MedKoo Cat#: 563111 | Name: A-331440 2HCl

Description:

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

A-331440 2HCl is a histamine H3 receptor antagonist.

Chemical Structure

A-331440 2HCl
A-331440 2HCl
CAS#1049740-32-0 (HCl)

Theoretical Analysis

MedKoo Cat#: 563111

Name: A-331440 2HCl

CAS#: 1049740-32-0 (HCl)

Chemical Formula: C22H29Cl2N3O

Exact Mass: 421.1688

Molecular Weight: 422.39

Elemental Analysis: C, 62.56; H, 6.92; Cl, 16.79; N, 9.95; O, 3.79

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
A-331440 2HCl; A331440 2HCl; A 331440 2HCl; A-331440 dihydrochloride; A 331440 dihydrochloride; A331440 dihydrochloride;
IUPAC/Chemical Name
(R)-4'-(3-(3-(dimethylamino)pyrrolidin-1-yl)propoxy)-[1,1'-biphenyl]-4-carbonitrile dihydrochloride
InChi Key
XFPYVTSGYYMTFS-GHVWMZMZSA-N
InChi Code
InChI=1S/C22H27N3O.2ClH/c1-24(2)21-12-14-25(17-21)13-3-15-26-22-10-8-20(9-11-22)19-6-4-18(16-23)5-7-19;;/h4-11,21H,3,12-15,17H2,1-2H3;2*1H/t21-;;/m1../s1
SMILES Code
[H]Cl.[H]Cl.N#CC1=CC=C(C2=CC=C(OCCCN3CC[C@@H](N(C)C)C3)C=C2)C=C1
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 422.39 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
1: Nieto-Alamilla G, Escamilla-Sánchez J, López-Méndez MC, Molina-Hernández A, Guerrero-Hernández A, Arias-Montaño JA. Differential expression and signaling of the human histamine H(3) receptor isoforms of 445 and 365 amino acids expressed in human neuroblastoma SH-SY5Y cells. J Recept Signal Transduct Res. 2018 Apr;38(2):141-150. doi: 10.1080/10799893.2018.1448995. Epub 2018 Mar 20. PubMed PMID: 29557708. 2: Mena-Avila E, Márquez-Gómez R, Aquino-Miranda G, Nieto-Alamilla G, Arias-Montaño JA. Clobenpropit, a histamine H(3) receptor antagonist/inverse agonist, inhibits [(3)H]-dopamine uptake by human neuroblastoma SH-SY5Y cells and rat brain synaptosomes. Pharmacol Rep. 2018 Feb;70(1):146-155. doi: 10.1016/j.pharep.2017.08.007. Epub 2017 Aug 30. PubMed PMID: 29414147. 3: Morales-Figueroa GE, Márquez-Gómez R, González-Pantoja R, Escamilla-Sánchez J, Arias-Montaño JA. Histamine H3 receptor activation counteracts adenosine A2A receptor-mediated enhancement of depolarization-evoked [3H]-GABA release from rat globus pallidus synaptosomes. ACS Chem Neurosci. 2014 Aug 20;5(8):637-45. doi: 10.1021/cn500001m. Epub 2014 Jun 11. PubMed PMID: 24884070; PubMed Central PMCID: PMC4140591. 4: Didone V, Quoilin C, Nyssen L, Closon C, Tirelli E, Quertemont E. Effects of L-histidine and histamine H3 receptor modulators on ethanol-induced sedation in mice. Behav Brain Res. 2013 Feb 1;238:113-8. doi: 10.1016/j.bbr.2012.10.019. Epub 2012 Oct 23. PubMed PMID: 23089647. 5: Coruzzi G, Adami M, Pozzoli C, de Esch IJ, Smits R, Leurs R. Selective histamine H₃ and H₄ receptor agonists exert opposite effects against the gastric lesions induced by HCl in the rat stomach. Eur J Pharmacol. 2011 Nov 1;669(1-3):121-7. doi: 10.1016/j.ejphar.2011.07.038. Epub 2011 Aug 5. PubMed PMID: 21839070. 6: Osorio-Espinoza A, Alatorre A, Ramos-Jiménez J, Garduño-Torres B, García-Ramírez M, Querejeta E, Arias-Montaño JA. Pre-synaptic histamine H₃ receptors modulate glutamatergic transmission in rat globus pallidus. Neuroscience. 2011 Mar 10;176:20-31. doi: 10.1016/j.neuroscience.2010.12.051. Epub 2010 Dec 31. PubMed PMID: 21195747. 7: Brabant C, Alleva L, Grisar T, Quertemont E, Lakaye B, Ohtsu H, Lin JS, Jatlow P, Picciotto MR, Tirelli E. Effects of the H3 receptor inverse agonist thioperamide on cocaine-induced locomotion in mice: role of the histaminergic system and potential pharmacokinetic interactions. Psychopharmacology (Berl). 2009 Mar;202(4):673-87. doi: 10.1007/s00213-008-1345-y. Epub 2008 Oct 9. PubMed PMID: 18843481. 8: Moreno-Delgado D, Torrent A, Gómez-Ramírez J, de Esch I, Blanco I, Ortiz J. Constitutive activity of H3 autoreceptors modulates histamine synthesis in rat brain through the cAMP/PKA pathway. Neuropharmacology. 2006 Sep;51(3):517-23. PubMed PMID: 16769092. 9: Hancock AA, Diehl MS, Fey TA, Bush EN, Faghih R, Miller TR, Krueger KM, Pratt JK, Cowart MD, Dickinson RW, Shapiro R, Knourek-Segel VE, Droz BA, McDowell CA, Krishna G, Brune ME, Esbenshade TA, Jacobson PB. Antiobesity evaluation of histamine H3 receptor (H3R) antagonist analogs of A-331440 with improved safety and efficacy. Inflamm Res. 2005 Apr;54 Suppl 1:S27-9. PubMed PMID: 15928821. 10: Hancock AA, Diehl MS, Faghih R, Bush EN, Krueger KM, Krishna G, Miller TR, Wilcox DM, Nguyen P, Pratt JK, Cowart MD, Esbenshade TA, Jacobson PB. In vitro optimization of structure activity relationships of analogues of A-331440 combining radioligand receptor binding assays and micronucleus assays of potential antiobesity histamine H3 receptor antagonists. Basic Clin Pharmacol Toxicol. 2004 Sep;95(3):144-52. PubMed PMID: 15447739. 11: Faghih R, Esbenshade TA, Krueger KM, Yao BB, Witte DG, Miller TM, Kang CH, Fox GB, Cowart M, Bennani YL, Hancock AA. Structure-activity relationships of A-331440: a new histamine-3 antagonist with anti-obesity properties. Inflamm Res. 2004 Mar;53 Suppl 1:S79-80. Epub 2004 Mar 5. PubMed PMID: 15054629. 12: Hancock AA, Bennani YL, Bush EN, Esbenshade TA, Faghih R, Fox GB, Jacobson P, Knourek-Segel V, Krueger KM, Nuss ME, Pan JB, Shapiro R, Witte DG, Yao BB. Antiobesity effects of A-331440, a novel non-imidazole histamine H3 receptor antagonist. Eur J Pharmacol. 2004 Mar 8;487(1-3):183-97. PubMed PMID: 15033391.