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HHS Public Access
Author manuscript
Int J Hyg Environ Health. Author manuscript; available in PMC 2022 June 01.
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Published in final edited form as:
Int J Hyg Environ Health. 2021 June ; 235: 113749. doi:10.1016/j.ijheh.2021.113749.
Harmonization of acronyms for volatile organic compound
metabolites using a standardized naming system
Denise S. Tevisa, Sharon R. Floresa, Brandon M. Kenwooda, Deepak Bhandaria,*, Peyton
Jacob 3rdb, Jia Liub, Pawel K. Lorkiewiczc, Daniel J. Conklinc, Stephen S. Hechtd, Maciej L.
Goniewicze, Benjamin C. Blounta, Víctor R. De Jesúsa
aTobaccoand Volatiles Branch, Division of Laboratory Sciences, National Center for
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Environmental Health, U.S. Centers for Disease Control and Prevention, Atlanta, GA, USA
bDepartment of Medicine, University of California San Francisco, Division of Cardiology, Clinical
Pharmacology Program, San Francisco General Hospital Medical Center, University of California
at San Francisco, San Francisco, CA, USA
cAmerican Heart Association - Tobacco Regulation and Addiction Center, Superfund Research
Center, Diabetes and Obesity Center, Christina Lee Brown Envirome Institute, University of
Louisville, Louisville, KY, USA
dMasonic Cancer Center, University of Minnesota, Minneapolis, MN, USA
eNicotine and Tobacco Product Assessment Resource, Department of Health Behavior, Division
of Cancer Prevention and Population Studies, Roswell Park Comprehensive Cancer Center,
Buffalo, NY, USA
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Abstract
Increased interest in volatile organic compound (VOC) exposure has led to an increased need
for consistent, systematic, and informative naming of VOC metabolites. As analytical methods
have expanded to include many metabolites in a single assay, the number of acronyms in use
for a single metabolite has expanded in an unplanned and inconsistent manner due to a lack
of guidance or group consensus. Even though the measurement of VOC metabolites is a well-
established means to investigate exposure to VOCs, a formal attempt to harmonize acronyms
amongst investigators has not been published. The aim of this work is to establish a system of
acronym naming that provides consistency in current acronym usage and a foundation for creating
acronyms for future VOC metabolites.
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*
Corresponding author. DBhandari@cdc.gov (D. Bhandari).
Publisher's Disclaimer: Disclaimers
Publisher's Disclaimer: The views and opinions expressed in this report are those of the authors and do not necessarily represent the
views, official policy or position of the US Department of Health and Human Services or any of its affiliated institutions or agencies or
the American Heart Association. Use of trade names is for identification purposes and does not imply endorsement by the US Centers
for Disease Control and Prevention, the Public Health Service, or the US Department of Health and Human Services.
Declaration of competing interest
None to declare.
Tevis et al. Page 2
Keywords
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Biomonitoring; Volatile organic compounds; Volatile organic compound metabolites; Mercapturic
acids; Naming systems; Acronyms
1. Introduction
Human exposure to volatile organic compounds (VOCs) is a major public health concern
due to their association with adverse health effects such as cancer, birth defects, and
neurological damage (Altmann et al., 1990; Lamplugh et al., 2019). Exposure to VOCs
is often assessed by measuring the urinary metabolite of the parent VOC (Alwis et
al., 2012; Bhandari et al., 2019; Carmella et al., 2007; Ding et al., 2009; Jacob et al.,
2013; Lorkiewicz et al., 2019; St Helen et al., 2014). VOC exposure is of interest to
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a wide range of researchers and regulatory agencies, such as the U.S. Food and Drug
Administration (FDA)(Husten and Deyton, 2013) and the Occupational Safety and Health
Administration (OSHA)(Papp and Miller, 2000). Biomonitoring data produced by laboratory
scientists is an important component for evaluating diverse sources of VOC exposure e.g.,
occupational (Belloc-Santaliestra et al., 2015; Brouwer et al., 2005; Jo and Song, 2001;
Zhong et al., 2019), environmental (Yeager et al., 2020), and tobacco (St Helen et al., 2020).
