A-381393
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 531353

CAS#: 726174-00-1

Description: A-381393 is a potent and selective agonist of the dopamine D4 receptor.


Chemical Structure

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A-381393
CAS# 726174-00-1

Theoretical Analysis

MedKoo Cat#: 531353
Name: A-381393
CAS#: 726174-00-1
Chemical Formula: C20H24N4
Exact Mass: 320.2001
Molecular Weight: 320.44
Elemental Analysis: C, 74.97; H, 7.55; N, 17.48

Price and Availability

Size Price Availability Quantity
100.0mg USD 950.0 2 Weeks
200.0mg USD 1550.0 2 Weeks
500.0mg USD 2250.0 2 Weeks
1.0g USD 3250.0 2 Weeks
2.0g USD 5650.0 2 Weeks
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Synonym: A-381393; A 381393; A381393;

IUPAC/Chemical Name: 2-[[4-(3,4-dimethylphenyl)piperazin-1-yl]methyl]-1H-benzimidazole

InChi Key: SAQMCVDGOIRQTC-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H24N4/c1-15-7-8-17(13-16(15)2)24-11-9-23(10-12-24)14-20-21-18-5-3-4-6-19(18)22-20/h3-8,13H,9-12,14H2,1-2H3,(H,21,22)

SMILES Code: CC1=CC=C(N2CCN(CC3=NC4=CC=CC=C4N3)CC2)C=C1C

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: 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

Product Data:

Biological target: A-381393 is a brain penetrate dopamine D4 receptor antagonist, with Kis of 1.5, 1.9 and 1.6 nM for human dopamine D4.4, D4.2, and D4.7 receptor, respectively, >2700-fold selectivity over D1, D2, D3 and D5 dopamine receptors.
In vitro activity: A-381393 binds to dopamine D4 receptor with nanomolar affinity (Ki = 1.5 nM), which is comparable with L-745870, and 36-fold higher than clozapine (Ki = 54 nM). A-381393 was more than 4000-fold selective for the dopamine D4 receptors as compared to dopamine D1, D2, D3 and D5 receptors. Reference: Neuropharmacology. 2005 Jul;49(1):112-21. https://pubmed.ncbi.nlm.nih.gov/15992586/
In vivo activity: It has been demonstrated that the dopamine D4 receptor selective agonist PD168077 induces penile erection in conscious rats by centrally mediated mechanisms with an effective dose of 0.3 μmol/kg. To determine if A-381393 would attenuate this effect, the compound was dosed subcutaneously at 30 μmol/kg before administration of PD168077. When the percent incidence of penile erection was examined, PD168077 induced 75% incidence at the efficacious dose. In animals treated with A-381393, this incidence was significantly reduced to 48% (Fig. 7). Reference: Neuropharmacology. 2005 Jul;49(1):112-21. https://pubmed.ncbi.nlm.nih.gov/15992586/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 51.67 161.25

Preparing Stock Solutions

The following data is based on the product molecular weight 320.44 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
Formulation protocol: 1. Nakane M, Cowart MD, Hsieh GC, Miller L, Uchic ME, Chang R, Terranova MA, Donnelly-Roberts DL, Namovic MT, Miller TR, Wetter JM, Marsh K, Stewart AO, Brioni JD, Moreland RB. 2-[4-(3,4-Dimethylphenyl)piperazin-1-ylmethyl]-1H benzoimidazole (A-381393), a selective dopamine D4 receptor antagonist. Neuropharmacology. 2005 Jul;49(1):112-21. doi: 10.1016/j.neuropharm.2005.02.004. Epub 2005 Apr 1. PMID: 15992586.
In vitro protocol: 1. Nakane M, Cowart MD, Hsieh GC, Miller L, Uchic ME, Chang R, Terranova MA, Donnelly-Roberts DL, Namovic MT, Miller TR, Wetter JM, Marsh K, Stewart AO, Brioni JD, Moreland RB. 2-[4-(3,4-Dimethylphenyl)piperazin-1-ylmethyl]-1H benzoimidazole (A-381393), a selective dopamine D4 receptor antagonist. Neuropharmacology. 2005 Jul;49(1):112-21. doi: 10.1016/j.neuropharm.2005.02.004. Epub 2005 Apr 1. PMID: 15992586.
In vivo protocol: 1. Nakane M, Cowart MD, Hsieh GC, Miller L, Uchic ME, Chang R, Terranova MA, Donnelly-Roberts DL, Namovic MT, Miller TR, Wetter JM, Marsh K, Stewart AO, Brioni JD, Moreland RB. 2-[4-(3,4-Dimethylphenyl)piperazin-1-ylmethyl]-1H benzoimidazole (A-381393), a selective dopamine D4 receptor antagonist. Neuropharmacology. 2005 Jul;49(1):112-21. doi: 10.1016/j.neuropharm.2005.02.004. Epub 2005 Apr 1. PMID: 15992586.

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1: Marona-Lewicka D, Nichols DE. WAY 100635 produces discriminative stimulus effects in rats mediated by dopamine D(4) receptor activation. Behav Pharmacol. 2009 Feb;20(1):114-8. doi: 10.1097/FBP.0b013e3283242f1a. PubMed PMID: 19179855.

2: Marona-Lewicka D, Chemel BR, Nichols DE. Dopamine D4 receptor involvement in the discriminative stimulus effects in rats of LSD, but not the phenethylamine hallucinogen DOI. Psychopharmacology (Berl). 2009 Apr;203(2):265-77. doi: 10.1007/s00213-008-1238-0. PubMed PMID: 18604600.

3: Bitner RS, Nikkel AL, Otte S, Martino B, Barlow EH, Bhatia P, Stewart AO, Brioni JD, Decker MW, Moreland RB. Dopamine D4 receptor signaling in the rat paraventricular hypothalamic nucleus: Evidence of natural coupling involving immediate early gene induction and mitogen activated protein kinase phosphorylation. Neuropharmacology. 2006 Apr;50(5):521-31. PubMed PMID: 16324724.

4: Nakane M, Cowart MD, Hsieh GC, Miller L, Uchic ME, Chang R, Terranova MA, Donnelly-Roberts DL, Namovic MT, Miller TR, Wetter JM, Marsh K, Stewart AO, Brioni JD, Moreland RB. 2-[4-(3,4-Dimethylphenyl)piperazin-1-ylmethyl]-1H benzoimidazole (A-381393), a selective dopamine D4 receptor antagonist. Neuropharmacology. 2005 Jul;49(1):112-21. PubMed PMID: 15992586.

A-381393

10.0mg / Not available