Xylazine

HCID 5707CAS 7361-61-7

Basic information

Standard SMILES
Cc1cccc(C)c1NC1=NCCCS1
InChIKey
BPICBUSOMSTKRF-UHFFFAOYSA-N
Molecular formula
C12H16N2S
Average molar mass
220.34 g/mol
Monoisotopic mass
220.10341951

Overview

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 analgesic, an alpha-adrenergic agonist, a sedative and a muscle relaxant. It is a methylbenzene, a 1,3-thiazine and a secondary amino compound. It is a conjugate base of a xylazine(1+).

Names & identifiers

Preferred name
Xylazine
IUPAC
N-(2,6-dimethylphenyl)-5,6-dihydro-4H-1,3-thiazin-2-amine
English name
Xylazine
Molecular formula
C12H16N2S
Molecular weight
220.33

Names & synonyms

xylazine7361-61-7N-(2,6-Dimethylphenyl)-5,6-dihydro-4H-1,3-thiazin-2-amineXilazinaChanazineXylazinumXylazinBAY 14705,6-Dihydro-2-(2,6-xylidino)-4H-1,3-thiazineWH 72864H-1,3-Thiazin-2-amine, N-(2,6-dimethylphenyl)-5,6-dihydro-2-(2,6-Dimethylanilino)-5,6-dihydro-4H-1,3-thiazine
Show more names
Xylazine (free base)wh7286bay1470Mobay RompunXylazine (CRM)Xylazine, >=99%
DTXSID30406432-(2,6-Dimethylphenylamino)-4H-5,6-dihydro-1,3-thiazine2KFG9TP5V8NSC-758142CHEBI:92386DTXCID1020643XylaxineRefChem:56228

Database identifiers

CAS
7361-61-7
PubChem CID
5707
DTXSID
DTXSID3040643
ChEMBL
CHEMBL297362
ChEBI
CHEBI:92386
UNII
2KFG9TP5V8
EC Number
230-902-1
Nikkaji
J8.925G

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
49.7 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
15

Experimental & physicochemical properties

Drugs · 2 items

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

Pharmaceuticals -> Listed in ZINC15

LogP1.34
Animal Drugs · 3 items

Active Ingredients (Xylazine) -> FDA Greenbook

Pharmaceuticals -> UK Veterinary Medicines Directorate List

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Collision Cross Section · 5 items

147.9 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

148.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated]

147.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

147.16 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

148.72 Ų [M+H]+

Physicochemical properties

Melting point
140 C · 140 C
Boiling point
334.2 · 334.2±52.0 °C(Predicted)
Density
1.0905 · 1.0905 (rough estimate)
refractive index
1.57 · 1.5700 (estimate)
storage temp.
-20 °C · -20°C
solubility
50 mg/ml · Soluble in methanol at 50mg/ml. Also soluble in dilute acid solutions.

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (98.1%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 54 reports by companies from 6 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationXylazine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - 4H-1,3-Thiazin-2-amine, N-(2,6-dimethylphenyl)-5,6-dihydro-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (98.1%)

Toxicology

Exposure RoutesIIntravenous (IV) administration was a common route for Xylazine as noted in case reports. Other routes included subcutaneous (SC), intramuscular (IM), and inhalation, with overall doses ranging from 40 mg to 4300 mg in humans.
Toxicity Summary · 2 items

Xylazine use can cause drowsiness, abnormally slow or absent breathing, low blood pressure, and a slow heart rate. A coma can develop and require the insertion of a breathing tube and hospitalization. The overdoes signs and symptoms are similar to those of heroin, fentanyl, and other opioids. If xylazine is added to opioids, severe toxicity and death can occur due to the combined effects of the drugs. Withdrawal can occur in people who abruptly discontinue use, and can result in markedly elevated blood pressure, rapid heart rate, and agitation. Headaches, insomnia, and nausea can also occur during withdrawal.