Volatile organic compound metabolites have a diverse set of naming conventions that can
create confusion among public health researchers and can impede clear communication
of analytical results among public health agencies, researchers, and the public. Clear
communication of these analytical results is critical for colleagues working in the same
discipline and other disciplines such as health policy, public health communication, and
epidemiology. Additionally, the lack of a clear naming convention can impede laboratories
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that measure VOC metabolites (VOCMs) from successful participation in proficiency testing
challenges due to the absence of a common set of acronyms. Successful proficiency testing
performance is important because it is typically an accreditation requirement.
Advances in mass spectrometry techniques, like multiple reaction monitoring mass
spectrometry, allows for the analysis of many metabolites at once. This technology, coupled
with an increase in the number of detectable metabolites, an increase in the understanding
of VOC metabolism and its usefulness for monitoring exposure to harmful VOCs, resulted
in the creation of single methods that can measure as many as 28 VOCMs (Alwis et al.,
2012; Pluym et al., 2015). As interest in these biomarkers of VOC exposure — VOCMs —
increased and the techniques to measure them improved, the collection of acronyms used
to describe them expanded. In the absence of a systematic method for creating acronyms or
consensus on which acronyms to use, VOCM acronyms have grown organically.
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The lack of a uniform naming convention for VOCMs has led to inconsistent acronym
use throughout the literature (Table 4). Specifically, a single VOCM may have multiple
acronyms or a single acronym may be used for multiple VOC metabolites. This is
particularly problematic for mercapturic acids (MA), which are N-acetyl-S-L-cysteine
conjugates of VOCs (Fig. 1, Table 4) formed in humans via the glutathione-S-transferase
pathway (Hanna and Anders, 2019). For example, 2-carboxyethyl mercapturic acid, an
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Tevis et al. Page 3
acrolein metabolite (Linhart et al., 1996), and 2-cyanoethyl mercapturic acid, a metabolite of
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acrylonitrile (Jakubowski et al., 1987), are both commonly represented as CEMA (Gregg
et al., 2013). Additionally, GAMA may refer to two different acrylamide metabolites:
2-carbamoyl-2-hydroxyethyl mercapturic acid (Boettcher et al., 2005) and 1-carbamoyl-2-
hydroxyethyl mercapturic acid (Ruenz et al., 2016). MHBMA, a metabolite of 1,3-
butadiene, may refer to 2-hydroxy-3-buten-1-yl-mercapturic acid or to a mixture of that
compound and 1-hydroxymethyl-2-propenyl mercapturic acid (Ding et al., 2009).
Some current naming conventions also fail to distinguish isomers. For example, DPMA
is a common abbreviation for the diphenyl mercapturic acids, but does not distinguish
between the ortho, para, or meta isomers. Additionally, PHEM and PHEMA represent
phenyl hydroxyethyl mercapturic acids, which are metabolites of styrene (Capella et al.,
2019). However, phenyl hydroxyethyl mercapturic acid is a mixture of two isomers: N-
acetyl-S-(1-phenyl-2-hydroxyethyl)-L-cysteine and N-acetyl-S-(2-phenyl-2-hydroxyethyl)-
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L-cysteine. When resolved chromatographically and quantitated separately, previous
abbreviations included the stereocenter as part of the acronym, e.g., (S, R)-M1 for N-
acetyl-S-(1-phenyl-2-hydroxyethyl)-L-cysteine and (S, R)-M2 for N-acetyl-S-(2-phenyl-2-
hydroxyethyl)-L-cysteine (De Palma et al., 2001; Linhart et al., 1998). Furthermore,
multiple isomers of metabolites of 1,3-butadiene (monohydroxy butenyl mercapturic acids
MHBMA1, MHBMA2, MHBMA3 (St Helen et al., 2014; Sterz et al., 2012) and isoprene
(isoprene mercapturic acids IPMA1, IPMA2, IPMA3 (Alwis et al., 2016) have been
described. None of these numeric designations provide specific structural information.
Conventional acronyms may also be derived from inconsistent sources. Some acronyms
use the parent VOC name or other metabolic precursor while others derive from the
metabolite chemical name. For example, acrylamide’s metabolites GAMA and AAMA
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refer to glycidamide and acrylamide mercapturic acid, respectively (Boettcher et al., 2005).
