Piberaline

Piberaline
Clinical data
Trade names	Trelibet
ATC code	none;
Identifiers
	IUPAC name [4-(Phenylmethyl)piperazin-1-yl]-pyridin-2-ylmethanone;
CAS Number	39640-15-8;
PubChem CID	65975;
ChemSpider	59374;
UNII	8M09P36809;
CompTox Dashboard (EPA)	DTXSID40192751 ;
Chemical and physical data
Formula	C17H19N3O
Molar mass	281.359 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(CCN1CC2=CC=CC=C2)C(=O)C3=CC=CC=N3;
	InChI InChI=1S/C17H19N3O/c21-17(16-8-4-5-9-18-16)20-12-10-19(11-13-20)14-15-6-2-1-3-7-15/h1-9H,10-14H2; Key:TZFUBYYADABEAV-UHFFFAOYSA-N;
	(verify)

Piberaline (EGYT-475; Trelibet) is a psychoactive drug and member of the piperazine chemical class which was developed in the 1980s. It has stimulant and antidepressant effects which are thought to be due largely to its active metabolite benzylpiperazine.^[1] It was studied to a limited extent in Hungary and Spain, but was not widely accepted and does not seem to be in current use, although a closely related drug befuraline with similar effects has been slightly more successful.

Synthesis

Piberaline can be prepared by reaction of picolinic acid with benzylpiperazine.^[2]^[3]^[4]

Synthesis of piberaline

Alternatively, it can be synthesized from 2-chloropyridine, carbon monoxide, and benzylpiperazine.

References

^ Tekes K, Tóthfalusi L, Malomvölgyi B, Hermán F, Magyar K (1987). "Studies on the biochemical mode of action of EGYT-475, a new antidepressant". Polish Journal of Pharmacology and Pharmacy. 39 (2): 203–211. PMID 2448760.
^ DE 2215545, Korösi J, Erdelyi L, Balla I, Lay A, Szabo G, Kiszelly E, "Pyridinderivate und ihre Salze sowie ihre Verwendung und Verfahren zur Herstellung derselben [Pyridine derivatives and their salts and their use and processes for the preparation thereof]", issued 11 March 1976, assigned to Egyt Gyogyszervegyeszeti Gyar, Budapest.
^ Kumar K, Michalik D, Garcia Castro I, Tillack A, Zapf A, Arlt M, et al. (February 2004). "Biologically Active Compounds through Catalysis: Efficient Synthesis of N -(Heteroarylcarbonyl)- N ′-(arylalkyl)piperazines". Chemistry. 10 (3): 746–757. doi:10.1002/chem.200305327. PMID 14767940.
^ Younes S, Labssita Y, Baziard-Mouysset G, Payard M, Rettori M, Renard P, et al. (January 2000). "Synthesis and structure-activity relationships of novel arylalkyl 4-benzyl piperazine derivatives as sigma site selective ligands". European Journal of Medicinal Chemistry. 35 (1): 107–121. doi:10.1016/S0223-5234(00)00113-6. PMID 10733608.

[pmid2448760-1] Tekes K, Tóthfalusi L, Malomvölgyi B, Hermán F, Magyar K (1987). "Studies on the biochemical mode of action of EGYT-475, a new antidepressant". Polish Journal of Pharmacology and Pharmacy. 39 (2): 203–211. PMID 2448760.

[2] DE 2215545, Korösi J, Erdelyi L, Balla I, Lay A, Szabo G, Kiszelly E, "Pyridinderivate und ihre Salze sowie ihre Verwendung und Verfahren zur Herstellung derselben [Pyridine derivatives and their salts and their use and processes for the preparation thereof]", issued 11 March 1976, assigned to Egyt Gyogyszervegyeszeti Gyar, Budapest.

[3] Kumar K, Michalik D, Garcia Castro I, Tillack A, Zapf A, Arlt M, et al. (February 2004). "Biologically Active Compounds through Catalysis: Efficient Synthesis of N -(Heteroarylcarbonyl)- N ′-(arylalkyl)piperazines". Chemistry. 10 (3): 746–757. doi:10.1002/chem.200305327. PMID 14767940.

[4] Younes S, Labssita Y, Baziard-Mouysset G, Payard M, Rettori M, Renard P, et al. (January 2000). "Synthesis and structure-activity relationships of novel arylalkyl 4-benzyl piperazine derivatives as sigma site selective ligands". European Journal of Medicinal Chemistry. 35 (1): 107–121. doi:10.1016/S0223-5234(00)00113-6. PMID 10733608.

[1]

[2]

[3]

[4]

Piberaline

Synthesis

See also

References