D-Phenylalanine

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

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| IUPAC_name = (2R)-2-amino-3-phenylpropanoic acid

| image = D-Phenylalanine.svg

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| tradename = Deprenon, Sabiben, Sabiden

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| routes_of_administration = By mouth

| class = Antidepressants; Enkephalinase inhibitors

| bioavailability =

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| CAS_number_Ref =

| CAS_number = 673-06-3

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| PubChem = 71567

| IUPHAR_ligand =

| DrugBank_Ref =

| DrugBank = DB02556

| ChemSpiderID_Ref =

| ChemSpiderID = 64639

| UNII = 032K16VRCU

| KEGG = C02265

| ChEBI = 16998

| ChEMBL = 379630

| synonyms = {{Small|D}}-(+)-Phenylalanine; (R)-(+)-Phenylalanine; (R)-Phenylalanine; {{Small|D}}-β-Phenylalanine; DPA; {{Small|D}}-Phe

| C=9 | H=11 | N=1 | O=2

| SMILES = C1=CC=C(C=C1)C[C@H](C(=O)O)N

| StdInChI_Ref =

| StdInChI = 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

| StdInChIKey_Ref =

| StdInChIKey = COLNVLDHVKWLRT-MRVPVSSYSA-N

}}

{{Small|D}}-Phenylalanine (DPA, {{Small|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.{{cite book | author=Schweizerischer Apotheker-Verein | title=Index Nominum 2000: International Drug Directory | publisher=Medpharm Scientific Publishers | year=2000 | isbn=978-3-88763-075-1 | url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA825 | access-date=23 July 2024 | page=825}}{{cite book | last=Negwer | first=M. | title=Organic-chemical Drugs and Their Synonyms: (an International Survey) | publisher=Akademie Verlag | year=1994 | isbn=978-3-05-500156-7 | url=https://books.google.com/books?id=1ghtAAAAMAAJ | access-date=23 July 2024 | page=323 | quote = D-Phenylalanine (●) D-α-Amino-β-phenylpropionic acid = (R)-α-Aminobenzenepropanoic acid S Deprenon "Promeco", D-Phenylalanine, Sabiden U Antidepressant}} The medication has been marketed since at least the 1970s{{cite book | title=Unlisted Drugs | publisher=Unlisted Drugs Committee of the Pharmaceutical Section, Science-Technology Group, Special Libraries Association | issue=v. 31 | year=1979 | url=https://books.google.com/books?id=WCZRAQAAIAAJ | access-date=23 July 2024 | page=}} and continued to be available by the 2000s.

{{Small|D}}-Phenylalanine has been found to act as an enkephalinase inhibitor, an inhibitor of enkephalinase enzymes that break down endogenous opioid peptides called enkephalins.{{cite journal | vauthors = Millinger GS | title = Neutral amino acid therapy for the management of chronic pain | journal = Cranio | volume = 4 | issue = 2 | pages = 157–163 | date = April 1986 | pmid = 3519793 | doi = 10.1080/08869634.1986.11678141| url = }}{{cite journal | vauthors = Thanawala V, Kadam VJ, Ghosh R | title = Enkephalinase inhibitors: potential agents for the management of pain | journal = Curr Drug Targets | volume = 9 | issue = 10 | pages = 887–894 | date = October 2008 | pmid = 18855623 | doi = 10.2174/138945008785909356 | url = }} It has been found to produce anti-inflammatory, analgesic, and anti-craving effects in animal studies.{{cite journal | vauthors = Trachtenberg MC, Blum K | title = Alcohol and opioid peptides: neuropharmacological rationale for physical craving of alcohol | journal = Am J Drug Alcohol Abuse | volume = 13 | issue = 3 | pages = 365–372 | date = 1987 | pmid = 2825513 | doi = 10.3109/00952998709001520 | url = }}{{cite journal | vauthors = Blum K, Baron D, McLaughlin T, Gold MS | title = Molecular neurological correlates of endorphinergic/dopaminergic mechanisms in reward circuitry linked to endorphinergic deficiency syndrome (EDS) | journal = J Neurol Sci | volume = 411 | issue = | pages = 116733 | date = April 2020 | pmid = 32088516 | doi = 10.1016/j.jns.2020.116733 | url = }}{{cite journal | vauthors = Blum K, Febo M, Badgaiyan RD, Braverman ER, Dushaj K, Li M, Demetrovics Z | title = Neuronutrient Amino-Acid Therapy Protects Against Reward Deficiency Syndrome: Dopaminergic Key to Homeostasis and Neuroplasticity | journal = Curr Pharm Des | volume = 22 | issue = 38 | pages = 5837–5854 | date = 2016 | pmid = 27510492 | doi = 10.2174/1381612822666160719111346 | url = }}