BPMA, derived from bromopropane mercapturic acid, originates from the parent compound
name rather than the metabolite chemical name, 1-propyl mercapturic acid (Cheever et
al., 2009). When the acronym derives from the metabolite’s chemical name, mercapturic
acid is almost universally shortened to MA. Typically, the mercapturic acid name is
used in the literature in tandem with the N-acetyl-S-L-cysteine name, the latter following
International Union of Pure and Applied Chemistry (IUPAC) rules. Examples of acronyms
derived from the IUPAC name are not as common in the literature as using MA and
include NANPC for N-acetyl-S-(4-nitrophenyl)-L-cysteine (4-nitrophenyl mercapturic acid,
parent VOC 4-chloronitrobenzene) and NASPC for N-acetyl-S-(propionamide)-L-cysteine
(2-carbamoylethyl mercapturic acid, parent VOC acrylamide) (Jones et al., 2007; Li et al.,
2005).
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However, previous acronym harmonization efforts have used alternative (non-IUPAC)
naming conventions to facilitate communication of chemicals with similar structures (Buck
et al., 2011). This has included environmental contaminants and compounds with public
health concern, such as brominated flame retardants (Bergman et al., 2012) and per- and
poly-fluoroalkyl substances (Buck et al., 2011). Thus, acronym-based naming systems do
not necessarily replace IUPAC naming conventions but serve as a tool for researchers and
public health professionals to communicate their findings.
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Our goal was to create a VOCM abbreviation system that provides unique, systematic, and
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structurally informative acronyms. We convened a group of subject matter experts to develop
a systematic naming convention, harmonize VOCM acronyms, and provide clear guidance
for creating harmonized acronyms and abbreviations for newly identified VOCMs.
2. Material and methods
2.1. Data collection
VOCMs included in this manuscript have parent VOCs in the FDA’s list of harmful or
potentially harmful constituents (Oldham et al., 2014) or are measured by a previously
published method (Alwis et al., 2012). While most of this work covers mercapturic acids,
other urinary VOCMs are also covered: hippuric acids (parent VOC xylene), carboxylic
acids (parent VOCs cyanide and carbon disulfide), glyoxylic acid and mandelic acid (parent
VOC styrene), and muconic acid (parent VOC benzene).
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We conducted literature searches to identify mercapturic acids of the VOCs identified
above and compiled a table of acronyms used for each metabolite. VOCM acronyms that
appear at least once in the literature and are detectable in human urine were included.
A few metabolites that did not meet these two criteria were also included for illustrative
purposes. One isomer of the isoprene metabolites, IPMA2b, was proposed but not measured,
while another, IPMA2a, was measured but not detected in human urine (Table 4) (Alwis
et al., 2016). These metabolites are included to demonstrate how a single, non-unique
acronym may arise from metabolites with complex structures. MHBMA is included as an
example where stereochemistry may be included. The E stereoisomer of MHBMA is the less
predominant isomer in human urine but can be used to quantitate (Z)-MHBMA (unpublished
spike-recovery results). We cited the oldest appearance of each abbreviation in the literature
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for those published multiple times. We used publicly available, free platforms like PubChem
and subscription services like SciFindern (American Chemical Society, Columbus, OH)
to compile and cross reference Chemical Abstracts Service registry numbers and confirm
accuracy of structures. Chemical structures in Fig. 1 and Table 4 were created using
ChemDraw (17.0 PerkinElmer, Waltham, MA). We noted instances where the same acronym
was used for metabolites of two different parent compounds, acronyms that referred to more
than one metabolite of the same parent compound, or acronyms that did not distinguish
between isomers of a metabolite. We also identified how acronyms in current use were
derived (e.g., based on the parent VOC or a common structure in the metabolites).
2.2. Creating harmonized VOCM acronyms
1. Identify and abbreviate the chemical group name in two letters to create a base
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for the new acronym. For example, use MA for the mercapturic acid (N-acetyl-
S-L-cysteine, R moiety in Fig. 1 and Table 4) as the base name. In the same
manner, abbreviate the hippuric, carboxylic, and glyoxylic acids to HA, CA, and
GA, respectively. Use these two letters as the last two letters of the new acronym.
