Asenapine free base | CAS#65576-45-6 | 1412458-61-7 | 85650-56-2

MedKoo Cat#: 317251 | Name: Asenapine free base

Description:

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

Asenapine, also known as Org 5222, shows high affinity (pKi) for numerous receptors, including the serotonin 5-HT1A (8.6), 5-HT1B (8.4), 5-HT2A (10.2), 5-HT2B (9.8), 5-HT2C (10.5), 5-HT5A (8.8), 5-HT6 (9.5), and 5-HT7 (9.9) receptors, the adrenergic α1 (8.9), α2A (8.9), α2B (9.5), and α2C (8.9) receptors, the dopamine D1 (8.9), D2 (8.9), D3 (9.4), and D4 (9.0) receptors, and the histamine H1 (9.0) and H2 (8.2) receptors. Asenapine behaves as an antagonist at all receptors. It exhibits potent activity in animal models predictive of antipsychotic efficacy. Note this product we supply is a racemic mixture.

Chemical Structure

Asenapine free base

CAS#65576-45-6 (free)

Theoretical Analysis

MedKoo Cat#: 317251

Name: Asenapine free base

CAS#: 65576-45-6 (free)

Chemical Formula: C17H16ClNO

Exact Mass: 285.0920

Molecular Weight: 285.77

Elemental Analysis: C, 71.45; H, 5.64; Cl, 12.41; N, 4.90; O, 5.60

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 Weeks
25mg	USD 650.00	2 Weeks

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Related CAS #

85650-56-2 (maleate) 65576-45-6 (free)

Synonym

Org 5222; Org5222; Org-5222; Asenapine; (+/-)-Asenapine;

IUPAC/Chemical Name

(3aR*,12bR*)-5-Chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrole

InChi Key

VSWBSWWIRNCQIJ-GJZGRUSLSA-N

InChi Code

InChI=1S/C17H16ClNO/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19/h2-8,14-15H,9-10H2,1H3/t14-,15-/m0/s1

SMILES Code

CN1C[C@](C2=CC=CC=C2OC3=CC=C(Cl)C=C34)([H])[C@@]4([H])C1

Appearance

Oily liquid or waxy semi-solid

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, not in water

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

More Info

Related: 65576-45-6 (Asenapine free) 1412458-61-7(Asenapine HCl) 85650-56-2 (Asenapine maleate)

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Asenapine (Org 5222) an antagonist of serotonin receptors (pKi: 8.4-10.5), adrenoceptors (pKi: 8.9-9.5), dopamine receptors (pKi: 8.9-9.4) and histamine receptors (pKi: 8.2-9.0).

In vitro activity:

To further determine whether AM (Asenapine maleate) act through ROS mediated signaling pathway, CFs were pretreated with or without AM followed by Ang II stimulation. The results demonstrated that AM could reduce the levels of ROS induced by Ang II (Fig. 4A). After pretreatment with 10 μM AM, the Ang II-induced activation of the TGFβ1/MAPK signal pathway was suppressed. Treatment with AM also reduced the expression of TGFβ1 and decreased the phosphorylation levels of ERK, JNK, and p38MAPK. Therefore, this study confirmed that AM can inhibit Ang II-induced cardiac fibrosis through the ROS/TGFβ1/MAPK signaling pathway (Fig. 4B and C). Reference: Biochem Biophys Res Commun. 2021 May 14;553:172-179. https://pubmed.ncbi.nlm.nih.gov/33773140/

In vivo activity:

As expected, administration of cumulative doses of the 5‐HT7 agonist LP‐44 (1‐4 mg/kg, i.v.) in control rats induced a dose‐dependent decrease in the firing activity of DR 5‐HT neurons with ED50=1.45 mg/kg (n=7; Figure 3A,B). Two‐way repeated‐measures ANOVA revealed a significant effect of SB 269970 pretreatment (F1,40=6.98, P<.05) on the potency of LP‐44 (F4,40=54.13, P<.001), but no SB 269970 x LP‐44 interaction. Similarly, an injection of Asenapine (1 mg/kg, i.v.) reduced the suppressant effect of LP‐44 on the firing activity of DR 5‐HT neurons, with ED50=3.54 mg/kg (n=7, Figure 3C,D). Two‐way repeated‐measures ANOVA indicated a significant effect of Asenapine (F1,55= 0.17, P<.01) on the potency of LP‐44 (F5,55=61.90, P<.001), and a significant interaction effect (F5,55=5.38, P<.001). Reference: CNS Neurosci Ther. 2017 Jun; 23(6): 518–525. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6492759/

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	174.97

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 285.77 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

Formulation protocol:

1. Wu HH, Meng TT, Chen JM, Meng FL, Wang SY, Liu RH, Chen JN, Ning B, Li Y, Su GH. Asenapine maleate inhibits angiotensin II-induced proliferation and activation of cardiac fibroblasts via the ROS/TGFβ1/MAPK signaling pathway. Biochem Biophys Res Commun. 2021 May 14;553:172-179. doi: 10.1016/j.bbrc.2021.03.042. Epub 2021 Mar 24. PMID: 33773140. 2. Grossini E, Gramaglia C, Farruggio S, Camillo L, Mary D, Vacca G, Zeppegno P. Asenapine modulates nitric oxide release and calcium movements in cardiomyoblasts. J Pharmacol Pharmacother. 2016 Jan-Mar;7(1):6-14. doi: 10.4103/0976-500X.179358. PMID: 27127388; PMCID: PMC4831496. 3. Foute Nelong T, Manduca JD, Zonneveld PM, Perreault ML. Asenapine maleate normalizes low frequency oscillatory deficits in a neurodevelopmental model of schizophrenia. Neurosci Lett. 2019 Oct 15;711:134404. doi: 10.1016/j.neulet.2019.134404. Epub 2019 Jul 26. PMID: 31356843. 4. Delcourte S, Abrial E, Etiévant A, Rovera R, Arnt J, Didriksen M, Haddjeri N. Asenapine modulates mood-related behaviors and 5-HT1A/7 receptors-mediated neurotransmission. CNS Neurosci Ther. 2017 Jun;23(6):518-525. doi: 10.1111/cns.12698. Epub 2017 Apr 17. PMID: 28417559; PMCID: PMC6492759.

In vitro protocol:

In vivo protocol:

1. Foute Nelong T, Manduca JD, Zonneveld PM, Perreault ML. Asenapine maleate normalizes low frequency oscillatory deficits in a neurodevelopmental model of schizophrenia. Neurosci Lett. 2019 Oct 15;711:134404. doi: 10.1016/j.neulet.2019.134404. Epub 2019 Jul 26. PMID: 31356843. 2. Delcourte S, Abrial E, Etiévant A, Rovera R, Arnt J, Didriksen M, Haddjeri N. Asenapine modulates mood-related behaviors and 5-HT1A/7 receptors-mediated neurotransmission. CNS Neurosci Ther. 2017 Jun;23(6):518-525. doi: 10.1111/cns.12698. Epub 2017 Apr 17. PMID: 28417559; PMCID: PMC6492759.

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