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MedKoo Cat#: 414981 | Name: Piquindone Free Base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Piquindone Free Base is an atypical antipsychotic and a rigid analog of molindone. Piquindone has a tricyclic structure and was developed in the 1980s but was never marketed.

Chemical Structure

Piquindone Free Base
Piquindone Free Base
CAS#78541-97-6 (free base)

Theoretical Analysis

MedKoo Cat#: 414981

Name: Piquindone Free Base

CAS#: 78541-97-6 (free base)

Chemical Formula: C15H22N2O

Exact Mass: 246.1732

Molecular Weight: 246.35

Elemental Analysis: C, 73.13; H, 9.00; N, 11.37; O, 6.49

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Related CAS #
83784-19-4 (H2O) 78541-97-6 (free base) 75689-38-2 (HCl)
Synonym
Piquindone Free Base; Ro 22-1319; Piquindona; Piquindonum
IUPAC/Chemical Name
4H-Pyrrolo(2,3-g)isoquinolin-4-one, 3-ethyl-1,4a,5,6,7,8,8a,9-octahydro-2,6-dimethyl-, trans-(+-)-
InChi Key
PVZMYDPRVUCJKV-CMPLNLGQSA-N
InChi Code
InChI=1S/C15H22N2O/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/t10-,12+/m0/s1
SMILES Code
O=C1C2=C(NC(C)=C2CC)C[C@]3([H])CCN(C)C[C@@]13[H]
Appearance
Solid powder
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 246.35 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.

Recalculate based on batch purity %
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
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Eur J Pharmacol. 1990 Jul 31;189(1):59-70. doi: 10.1016/0922-4106(90)90230-u. PMID: 1977603. 6: Vezina P, Stewart J. The effect of dopamine receptor blockade on the development of sensitization to the locomotor activating effects of amphetamine and morphine. Brain Res. 1989 Oct 9;499(1):108-20. doi: 10.1016/0006-8993(89)91140-2. PMID: 2679971. 7: 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. 8: Kaneda H, Shintani T, Kakigi T, Terada T, Tanimoto K. Comparison of prolactin responses to D-1 and D-2 antagonists in rats: Ro 22-1319 is a potent D-2 antagonist. Biol Psychiatry. 1989 Feb 15;25(4):517-22. doi: 10.1016/0006-3223(89)90210-2. PMID: 2564788. 9: Murray AM, Waddington JL. The induction of grooming and vacuous chewing by a series of selective D-1 dopamine receptor agonists: two directions of D-1:D-2 interaction. Eur J Pharmacol. 1989 Feb 7;160(3):377-84. doi: 10.1016/0014-2999(89)90093-9. PMID: 2565818. 10: Murray AM, Waddington JL. Further evidence for two directions of D-1:D-2 dopamine receptor interaction revealed concurrently in distinct elements of typical and atypical behaviour: studies with the new enantioselective D-2 agonist LY 163502. Psychopharmacology (Berl). 1989;98(2):245-50. doi: 10.1007/BF00444699. PMID: 2569218. 11: Warenycia MW, McKenzie GM. Pharmacological activity profiles of dopamine D-1 and D-2 reception agonists and antagonists on striatal neuronal activity and the response to dexamphetamine in freely moving rats. Gen Pharmacol. 1989;20(3):295-301. doi: 10.1016/0306-3623(89)90262-0. PMID: 2568305. 12: Thaker GK, Wagman AM, Kirkpatrick B, Tamminga CA. Alterations in sleep polygraphy after neuroleptic withdrawal: a putative supersensitive dopaminergic mechanism. Biol Psychiatry. 1989 Jan;25(1):75-86. doi: 10.1016/0006-3223(89)90149-2. PMID: 2563233. 13: Collin S, Evrard G, Vercauteren DP, Durant F, Carrupt PA, van de Waterbeemd H, Testa B. Stereoelectronic study of zetidoline, a dopamine D2 receptor antagonist. J Med Chem. 1989 Jan;32(1):38-42. doi: 10.1021/jm00121a008. PMID: 2521253. 14: Högberg T, Norinder U, Rämsby S, Stensland B. Crystallographic, theoretical and molecular modelling studies on the conformations of the salicylamide, raclopride, a selective dopamine-D2 antagonist. J Pharm Pharmacol. 1987 Oct;39(10):787-96. doi: 10.1111/j.2042-7158.1987.tb05120.x. PMID: 2891816. 15: 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. 16: Cadet JL, Braun T, Freed WJ. The dopamine D-2 antagonist, Ro 22-1319, inhibits the persistent behavioral syndrome induced by iminodipropionitrile (IDPN) in mice. Exp Neurol. 1987 Jun;96(3):594-600. doi: 10.1016/0014-4886(87)90221-4. PMID: 2953619. 17: Foreman MM, Hall JL. Effects of D2-dopaminergic receptor stimulation on male rat sexual behavior. J Neural Transm. 1987;68(3-4):153-70. doi: 10.1007/BF02098495. PMID: 2951493. 18: 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. 19: 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. 20: Molloy AG, O'Boyle KM, Pugh MT, Waddington JL. Locomotor behaviors in response to new selective D-1 and D-2 dopamine receptor agonists, and the influence of selective antagonists. Pharmacol Biochem Behav. 1986 Jul;25(1):249-53. doi: 10.1016/0091-3057(86)90262-5. PMID: 3529126.