34834-67-8 Usage
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
Different sources of media describe the Uses of 34834-67-8 differently. You can refer to the following data:
1. A metabolite of Nicotine. Carcinogen.
2. 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.
Check Digit Verification of cas no
The CAS Registry Mumber 34834-67-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,4,8,3 and 4 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 34834-67:
(7*3)+(6*4)+(5*8)+(4*3)+(3*4)+(2*6)+(1*7)=128
128 % 10 = 8
So 34834-67-8 is a valid CAS Registry Number.
InChI:InChI=1/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
34834-67-8Relevant articles and documents
Synthesis of (3′R,5′S)-3′-hydroxycotinine using 1,3-dipolar cycloaddition of a nitrone
Tamura, Osamu,Kanoh, Ayano,Yamashita, Masayuki,Ishibashi, Hiroyuki
, p. 9997 - 10003 (2007/10/03)
To synthesize (3′R,5′S)-3′-hydroxycotinine [(+)-1], the main metabolite of nicotine (2), cycloaddition of C-(3-pyridyl)nitrones 3a, 3c, and 15 with (2R)- and (2S)-N-(acryloyl)bornane-10,2-sultam [(2R)- and (2S)-8] was examined. Among them, l-gulose-derived nitrone 15 underwent stereoselective cycloaddition with (2S)-8 to afford cycloadduct 16, which was elaborated to (+)-1. Graphical Abstract
Synthesis of (3'R,5'S)-trans-3'-hydroxycotinine, a major metabolite of nicotine. Metabolic formation of 3'-hydroxycotinine in humans is highly stereoselective
Jacob III,Shulgin,Benowitz
, p. 1888 - 1891 (2007/10/02)
A method for the synthesis of (3'R,5'S-trans-3'-hydroxycotinine, a major metabolite of nicotine in humans, is described. The method involves deprotonation of (S)-cotinine with lithium diisopropylamide (LDA) followed by oxidation with the transition metal peroxide oxodiperoxymolybdenum (pyridine)(hexamethylphosphoric triamide)(MoOPH) to give an 80:20 mixture of trans-/cis-3'-hydroxycotinine. The pure (>98%) trans isomer is obtained by conversion to the solid hexanoate ester, recrystallization, and cleavage of the ester by heating with n-butylamine. GC-MS analysis of urine extracts from several smokers indicated that in humans metabolic 3'-hydroxycotinine is 95-98% trans.
Deuterium isotope effects in the in vivo metabolism of cotinine
Dagne,Gruenke,Castagnoli Jr.
, p. 1330 - 1333 (2007/10/04)
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