Compound: cotinine
SMILES: O=C1N([C@H](c2cnccc2)CC1)C
InChIKey: UIKROCXWUNQSPJ-VIFPVBQESA-N
Synonyms: cotinine, (-)-Cotinine, 486-56-6, (S)-Cotinine, Cotinina, Cotininum, S-(-)-Cotinine, (S)-(-)-Cotinine, (5S)-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one, DTXSID1047576, (S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone, 2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-, (5S)-, (5S)-1-methyl-5-pyridin-3-ylpyrrolidin-2-one, CHEBI:68641, K5161X06LL, n-methyl-2-(3-pyridyl)-5-pyrrolidone, 2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-, (S)-, DTXCID9027576, Scotine, RefChem:128208, 207-634-9, 1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone, 1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one, (S)-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one, Cotinine [INN], Cotinine (-), MFCD00077696, (5S)-1-methyl-5-(3-pyridyl)pyrrolidin-2-one, (-)-Cotinine 100 microg/mL in Acetonitrile, (5~{S})-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one, BRD4010, Nicotine EP Impurity C, BRD-4010, (5S)-1-Methyl-5-(pyridin-3-yl)pyrrolidin-2-one ((-)-Cotinine), SMR000449278, S-(-)-Cotinine (1.0 mg/mL in Methanol), Cotininum [INN-Latin], SR-01000075768, Cotinina [INN-Spanish], UNII-K5161X06LL, CCRIS 7625, HSDB 7805, NCGC00093739-04, (5S)-1-methyl-5-(3-pyridinyl)-2-pyrrolidinone, CAS-486-56-6, Prestwick_134, EINECS 207-634-9, (-)-Cotinine;(S)-Cotinine;NIH-10498, Cotinine (Standard), NIH 10498, BRN 0083099, (S)-1-Methyl-5-(3-pyridyl)-2-pyrrolidinone, Spectrum_001984, COTININE [HSDB], COTININE [MI], Prestwick0_000082, Prestwick1_000082, Prestwick2_000082, Prestwick3_000082, Spectrum3_000700, Spectrum4_001793, Spectrum5_000465, bmse000577, (-)-Cotinine, 98%, Epitope ID:2272242, Lopac0_000285, SCHEMBL49060, BSPBio_000004, BSPBio_002459, KBioGR_002368, KBioSS_002550, 5-24-02-00504 (Beilstein Handbook Reference), MLS000758262, MLS001423950, NIH 10498(Cotinine)?, DivK1c_000861, SPECTRUM1500208, SPBio_001943, (-)-Cotinine, >=98%, BPBio1_000006, CHEMBL578211, MEGxp0_001870, orb1309427, SCHEMBL29404962, ACon1_000202, HY-B1178R, KBio1_000861, KBio2_002541, KBio2_005109, KBio2_007677, KBio3_001679, NINDS_000861, US8609708, 91 Cotinine, HMS1568A06, HMS1920A14, HMS2051A15, HMS2091G22, HMS2095A06, HMS2232F15, HMS3260J12, Pharmakon1600-01500208, (-)-Cotinine, analytical standard, HY-B1178, MSK10040, Tox21_111219, Tox21_300615, Tox21_500285, BBL102262, BDBM50370573, NSC756704, s9339, STL556061, AKOS007930814, Tox21_111219_1, (-)-Cotinine 1.0 mg/ml in Methanol, CCG-100799, CS-4787, EBC-612610, FC20565, LP00285, NC00049, NSC-756704, SDCCGMLS-0066565.P001, SDCCGSBI-0050273.P004, IDI1_000861, NC01 - Nicotine and Cotinine in Urine, NCGC00093739-08, NCGC00093739-13, NCGC00093739-20, NCGC00254396-01, NCGC00260970-01, AC-35718, AS-50387, NICOTINE IMPURITY C [EP IMPURITY], S-(-)-Cotinine (1 mg/mL in Methanol), ST057157, SY075839, SBI-0050273.P003, EU-0100285, NS00010263, C 5923, P10066, S(-)-1-Methyl-5-(3-pyridyl)-2-pyrrolidone, AB00053721_08, NICOTINE RESINATE IMPURITY C [EP IMPURITY], Q421177, SR-01000075768-1, SR-01000075768-5, SR-01000075768-6, (-)-1-METHYL-5-(3-PYRIDYL)-2-PYRROLIDINONE, (S)-(-)-1-Methyl-5-(3-pyridiyl)-2-pyrrolidinone, BRD-K94144010-001-04-8, BRD-K94144010-001-05-5, BRD-K94144010-001-09-7, BRD-K94144010-001-13-9, NICOTINE DITARTRATE DIHYDRATE IMPURITY C [EP IMPURITY], U5H
Theoretical properties:
molecular_formula: C10H12N2O
molecular_weight: 176.21 g/mol
exact_mass: 176.094963011 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 13
topological_polar_surface_area: 33.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Viscous oil
color: Viscous oil
boiling_point: 210-211 °C at 6 mm Hg
Descriptions:
{"pubchem": "(-)-cotinine is an N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum. It has a role as an antidepressant, a biomarker, a plant metabolite and a human xenobiotic metabolite. It is a member of pyridines, a pyrrolidine alkaloid, a N-alkylpyrrolidine and a member of pyrrolidin-2-ones.", "chebi": "An <em>N</em>-alkylpyrrolidine that consists of <em>N</em>-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5<i>S</i>-enantiomer). It is an alkaloid commonly found in <em>Nicotiana tabacum</em>.", "chembl": "COTININE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.", "wikipedia": "Cotinine is an alkaloid found in tobacco and is also the predominant metabolite of nicotine, typically used as a biomarker for exposure to tobacco smoke. Cotinine is currently being studied as a treatment for depression, post-traumatic stress disorder (PTSD), schizophrenia, Alzheimer's disease and Parkinson's disease. Cotinine was developed as an antidepressant as a fumaric acid salt, cotinine fumarate, to be sold under the brand name Scotine, but it was never marketed.\nSimilarly to nicotine, cotinine binds to, activates, and desensitizes neuronal nicotinic acetylcholine receptors, though at much lower potency in comparison. It has demonstrated nootropic and antipsychotic-like effects in animal models. Cotinine treatment has also been shown to reduce depression, anxiety, and fear-related behavior as well as memory impairment in animal models of depression, post-traumatic stress disorder, and Alzheimer's disease. Nonetheless, treatment with cotinine in humans was reported to have no significant physiologic, subjective, or performance effects in one study, though others suggest that this may not be the case. \nBecause cotinine is the main metabolite to nicotine and has been shown to be pharmacologically active, it has been suggested that some of nicotine's effects in the nervous system may be mediated by cotinine and/or complex interactions with nicotine itself."}