Cyclazosin Free Base | CAS# 139953-73-4 (Free Base) | adenosine A2A receptor antagonist

MedKoo Cat#: 413401 | Name: Cyclazosin Free Base

Description:

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

Cyclazosin Free Base is a monocarboxylic acid amide obtained by formal condensation of the carboxy group of furoic acid with the secondary amino group of 6,7-dimethoxy-2-[(4aR,8aS)-octahydroquinoxalin-1-yl]quinazolin-4-amine. It has a role as an adenosine A2A receptor antagonist. It is a member of quinazolines, a member of furans, an aromatic ether, a quinoxaline derivative, an aromatic amide and a monocarboxylic acid amide.

Chemical Structure

Cyclazosin Free Base

CAS#139953-73-4 (Free Base)

Theoretical Analysis

MedKoo Cat#: 413401

Name: Cyclazosin Free Base

CAS#: 139953-73-4 (Free Base)

Chemical Formula: C23H27N5O4

Exact Mass: 437.2063

Molecular Weight: 437.50

Elemental Analysis: C, 63.14; H, 6.22; N, 16.01; O, 14.63

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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Related CAS #

139953-73-4 (Free Base) 146929-33-1 (HCl)

Synonym

Cyclazosin Free Base

IUPAC/Chemical Name

Quinoxaline, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)decahydro-, cis-

InChi Key

XBRXTUGRUXGBPX-DLBZAZTESA-N

InChi Code

InChI=1S/C23H27N5O4/c1-30-19-12-14-15(13-20(19)31-2)25-23(26-21(14)24)28-10-9-27(16-6-3-4-7-17(16)28)22(29)18-8-5-11-32-18/h5,8,11-13,16-17H,3-4,6-7,9-10H2,1-2H3,(H2,24,25,26)/t16-,17+/m0/s1

SMILES Code

O=C(N1CCN(C2=NC(N)=C3C=C(OC)C(OC)=CC3=N2)[C@]4([H])CCCC[C@]14[H])C5=CC=CO5

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

More Info

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	0.0	100.00

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 437.50 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

1: Sagratini G, Buccioni M, Marucci G, Poggesi E, Skorski M, Costanzi S, Giardinà D. Chiral analogues of (+)-cyclazosin as potent α1B-adrenoceptor selective antagonist. Bioorg Med Chem. 2018 Jul 23;26(12):3502-3513. doi: 10.1016/j.bmc.2018.05.023. Epub 2018 May 17. PMID: 29784274; PMCID: PMC6008244. 2: Marucci G, Angeli P, Buccioni M, Gulini U, Melchiorre C, Sagratini G, Testa R, Giardinà D. (+)-Cyclazosin, a selective alpha1B-adrenoceptor antagonist: functional evaluation in rat and rabbit tissues. Eur J Pharmacol. 2005 Oct 17;522(1-3):100-7. doi: 10.1016/j.ejphar.2005.08.044. Epub 2005 Oct 6. PMID: 16213480. 3: Giardinà D, Sagratini G, Grelli M, Gulini U, Melchiorre C, Antolini L. Absolute configuration of the alpha (1B)-adrenoceptor antagonist (+)-cyclazosin. Farmaco. 2004 Dec;59(12):965-9. doi: 10.1016/j.farmac.2004.07.013. PMID: 15598431. 4: Sagratini G, Angeli P, Buccioni M, Gulini U, Marucci G, Melchiorre C, Leonardi A, Poggesi E, Giardinà D. Synthesis and alpha(1)-adrenoceptor antagonist activity of derivatives and isosters of the furan portion of (+)-cyclazosin. Bioorg Med Chem. 2007 Mar 15;15(6):2334-45. doi: 10.1016/j.bmc.2007.01.028. Epub 2007 Jan 19. PMID: 17276073. 5: Giardinà D, Polimanti O, Sagratini G, Angeli P, Gulini U, Marucci G, Melchiorre C, Poggesi E, Leonardi A. Searching for cyclazosin analogues as alpha(1B)-adrenoceptor antagonists. Farmaco. 2003 Jul;58(7):477-87. doi: 10.1016/s0014-827x(02)00025-3. PMID: 12818686. 6: Gao X, Abdelkarim H, Albee LJ, Volkman BF, Gaponenko V, Majetschak M. Partial agonist activity of α1-adrenergic receptor antagonists for chemokine (C-X-C motif) receptor 4 and atypical chemokine receptor 3. PLoS One. 2018 Sep 24;13(9):e0204041. doi: 10.1371/journal.pone.0204041. PMID: 30248140; PMCID: PMC6152952. 7: Giardinà D, Crucianelli M, Melchiorre C, Taddei C, Testa R. Receptor binding profile of cyclazosin, a new alpha 1B-adrenoceptor antagonist. Eur J Pharmacol. 1995 Dec 4;287(1):13-6. doi: 10.1016/0014-2999(95)00471-7. PMID: 8666020. 8: Alsufyani HA, McCormick PA, Docherty JR. Both α1B- and α1A-adrenoceptor subtypes are involved in contractions of rat spleen. Pharmacol Rep. 2021 Feb;73(1):255-260. doi: 10.1007/s43440-020-00118-x. Epub 2020 Aug 28. PMID: 32860192. 9: Giardinà D, Crucianelli M, Romanelli R, Leonardi A, Poggesi E, Melchiorre C. Synthesis and biological profile of the enantiomers of [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)-cis-octahydroquinoxalin- 1-yl]furan-2-ylmethanone (cyclazosin), a potent competitive alpha 1B- adrenoceptor antagonist. J Med Chem. 1996 Nov 8;39(23):4602-7. doi: 10.1021/jm960510x. PMID: 8917649. 10: Proudman RGW, Pupo AS, Baker JG. The affinity and selectivity of α-adrenoceptor antagonists, antidepressants, and antipsychotics for the human α1A, α1B, and α1D-adrenoceptors. Pharmacol Res Perspect. 2020 Aug;8(4):e00602. doi: 10.1002/prp2.602. PMID: 32608144; PMCID: PMC7327383.