Showing Compound Card for Cotinined (CDB005650)

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Record Information
Version1.0
Created at2020-04-27 16:41:57 UTC
Updated at2021-01-04 18:49:03 UTC
CannabisDB IDCDB005650
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCotinined
DescriptionCotinine, also known as (S)-cotinine or cotininum, belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. Cotinine is an alkaloid found in tobacco and is also the predominant metabolite of nicotine. Within humans, cotinine participates in a number of enzymatic reactions. In particular, cotinine can be biosynthesized from nicotine imine through the action of the enzyme aldehyde oxidase. In addition, cotinine can be converted into hydroxycotinine through the action of the enzyme cytochrome P450 2A6. Indeed, most of the reported urinary metabolites of nicotine are derived from cotinine. While cotinine is normally associated with tobacco, it has been detected, but not quantified in, several different plants and foods, such as medlars, cannabis, arrowhead, lotus, alaska blueberries, and thistles. Similarly, to nicotine, cotinine binds to, activates, and desensitizes neuronal nicotinic acetylcholine receptors (especially the alpha-7 nicotinic acetylcholine receptor), though at much lower potency in comparison to nicotine (PMID: 9833639 ). Cotinine has demonstrated nootropic and antipsychotic-like effects in animal models (PMID 19577545 ). Cotinine intake has also been shown to reduce depression, anxiety, and fear-related behavior as well as memory impairment in animal models of depression, PTSD, and Alzheimer's disease (PMID: 24970109 ). Serum cotinine concentration has been used for decades in US population surveys of the Centers for Disease Control and Prevention to monitor tobacco use, to monitor levels and trends in exposure to environmental tobacco smoke, and to study the relationship between tobacco smoke and chronic health conditions. The level of cotinine in the blood, saliva, and urine is proportionate to the amount of exposure to tobacco smoke, so it is a valuable indicator of tobacco smoke exposure, including secondary (passive) smoke. Serum cotinine levels <10 ng/mL are considered to be consistent with no active smoking. Values of 10 ng/mL to 100 ng/mL are associated with light smoking or moderate passive exposure, and levels above 300 ng/mL are seen in heavy smokers - more than 20 cigarettes a day. In urine, values between 11 ng/mL and 30 ng/mL may be associated with light smoking or passive exposure, and levels in active smokers typically reach 500 ng/mL or more. In saliva, values between 1 ng/mL and 30 ng/mL may be associated with light smoking or passive exposure, and levels in active smokers typically reach 100 ng/mL or more (PMID: 18783507 ). African American smokers generally have higher plasma cotinine levels than Caucasian smokers (PMID: 2382740 ) while males generally have higher plasma cotinine levels than females (PMID: 18686176 ). Cotinine is also found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-(-)-CotinineChEBI
(S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinoneChEBI
(S)-CotinineChEBI
CotininaChEBI
CotinineChEBI
CotininumChEBI
ScotineMeSH
Chemical FormulaC10H12N2O
Average Molecular Weight176.22
Monoisotopic Molecular Weight176.095
IUPAC Name(5S)-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
Traditional Namecotinine
CAS Registry Number486-56-6
SMILES
CN1[C@@H](CCC1=O)C1=CN=CC=C1
InChI Identifier
InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1
InChI KeyUIKROCXWUNQSPJ-VIFPVBQESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyrrolidinylpyridines
Direct ParentPyrrolidinylpyridines
Alternative Parents
Substituents
  • Pyrrolidinylpyridine
  • Alkaloid or derivatives
  • Pyrrolidone
  • 2-pyrrolidone
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Lactam
  • Carboxamide group
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.39ALOGPS
logP0.21ChemAxon
logS-0.18ALOGPS
pKa (Strongest Basic)4.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area33.2 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.28 m³·mol⁻¹ChemAxon
