Compound Summary

General Compound Information

Phenylthiocarbamide

Description
N-phenylthiourea is a member of the class of thioureas that is thiourea in which one of the hydrogens is replaced by a phenyl group. Depending on their genetic makeup, humans find it either very bitter-tasting or tasteless. This unusual property resulted in N-phenylthiourea being used in paternity testing prior to the advent of DNA testing. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor. It derives from a thiourea.
Synonyms
Phenylthiourea;  103-85-5;  N-Phenylthiourea;  1-Phenylthiourea;  1-PHENYL-2-THIOUREA;
FlavorDB ID
41
PUBCHEM ID
Molecular Weight
152.22
Molecular Formula
C7H8N2S
Openeye Can Smiles
C1=CC=C(C=C1)NC(=S)N
IUPAC Inchikey
FULZLIGZKMKICU-UHFFFAOYSA-N
Compound Classification
  • ClassyFire Ontology
Compound Quality
Quality information of this compound is not available!
Compound Toxicity and Food Additive Safety (OFAS)
Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database
IDENTIFICATION AND USE: 1-Phenyl-2-thiourea is a bitter or tasteless (depending on the individual"s genetic background) needle- or prism-like solid material used in medical genetics studies, as a repellent for rats, rabbits, and weasels, and in the production of rodenticides.
HUMAN EXPOSURE AND TOXICITY: 1-Phenyl-2-thiourea can be absorbed by ingestion and parenterally; it may be absorbed and cause systemic toxicity following inhalation or dermal exposure. The bitter taste perception (associated with the ability or inability to taste 1-phenyl-2-thiourea) is mediated by the tas2r38 gene. Some studies have found higher proportions of nontasters among those with a family history of alcoholism than controls, whereas others have not.
ANIMAL STUDIES: Vomiting, noisy or difficult breathing, cyanosis, and hypothermia may occur. Pleural effusions and pulmonary edema have been seen in exposed experimental animals, and this compound destroys cytochrome P450 in vivo. Hypoglycemia lasting for up to 5 hours was seen in rats injected with 1-phenyl-2-thiourea. In mice it was nearly as effective as a strong dose of licl in reducing sucrose drinking. 1-Phenyl-2-thiourea produced a concn-dependent inhibition of rat lung acetylcholinesterase activity in vitro. Phenylthiourea caused mutagenicity in the Salmonella typhimurium assay without S9 activation, but was negative in the salmonella/microsome preincubation assay. At the standard concentration of 0.003% (200 uM), 1-phenyl-2-thiourea inhibits melanogenesis and reportedly has minimal other effects on zebrafish embryogenesis. The administration of 0.003% 1-phenyl-2-thiourea altered retinoic acid and insulin-like growth factor regulation of neural crest and mesodermal components of craniofacial development. 1-Phenyl-2-thiourea also decreased retinoic acid-induced teratogenic effects on pharyngeal arch and jaw cartilage despite morphologically normal appearing 1-phenyl-2-thiourea -treated controls. 1-Phenyl-2-thiourea inhibited neural crest development at higher concentrations (0.03%) and had the greatest inhibitory effect when added prior to 22 hours post fertilization (hpf). Addition of 0.003% 1-phenyl-2-thiourea between 4 and 20 hpf decreased thyroxine (T4) in thyroid follicles in the nasopharynx of 96 hpf embryos. 1-Phenyl-2-thiourea is an experimental teratogen in mice. In NTP 78 weeks feeding study 1-phenyl-2-thiourea was not carcinogenic to rats (120 and 60 ppm) and mice (300 and 150 ppm) in both males or females.
Source: DrugBank or Hazardous Substances Data Bank (HSDB)
Receptors
Receptor REFERENCE EC50 [µM] Effective Concentration [µM]
TAS2R38 details Activated
Consensus Spectra
Spectrum Type Spectrum View Description Polarity
Experimental LCMS view LCMS_Positive positive
Experimental LCMS view LCMS_Negative negative