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MedKoo Cat#: 571149 | Name: Phenoxybenzamine

Description:

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

Phenoxybenzamine is an α-1 adrenergic receptor antagonist used to treat hypertension and as a peripheral vasodilator. Phenoxybenzamine reduced neuronal death in rat hippocampal slice cultures following exposure to oxygen glucose deprivation. Phenoxybenzamine treated TBI (traumatic brain injury) animals also showed a significant improvement in both learning and memory compared to saline treated controls. At 32 h post-TBI phenoxybenzamine treated animals had significantly lower expression of pro-inflammatory signaling proteins CCL2, IL1β, and MyD88, suggesting that phenoxybenzamine may exert a neuroprotective effect by reducing neuroinflammation after TBI.

Chemical Structure

Phenoxybenzamine
Phenoxybenzamine
CAS#59-96-1 (free)

Theoretical Analysis

MedKoo Cat#: 571149

Name: Phenoxybenzamine

CAS#: 59-96-1 (free)

Chemical Formula: C18H22ClNO

Exact Mass: 303.1390

Molecular Weight: 303.83

Elemental Analysis: C, 71.16; H, 7.30; Cl, 11.67; N, 4.61; O, 5.27

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 #
63-92-3 (HCl) 59-96-1 (free)
Synonym
Phenoxybenzamine; NSC 37448; NSC-37448; NSC37448; A-688; A688; A 688
IUPAC/Chemical Name
Benzenemethanamine, N-(2-chloroethyl)-N-(1-methyl-2-phenoxyethyl)-
InChi Key
QZVCTJOXCFMACW-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H22ClNO/c1-16(15-21-18-10-6-3-7-11-18)20(13-12-19)14-17-8-4-2-5-9-17/h2-11,16H,12-15H2,1H3
SMILES Code
CC(N(CCCl)CC1=CC=CC=C1)COC2=CC=CC=C2
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

Preparing Stock Solutions

The following data is based on the product molecular weight 303.83 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: van der Zee PA, de Boer A. Pheochromocytoma: a review on preoperative treatment with phenoxybenzamine or doxazosin. Neth J Med. 2014 May;72(4):190-201. Review. PubMed PMID: 24829175. 2: National Toxicology Program. Phenoxybenzamine hydrochloride. Rep Carcinog. 2011;12:344-5. PubMed PMID: 21863081. 3: Rau TF, Kothiwal A, Rova A, Rhoderick JF, Poulsen DJ. Phenoxybenzamine is neuroprotective in a rat model of severe traumatic brain injury. Int J Mol Sci. 2014 Jan 20;15(1):1402-17. doi: 10.3390/ijms15011402. PubMed PMID: 24447929; PubMed Central PMCID: PMC3907876. 4: Lin XB, Jiang L, Ding MH, Chen ZH, Bao Y, Chen Y, Sun W, Zhang CR, Hu HK, Cai Z, Lu CY, Zhou JY, Qian J, Wu XJ, Jin WL, Hu GH. Anti-tumor activity of phenoxybenzamine hydrochloride on malignant glioma cells. Tumour Biol. 2016 Mar;37(3):2901-8. doi: 10.1007/s13277-015-4102-y. Epub 2015 Sep 26. PubMed PMID: 26409450. 5: Lim LY, Tan LL, Chan EW, Yow KL, Chan SY, Ho PC. Stability of phenoxybenzamine hydrochloride in various vehicles. Am J Health Syst Pharm. 1997 Sep 15;54(18):2073-8. PubMed PMID: 9377206. 6: Phenoxybenzamine and phenoxybenzamine hydrochloride. IARC Monogr Eval Carcinog Risk Chem Hum. 1980;24:185-94. Review. PubMed PMID: 7009392. 7: Sambhunath D, Pankaj K, Usha K. Role of phenoxybenzamine in perioperative clinical practice. Ann Card Anaesth. 2015 Oct-Dec;18(4):577-8. doi: 10.4103/0971-9784.166473. PubMed PMID: 26440247; PubMed Central PMCID: PMC4881667. 8: Phenoxybenzamine hydrochloride. Rep Carcinog. 2004;11:III216. PubMed PMID: 21089945. 9: National Toxicology Program. Phenoxybenzamine hydrochloride. Rep Carcinog. 2002;10:197-8. Update in: Rep Carcinog. 2004;11:III216. PubMed PMID: 15332291. 10: Agrawal R, Mishra SK, Bhatia E, Mishra A, Chand G, Agarwal G, Agarwal A, Verma AK. Prospective study to compare peri-operative hemodynamic alterations following preparation for pheochromocytoma surgery by phenoxybenzamine or prazosin. World J Surg. 2014 Mar;38(3):716-23. PubMed PMID: 24233658. 11: Khanna OP, Gonick P. Effects of phenoxybenzamine hydrochloride on canine lower urinary tract: clinical implications. Urology. 1975 Sep;6(3):323-30. PubMed PMID: 1167189. 12: Phenoxybenzamine (hydrochloride). IARC Monogr Eval Carcinog Risk Chem Man. 1975;9:223-8. Review. PubMed PMID: 791836. 13: Ramachandran R, Rewari V. Preoperative optimization in pheochromocytoma: phenoxybenzamine may be redundant but not alpha blockade. Can J Anaesth. 2016 May;63(5):629. doi: 10.1007/s12630-015-0557-y. Epub 2015 Dec 7. PubMed PMID: 26643509. 14: Portoghese PS, Riley TN, Miller JW. Stereochemical studies on medicinal agents. 10. The role of chirality in alpha-adrenergic receptor blockage by (plus)-and(minus)-phenoxybenzamine hydrochloride. J Med Chem. 1971 Jul;14(17):561-4. PubMed PMID: 4151883. 15: Sharma PL. Comparative effect of prophylactic administration of isoxsuprine hydrochloride and phenoxybenzamine hydrochloride on the survival rate of dogs subjected to acute blood loss. Indian J Med Res. 1969 Oct;57(10):1902-10. PubMed PMID: 5372176. 16: Collado Mdel C, Nedergaard M. [On the stability of phenoxybenzamine hydrochloride in solution]. Ann Pharm Fr. 1968 May;26(5):409-12. French. PubMed PMID: 5708743. 17: Mitchell JC, Maibach HI. Allergic contact dermatitis from phenoxybenzamine hydrochloride: cross-sensitivity to some related haloalkylamine compounds. Contact Dermatitis. 1975 Dec;1(6):363-6. PubMed PMID: 1235295. 18: Dunzendorfer U. alpha-Difluoromethylornithine (alpha DFMO) and phenoxybenzamine hydrochloride in the treatment of chronic non-suppurative prostatitis. Arzneimittelforschung. 1981;31(2):382-5. PubMed PMID: 6784733. 19: Cimino M, Weiss B. Characteristics of the binding of phenoxybenzamine to calmodulin. Biochem Pharmacol. 1988 Jul 15;37(14):2739-45. PubMed PMID: 3134891. 20: Lewis JE, Miller JW. The synthesis of tritium-labeled phenoxybenzamine hydrochloride. J Med Chem. 1966 Mar;9(2):261-2. PubMed PMID: 5911816.