''n''-Butyl cyanoacrylate (n-BCA, NBCA), a

cyanoacrylate Cyanoacrylates are a family of strong fast-acting adhesives with industrial, medical, and household uses. They are derived from ethyl cyanoacrylate and related esters. The cyanoacrylate group in the monomer rapidly polymerizes in the presence ...

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

, is a

butyl In organic chemistry, butyl is a four- carbon alkyl radical or substituent group with general chemical formula , derived from either of the two isomers (''n''-butane and isobutane) of butane. The isomer ''n''-butane can connect in two ways, gi ...

of 2-cyano-2-propenoic acid. It is a colorless liquid with a sharp, irritating odor. It is insoluble in water. Its chief use is as the main component of medical cyanoacrylate glues. It can be encountered under various

trade name A trade name, trading name, or business name, is a pseudonym used by companies that do not operate under their registered company name. The term for this type of alternative name is a "fictitious" business name. Registering the fictitious name w ...

s, e.g. Cutseal, MediBond, MediCryl, PeriAcryl, GluStitch, Xoin, Gesika, VetGlu, Vetbond, LiquiVet, Indermil, LiquiBand, Histoacryl, IFABond, CutisSeal and others. The generic international nonproprietary name (INN) for NBCA is enbucrilate. In medical and veterinary applications, NBCA,

isobutyl cyanoacrylate Isobutyl cyanoacrylate is an isomer of butyl cyanoacrylate. It is used in medical procedures either to close incisions and lacerations without the use of sutures, or as an adjunct to strengthen the suturing. This use is possible because it is a ...

, and octyl cyanoacrylate are commonly used. They are

bacteriostatic A bacteriostatic agent or bacteriostat, abbreviated Bstatic, is a biological or chemical agent that stops bacteria from reproducing, while not necessarily killing them otherwise. Depending on their application, bacteriostatic antibiotics, disinfect ...

and their use is usually painless. Butyl esters provide stronger bond, but are rigid. Octyl esters, while providing weaker bond, are more flexible. Blends of octyl cyanoacrylate and n-butyl cyanoacrylate are available (such as GLUture) which offer both flexibility and a strong bond. n-Butyl cyanoacrylate is also used for embolization of cerebral arteriovenous malformations before their surgical treatment. NBCA in monomer form is soluble in

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...

methyl ethyl ketone Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nat ...

nitromethane Nitromethane, sometimes shortened to simply "nitro", is an organic compound with the chemical formula . It is the simplest organic nitro compound. It is a polar liquid commonly used as a solvent in a variety of industrial applications such as in ...

, and

methylene chloride Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with ...

. It polymerizes rapidly in presence of ionic substances such as moisture, blood, or tissue fluids. NBCA has unique properties compared to other cyanoacrylates such as octyl cyanoacrylate or isoamyl cyanoacrylate. The polymerized form has excellent tensile strength and is very effective in closing surgical or wound incisions. The closure of the wound or cut is quick (about 30 to 45 seconds) and the product has inherently some valuable bacteriostatic properties. The cosmetic outcome of the closure is comparable or generally better than an equivalent suture substitute with least amount of scarring visible after three to six months. Also important is the degradation properties of polymerized NBCA within the body. This property of NBCA has made it a very useful polymer to create various nanoparticles for delivery of drugs into the body with sustained release profiles. Heating to higher temperatures causes

pyrolysis The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''py ...

and depolymerization of the cured glue, producing gaseous products strongly irritating to lungs and eyes.

