D-Phenylalanine

D-Phenylalanine
Clinical data
Trade namesDeprenon, Sabiben, Sabiden
Other namesD-(+)-Phenylalanine; (R)-(+)-Phenylalanine; (R)-Phenylalanine; D-β-Phenylalanine; DPA; D-Phe
Routes of
administration		By mouth
Drug classAntidepressants; Enkephalinase inhibitors
Identifiers
  • (2R)-2-amino-3-phenylpropanoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.010.549 Edit this at Wikidata
Chemical and physical data
FormulaC9H11NO2
Molar mass165.192 g·mol−1
3D model (JSmol)
  • C1=CC=C(C=C1)C[C@H](C(=O)O)N
  • InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m1/s1
  • Key:COLNVLDHVKWLRT-MRVPVSSYSA-N

D-Phenylalanine (DPA, D-Phe), sold under the brand names Deprenon, Sabiben, and Sabiden, is an enantiomer of phenylalanine which is described as an antidepressant and is marketed as a prescription drug for medical use in Argentina.[1][2] The medication has been marketed since at least the 1970s[3] and continued to be available by the 2000s.[1]

D-Phenylalanine has been found to act as an enkephalinase inhibitor, an inhibitor of enkephalinase enzymes that break down endogenous opioid peptides called enkephalins.[4][5] It has been found to produce anti-inflammatory, analgesic, and anti-craving effects in animal studies.[4][6][7][8]

  1. ^ a b Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 825. ISBN 978-3-88763-075-1. Retrieved 23 July 2024.
  2. ^ Negwer, M. (1994). Organic-chemical Drugs and Their Synonyms: (an International Survey). Akademie Verlag. p. 323. ISBN 978-3-05-500156-7. Retrieved 23 July 2024. D-Phenylalanine (●) D-α-Amino-β-phenylpropionic acid = (R)-α-Aminobenzenepropanoic acid S Deprenon "Promeco", D-Phenylalanine, Sabiden U Antidepressant
  3. ^ Unlisted Drugs. Unlisted Drugs Committee of the Pharmaceutical Section, Science-Technology Group, Special Libraries Association. 1979. Retrieved 23 July 2024.
  4. ^ a b Millinger GS (April 1986). "Neutral amino acid therapy for the management of chronic pain". Cranio. 4 (2): 157–163. doi:10.1080/08869634.1986.11678141. PMID 3519793.
  5. ^ Thanawala V, Kadam VJ, Ghosh R (October 2008). "Enkephalinase inhibitors: potential agents for the management of pain". Curr Drug Targets. 9 (10): 887–894. doi:10.2174/138945008785909356. PMID 18855623.
  6. ^ Trachtenberg MC, Blum K (1987). "Alcohol and opioid peptides: neuropharmacological rationale for physical craving of alcohol". Am J Drug Alcohol Abuse. 13 (3): 365–372. doi:10.3109/00952998709001520. PMID 2825513.
  7. ^ Blum K, Baron D, McLaughlin T, Gold MS (April 2020). "Molecular neurological correlates of endorphinergic/dopaminergic mechanisms in reward circuitry linked to endorphinergic deficiency syndrome (EDS)". J Neurol Sci. 411: 116733. doi:10.1016/j.jns.2020.116733. PMID 32088516.
  8. ^ Blum K, Febo M, Badgaiyan RD, Braverman ER, Dushaj K, Li M, Demetrovics Z (2016). "Neuronutrient Amino-Acid Therapy Protects Against Reward Deficiency Syndrome: Dopaminergic Key to Homeostasis and Neuroplasticity". Curr Pharm Des. 22 (38): 5837–5854. doi:10.2174/1381612822666160719111346. PMID 27510492.