Pivenfrine

Pivenfrine (INNTooltip International Nonproprietary Name), also known as pivalylphenylephrine or phenylephrine pivalate, is a sympathomimetic and mydriatic agent which was never marketed.^[1][2][3][4] It is the 3-pivalyl ester of phenylephrine.^[1] Pivenfrine has much greater lipophilicity than phenylephrine.^[5] Higher lipophilicity is known to greatly improve corneal permeability, as in dipivefrine (epinephrine dipivalate).^[6] Another related compound is etilefrine pivalate (ethylnorphenylephrine pivalate).^[1]

Pivenfrine

Clinical data
Other names	Pivalylphenylephrine; Phenylephrine pivalate; β,3-Dihydroxy-N-methylphenethylamine 3-pivalate
ATC code	None
Identifiers
IUPAC name 3-[1-Hydroxy-2-(methylamino)ethyl]phenyl pivalate
CAS Number	67577-23-5
PubChem CID	130545
ChemSpider	115481
UNII	RB4XQ0T71U
ChEMBL	ChEMBL2107163
CompTox Dashboard (EPA)	DTXSID80867279
Chemical and physical data
Formula	C14H21NO3
Molar mass	251.326 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)(C)C(=O)Oc1cccc(c1)C(CNC)O
InChI InChI=1S/C14H21NO3/c1-14(2,3)13(17)18-11-7-5-6-10(8-11)12(16)9-15-4/h5-8,12,15-16H,9H2,1-4H3 Key:DQCAWJLMFJKICG-UHFFFAOYSA-N