Medical applications

The medical applications of butyl cyanoacrylate include its use as an adhesive for

laceration A wound is a rapid onset of injury that involves lacerated or punctured skin (an ''open'' wound), or a contusion (a ''closed'' wound) from blunt force trauma or compression. In pathology, a ''wound'' is an acute injury that damages the epiderm ...

s of the skin, and in the treatment of bleeding from vascular structures. Butyl cyanoacrylate has been used to treat

arteriovenous malformation Arteriovenous malformation is an abnormal connection between arteries and veins, bypassing the capillary system. This vascular anomaly is widely known because of its occurrence in the central nervous system (usually cerebral AVM), but can appea ...

s by application of the glue into the abnormality through

angiography Angiography or arteriography is a medical imaging technique used to visualize the inside, or lumen, of blood vessels and organs of the body, with particular interest in the arteries, veins, and the heart chambers. Modern angiography is performe ...

. In gastroenterology, butyl cyanoacrylate is used to treat bleeding

gastric varices Gastric varices are dilated submucosal veins in the lining of the stomach, which can be a life-threatening cause of bleeding in the upper gastrointestinal tract. They are most commonly found in patients with portal hypertension, or elevated pr ...

, which are dilated

vein Veins are blood vessels in humans and most other animals that carry blood towards the heart. Most veins carry deoxygenated blood from the tissues back to the heart; exceptions are the pulmonary and umbilical veins, both of which carry oxygenated b ...

s that occur in the setting of liver

cirrhosis Cirrhosis, also known as liver cirrhosis or hepatic cirrhosis, and end-stage liver disease, is the impaired liver function caused by the formation of scar tissue known as fibrosis due to damage caused by liver disease. Damage causes tissue repai ...

thrombosis Thrombosis (from Ancient Greek "clotting") is the formation of a blood clot inside a blood vessel, obstructing the flow of blood through the circulatory system. When a blood vessel (a vein or an artery) is injured, the body uses platelets (thro ...

of the

splenic vein The spleen is an organ (biology), organ found in almost all vertebrates. Similar in structure to a large lymph node, it acts primarily as a blood filter. The word spleen comes .

. The gastric varices are accessed by

endoscopy An endoscopy is a procedure used in medicine to look inside the body. The endoscopy procedure uses an endoscope to examine the interior of a hollow organ or cavity of the body. Unlike many other medical imaging techniques, endoscopes are insert ...

, which uses a flexible fibre-optic camera to enter the stomach. They are injected with a catheter needle inserted into the varix through the endoscope. Other sites of varices, including

esophageal varices Esophageal varices are extremely dilated sub-mucosal veins in the lower third of the esophagus. They are most often a consequence of portal hypertension, commonly due to cirrhosis. People with esophageal varices have a strong tendency to develop ...

, duodenal varices and colonic varices. Gastric varices have also been obliterated with recurrent injection treatment with butyl cyanoacrylate.

