Compound: prilocaine
SMILES: O=C(Nc1c(cccc1)C)C(NCCC)C
InChIKey: MVFGUOIZUNYYSO-UHFFFAOYSA-N
Synonyms: prilocaine, 721-50-6, Propitocaine, prilocaine base, N-(2-Methylphenyl)-2-(propylamino)propanamide, Prilocaina, Prilocainum, Astra 1515, Propanamide, N-(2-methylphenyl)-2-(propylamino)-, o-Methyl-2-propylaminopropionanilide, o-Propionotoluidide, 2-(propylamino)-, 2-(Propylamino)-o-propionotoluidide, Astra 1512, o-Methyl-alpha-propylaminopropionanilide, 2-Methyl-alpha-propylaminopropionanilide, alpha-n-Propylamino-2-methylpropionanilide, NSC-40027, ASTRA-1512, ASTRA-1515, CHEBI:8404, 046O35D44R, DTXSID7031955, FORTACIN COMPONENT PRILOCAINE, NSC40027, N-(2-methylphenyl)-2-(propylamino)propanimidic acid, RefChem:56655, DTXCID5011955, N01BB04, 211-957-0, Citanest, 2-(Propylamino)-N-(o-tolyl)propanamide, NSC 40027, Propitocaine (JAN), 2-Methyl-.alpha.-propylaminopropionanilide, MFCD00048681, o-Propionotuluidide, 2-propylamino-, Prilocaine [USAN], N-(2-methylphenyl)-N~2~-propylalaninamide, PROPITOCAINE [JAN], Prilocainum [INN-Latin], Prilocaina [INN-Spanish], (R)-Prilocaine, (S)-Prilocaine, (+/-)-Prilocaine, HSDB 3386, Prilocaine (USP/INN), o-Propionotoluidide, 2-propylamino-, EINECS 211-957-0, BRN 2108498, Prilotekal, Prilocain, Prilocaine CRS, UNII-046O35D44R, Prilocaine [USAN:USP:INN:BAN], Prilocaine (Standard), N-(o-tolyl)-2-(propylamino)propanamide, Spectrum_001649, PRILOCAINE [MI], PRILOCAINE [INN], N-(2-methylphenyl)-N(2)-propylalaninamide, Prestwick0_000199, Prestwick1_000199, Prestwick2_000199, Prestwick3_000199, Spectrum2_001549, Spectrum3_001052, Spectrum4_001192, Spectrum5_001175, (.+/-.)-Prilocaine, PRILOCAINE [HSDB], PRILOCAINE [VANDF], PRILOCAINE [MART.], CHEMBL1194, PRILOCAINE [USP-RS], PRILOCAINE [WHO-DD], Lopac0_001005, SCHEMBL25467, BSPBio_000157, BSPBio_002604, KBioGR_001883, KBioSS_002129, DivK1c_000846, SCHEMBL448102, SPBio_001398, SPBio_002078, BPBio1_000173, GTPL7276, orb1300315, orb3141414, DL-(+/-)-PRILOCAINE, EMLA COMPONENT PRILOCAINE, PRILOCAINE [ORANGE BOOK], SCHEMBL31333079, HY-B0137R, KBio1_000846, KBio2_002129, KBio2_004697, KBio2_007265, KBio3_001824, PRILOCAINE [EP MONOGRAPH], NINDS_000846, ORAQIX COMPONENT PRILOCAINE, GLXC-05261, HMS3604H09, HMS3651M13, HMS3884A04, HMS5079M20, PRILOCAINE [USP MONOGRAPH], HY-B0137, MSK15263, PAA28931, PAA28932, BDBM50225477, EBC-11101, s1619, STL257086, AKOS015889404, AC-2100, CCG-205085, CS-1929, DB00750, SDCCGSBI-0050978.P004, IDI1_000846, NCGC00015860-02, NCGC00015860-03, NCGC00015860-15, NCGC00162312-01, AS-14851, FP137966, o-Methyl-.alpha.-propylaminopropionanilide, SY163181, SBI-0050978.P003, DB-055611, AB00053665, NS00000546, SW196783-3, .alpha.-n-Propyl-amino-2-methylpropionanilide, C07531, D00553, EN300-188120, AB00053665-12, AB00053665_13, AB00053665_14, F468387, N-(2-Methylphenyl)-2-(propylamino)propanamide #, Q413598, Propranamide, N-(2-methylphenyl)-2-(propylamino)-, BRD-A53952395-001-02-4, BRD-A53952395-003-05-3, BRD-A53952395-003-15-2, BRD-A53952395-003-25-1, Z44530398, (+/-)-N-(2-PROPYLAMINOPROPIONYL)-2-TOLUIDINE, N-(2,6-DIMETHYLPHENYL)-2-(PROPYLAMINO)PROPANAMIDE
Theoretical properties:
molecular_formula: C13H20N2O
molecular_weight: 220.31 g/mol
exact_mass: 220.157563266 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 5
heavy_atom_count: 16
topological_polar_surface_area: 41.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Needles
color: Needles
odor: ODORLESS
boiling_point: 159-162 °C at 1.00E-01 mm Hg
melting_point: 37-38 °C
Descriptions:
pubchem: Prilocaine is an amino acid amide in which N-propyl-DL-alanine and 2-methylaniline have combined to form the amide bond; used as a local anaesthetic. It has a role as an anticonvulsant and a local anaesthetic. It is an amino acid amide and a monocarboxylic acid amide.
chebi: An  amino acid amide in which <em>N</em>-propyl-<small>D</small><small>L</small>-alanine and 2-methylaniline have combined to form the amide bond; used as a local anaesthetic.
chembl: PRILOCAINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Prilocaine () is a local anesthetic of the amino amide type first prepared by Claes Tegner and Nils Löfgren.  In its injectable form (trade name Citanest), it is often used in dentistry.  It is also often combined with lidocaine as a topical preparation for dermal anesthesia (lidocaine/prilocaine or EMLA), for treatment of conditions like paresthesia.  As it has low cardiac toxicity, it is commonly used for intravenous regional anaesthesia (IVRA).