Polarizability18.66 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 5V, positivesplash10-004i-0900000000-129b8a08a240554c37ac2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 10V, positivesplash10-004i-0900000000-8c4a53b0d07d21a872932020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 15V, positivesplash10-004i-4900000000-e0b92757f9bd47b7d2832020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 21V, positivesplash10-001i-9300000000-7506b36c886e3cda57512020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 26V, positivesplash10-001i-9100000000-c95ef51b2d0c5e5977c42020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 31V, positivesplash10-001i-9000000000-8591e08a8b8855fc7f8a2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 42V, positivesplash10-001i-9000000000-6e9ecbf549e02269478a2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 52V, positivesplash10-001i-9000000000-11fbeb248c673ceccce02020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 63V, positivesplash10-001i-9000000000-d7fde53a7bedf65d84852020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 40V, positivesplash10-0002-4900000000-1401eaf39c30b52e574f2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 19V, positivesplash10-004i-5900000000-06f0fb1121618a8c5ab82020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 28V, positivesplash10-001i-9100000000-f989f8c76edc4e5555462020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 12V, positivesplash10-004j-2900000000-de77a633fb427b5685432020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QIT 8V, positivesplash10-0032-9900000000-f50b3140ed2e34c5c54b2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-1900000000-9adddcdbdffdccf7cebe2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0059-8900000000-275b870020bc0afcb8ce2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-004i-0900000000-09558c5d6d77a87987472020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-004i-0900000000-e5dd1f650b676b9b77ec2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-004i-0900000000-3e0ba6bec3be80c607512020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-2d0273ce1bbe69dbc29f2019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0900000000-6acb3339c78e32056d722019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9400000000-39a2725cb83b9d78a3a82019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-aa2ec7964920c590b4182019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-4b4d2d3e9eebd29517e12019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9700000000-39765f3dfdc8e2642f2a2019-02-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00034470
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-2742
BiGG IDNot Available
Wikipedia LinkCotinine
METLIN IDNot Available
PubChem Compound854019
PDB IDNot Available
ChEBI ID68641
References
General References
  1. Briggs CA, McKenna DG: Activation and inhibition of the human alpha7 nicotinic acetylcholine receptor by agonists. Neuropharmacology. 1998 Sep;37(9):1095-102. doi: 10.1016/s0028-3908(98)00110-5. [PubMed:9833639 ]
  2. Buccafusco JJ, Terry AV Jr: A reversible model of the cognitive impairment associated with schizophrenia in monkeys: potential therapeutic effects of two nicotinic acetylcholine receptor agonists. Biochem Pharmacol. 2009 Oct 1;78(7):852-62. doi: 10.1016/j.bcp.2009.06.102. Epub 2009 Jul 3. [PubMed:19577545 ]
  3. Grizzell JA, Echeverria V: New Insights into the Mechanisms of Action of Cotinine and its Distinctive Effects from Nicotine. Neurochem Res. 2015 Oct;40(10):2032-46. doi: 10.1007/s11064-014-1359-2. Epub 2014 Jun 27. [PubMed:24970109 ]
  4. Jarvis MJ, Fidler J, Mindell J, Feyerabend C, West R: Assessing smoking status in children, adolescents and adults: cotinine cut-points revisited. Addiction. 2008 Sep;103(9):1553-61. doi: 10.1111/j.1360-0443.2008.02297.x. [PubMed:18783507 ]
  5. Wagenknecht LE, Cutter GR, Haley NJ, Sidney S, Manolio TA, Hughes GH, Jacobs DR: Racial differences in serum cotinine levels among smokers in the Coronary Artery Risk Development in (Young) Adults study. Am J Public Health. 1990 Sep;80(9):1053-6. doi: 10.2105/ajph.80.9.1053. [PubMed:2382740 ]
  6. Gan WQ, Cohen SB, Man SF, Sin DD: Sex-related differences in serum cotinine concentrations in daily cigarette smokers. Nicotine Tob Res. 2008 Aug;10(8):1293-300. doi: 10.1080/14622200802239132. [PubMed:18686176 ]