Äntu

α-Naphthylthiourea

Names
IUPAC name Naphthalen-1-ylthiourea
Other names 1-(1-Naphthyl)-2-thiourea; ANTU; Dirax; 1-Naphthylthiourea; Anturat; Rattrack; Smeesana; Alrato; alpha-Naphthylthiourea; 1-Naphthyl thiourea
Identifiers
CAS Number	86-88-4 N
3D model (Jmol)	Interactive image Interactive image
Abbreviations	ANTU
ChemSpider	643492 Y
ECHA InfoCard	100.001.552
KEGG	C19136 N
PubChem CID	736366
InChI InChI=1S/C11H10N2S/c12-11(14)13-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,(H3,12,13,14) Y Key: PIVQQUNOTICCSA-UHFFFAOYSA-N Y InChI=1/C11H10N2S/c12-11(14)13-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,(H3,12,13,14) Key: PIVQQUNOTICCSA-UHFFFAOYAV
SMILES C1=CC=C2C(=C1)C=CC=C2NC(=S)N S=C(N)Nc2cccc1ccccc12
Properties
Chemical formula	C11H10N2S
Molar mass	202.28 g·mol−1
Appearance	White solid, crystallizes in prisms from alcohol Colorless, solid. White. White, crystalline or gray powder.
Melting point	197.8 °C (388.0 °F; 470.9 K)
Boiling point	Decomposes
Solubility in water	600 mg/L
Solubility in other solvents	2.43 g/100mL (acetone) 8.6 g/100mL (triethylene glycol)
log P	1.65
Vapor pressure	6.6x10−6 mmHg
Henry's law constant (kH)	8.51x10−9 atm-cu m/mol
Hazards
Main hazards	Toxic
Flash point	noncombustible
Lethal dose or concentration (LD, LC):
LD50 (median dose)	0.38 mg/kg (dog, oral) 6 mg/kg (rat, oral) 4250 mg/kg (monkey, oral) 5 mg/kg (mouse, oral)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 0.3 mg/m3
REL (Recommended)	TWA 0.3 mg/m3
IDLH (Immediate danger)	100 mg/m3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

α-Naphthylthiourea (ANTU) is an organosulfur compound with the formula C₁₀H₇NHC(S)NH₂. This a white, crystalline powder although commercial samples may be off-white. It is used as a rodenticide and as such is fairly toxic. Naphthylthiourea is available as 10% active baits in suitable protein- or carbohydrate-rich materials and as a 20% tracking powder.

Like other thioureas, ANTU can be prepared by several routes. The usual method is the reaction of 1-naphthylamine hydrochloride with ammonium thiocyanate:

It is produced from the reaction of 1-naphthyl isothiocyanate with ammonia.

Alpha-Naphthylthiourea is toxic to inhalation, ingestion, or skin contact, although the intoxication may be delayed. According to the U.S. National Institute for Occupational Safety and Health (NIOSH), the recommended workplace airborne exposure limit is 0.3 mg/m³ averaged over a 10-hour workshift. Exposure to 100 mg/m³ is immediately dangerous to life and health. The lethal dose in humans is approximately 4 g/kg.

A oral dose of 3 mg per kilogram of body weight causes the death of 50% of the rats exposed (LD₅₀), showing a very high selectivity when compared for example to monkeys ( 4000 mg per kilogram of body weight). However other studies have shown a much higher efficacy for dogs (a LD₅₀ of 0.38 mg/Kg).

The mortality of rats caused by 5 mg/kg of ANTU is reduced when allylthiourea, isopropylthiourea, ethylenethiourea, or ethylidenethiourea are administered simultaneously with ANTU.Superoxide dismutase, catalase and dimethylsulfoxide all protect against the lung damage by ANTU (although the results are diverse). This indicates that OH radicals are responsible for this type of lung injury. Given hydroxurea over 2 days doesn’t block the ANTU damage when neutrophils are decreased or when administered acutely. Cyclooxygenase pathway may generate the free radicals since ibuprofen blocked as well the ANTU damage.