3-hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one Chemical Properties

Melting point:

107-109°C

Boiling point:

416.5±45.0 °C(Predicted)

Density 

1.275±0.06 g/cm3(Predicted)

Flash point:

9℃

storage temp. 

Hygroscopic, -20°C Freezer, Under Inert Atmosphere

solubility 

DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml; PBS (pH 7.2): 10 mg/ml

form 

A crystalline solid

pka

13.02±0.40(Predicted)

color 

White to off-white

Major Application

cell analysis
clinical research
general analytical
life science and biopharma
metabolomics

InChI

InChI=1S/C10H12N2O2/c1-12-8(5-9(13)10(12)14)7-3-2-4-11-6-7/h2-4,6,8-9,13H,5H2,1H3/t8-,9+/m0/s1

InChIKey

XOKCJXZZNAUIQN-DTWKUNHWSA-N

SMILES

CN1[C@@H](C[C@@H](O)C1=O)C=2C=CC=NC2

Safety Information

Hazard Codes 

F,T

Risk Statements 

11-23/24/25-39/23/24/25

Safety Statements 

16-36/37-45

RIDADR 

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 

1

Storage Class

6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects

Hazard Classifications

Acute Tox. 3 Oral

3-hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one Usage And Synthesis

Description

trans-3’-Hydroxycotinine (3HC) is a product of CYP2A6 metabolism of the primary nicotine metabolite, cotinine . Cotinine has a longer metabolic half-life compared to 3HC (16 hours vs. 5 hours). The ratio of 3HC to cotinine, termed the nicotine metabolite ratio, correlates with nicotine clearance from the body and is used as a biomarker of CYP2A6 activity. This measure of nicotine metabolism has been used to study tobacco and secondhand smoke exposure as well as to develop pharmacological intervention strategies for smoking cessation.

Chemical Properties

Off-White to Pale-Yellow Solid

Uses

A metabolite of Nicotine. Carcinogen.

Uses

trans-3''-Hydroxy Cotinine is a metabolite of Nicotine (N412450, (S)-(-)-Nicotine).

Definition

ChEBI: An N-alkylpyrrolidine that is cotinine substituted at position C-3 by a hydroxy group (the 3R,5S-diastereomer).

General Description

Trans-3′-Hydroxycotinine is a major nicotine metabolite excreted in the urine of smokers and users of other tobacco or nicotine products including cigars, chewing tobacco and snuff. This Certified Spiking Solution^? is suitable for use in nicotine testing methods or clinical and diagnostic testing of nicotine biomarkers by LC-MS/MS or GC/MS.

References

[1] ANDY Z X ZHU. Variation in trans-3’-hydroxycotinine glucuronidation does not alter the nicotine metabolite ratio or nicotine intake.[J]. PLoS ONE, 2013: e70938. DOI: 10.1371/journal.pone.0070938
[2] LINDA B VON WEYMARN S E M Cassandra Retzlaff. CYP2A6- and CYP2A13-catalyzed metabolism of the nicotine Δ5’(1’)iminium ion.[J]. Journal of Pharmacology and Experimental Therapeutics, 2012, 343 2: 307-315. DOI: 10.1124/jpet.112.195255
[3] SHARON E MURPHY. Cotinine and trans 3′-hydroxycotinine in dried blood spots as biomarkers of tobacco exposure and nicotine metabolism[J]. Journal of Exposure Science and Environmental Epidemiology, 2013, 23 5: 513-518. DOI: 10.1038/jes.2013.7

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