Pyrrocaine

Last updated
Pyrrocaine
Pyrrocaine.svg
Names
Preferred IUPAC name
N-(2,6-Dimethylphenyl)-2-(pyrrolidin-1-yl)acetamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 218-642-7
KEGG
PubChem CID
UNII
  • InChI=1S/C14H20N2O/c1-11-6-5-7-12(2)14(11)15-13(17)10-16-8-3-4-9-16/h5-7H,3-4,8-10H2,1-2H3,(H,15,17)
    Key: OYCGKECKIVYHTN-UHFFFAOYSA-N
  • Cc1cccc(c1NC(=O)CN2CCCC2)C
Properties
C14H20N2O
Molar mass 232.327
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pyrrocaine is a local anesthetic drug. The cogency of pyrrocaine is equivalent to lidocaine in blocking the motor nerve and sensory. Pyrrocaine was proven to be somewhat harmless compared to lidocaine. No signs of methemoglobinemia was found while observing. It was considered unsafe for acute porphyria treatment. No evidence is found that it is profitly used now. [1]

Contents

History

In the 1960s it was most of the time used as a nerve blocker dental anesthetic and dentists recommended it due to its fast commencement. [1]

Adverse effects

Pyrrocane has very similar side effects on blood pressure and heart rate compared to lidocaine. [2]

Synthesis

Selfsame as lidocaine, albeit interposing pyrrolidine for diethylamine.

Synthesis: Patents: Pyrrocaine synthesis.svg
Synthesis: Patents:

Amide formation between 2,6-Dimethylaniline (1) and Chloroacetyl chloride (2) gives [1131-01-7] (3). Displacement of the remaining halogen by pyrrolidine (4) completed the synthesis of Pyrrocaine (5).

See also

Related Research Articles

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Anesthesia or anaesthesia is a state of controlled, temporary loss of sensation or awareness that is induced for medical or veterinary purposes. It may include some or all of analgesia, paralysis, amnesia, and unconsciousness. An individual under the effects of anesthetic drugs is referred to as being anesthetized.

Local anesthesia is any technique to induce the absence of sensation in a specific part of the body, generally for the aim of inducing local analgesia, i.e. local insensitivity to pain, although other local senses may be affected as well. It allows patients to undergo surgical and dental procedures with reduced pain and distress. In many situations, such as cesarean section, it is safer and therefore superior to general anesthesia.

<span class="mw-page-title-main">Local anesthetic</span> Medications to reversibly block pain

A local anesthetic (LA) is a medication that causes absence of all sensation in a specific body part without loss of consciousness, as opposed to a general anesthetic, which eliminates all sensation in the entire body and causes unconsciousness. Local anesthetics are most commonly used to eliminate pain during or after surgery. When it is used on specific nerve pathways, paralysis also can be induced.

<span class="mw-page-title-main">Procaine</span> Local anesthetic drug

Procaine is a local anesthetic drug of the amino ester group. It is most commonly used in dental procedures to numb the area around a tooth and is also used to reduce the pain of intramuscular injection of penicillin. Owing to the ubiquity of the trade name Novocain or Novocaine, in some regions, procaine is referred to generically as novocaine. It acts mainly as a sodium channel blocker. Today, it is used therapeutically in some countries due to its sympatholytic, anti-inflammatory, perfusion-enhancing, and mood-enhancing effects.

<span class="mw-page-title-main">Lidocaine</span> Local anesthetic

Lidocaine, also known as lignocaine and sold under the brand name Xylocaine among others, is a local anesthetic of the amino amide type. It is also used to treat ventricular tachycardia. When used for local anaesthesia or in nerve blocks, lidocaine typically begins working within several minutes and lasts for half an hour to three hours. Lidocaine mixtures may also be applied directly to the skin or mucous membranes to numb the area. It is often used mixed with a small amount of adrenaline (epinephrine) to prolong its local effects and to decrease bleeding.

<span class="mw-page-title-main">Bupivacaine</span> Pair of enantiomers

Bupivacaine, marketed under the brand name Marcaine among others, is a medication used to decrease feeling in a specific area. In nerve blocks, it is injected around a nerve that supplies the area, or into the spinal canal's epidural space. It is available mixed with a small amount of epinephrine to increase the duration of its action. It typically begins working within 15 minutes and lasts for 2 to 8 hours.

<span class="mw-page-title-main">Nerve block</span> Deliberate inhibition of nerve impulses

Nerve block or regional nerve blockade is any deliberate interruption of signals traveling along a nerve, often for the purpose of pain relief. Local anesthetic nerve block is a short-term block, usually lasting hours or days, involving the injection of an anesthetic, a corticosteroid, and other agents onto or near a nerve. Neurolytic block, the deliberate temporary degeneration of nerve fibers through the application of chemicals, heat, or freezing, produces a block that may persist for weeks, months, or indefinitely. Neurectomy, the cutting through or removal of a nerve or a section of a nerve, usually produces a permanent block. Because neurectomy of a sensory nerve is often followed, months later, by the emergence of new, more intense pain, sensory nerve neurectomy is rarely performed.

