Compound: Icaridin
SMILES: O=C(OC(CC)C)N1C(CCCC1)CCO
InChIKey: QLHULAHOXSSASE-UHFFFAOYSA-N
Synonyms: Icaridin, Picaridin, 119515-38-7, Bayrepel, Icaridine, Pikaridin, Propidine, sec-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate, Icaridina, Cutter Advanced, Icaridinum, Saltidin, butan-2-yl 2-(2-hydroxyethyl)piperidine-1-carboxylate, 1-Piperidinecarboxylic acid, 2-(2-hydroxyethyl)-, 1-methylpropyl ester, 1-(1-Methylpropoxycarbonyl)-2-(2-hydroxyethyl)piperidine, 2-(2-Hydroxyethyl)-1-piperidinecarboxylic acid 1-methylpropyl ester, DTXSID0034227, N51GQX0837, 1-Methylpropyl 2-(2-hydroxyethyl)-1-piperidinecarboxylate, 1-Methylpropyl 2-(2-hydroxyethyl)piperidine-1-carboxylate, hydroxyethyl isobutyl piperidine carboxylate, DTXCID8014227, RefChem:55390, SG Plus Repellent Aroma Mist, 423-210-8, Kbr 3023, Icaridin [INN], Lcaridin, MFCD01756488, Icaridine [INN-French], Icaridinum [INN-Latin], Icaridina [INN-Spanish], Icaridin-d3, HSDB 7374, UNII-N51GQX0837, CCRIS 8576, Icaridin (Picaridin), ICARIDIN [HSDB], PICARIDIN [MI], ICARIDIN [MART.], ICARIDIN [WHO-DD], EC 423-210-8, SCHEMBL135432, orb1307877, orb3025192, 119515-38-7 unlabeled, CHEMBL2104314, CHEBI:143733, MSK20488, Tox21_301141, 2-(2-Hydroxyethyl)-1-piperidinecarboxylic Acid 1-Methyl-propyl Ester, 2-(2-Hydroxyethyl)-1-piperidinecarboxylic Acid 1-Methyl-d3-propyl Ester, AKOS005145519, AC-6795, DB14074, DS-3268, FP27035, NCGC00163920-01, NCGC00163920-02, NCGC00163920-03, NCGC00255039-01, Picaridin 100 microg/mL in Acetonitrile, SY111276, DB-188907, HY-116144, CAS-119515-38-7, CS-0064147, NS00008107, D70300, Q418792, (RS)-SEC-BUTYL (RS)-2-(2-HYDROXYETHYL)PIPERIDINE-1-CARBOXYLATE, sec-Butyl 2-(2-hydroxyethyl)piperidine-1- carboxylate/icaridine (icaridine), 658051-75-3
Theoretical properties:
molecular_formula: C12H23NO3
molecular_weight: 229.32 g/mol
exact_mass: 229.16779360 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 5
heavy_atom_count: 16
topological_polar_surface_area: 49.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Colorless liquid
color: Colorless liquid
odor: Nearly odorless
melting_point: < -170
density: 1.07 at 20 °C
solubility: Insoluble
vapor_pressure: 0.00044 [mmHg]
Descriptions:
pubchem: Butan-2-yl 2-(2-hydroxyethyl)piperidine-1-carboxylate is a member of piperidines and a carboxylic acid.
chembl: ICARIDIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Picaridin, also known as icaridin, is an insect repellent which can be used directly on skin or clothing. It has broad efficacy against various arthropods such as mosquitos, ticks, gnats, flies and fleas, and is almost colorless and odorless. A study performed in 2010 showed that picaridin spray and cream at the 20% concentration provided 12 hours of protection against ticks. Unlike DEET, picaridin does not dissolve plastics, synthetics or sealants, is odorless and non-greasy and presents a lower risk of toxicity when used with sunscreen, as it may reduce skin absorption of both compounds.
The name picaridin was proposed as an International Nonproprietary Name (INN) to the World Health Organization (WHO), but the official name that has been approved by the WHO is icaridin. The chemical is part of the piperidine family, along with many pharmaceuticals and alkaloids such as piperine, which gives black pepper its spicy taste.
Trade names include Bayrepel and Saltidin among others. The compound was developed by the German chemical company Bayer in the 1980s  and was given the name Bayrepel. In 2005, Lanxess AG and its subsidiary Saltigo GmbH were spun off from Bayer and the product was renamed Saltidin in 2008.
Picaridin has been sold in Europe, where it is the best-selling insect repellent, since 1998. On 23 July 2020, the EU Commission approved it again for use in repellent products. The approval entered into force on 1 February 2022 and is valid for ten years.