HP-505

HP-505
Identifiers
	IUPAC name 3-phenyl-3H-spiro[isobenzofuran-1,4'-piperidine];
JSmol)	Interactive image;
	SMILES C1(C2OC3(CCNCC3)C4=C2C=CC=C4)=CC=CC=C1;
	InChI InChI=1S/C18H19NO/c1-2-6-14(7-3-1)17-15-8-4-5-9-16(15)18(20-17)10-12-19-13-11-18/h1-9,17,19H,10-13H2; Key:ZFJQWOMHWFYLPD-UHFFFAOYSA-N;

HP-505 is a

Hoechst-Roussel Pharmaceuticals.^[1] In mice, HP-505 was a potent inhibitor of tetrabenazine-induced ptosis which may indicate antidepressant activity.^[2]

Pharmacology

HP-505 IC₅₀ (µM)^[1]
5-HT	NE	DA	NE:5-HT	DA:5-HT
0.19 ± 0.04	0.34 ± 0.1	0.66 ± 0.15	1.8	3.5

The inhibitory effect of HP-505 on serotonin reuptake is approximately 1.8 and 3.5 times stronger than on norepinephrine and dopamine, respectively.^[1] Subsequent investigations have found that HP-505 acts on presynaptic dopamine transporters and is devoid of anticholinergic effects.^[3]

Synthesis

The N-methylated analog is called HP-365 [59142-29-9].

An older synthesis is available, although more modern methods exist now:^[4]

References

^
S2CID 45400599
.

PMID 850252
.

ISBN 978-1-4832-8363-0
.

ISSN 0022-2623
.

^ Victor J. Bauer & Raymond W. Kosley, Jr., U.S. patent 3,959,475 (1976 to CNA Holdings LLC).

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[BETA-1] 
S2CID 45400599
.

[2] PMID 850252
.

[3] ISBN 978-1-4832-8363-0
.

[4] ISSN 0022-2623
.

[5] Victor J. Bauer & Raymond W. Kosley, Jr., U.S. patent 3,959,475 (1976 to CNA Holdings LLC).

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