Synonym
Phentolamine HCl; Phentolamine chloride; Regitine hydrochloride;
IUPAC/Chemical Name
3-(((4,5-dihydro-1H-imidazol-2-yl)methyl)(p-tolyl)amino)phenol hydrochloride
InChi Key
TUEJFGFQYKDAPM-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H19N3O.ClH/c1-13-5-7-14(8-6-13)20(12-17-18-9-10-19-17)15-3-2-4-16(21)11-15;/h2-8,11,21H,9-10,12H2,1H3,(H,18,19);1H
SMILES Code
Oc1cccc(N(c2ccc(C)cc2)CC3=NCCN3)c1.Cl
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
Biological target:
Phentolamine hydrochloride is an orally active adrenergic α receptor-blocking agent.
In vitro activity:
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:
Changes in pain behavior and GLT-1 protein levels in the SNI rat spinal cords were then examined by intrathecal administration of the α1 adrenergic antagonist phentolamine, followed by von Frey test and western blotting. SNI resulted in the development of MIP and bilateral downregulation of GLT-1 protein in the rat spinal cord. Intrathecal phentolamine increased contralateral GLT-1 protein levels and partially ameliorated the 50% paw withdrawal threshold in the contralateral hind paw. Spinal GLT-1 upregulation by intrathecal phentolamine ameliorates MIP.
Reference: Acta Med Okayama. 2022 Jun;76(3):255-263. https://pubmed.ncbi.nlm.nih.gov/35790355/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
125.0 |
393.31 |
|
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
317.82
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. 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. Ahn SW, Kim SH, Kim JH, Choi S, Yeum CH, Wie HW, Sun JM, So I, Jun JY. Phentolamine inhibits the pacemaker activity of mouse interstitial cells of Cajal by activating ATP-sensitive K+ channels. Arch Pharm Res. 2010 Mar;33(3):479-89. doi: 10.1007/s12272-010-0319-x. Epub 2010 Mar 30. PMID: 20361315.
3. Nakatsuka K, Matsuoka Y, Kurita M, Wang R, Tsuboi C, Sue N, Kaku R, Morimatsu H. Intrathecal Administration of the α1 Adrenergic Antagonist Phentolamine Upregulates Spinal GLT-1 and Improves Mirror Image Pain in SNI Model Rats. Acta Med Okayama. 2022 Jun;76(3):255-263. doi: 10.18926/AMO/63719. PMID: 35790355.
4. Zainul Z, Ma B, Koka M, Wilkerson JL, Ortiz YT, Kerosuo L, Chandran V. Novel roles of phentolamine in protecting axon myelination, muscle atrophy, and functional recovery following nerve injury. Sci Rep. 2022 Feb 28;12(1):3344. doi: 10.1038/s41598-022-07253-w. PMID: 35228612; PMCID: PMC8885794.
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. Ahn SW, Kim SH, Kim JH, Choi S, Yeum CH, Wie HW, Sun JM, So I, Jun JY. Phentolamine inhibits the pacemaker activity of mouse interstitial cells of Cajal by activating ATP-sensitive K+ channels. Arch Pharm Res. 2010 Mar;33(3):479-89. doi: 10.1007/s12272-010-0319-x. Epub 2010 Mar 30. PMID: 20361315.
In vivo protocol:
1. Nakatsuka K, Matsuoka Y, Kurita M, Wang R, Tsuboi C, Sue N, Kaku R, Morimatsu H. Intrathecal Administration of the α1 Adrenergic Antagonist Phentolamine Upregulates Spinal GLT-1 and Improves Mirror Image Pain in SNI Model Rats. Acta Med Okayama. 2022 Jun;76(3):255-263. doi: 10.18926/AMO/63719. PMID: 35790355.
2. Zainul Z, Ma B, Koka M, Wilkerson JL, Ortiz YT, Kerosuo L, Chandran V. Novel roles of phentolamine in protecting axon myelination, muscle atrophy, and functional recovery following nerve injury. Sci Rep. 2022 Feb 28;12(1):3344. doi: 10.1038/s41598-022-07253-w. PMID: 35228612; PMCID: PMC8885794.
1: Zimina OA, Kovalenko RI, Nozdrachev AD. The effects of epiphyseal peptides on the release of immunoglobulins in Peyer's patches in rats in vitro. Neurosci Behav Physiol. 2003 Nov;33(9):893-7. doi: 10.1023/a:1025900922645. PMID: 14969428.
2: Wilkins AS, Marota JJ, Tabit E, Kosofsky BE. Transplacental cocaine exposure. 3: Mechanisms underlying altered brain development. Neurotoxicol Teratol. 1998 May-Jun;20(3):239-49. doi: 10.1016/s0892-0362(97)00128-1. PMID: 9638681.
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5: Dembe K, Jasik M, Piechna K. Ocena przydatności klinicznej wstrzyknieć do ciał jamistych leków zwiekszajacych miejscowy przepływ naczyniowy w leczeniu impotencji erekcyjnej u chorych na cukrzyce [Evaluation of clinical usefulness of direct drug injections for increasing local circulation, into cavernous bodies of the penis for treatment of erection impotence in patients with diabetes mellitus]. Pol Tyg Lek. 1994 Jan 3-17;49(1-3):19-20. Polish. PMID: 8008670.
6: Richter S, Shalev M, Nissenkorn I. [Intracavernous pharmacotherapy for organic impotence in the elderly]. Harefuah. 1990 Aug;119(3-4):66-7. Hebrew. PMID: 2227669.
7: Bischoff E, Schneider K. A conscious-rabbit model to study vardenafil hydrochloride and other agents that influence penile erection. Int J Impot Res. 2001 Aug;13(4):230-5. doi: 10.1038/sj.ijir.3900703. PMID: 11494080.
8: Lin SB, Hu C, Qin YP, Miao J, Feng SY, Shu SQ, Nan F, Wang Y, Zhu XH, Liang MZ. [Pharmacokinetics Study of Phentolamine Mesylate Injection in Healthy Volunteers]. Sichuan Da Xue Xue Bao Yi Xue Ban. 2018 Nov;49(6):929-933. Chinese. PMID: 32677407.
