	D08042
PubChem CID	28281
UNII	H473MVB16U LK8EOC1M6K (Calcium salt)
CompTox Dashboard (EPA)	DTXSID6048331
InChI InChI=1S/C10H19NO5/c1-10(2,6-12)8(15)9(16)11-5-3-4-7(13)14/h8,12,15H,3-6H2,1-2H3,(H,11,16)(H,13,14)/t8-/m0/s1 Key: SBBDHANTMHIRGW-QMMMGPOBSA-N
SMILES CC(C)(CO)[C@@H](O)C(=O)NCCCC(O)=O
Properties
Chemical formula	C10H19NO5
Molar mass	233.264 g·mol^−1
Related compounds
Related alkanoic acids	Theanine Pantothenic acid 4-(γ-Glutamylamino)butanoic acid
Related compounds	Panthenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Chemistry

Hopantenic acid is a homologue of pantothenic acid. While pantothenic acid is the amide of D-pantoate and β-alanine, hopantenic acid is the amide of D-pantoate and γ-aminobutyric acid (GABA). This change leads to an additional CH₂ in the molecule.[2]

See also

• Methyl pentanoate
• Menthyl isovalerate

References

1. Pantogam, drugs.com
2. Kopelevich VM, Evdokimova GS, Marieva TD, Shmuilovich LM (1971). "Synthesis of D-homopantothenic acid". Pharmaceutical Chemistry Journal. 5 (9): 534–536. doi:10.1007/BF00771659 (inactive 2021-02-06).CS1 maint: DOI inactive as of February 2021 (link)

External links

• pantogab (hopantenic acid) - Curehunter.com