D-Phenylalanine

D-Phenylalanine
Clinical data
Trade names	Deprenon, Sabiben, Sabiden
Other names	D-(+)-Phenylalanine; (R)-(+)-Phenylalanine; (R)-Phenylalanine; D-β-Phenylalanine; DPA; D-Phe
Routes of; administration	By mouth
Drug class	Antidepressants; Enkephalinase inhibitors
Identifiers
	IUPAC name (2R)-2-amino-3-phenylpropanoic acid;
CAS Number	673-06-3;
PubChem CID	71567;
DrugBank	DB02556;
ChemSpider	64639;
UNII	032K16VRCU;
KEGG	C02265;
ChEBI	CHEBI:16998;
ChEMBL	ChEMBL379630;
CompTox Dashboard (EPA)	DTXSID4025876 ;
ECHA InfoCard	100.010.549
Chemical and physical data
Formula	C9H11NO2
Molar mass	165.192 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC=C(C=C1)C[C@H](C(=O)O)N;
	InChI 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]

References

^ ^a ^b Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Index nominum. Medpharm Scientific Publishers. p. 825. ISBN 978-3-88763-075-1. Retrieved 23 July 2024.
^ Negwer, M. (1994). Organic-chemical Drugs and Their Synonyms: (an International Survey). Organic-chemical Drugs and Their Synonyms:. 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{{cite book}}: CS1 maint: extra punctuation (link)
^ Unlisted Drugs. Unlisted Drugs Committee of the Pharmaceutical Section, Science-Technology Group, Special Libraries Association. 1979. Retrieved 23 July 2024.
^ ^a ^b Millinger GS (April 1986). "Neutral amino acid therapy for the management of chronic pain". Cranio. 4 (2): 157–163. PMID 3519793.
^ 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.
^ 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.
^ 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.
^ 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.

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[IndexNominum2000-1] Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Index nominum. Medpharm Scientific Publishers. p. 825. ISBN 978-3-88763-075-1. Retrieved 23 July 2024.

[Negwer1994-2] Negwer, M. (1994). Organic-chemical Drugs and Their Synonyms: (an International Survey). Organic-chemical Drugs and Their Synonyms:. 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{{cite book}}: CS1 maint: extra punctuation (link)

[UnlistedDrugs1979-3] Unlisted Drugs. Unlisted Drugs Committee of the Pharmaceutical Section, Science-Technology Group, Special Libraries Association. 1979. Retrieved 23 July 2024.

[Millinger1986-4] Millinger GS (April 1986). "Neutral amino acid therapy for the management of chronic pain". Cranio. 4 (2): 157–163. PMID 3519793.

[ThanawalaKadamGhosh2008-5] 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.

[TrachtenbergBlum1987-6] 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.

[BlumBaronMcLaughlin2020-7] 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.

[BlumFeboBadgaiyan2016-8] 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.

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[5]

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See also

References