Synonym
Piquindone hydrochloride; Piquindone HCl; Piquindona; Piquindonum; Ro 22-1319
IUPAC/Chemical Name
(+-)-trans-3-Ethyl-1,4a,5,6,7,8,8a,9-octahydro-2,6-dimethyl-4H-pyrrolo(2,3-g)isoquinolin-4-one monohydrochloride dihydrate
InChi Key
GEAXXUIYNZBBLU-ZTALITPHSA-N
InChi Code
InChI=1S/C15H22N2O.ClH.2H2O/c1-4-11-9(2)16-13-7-10-5-6-17(3)8-12(10)15(18)14(11)13;;;/h10,12,16H,4-8H2,1-3H3;1H;2*1H2/t10-,12+;;;/m0.../s1
SMILES Code
O=C1C2=C(NC(C)=C2CC)C[C@]3([H])CCN(C)C[C@@]13[H].[H]Cl.[H]O[H].[H]O[H]
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
318.84
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 |
1: Cohen JD, Van Putten T, Marder S, Berger PA, Stahl SM. The efficacy of piquindone, a new atypical neuroleptic, in the treatment of the positive and negative symptoms of schizophrenia. J Clin Psychopharmacol. 1987 Oct;7(5):324-9. PMID: 2890671.
2: Uhr SB, Pruitt B, Berger PA, Stahl SM. Improvement of symptoms in Tourette syndrome by piquindone, a novel dopamine-2 receptor antagonist. Int Clin Psychopharmacol. 1986 Jul;1(3):216-20. doi: 10.1097/00004850-198607000-00004. PMID: 3549873.
3: Nakajima T, Iwata K. [3H]Ro 22-1319 (piquindone) binds to the D2 dopaminergic receptor subtype in a sodium-dependent manner. Mol Pharmacol. 1984 Nov;26(3):430-8. PMID: 6149457.
4: Brooks MA, Lee TL. Determination of piquindone in canine plasma and urine by high-performance liquid chromatography. J Chromatogr. 1986 Mar 7;375(2):349-57. doi: 10.1016/s0378-4347(00)83727-5. PMID: 2871038.
5: Nock B, Sedvall G, Mcewen BS. Quantitative autoradiography of [3H]piquindone binding sites (dopamine D2 receptors) in rat brain. Eur J Pharmacol. 1986 Mar 4;121(3):387-93. doi: 10.1016/0014-2999(86)90259-1. PMID: 3699100.
6: Jiménez-Jiménez FJ, García-Ruiz PJ. Pharmacological options for the treatment of Tourette's disorder. Drugs. 2001;61(15):2207-20. doi: 10.2165/00003495-200161150-00005. PMID: 11772131.
7: Kilpatrick GJ, el Tayar N, Van de Waterbeemd H, Jenner P, Testa B, Marsden CD. The thermodynamics of agonist and antagonist binding to dopamine D-2 receptors. Mol Pharmacol. 1986 Sep;30(3):226-34. PMID: 2943980.
8: Collin S, Vercauteren DP, Vanderveken D, Evrard G, Durant F. Structural requirements of Na+-dependent antidopaminergic agents: Tropapride, Piquindone, Zetidoline, and Metoclopramide. Comparison with Na+-independent ligands. J Comput Aided Mol Des. 1989 Mar;3(1):39-53. doi: 10.1007/BF01590994. PMID: 2715795.
9: Teeter MM, Durand CJ. Dopamine D2 receptor model explains binding affinity of neuroleptics: piquindone and its structure activity relationships. Drug Des Discov. 1996 Apr;13(3-4):49-62. PMID: 8874043.
10: Uhr SB, Pruitt B, Berger PA, Stahl SM. Case report of four patients with Tourette syndrome treated with piquindone, a D2 receptor antagonist. J Clin Psychopharmacol. 1986 Apr;6(2):128-30. PMID: 2871057.
