Xylazine Chemical Properties

Melting point:

140 C

Boiling point:

334.2±52.0 °C(Predicted)

Density 

1.0905 (rough estimate)

refractive index 

1.5700 (estimate)

storage temp. 

-20°C

solubility 

Soluble in methanol at 50mg/ml. Also soluble in dilute acid solutions.

pka

7.67±0.20(Predicted)

form 

Powder

InChI

InChI=1S/C12H16N2S/c1-9-5-3-6-10(2)11(9)14-12-13-7-4-8-15-12/h3,5-6H,4,7-8H2,1-2H3,(H,13,14)

InChIKey

BPICBUSOMSTKRF-UHFFFAOYSA-N

SMILES

S1CCCN=C1NC1=C(C)C=CC=C1C

CAS DataBase Reference

7361-61-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

25-36/37/38

Safety Statements 

45-37/39-26

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

XJ0776300

HazardClass 

6.1

HS Code 

2934990002

Toxicity

LD50 in mice (mg/kg): 43 i.v.; 121 s.c.; 240 orally; LD50 in rats (mg/kg): 130 orally (Sagner)

MSDS

• Language:English Provider:N-(2,6-Dimethylphenyl)-5,6-dihydro-4H-1,3-thiazin-2-amine
• Language:English Provider:SigmaAldrich

Xylazine Usage And Synthesis

Description

Xylazine is an agonist of α₂-adrenergic receptors (K_i = 194 nM). It is an analog of clonidine, an α₂-adrenergic receptor agonist used to reduce blood pressure. Xylazine is used for sedation, anesthesia, and analgesia in non-human mammals. This product is also available as an analytical reference standard .

Originator

Xylazine,Bayer

Uses

Antinociceptive;Alpha-2 adrenergic agonist

Uses

Xylazine is an α2 class of adrenergic receptor agonist. Xylazine is a clonidine analoque that acts on presynaptic and postsynaptic receptors as an a 2-adrenergic agonist.

Definition

ChEBI: Xylazine is a methyl benzene that is 1,3-dimethylbenzene which is substituted by a 5,6-dihydro-4H-1,3-thiazin-2-ylnitrilo group at position 2. It is an alpha2 adrenergic receptor agonist and frequently used in veterinary medicine as an emetic and sedative with analgesic and muscle relaxant properties. It has a role as an emetic, an alpha-adrenergic agonist, a sedative, a muscle relaxant and an analgesic. It is a methylbenzene, a 1,3-thiazine and a secondary amino compound. It is a conjugate base of a xylazine(1+).

Manufacturing Process

2,6-Dimethylphenyl isothiocyanate, 31.0 g (0.2 mole), prepared from 2,6- dimethylaniline with thiophosgene, were added dropwise during 15 min to a well-stirred suspension of 15.0 g (0.2 mole) of 3-aminopropanol-1 in 100 ml of ether. The ether started to boil. Stirring under reflux was continued for 30 min, and the ether was then distilled off. The residue was treated with 100 ml of concentrated hydrochloric acid and boiled under reflux for 30 min. After cooling, it was diluted with water, filtered free from impurities, and the base was precipitated by the addition of concentrated sodium hydroxide solution. When recrystallized from benzene-ligroin, the resulting compound 2-(2,6- dimethyl-phenylamino)-4H-5,6-dihydro-1,3-thiazine, melting point 140-142°C (yield 90% of the theoretical).

Therapeutic Function

Analgesic, Anesthetic

Origin

Xylazine was discovered as an antihypertensive agent in 1962 by Farbenfabriken Bayer in Leverkusen, Germany. Accounts of the actions and uses of xylazine in animals were reported as early as the late 1960s and early 1970s. Results from early human clinical studies confirmed that xylazine has several central nervous system depressant effects.

General Description

Xylazine is soluble in methanol (50 mg/ml), yielding a clear, colorless solution. It is also soluble in dilute HCl acid and in chloroform. Xylazine is practically insoluble in water and in alkali solutions.

Biochem/physiol Actions

Xylazine when used along with ketamine is considered to be a potent and safe anaesthetic in experimental animal. It is known to elevate the hepatic release of glucose, which aggravates to hyperglycemia.

Mechanism of action

Xylazine is marketed as its hydrochloride salt as Rompun (100 mg/mL) and Anased (20 mg/mL) injectable solutions for intravenous administration to horses and dogs, respectively. The actions of xylazine may be reversed by the administration of yohimbine, an indolalkylamine alkaloid, that blocks those α2- adrenoreceptors that are stimulated by xylazine.

Side effects

High doses of Xylazine can cause dizziness, vomiting, high blood sugar, blurry vision and even overdose deaths. If you inject xylazine into your body, you also may develop skin ulcers and severe wounds that can spread and worsen quickly. Xylazine can lead to depression of the central nervous system along with other adverse effects. As for animals, they may show profound salivation following an injection with xylazine. Other adverse effects for dogs and cats include: muscle tremors, bradycardia with AV-block, hypotension, reduced respiratory rate, movement in response to strong auditory stimuli, and increased urination in cats.

Safety Profile

Poison by ingestion, subcutaneous, and intravenous routes. Human systemic effects: change in motor activity, fall in blood pressure, miosis, pleural thickening, pulse rate decrease, somnolence. When heated to decomposition it emits very toxic fumes of NOx and SOx.

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