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A3104

Sigma-Aldrich

A-331440 L-tartrate hydrate

≥98% (HPLC), solid

Synonym(s):

4′-[3-[3(R)-Dimethylamino-1-pyrrolidinyl]propoxy]-[1,1-biphenyl]-4′-carbonitrile L-tartrate hydrate

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About This Item

Empirical Formula (Hill Notation):
C22H27N3O · xC4H6O6 · yH2O
CAS Number:
Molecular Weight:
349.47 (anhydrous free base basis)
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

DMSO: ≥10 mg/mL
H2O: insoluble
ethanol: insoluble
methanol: insoluble

originator

Abbott

SMILES string

[H]O[H].O[C@H]([C@@H](O)C(O)=O)C(O)=O.CN(C)[C@@H]1CCN(CCCOc2ccc(cc2)-c3ccc(cc3)C#N)C1

InChI

1S/C22H27N3O.C4H6O6.H2O/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;5-1(3(7)8)2(6)4(9)10;/h4-11,21H,3,12-15,17H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10);1H2/t21-;1-,2-;/m11./s1

InChI key

BWZMVOINNVPOGW-LZXZYUBDSA-N

Biochem/physiol Actions

Histamine affects homeostatic mechanisms, including food and water consumption, by acting on central nervous system (CNS) receptors. Presynaptic histamine H3 receptors regulate release of histamine and other neurotransmitters, and histamine H3 receptor antagonists enhance neurotransmitter release. A-331440 [4′-[3-(3(R)-(dimethylamino)-pyrrolidin-1-yl)-propoxy]-biphenyl-4-carbonitrile] is a histamine H3 receptor antagonist which binds potently and selectively to both human and rat histamine H3 receptors (Ki<=25 nM). Mice were stabilized on a high-fat diet (45 kcal % lard) prior to 28-day oral b.i.d. dosing for measurement of obesity-related parameters. A-331440 administered at 0.5 mg/kg had no significant effect on weight, whereas 5 mg/kg decreased weight comparably to dexfenfluramine (10 mg/kg). A-331440 administered at 15 mg/kg reduced weight to a level comparable to mice on the low-fat diet. The two higher doses reduced body fat and the highest dose also normalized an insulin tolerance test. These data show that the histamine H3 receptor antagonist, A-331440, has potential as an antiobesity agent.

Features and Benefits

This compound is featured on the Histamine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Abbott. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

Subject to U.S. Patent numbers 6,515,013 and 6,620,839. Sold under license from Abbott Laboratories

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Structure-activity relationships of A-331440: a new histamine-3 antagonist with anti-obesity properties.
R Faghih et al.
Inflammation research : official journal of the European Histamine Research Society ... [et al.], 53 Suppl 1, S79-S80 (2004-04-01)
Arthur A Hancock et al.
European journal of pharmacology, 487(1-3), 183-197 (2004-03-23)
Histamine affects homeostatic mechanisms, including food and water consumption, by acting on central nervous system (CNS) receptors. Presynaptic histamine H(3) receptors regulate release of histamine and other neurotransmitters, and histamine H(3) receptor antagonists enhance neurotransmitter release. A-331440 [4'-[3-(3(R)-(dimethylamino)-pyrrolidin-1-yl)-propoxy]-biphenyl-4-carbonitrile] is a

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