MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 318485 | Name: Phentolamine Mesylate
Featured New

Description:

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

Phentolamine is a reversible antagonist of α-adrenergic receptors, non-specifically binding all α1- and α2-adrenoceptors with nanomolar affinities. When given intravenously, phentolamine rapidly and transiently increases local blood flow, which has proven useful for the management of hypertensive emergencies. Phentolamine also has applications in controlling chronic and emergent pain.

Chemical Structure

Phentolamine Mesylate
Phentolamine Mesylate
CAS#65-28-1 (mesylate)

Theoretical Analysis

MedKoo Cat#: 318485

Name: Phentolamine Mesylate

CAS#: 65-28-1 (mesylate)

Chemical Formula: C18H23N3O4S

Exact Mass: 0.0000

Molecular Weight: 377.46

Elemental Analysis: C, 57.28; H, 6.14; N, 11.13; O, 16.95; S, 8.49

Price and Availability

Size Price Availability Quantity
50mg USD 150.00 Ready to ship
100mg USD 250.00 Ready to ship
200mg USD 450.00 Ready to ship
500mg USD 850.00 Ready to ship
1g USD 1,250.00 2 weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
73-05-2 (HCl) 50-60-2 (free base) 65-28-1 (mesylate)
Synonym
Phentolamine Mesylate, Phentolamine mesilate, Phentolamine methanesulfonate, OraVerse, Regitine mesylate, Regitine, Regityn, Rogitine, Z-Max
IUPAC/Chemical Name
3-(((4,5-dihydro-1H-imidazol-2-yl)methyl)(p-tolyl)amino)phenol methanesulfonate
InChi Key
OGIYDFVHFQEFKQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H19N3O.CH4O3S/c1-13-5-7-14(8-6-13)20(12-17-18-9-10-19-17)15-3-2-4-16(21)11-15;1-5(2,3)4/h2-8,11,21H,9-10,12H2,1H3,(H,18,19);1H3,(H,2,3,4)
SMILES Code
CC1=CC=C(N(C2=CC(O)=CC=C2)CC3=NCCN3)C=C1.CS(=O)(O)=O
Appearance
White to off-white 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, 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
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#A23K11S10
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Phentolamine mesylate (Phentolamine methanesulfonate) is a reversible, non-selective, and orally active blocker of α1 and α2 adrenergic receptor.
In vitro activity:
Moreover, these results indicate that phentolamine inhibits the proliferation, migration, and tubulogenesis of HDMECs and HBMECs. Finally, VEGFR-2 and Ang1/2 expression of HDMECs was suppressed by phentolamine. Together, these results indicate that phentolamine impairs several critical events of neovascularization, and α-ARs, as well as the VEGF/VEGFR-2 and Ang/Tie-2 signaling pathways, may be involved in these processes. Reference: Clin Hemorheol Microcirc. 2017;65(1):31-41. https://pubmed.ncbi.nlm.nih.gov/27314442/
In vivo activity:
This study sought to determine if pretreatment with phentolamine could reduce acute myocardial injury and mortality in rats administered an overdose of phenylpropanolamine. Twelve rats died within 6 hours of phenylpropanolamine administration. Mortality was significantly lower in the phentolamine-pretreated rats (2/14; 14%) as compared to the control group (10/14; 71%; p = 0.006). The degree of myocardial injury was significantly lower in the phentolamine-pretreated rats (0) as compared to the control group (1.4 +/- 1.6; p = 0.012). Reference: J Toxicol Clin Toxicol. 2001;39(2):129-34. https://pubmed.ncbi.nlm.nih.gov/11407498/
Solvent mg/mL mM comments
Solubility
DMF 50.0 132.46
DMSO 47.9 126.95
Ethanol 45.5 120.54
PBS (pH 7.2) 10.0 26.49
Water 54.6 144.61
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 377.46 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