* Octyl cyanoacrylate .Galil, K.A., Schofield, I and Wright, G.Z. (1980) Localization of cyanoacrylates in tissue sections. International Assoc. for Dental Res. Joint meeting of Buffalo, Toronto, Western, and Rochester Chapters, Rochester, N.Y. Session #1, 7. .Galil, K.A. and Wright, G.Z. Bonding of adhesive resins to acid etched enamel of primary tooth surfaces. J. Dent Res. 60: 313 #10, Special Issue. ..Galil, K.A., Schofield, I. and Wright. G.Z. (1981) Cyanoacrylate tissue adhesive detection in histological sections. J. Dent. Res. 60: 561 #1005, Special Issue .Galil, K.A., Schofield, I. and Wright, G.Z. (1981) A studies on incisional wound healing in hamster using N-Butyl-2-C Cyanoacrylate (Histoacryl Blue). Intern. Assoc. for Dent. Res., Ontario Section. Joint meeting of Buffalo, Toronto Western and Rochester Chapters, Ontario. Session # 2, 5. .Galil, K.A., Wright, G.Z. and Schofield, I. (1982) Effect of N-Butyl-2 Cyanoacrylate (Histoacryl Blue) on the healing of skin wounds. J. Dent. Res. 61: 258, # 718. Special Issue. .Galil, K.A., Wright, G.Z. and Schofield, I. (1982) the response of hamster cheek pouches to cyanoacrylate tissue adhesive (Histoacryl Blue). J. Dent. Res. 61: 259, # 723. Special Issue. .Marck, P.A., Cummins, J.E., Galil, K.A., Schofield, I. and Wright, G.Z. (1982) Weak mutagen city of an N-Butyl- 2-Cyanoacrylate tissue adhesive. J. Dent. Res. 61:288, #983. Special Issue. 21.Pinto, J. and Galil, K.A. (1982) Epithelial wound closure in the oral cavity of the rat. J. Dent. Res. 61: 307, #62. Special Issue .Galil, K.A., Schofield, I.D. and Wright, G.Z. (1982) Isobutyl cyanoacrylate tissue adhesive (Histoacryl) as a surface an adhesive in skin ulcers. XII biennial Conference on Dental Res. ACFD/CADR. Dalhousie Univ., Halifax, Nova Scotia. ACFD/CADR 14:19 #11 Special Issues. J. Dent. Res. 62: 445 #24 (1983) Special Issue .Galil, K.A., Schofield, I.D. and Wright, G.Z. (1983) Effects of Histoacryl Blue on ulcers of hamster cheek pouch. J. D Dent. Res. 62:245, #683. .Ryall, L., Galil, K.A., Wright, G.Z. (1983) In vitro cytotoxicity of two Cyano-acrylates using the agar overlay Technique. Int. Assn. Dent. Res., Lake Ont. Region, Buffalo, N.Y. November. 7, # 10 .Galil, K.A., Schofield, I.D., Wright, G.Z. and Ryall, L. (1984) Cytotoxic effect of two cyanoacrylates. An in vitro study. I.A.D.R. meeting, Dallas, Texas. J. Dent. Res. 63:325, #1389. .Galil, K. A., Schofield, I.D. and Wright, G.Z. (1984). The effect of repeated application of tissue adhesive on the mucosa of the hamster cheek pouch. I.A.D.R. meeting, Dallas, Texas. J. Dent. Res. 63: 324, #1382 .Galil, K.A. and Schofield, I.D. (1984) Evaluation of the biocompatibility of cyanoacrylate material (Histoacryl Blue) in hamsters. Int. Assn. Dent. Res., Lake Ontario Region, Niagara-on-the-Lake, Ontario. October. 9, # 6. .Way. D.C., MacPhee, C.A., and Galil, K.A. (1984) Comparing the polyacrylic acid technique with a conventional p phosphoric acid etch bonding technique. U.W.O. Research Conference, October. 2, # 4. .Galil, K.A. and Schofield, I.D. (1985) A Study of possible oncogenic action of tissue adhesive-Histoacryl-blue by Implantation in hamster and mice. J. dent. Res. 64: 304, # 1163. .Schofield, I.D. and Galil, K.A. (1986) Local and systemic response to a tissue adhesive (Histoacryl blue). 9th International Conference on Oral and Maxillofacial Surgery, 90, # 24. .Galil, K.A., Wright, G.Z. and Schofield, I.D. (1984) The healing of hamster skin ulcers treated with N-butyl-2- Cyanoacrylate (Histoacryl Blue). J. Biomed. Mater. Res. 18, 601-607. .Galil, K.A., Scholfield, I.D. and Wright, G.Z. (1984) Detection of cyanoacrylate tissue adhesives in histological Sections. J. Biomed. Mater. Res., 18, 609-616. .Galil, K.A., Schofield, I.D. and Wright, G.Z. (1984) Effect of N-butyl-2-cyanoacrylate (Histoacryl Blue) on Healing of skin wounds. J. Canad. Dent. Assn. 50, 565-569. Vinters, H.V., Galil, K.A., Lundi, M. and Kaufman, J.C. (1985) Review article. The Histotoxicity of cyanoacrylate. Neuroradiology. 27, 279-291.

References

{{reflist, 2 Cyanoacrylate esters Monomers Butyl compounds

Medical applications

See also

References