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Phentolamine

Clinical data
Trade names	Regitine
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	C (U.S.)
Routes of administration	Usually IV or IM
ATC code	C04AB01 (WHO) V03AB36 (WHO)
Pharmacokinetic data
Metabolism	Hepatic
Elimination half-life	19 minutes
Identifiers
IUPAC name 3-phenol
CAS Number	50-60-2
PubChem CID	5775
IUPHAR/BPS	502
DrugBank	APRD00615
ChemSpider	5571
UNII	Z468598HBV
KEGG	D08362
ChEMBL	ChEMBL597
CompTox Dashboard (EPA)	DTXSID4023462
ECHA InfoCard	100.000.049
Chemical and physical data
Formula	C17H19N3O
Molar mass	281.352 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES Oc3cc(N(c1ccc(cc1)C)CC/2=N/CCN\2)ccc3
InChI InChI=1S/C17H19N3O/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) Key:MRBDMNSDAVCSSF-UHFFFAOYSA-N
(verify)

Phentolamine (Regitine) is a reversible nonselective alpha-adrenergic antagonist.

Mechanism

Its primary action is vasodilation due to α₁ blockade.

It also can lead to reflex tachycardia because of hypotension and α₂ inhibition, which increases sympathetic tone.

Uses

The primary application for phentolamine is for the control of hypertensive emergencies, most notably due to pheochromocytoma.

It also has usefulness in the treatment of cocaine induced hypertension, where one would generally avoid beta blockers and where calcium channel blockers are not effective. Beta-blockers (i.e. metoprolol) or combined alpha and beta adrenergic blocking agents (i.e. labetalol) should be avoided in patients with a history of cocaine abuse. They can cause an unopposed alpha-adrenergic mediated coronary vasoconstriction, causing the worsening of myocardial ischemia and hypertension.

In this context it is probably most safely given by infusion since bolus doses have a propensity towards causing precipitous falls in blood pressure.

When given by injection it causes blood vessels to expand, thereby increasing blood flow. When injected into the penis (intracavernosal), it increases blood flow to the penis, which results in an erection.

It may be stored in crash carts to counteract severe peripheral vasoconstriction secondary to extravasation of peripherally placed vasopressor infusions, typically of norepinephrine. Epinephrine infusions are less vasoconstrictive than norepinephrine as they primarily stimulate beta receptor more than alpha receptors, but the effect remains dose dependent.

Phentolamine also has diagnostic and therapeutic roles in complex regional pain syndrome (reflex sympathetic dystrophy).

Phentolamine has recently been introduced in the dental field as a local anesthetic reversal agent. Distributed by Septodont, OraVerse is a Phentolamine Mesylate injection designed to reverse the local vasoconstrictor properties used in many local anesthetics to prolong anesthesia. OraVerse has been shown to accelerate the reversal of the lingering soft-tissue numbness associated with the widely used anesthetic-vasoconstrictor combinations.

Chemistry

Phentolamine, 2-methyl]-2-imidazoline, is synthesized by alkylation of 3-(4-methylanilino)phenol using 2-chloromethylimidazoline.

• K. Miescher, A. Marxer, E. Urech, U.S. patent 2,503,059 (1950).
• E. Urech, A. Marxer, K. Miescher, Helv. Chim. Acta, 33, 1386 (1950).

References

1. Jewell, John R.; Longworth, David L.; Stoller, James K.; Casey, David (2003). The Cleveland Clinic internal medicine case reviews. Hagerstown, MD: Lippincott Williams & Wilkins. p. 32. ISBN 0-7817-4266-8.{{cite book}}: CS1 maint: multiple names: authors list (link)
2. Phentolamine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
3. Brock G. Oral phentolamine (Vasomax). Drugs Today (Barcelona). 2000 Feb-Mar;36(2-3):121-4.
4. Shen, Howard (2008). Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. p. 14. ISBN 1-59541-101-1.
5. Tuncel M, Ram VC. Hypertensive emergencies. Etiology and management. American Journal of Cardiovascular Drugs. 2003;3(1):21-31.
6. Hollander JE, Henry TD. Evaluation and management of the patient who has cocaine-associated chest pain. Cardiology Clinics. 2006 Feb;24(1):103-14.
7. Chan GM, Sharma R, Price D, Hoffman RS, Nelson LS. Phentolamine Therapy for Cocaine-Association Acute Coronary Syndrome (CAACS). Journal of Medical Toxicology. 2006 Sep;2(3):108-11.
8. Bella AJ, Brock GB. Intracavernous pharmacotherapy for erectile dysfunction. Endocrine. 2004 Mar-Apr;23(2-3):149-55.
9. Rowbotham MC. Pharmacologic management of complex regional pain syndrome. Clinical Journal of Pain. 2006 Jun;22(5):425-9.
10. http://www.novalar.com/oraverse-dental-specialty-pharmaceutical
11. Malamed S. What's new in local anaesthesia? Society For The Advancement Of Anaesthesia In Dentistry Digest. 2009 Jan;25:4-14.

• Antihypertensive agents
• Vasodilators
• Imidazolines
• Alpha blockers
• Phenols
• Anilines