Formulation protocol:
1. Pan L, Liu C, Kong Y, Piao Z, Cheng B. Phentolamine inhibits angiogenesis in vitro: Suppression of proliferation migration and differentiation of human endothelial cells. Clin Hemorheol Microcirc. 2017;65(1):31-41. doi: 10.3233/CH-162070. PMID: 27314442. 2. Traish A, Gupta S, Gallant C, Huang YH, Goldstein I. Phentolamine mesylate relaxes penile corpus cavernosum tissue by adrenergic and non-adrenergic mechanisms. Int J Impot Res. 1998 Dec;10(4):215-23. doi: 10.1038/sj.ijir.3900351. PMID: 9884917 3. Burns MJ, Dickson EW, Sivilotti ML, Cuenoud H. Phentolamine reduces myocardial injury and mortality in a rat model of phenylpropanolamine poisoning. J Toxicol Clin Toxicol. 2001;39(2):129-34. doi: 10.1081/clt-100103828. PMID: 11407498. 4. Ahrén B, Lundquist I. Alpha-adrenoceptor blockade by phentolamine inhibits beta-adrenergically and cholinergically induced glucagon secretion in the mouse. Horm Metab Res. 1987 Dec;19(12):600-3. doi: 10.1055/s-2007-1011889. PMID: 2894339.
In vitro protocol:
1. Pan L, Liu C, Kong Y, Piao Z, Cheng B. Phentolamine inhibits angiogenesis in vitro: Suppression of proliferation migration and differentiation of human endothelial cells. Clin Hemorheol Microcirc. 2017;65(1):31-41. doi: 10.3233/CH-162070. PMID: 27314442. 2. Traish A, Gupta S, Gallant C, Huang YH, Goldstein I. Phentolamine mesylate relaxes penile corpus cavernosum tissue by adrenergic and non-adrenergic mechanisms. Int J Impot Res. 1998 Dec;10(4):215-23. doi: 10.1038/sj.ijir.3900351. PMID: 9884917
In vivo protocol:
1. Burns MJ, Dickson EW, Sivilotti ML, Cuenoud H. Phentolamine reduces myocardial injury and mortality in a rat model of phenylpropanolamine poisoning. J Toxicol Clin Toxicol. 2001;39(2):129-34. doi: 10.1081/clt-100103828. PMID: 11407498. 2. Ahrén B, Lundquist I. Alpha-adrenoceptor blockade by phentolamine inhibits beta-adrenergically and cholinergically induced glucagon secretion in the mouse. Horm Metab Res. 1987 Dec;19(12):600-3. doi: 10.1055/s-2007-1011889. PMID: 2894339.
1: Prados-Frutos JC, Rojo R, González-Serrano J, González-Serrano C, Sammartino G, Martínez-González JM, Sánchez-Monescillo A. Phentolamine mesylate to reverse oral soft-tissue local anesthesia: A systematic review and meta-analysis. J Am Dent Assoc. 2015 Oct;146(10):751-9.e3. doi: 10.1016/j.adaj.2015.04.018. Review. PubMed PMID: 26409985. 2: Grover HS, Gupta A, Saksena N, Saini N. Phentolamine mesylate: It's role as a reversal agent for unwarranted prolonged local analgesia. J Indian Soc Pedod Prev Dent. 2015 Oct-Dec;33(4):265-8. doi: 10.4103/0970-4388.165646. PubMed PMID: 26381625. 3: Boynes SG, Riley AE, Milbee S, Bastin MR, Price ME, Ladson A. Evaluating complications of local anesthesia administration and reversal with phentolamine mesylate in a portable pediatric dental clinic. Gen Dent. 2013 Aug;61(5):70-6. PubMed PMID: 23928444. 4: Nourbakhsh N, Shirani F, Babaei M. Effect of phentolamine mesylate on duration of soft tissue local anesthesia in children. J Res Pharm Pract. 2012 Oct;1(2):55-9. doi: 10.4103/2279-042X.108371. PubMed PMID: 24991590; PubMed Central PMCID: PMC4076863. 5: Yagiela JA. What's new with phentolamine mesylate: a reversal agent for local anaesthesia? SAAD Dig. 2011 Jan;27:3-7. Review. PubMed PMID: 21323030. 6: Hersh EV, Lindemeyer RG. Phentolamine mesylate for accelerating recovery from lip and tongue anesthesia. Dent Clin North Am. 2010 Oct;54(4):631-42. doi: 10.1016/j.cden.2010.06.004. Review. PubMed PMID: 20831927. 