<span class="mw-page-title-main">Articaine</span> Chemical compound

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<span class="mw-page-title-main">Prilocaine</span> Local anesthetic of the amino amide type

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<span class="mw-page-title-main">Chloroprocaine</span> Chemical compound

Chloroprocaine is a local anesthetic given by injection during surgical procedures and labor and delivery. Chloroprocaine vasodilates; this is in contrast to cocaine which vasoconstricts. Chloroprocaine is an ester anesthetic.

<span class="mw-page-title-main">Alfred Einhorn</span> German chemist (1856–1917)

Alfred Einhorn was a German chemist most notable for first synthesizing procaine in 1905 which he patented under the name Novocain. Until that time the primary anesthetic in use was cocaine, however its undesirable side effects led scientists to seek out newer anesthetic drugs. Novocain was found to be comparatively safe and effective, although its anesthetic effects were weaker than cocaine and some patients proved highly allergic. However, none of the other anesthetics developed during this period proved more effective and Novocain quickly became the standard local anesthesia. Although its use has largely been replaced by lidocaine, it is still in use today, most frequently in dentistry.

A retrobulbar block is a regional anesthetic nerve block in the retrobulbar space, the area located behind the globe of the eye. Injection of local anesthetic into this space constitutes the retrobulbar block. This injection provides akinesia of the extraocular muscles by blocking cranial nerves II, III, and VI, thereby preventing movement of the globe. Cranial nerve IV lies outside the muscle cone, and therefore is not affected by the local anesthesia. As a result, intorsion of the eye is still possible. It also provides sensory anesthesia of the conjunctiva, cornea and uvea by blocking the ciliary nerves. This block is most commonly employed for cataract surgery, but also provides anesthesia for other intraocular surgeries.

Dental anesthesia is the application of anesthesia to dentistry. It includes local anesthetics, sedation, and general anesthesia.

<span class="mw-page-title-main">Dimethocaine</span> Stimulant

Dimethocaine, also known as DMC or larocaine, is a compound with a stimulatory effect. This effect resembles that of cocaine, although dimethocaine appears to be less potent. Just like cocaine, dimethocaine is addictive due to its stimulation of the reward pathway in the brain. However, dimethocaine is a legal cocaine replacement in some countries and is even listed by the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) under the category “synthetic cocaine derivatives”. The structure of dimethocaine, being a 4-aminobenzoic acid ester, resembles that of procaine. It is found as a white powder at room temperature.

A paracervical block is an anesthetic procedure used in obstetrics and gynecology, in which a local anesthetic is injected into between two and six sites at a depth of 3–7 mm alongside the vaginal portion of the cervix in the vaginal fornices. In the United States, the paracervical block is underutilized during insertion of intrauterine devices (IUDs). There is speculation that this is related to the disproportionate under-researching of women's health.

<span class="mw-page-title-main">Brachial plexus block</span>

Brachial plexus block is a regional anesthesia technique that is sometimes employed as an alternative or as an adjunct to general anesthesia for surgery of the upper extremity. This technique involves the injection of local anesthetic agents in close proximity to the brachial plexus, temporarily blocking the sensation and ability to move the upper extremity. The subject can remain awake during the ensuing surgical procedure, or they can be sedated or even fully anesthetized if necessary.

<span class="mw-page-title-main">Intravenous regional anesthesia</span>

Intravenous regional anesthesia (IVRA) or Bier's block anesthesia is an anesthetic technique on the body's extremities where a local anesthetic is injected intravenously and isolated from circulation in a target area. The technique usually involves exsanguination of the target region, which forces blood out of the extremity, followed by the application of pneumatic tourniquets to safely stop blood flow. The anesthetic agent is intravenously introduced into the limb and allowed to diffuse into the surrounding tissue while tourniquets retain the agent within the desired area.

Fascia iliaca blocks is a local anesthetic nerve block, a type of regional anesthesia technique, used to provide analgesia or anaesthesia to the hip and thigh. FICB can performed by using ultrasound or with a loss of resistance technique, the latter sometimes referred to as the "two-pop-method". FICB works by affecting the femoral, obturator and the lateral cutaneous nerves with a local anesthetic.

Hypokalemic sensory overstimulation is characterized by a subjective experience of sensory overload and a relative resistance to lidocaine local anesthesia. The sensory overload is treatable with oral potassium gluconate. Individuals with this condition are sometimes diagnosed as having attention deficit hyperactivity disorder (ADHD), raising the possibility that a subtype of ADHD has a cause that can be understood mechanistically and treated in a novel way.

References

  1. 1 2 "NCATS Inxight: Drugs". drugs.ncats.io. Retrieved 2018-08-07.
  2. Annals of Dentistry. New York Academy of Dentistry. 1983.
  3. Löfgren, Nils; Tegnér, Claës; Takman, Bertil (1957). "Studies on Local Anesthetics. XVI.". Acta Chemica Scandinavica 11: 1724–1737. doi:10.3891/acta.chem.scand.11-1724.
  4. US 2813861,Schlesinger, Albert&Gordon, Samuel M.,"Pyrrolidino-2, 6-dimethyl anilide salt of 8-[2'-methoxy-3'-(7-theophyllinyl mercuri)] propyl-coumarin-3-carboxylic acid",published 1957-11-19, assigned to Endo Laboratories, Inc.
  5. GB 986993,"Local anesthetics",published 1965-03-24, assigned to Graham Chemical Corp.