DA-Phen

DA-Phen, also known as dopamine–phenylalanine conjugate, is a synthetic dopamine prodrug which is under preclinical evaluation.^{[1][2][3][4][5][6][7]} Dopamine itself is hydrophilic and is unable to cross the blood–brain barrier, thus showing peripheral selectivity.^[2] DA-Phen was developed as a dopamine prodrug that would allow for entry into the central nervous system via passive diffusion and/or active transport.^[1][2]

DA-Phen

Clinical data
Other names	DA-Phe; DA-PHEN; Dopamine–phenylalanine conjugate
Drug class	Monoamine precursor; Dopamine receptor agonist
Identifiers
IUPAC name 2-amino-N-[2-(3,4-dihydroxyphenyl)ethyl]-3-phenylpropanamide
CAS Number	54653-55-3 Y
PubChem CID	21426279
ChemSpider	9522051
Chemical and physical data
Formula	C17H20N2O3
Molar mass	300.358 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC=C(C=C1)CC(C(=O)NCCC2=CC(=C(C=C2)O)O)N
InChI InChI=1S/C17H20N2O3/c18-14(10-12-4-2-1-3-5-12)17(22)19-9-8-13-6-7-15(20)16(21)11-13/h1-7,11,14,20-21H,8-10,18H2,(H,19,22) Key:NBYUYHYHFPOSLI-UHFFFAOYSA-N

DA-Phen is a conjugate of dopamine and the amino acid phenylalanine (Phe or Phen).^[1][2] It is slowly cleaved by brain enzymes (t_½ = 460 minutes) to yield free dopamine but is also rapidly hydrolyzed in human blood plasma (t_½ = 28 minutes).^[2] The drug was intended as a prodrug but may also directly interact with the dopamine D₁-like and/or D₂-like receptors.^[1][5][4][6] DA-Phen has shown centrally mediated effects in animals, including increased cognitive flexibility, improved spatial learning and memory, antidepressant- and anxiolytic-like effects, and decreased ethanol intake.^[1][7][5]

Other analogues, such as DA-Trp and DA-Leu, have also been developed and studied.^[4]

See also

• Neurotransmitter prodrug
• Lisdexamfetamine (dextroamphetamine–lysine conjugate)
• DopAmide
• Docarpamine