Acute xylazine exposure can lead to severe central nervous system (CNS) depression, respiratory depression, bradycardia, hypotension, and, in extreme cases, cardiac arrest. Long-term use of xylazine-mixed illicit substances can result in cumulative toxic effects, e.g., chronic wounds and ulcers on the skin. The primary metabolite of xylazine, 2,6-xylidine, has carcinogenic and genotoxic effects, and long-term users of xylazine appear to be at increased risk for malignancies. There are no human data on the effect of xylazine on embryogenesis and pregnancy. Studies have found increased uterine contractions, decreased uterine blood flow, and fetal loss when used in pregnant cattle and goats.

Antidote and Emergency Treatment · 1 item

Identification of xylazine toxicity is difficult due to its use as an adulterant and possible polysubstance use. Identifying xylazine toxicity based on history and physical examination is challenging since other substances and their toxidromes may be present. The authors of this publication suggest having a low threshold of suspicion for coadministration of xylazine and any available illicit drug. Xylazine toxicity by itself is characterized by CNS depression. Symptoms may include a "high" feeling, sedation, dry mouth, dysarthria, hyporeflexia, disorientation, dysmetria, miosis, hypotension, bradycardia, hypothermia, and hyperglycemia. Xylazine combined with other CNS depressants such as opioids, benzodiazepines, or alcohol can cause severe CNS depression with signs and symptoms of obtundation, coma, muscle relaxation, hypotension or hypertension, respiratory depression, areflexia, asthenia or apnea, cardiac arrhythmias or cardiac arrest. As of June 2023, no pharmacological antidote for xylazine intoxication has been approved by the United States Food and Drug Administration (FDA). Management of xylazine intoxication involves supportive care, monitoring for adverse effects, and interventional management as symptoms present. The few studies on humans and animals indicate potentially life-threatening complications of xylazine use, including biventricular failure, pulmonary edema, cardiac necrosis, valvular dysfunction, and insulin-dependent diabetes mellitus.

Human Toxicity Values · 1 item

The doses in case reports ranged from 40 mg to 4300 mg in humans. The average dose in fatal cases was 1,200 mg, compared to 525 mg in non-fatal cases. Concurrent administration of other drugs, primarily opioids, occurred in 28 cases (47.5%).

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
rtecs
XJ0776300
ridadr
UN 2811 6.1/PG 3
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)

Chemistry & industry

Pharmacology

ATC CodeQN - Nervous system
MeSH Pharmacological Classification · 4 items

Compounds capable of relieving pain without the loss of CONSCIOUSNESS.

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.

A heterogeneous group of drugs used to produce muscle relaxation, excepting the neuromuscular blocking agents. They have their primary clinical and therapeutic uses in the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. They have been used also for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in MULTIPLE SCLEROSIS. (From Smith and Reynard, Textbook of Pharmacology, 1991, p358)

Compounds that bind to and activate ADRENERGIC ALPHA-2 RECEPTORS.

Uses & manufacturing

Consumer Uses · 2 items

Xylazine is available for veterinary usage for injection in concentrations of 20 mg/mL, 100 mg/mL, and 300 mg/mL. The solution may be dried into a powder or salted. Xylazine may be added to other illicit substances for many reasons.

Xylazine is an animal tranquilizer used to provide sedation, pain relief, and muscle relaxation. It was initially studied in humans as a potential blood pressure-lowering drug; however, it was found to cause excessive sleepiness. Currently, xylazine is not approved for human use by the U.S. Food and Drug Administration. Xylazine was initially discovered as an illicit drug contaminant in the U.S. in the early 2000s, e.g., it has been found in cocaine, heroin, and fentanyl.

Use Classification · 3 items

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Veterinary Drug -> ADRENOCEPTOR_AGONIST -> JECFA Functional Classes

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Applications · 4 items

DescriptionXylazine is an agonist of α2-adrenergic receptors (Ki = 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 .

UsesAntinociceptive;Alpha-2 adrenergic agonist

UsesXylazine 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.

General DescriptionXylazine 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.

Upstream & downstream products

Additional notes · 1 item

DefinitionChEBI: 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+).

Related reactions

25 records

Linked notes

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