S-(-)-Cotinine - Moligand™,≥98% , CAS No.486-56-6

CAS: 486-56-6 Cat. No.: S303802 Molecular Weight: 176.22 EC Number: 207-634-9

GRADE & PURITY Moligand™, ≥98%

Synonyms

HMS1920A14 | NC00049 | SDCCGMLS-0066565.P001 | KBio3_001679 | Pharmakon1600-01500208 | Prestwick2_000082 | STL556061 | (-)-Cotinine, 98% | HMS2091G22 | MEGxp0_001870 | MFCD00077696 | 2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-, (S)- | K5161X06LL | NICOTINE

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Application

(-)-Cotinine is used to activate a subpopulation of α3/ α6β2 nAChRs in monkey striatum. It binds nicotinic- and muscarinic-type acetylcholine receptors with minimal receptor desensitization and demonstrates antipsychotic drug-like properties in behavioral models, neuroprotective properties in neurodegenerative disease models, and enhances attention in a delayed matching-to-sample task.

Specifications

Synonyms

HMS1920A14 | NC00049 | SDCCGMLS-0066565.P001 | KBio3_001679 | Pharmakon1600-01500208 | Prestwick2_000082 | STL556061 | (-)-Cotinine, 98% | HMS2091G22 | MEGxp0_001870 | MFCD00077696 | 2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-, (S)- | K5161X06LL | NICOTINE

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Major metabolite of nicotine in humans. Displays cognition-enhancing effects in vivo ; reduces amyloid β (Aβ) aggregation and improves memory in an Alzheimer's disease mouse model. Activates a subpopulation of α3/α6β2 nAChRs in

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504760285
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504760285
• Canonical Smiles: CN1C(CCC1=O)C2=CN=CC=C2
• IUPAC Name: (5S)-1-methyl-5-pyridin-3-ylpyrrolidin-2-one
• InChIKey: UIKROCXWUNQSPJ-VIFPVBQESA-N
• 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
• Isomeric SMILES: CN1[C@@H](CCC1=O)C2=CN=CC=C2
• Molecular Weight: 176.22
• Reaxy-Rn: 141449
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=141449&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyridines and derivatives
      • Subclass Pyrrolidinylpyridines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyridines and derivatives
• Subclass: Pyrrolidinylpyridines
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrrolidinylpyridines
• Alternative Parents: Alkaloids and derivatives Pyrrolidine-2-ones N-alkylpyrrolidines Tertiary carboxylic acid amides Heteroaromatic compounds Lactams Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• 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
• Description: This compound belongs to the class of organic compounds known as pyrrolidinylpyridines. These are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.
• External Descriptors: pyrrolidine alkaloid - pyridines - pyrrolidin-2-ones - N-alkylpyrrolidine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

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ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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DRD4 Tchem Dopamine D4 receptor (7907 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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HTR1D Tclin Serotonin 1d (5-HT1d) receptor (2897 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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HTR4 Tclin Serotonin 4 (5-HT4) receptor (2068 Activities)

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CYSLTR1 Tclin Cysteinyl leukotriene receptor 1 (2118 Activities)

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CHRM4 Tclin Muscarinic acetylcholine receptor M4 (6041 Activities)

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CHRM5 Tclin Muscarinic acetylcholine receptor M5 (4677 Activities)

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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

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CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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EDNRA Tclin Endothelin receptor ET-A (5008 Activities)

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TACR1 Tclin Neurokinin 1 receptor (6273 Activities)

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ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

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BDKRB2 Tclin Bradykinin B2 receptor (3970 Activities)

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GABBR1 Tclin GABA-B receptor 1 (184 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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NPY2R Tchem Neuropeptide Y receptor type 2 (3731 Activities)

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LTB4R Tchem Leukotriene B4 receptor 1 (1083 Activities)

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PRKCA Tchem Protein kinase C alpha (5923 Activities)

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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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CYP2A6 Tchem Cytochrome P450 2A6 (2861 Activities)

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Homo sapiens (32628 Activities)

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FEN1 Tchem Flap endonuclease 1 (12055 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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Associated Targets(non-human)

Htr7 Serotonin 7 (5-HT7) receptor (19 Activities)

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Sigmar1 Sigma opioid receptor (160 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Galc Galactocerebrosidase (11 Activities)

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Cyp2a5 Cytochrome P450 2A5 (126 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Musca domestica (713 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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BCHE Cholinesterase (8742 Activities)

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Cacna1c Voltage-gated L-type calcium channel (1164 Activities)

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nAChRalpha5 Nicotinic acetylcholine receptor alpha 5 subunit (134 Activities)

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Tmem97 Sigma intracellular receptor 2 (922 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Flash Point(°F): 230°F
• Flash Point(°C): >110°
• Boil Point(°C): 145-147°/3 mm
• Molecular Weight: 176.210 g/mol
• XLogP3: -0.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 176.095 Da
• Monoisotopic Mass: 176.095 Da
• Topological Polar Surface Area: 33.200 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 205.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Gao-Feng Wu, Jian Zhu, Guo-Jun Weng, Jian-Jun Li, Jun-Wu Zhao.  (2025)  3D composite SERS substrate constructed by Au–Ag core-satellite NPs and polystyrene sphere for ultrasensitive ratiometric Raman detection of cotinine.  TALANTA,      [PMID:39985926] [10.1016/j.talanta.2025.127742]

2. SunHongzheng , HanLongsen , GuoYueshuai , AnHuiqing , WangBing , ZhangXiangzheng , LiJiashuo , JiangYingtong , WangYue , SunGuangyi , ZhuShuai , TangShoubin , GeJuan , ChenMinjian , GuoXuejiang , WangQiang.  (2024)  The global phosphorylation landscape of mouse oocytes during meiotic maturation.  EMBO JOURNAL,      [PMID:39256562] [10.1038/s44318-024-00222-1]