2. Identify the substituent abbreviation using the metabolite name and Table 3.
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3. Incorporate the number of the position of the first substituent. Avoid using “n”
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for normal, instead use “1” for the position (e.g., for n-propyl mercapturic acid
use 1-propyl).
a. If different substituents are in the same first position (i.e., structural
moiety left of R in Fig. 1 and Table 4), use the abbreviation for the first
substituent and remove all other position numbers.
b. If two or more of the same substituents are present in the same first
position, use the numbers of the positions of multiples of the first
substituent.
4. Where stereochemistry is indicated, use the E/Z Sequence Rules (Blackwood et
al., 1968; Cahn et al., 1966) rather than trans/cis nomenclature. Use of E and Z
removes the potential for ambiguity that comes with using trans/cis designations
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with tri- and tetra-substituted alkenes.
Examples of using these steps to obtain harmonized acronyms are found in Tables 1 and 2.
2.3. Exceptions to harmonized VOCM acronyms
We used non-systematic acronym naming for three non-mercapturic acids: trans, trans-
muconic acid, mandelic acid, and 2-thioxothiazolidine-4-carboxylic acid. The chemical
names of the first two metabolites do not follow the same form as the other metabolites.
Acronyms for these two chemicals have been inconsistent. For example, trans, trans-
muconic acid has been variously referred to as MU (Jain, 2015), MA (Inoue et al.,
1989), MUC (Medinsky et al., 1989), and tt-MA (Ducos et al., 1990), among others
(see Table 4). Mandelic acid has also been shortened to MA (Jain, 2015), which is
non-unique, and can be confused with trans, trans-muconic acid. We propose consensus
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acronyms for these metabolites that are unique and still easy to interpret: trans, trans-
muconic acid (MUCA), mandelic acid (MADA). For the carbon disulfide metabolite 2-
thioxothiazolidine-4-carboxylic acid we propose the acronym currently in use, TTCA.
3. Results
We added many common substituents Table 3 to make it as comprehensive as possible. This
table may be updated in the future to list acronyms for newly identified VOC metabolites or
to add to the list of substituents. Table 4 provides a list of selected parent VOCs, previously
used VOCM acronyms, and the harmonized acronym created using the system described in
this work.
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4. Discussion
Previous systems for creating VOCM acronyms ranged widely, including using the
parent VOC as the basis for the acronym (e.g., AAMA, for acrylamide mercapturic
acid), numbering isomers sequentially as they were described (e.g. IPMA1, IPMA2,
IPMA3), using a common structural feature of the metabolite not related to its name
(e.g. MHBMA), or using the metabolite chemical name (e.g. CEMA) without additional
structural information. When working with urinary biomarkers of a single VOC, non-
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systematic naming may not be noticeable. However, taken as a collection of related
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acronyms, the inconsistencies are harder to ignore. For example, because the authors of
previous publications were aware of confusion with the acronym CEMA, commonly used
for 2-carboxyethyl mercapturic acid and 2-cyanoethyl mercapturic acid, they created a new
acronym, CNEMA (St Helen et al., 2014, 2019). They used CNEMA instead of CEMA to
create clarity by using the chemical designation for the cyano-group (CN).
The VOCM acronym system described here resolves the conflicts and confusion outlined
in the introduction by unifying the naming convention across VOCMs to provide structural
information derived from the chemical names of metabolites. CEMA and GAMA each refer
to more than one metabolite, but using harmonized acronyms resolves separate metabolites
as 2CyEMA and 2CoEMA, and 1CaHEMA and 2CaHEMA, respectively. Similarly, the
three isomers that comprise the monohydroxy butenyl mercapturic acids, MHBMA, are
differentiated as 1HMPeMA, 2HBeMA, and 4HBeMA, making it easier to identify the
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specific metabolites in a mixture. Harmonized acronyms for the isomers of dimethylphenyl
mercapturic acids, phenyl hydroxyethyl mercapturic acids, and isoprene mercapturic acids
capture the structural differences among them.
