Synonym
Gepirone; Gepirona; Gepironum; BMY-13805; BMY 13805; BMY13805; MJ-13805; MJ 13805; MJ13805;
IUPAC/Chemical Name
4,4-Dimethyl-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]piperidine-2,6-dione
InChi Key
QOIGKGMMAGJZNZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H29N5O2/c1-19(2)14-16(25)24(17(26)15-19)9-4-3-8-22-10-12-23(13-11-22)18-20-6-5-7-21-18/h5-7H,3-4,8-15H2,1-2H3
SMILES Code
O=C(CC(C)(C)C1)N(CCCCN2CCN(C3=NC=CC=N3)CC2)C1=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
A selective 5-HT(1A) agonist.
In vivo activity:
GEP (gepirone) increased the escape latency of W animals exposed or non-exposed to IS, but did not affect the response of PCM animals, while chlordiazepoxide reduced the escape deficit of both W and PCM rats. The data suggest that PCM animals were more sensitive to the impairment produced by LH and that PCM led to neurochemical changes in the serotonergic system, resulting in hyporeactivity to the anxiogenic effects of GEP in the LH paradigm.
Reference: Braz J Med Biol Res. 2008 Jan;41(1):54-9. https://pubmed.ncbi.nlm.nih.gov/17952336/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
359.47
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Camargo LM, Nascimento AB, Almeida SS. Differential response to gepirone but not to chlordiazepoxide in malnourished rats subjected to learned helplessness. Braz J Med Biol Res. 2008 Jan;41(1):54-9. doi: 10.1590/s0100-879x2006005000187. Epub 2007 Dec 17. PMID: 17952336.
2. Pruus K, Skrebuhhova-Malmros T, Rudissaar R, Matto V, Allikmets L. 5-HT1A receptor agonists buspirone and gepirone attenuate apomorphine-induced aggressive behaviour in adult male Wistar rats. J Physiol Pharmacol. 2000 Dec;51(4 Pt 2):833-46. PMID: 11220492.
In vivo protocol:
1. Camargo LM, Nascimento AB, Almeida SS. Differential response to gepirone but not to chlordiazepoxide in malnourished rats subjected to learned helplessness. Braz J Med Biol Res. 2008 Jan;41(1):54-9. doi: 10.1590/s0100-879x2006005000187. Epub 2007 Dec 17. PMID: 17952336.
2. Pruus K, Skrebuhhova-Malmros T, Rudissaar R, Matto V, Allikmets L. 5-HT1A receptor agonists buspirone and gepirone attenuate apomorphine-induced aggressive behaviour in adult male Wistar rats. J Physiol Pharmacol. 2000 Dec;51(4 Pt 2):833-46. PMID: 11220492.
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2: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Apr;27(3):193-219. PubMed PMID: 15834452.
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4: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Nov;26(9):723-53. PubMed PMID: 15632957.
5: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Mar;26(2):129-61. PubMed PMID: 15071612.
6: Caccia S. Metabolism of the newest antidepressants: comparisons with related predecessors. IDrugs. 2004 Feb;7(2):143-50. Review. PubMed PMID: 15057659.
7: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Jan-Feb;26(1):53-84. Review. PubMed PMID: 14988742.
8: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2002 Dec;24(10):703-29. PubMed PMID: 12616965.
9: Gu CH, Grant DJ. Estimating the relative stability of polymorphs and hydrates from heats of solution and solubility data. J Pharm Sci. 2001 Sep;90(9):1277-87. PubMed PMID: 11745780.
10: Canto-de-Souza A, Nunes de Souza RL, Pelá IR, Graeff FG. Involvement of the midbrain periaqueductal gray 5-HT1A receptors in social conflict induced analgesia in mice. Eur J Pharmacol. 1998 Mar 26;345(3):253-6. PubMed PMID: 9592023.
11: Dursun SM, Handley SL. The effects of alpha 2-adrenoceptor antagonists on the inhibition of 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI)-induced head shakes by 5-HT1A receptor agonists in the mouse. Br J Pharmacol. 1993 Aug;109(4):1046-52. PubMed PMID: 8104640; PubMed Central PMCID: PMC2175745.
12: Amsterdam JD. Gepirone, a selective serotonin (5HT1A) partial agonist in the treatment of major depression. Prog Neuropsychopharmacol Biol Psychiatry. 1992 May;16(3):271-80. PubMed PMID: 1350353.
13: Yevich JP, Eison MS, Eison AS, Taylor DP, Yocca FD, VanderMaelen CP, Riblet LA, Robinson DS, Roberts DL, Temple DL. Gepirone hydrochloride: preclinical pharmacology and recent clinical findings. Prog Clin Biol Res. 1990;361:443-51. Review. PubMed PMID: 1981261.
14: Behme RJ, Brooke D, Farney RF, Kensler TT. Characterization of polymorphism of gepirone hydrochloride. J Pharm Sci. 1985 Oct;74(10):1041-6. PubMed PMID: 4078700.