7: Froum SJ, Froum SH, Malamed SF. The use of phentolamine mesylate to evaluate mandibular nerve damage following implant placement. Compend Contin Educ Dent. 2010 Sep;31(7):520, 522-8. PubMed PMID: 20879205. 8: Wynn RL. Phentolamine mesylate--an old medical drug becomes a new dental drug. Gen Dent. 2009 May-Jun;57(3):200-2. PubMed PMID: 19819806. 9: Rutherford B, Zeller JR, Thake D. Local and systemic toxicity of intraoral submucosal injections of phentolamine mesylate (OraVerse). Anesth Prog. 2009 Winter;56(4):123-7. doi: 10.2344/0003-3006-56.4.123. PubMed PMID: 20020792; PubMed Central PMCID: PMC2796381. 10: Tavares M, Goodson JM, Studen-Pavlovich D, Yagiela JA, Navalta LA, Rogy S, Rutherford B, Gordon S, Papas AS; Soft Tissue Anesthesia Reversal Group. Reversal of soft-tissue local anesthesia with phentolamine mesylate in pediatric patients. J Am Dent Assoc. 2008 Aug;139(8):1095-104. Erratum in: J Am Dent Assoc. 2008 Oct;139(10):1312. PubMed PMID: 18682624. 11: Poulet FM, Berardi MR, Halliwell W, Hartman B, Auletta C, Bolte H. Development of hibernomas in rats dosed with phentolamine mesylate during the 24-month carcinogenicity study. Toxicol Pathol. 2004 Sep-Oct;32(5):558-66. PubMed PMID: 15603540. 12: Padma-Nathan H, Goldstein I, Klimberg I, Coogan C, Auerbach S, Lammers P; Vasomax Study Group. Long-term safety and efficacy of oral phentolamine mesylate (Vasomax) in men with mild to moderate erectile dysfunction. Int J Impot Res. 2002 Aug;14(4):266-70. PubMed PMID: 12152116. 13: Lammers PI, Rubio-Aurioles E, Castell R, Castaneda J, Ponce de Leon R, Hurley D, Lipezker M, Loehr LA, Lowrey F. Combination therapy for erectile dysfunction: a randomized, double blind, unblinded active-controlled, cross-over study of the pharmacodynamics and safety of combined oral formulations of apomorphine hydrochloride, phentolamine mesylate and papaverine hydrochloride in men with moderate to severe erectile dysfunction. Int J Impot Res. 2002 Feb;14(1):54-9; discussion 60. PubMed PMID: 11896479. 14: Dinsmore WW, Gingell C, Hackett G, Kell P, Savage D, Oakes R, Frentz GD. Treating men with predominantly nonpsychogenic erectile dysfunction with intracavernosal vasoactive intestinal polypeptide and phentolamine mesylate in a novel auto-injector system: a multicentre double-blind placebo-controlled study. BJU Int. 1999 Feb;83(3):274-9. PubMed PMID: 10233493. 15: McCleane GJ. Intravenous phentolamine mesylate alleviates the pain of pancreatic carcinoma. Pain. 1997 Nov;73(2):263-4. PubMed PMID: 9415515. 16: McCleane GJ. Phentolamine mesylate can alleviate the nausea and vomiting associated with liver metastasis. Ulster Med J. 1996 Nov;65(2):165-6. PubMed PMID: 8979787; PubMed Central PMCID: PMC2448593. 17: McCleane GJ. Oral phentolamine mesylate in the treatment of complex regional pain syndrome. Ulster Med J. 1996 May;65(1):87-8. PubMed PMID: 8686109; PubMed Central PMCID: PMC2448742. 18: Hadzija BW, Mattocks AM, Stahl GM. Physicochemical stability of papaverine hydrochloride-phentolamine mesylate mixtures used for intracavernous injection: a preliminary evaluation. J Urol. 1988 Jul;140(1):64-5. PubMed PMID: 2454330. 19: Tu YH, Allen LV Jr, Wang DP. Stability of papaverine hydrochloride and phentolamine mesylate in injectable mixtures. Am J Hosp Pharm. 1987 Nov;44(11):2524-7. PubMed PMID: 2446497. 20: Okabe S, Takeuchi K, Honda K, Takagi K. Effects of phentolamine mesylate and propranolol hydrochloride on aspirin-induced gastric lesions and gastric secretions in the rat. Jpn J Pharmacol. 1974 Jun;24(3):490-2. PubMed PMID: 4449157.