This work provides a reference for laboratories to create and use VOCM acronyms
consistently, as acronyms used in publications can change slightly over time even when
authored by the same laboratory or institution. For example, the Tobacco and Volatiles
Branch at the U.S. Centers for Disease Control and Prevention (CDC) published an
analytical method using the acronyms IPMA3 and MHBMA3 (Alwis et al., 2016), but also
used IPM3 (Biren et al., 2020) and MHB3 (Etemadi et al., 2019) in publications reporting
on exposures as well as in those written with external collaborators. This discrepancy
resulted from the acronym-length limitation (no more than four numbers/characters)
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imposed by large studies such as the National Health and Nutrition Examination Survey
(NHANES) and the Population Assessment of Tobacco and Health Study (PATH). If the
same restricted acronyms are used to report results to collaborators, they may also use
them in their manuscripts, perpetuating the use of non-systematic acronyms. Analytical
method publications do not have acronym length restrictions, thus the acronyms used in the
method publication were slightly longer. This subtle example is a reminder that study report
acronyms can influence publication acronyms. Thus, laboratory information systems may
need flexibility to use different acronym sets depending on which institution is receiving the
results. Unfortunately, due to the limitation on available acronyms and acronym size, and
changes made to acronyms before they are published (e.g., in published NHANES, IPM3
and HPMA become laboratory variables URXIPM3 and URXHPM, respectively (Centers
for Disease Control and Prevention (CDC et al., 2013–2014)).Currently, it is not possible to
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use harmonized acronyms in large, national, studies like NHANES and PATH. Fortunately,
the chemical names and NHANES variables are provided in the data documentation.
This naming system is limited in how well it can provide reasonable acronyms for long-
chain or complex alkyls the more complexity, the longer the acronym. A second limitation is
that not all positional isomers produce unique acronyms, since the position of additional
substituents beyond the first one is dropped. For example, two possible metabolites
of isoprene, 2-hydroxy-3-methyl-3-buten-1-yl mercapturic acid and 2-hydroxy-2-methyl-3-
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buten-1-yl (proposed metabolite not detected in human urine (Alwis et al., 2016)) yield
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the same acronym, 2HMBeMA, using this scheme. In another example, Chen et al. (2020)
recently described an analytical method that resolves two novel isomers previously ascribed
solely to 3-hydroxy-1-methylpropyl mercapturic acid (parent VOC crotonaldehyde): 3-
hydroxy-2-methylpropyl mercapturic acid and 3-hydroxy-3-methylpropyl mercapturic acid.
Again, this system yields the acronym 3HMPMA for all three isomers. The authors used
the acronyms HMPMA-1, HMPMA-2, and HMPMA-3, respectively. As we have previously
described, the addition of a number to the end of the acronym is not necessarily related
to the position of a particular substituent (e.g. IPMA1, IPMA2, and IPMA3). However,
Chen et al. (2020) used numbers at the end of the acronyms that corresponded to the
position of the methylpropyl substituent, a practice that provides a good solution for
isomers that create non-unique acronyms. While cysteine is a single enantiomer, generation
of new chiral centers in the metabolite could lead to diastereomers that might separate
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chromatographically and cause confusion. We did not address R/S notation because its
biological relevance is unclear.
5. Conclusions
We developed a systematic and practical naming convention to produce harmonized VOCM
acronyms that are unique and structurally informative. These acronyms reduce confusion
that arises from the non-systematic acronyms currently in use and improve communication
between analytical chemists who produce VOCM data and health scientists who use it
to investigate VOC exposure. The system described in this work makes the transition to
harmonized acronyms easy, since the acronym derives from the chemical name and is
relatively simple to construct. This work offers useful guidance and clear justification for
laboratories to adopt the harmonized acronym system. Laboratories at CDC and elsewhere
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have committed to using this acronym system for VOCMs. Papers using this system have
already been published (De Jesús et al., 2020; De Jesus et al., 2021; Nieto et al., In
Press). The National Center for Environmental Health at CDC is routinely involved in
projects examining VOCMs and plans to report results to external collaborators using these
harmonized acronyms.
Acknowledgements
Pawel K. Lorkiewicz and Daniel J. Conklin acknowledge National Institute on Drug Abuse grants: P42 ES023716,
P54 HL120163, P30 GM127607. Peyton Jacob acknowledges NIH grant P30 DA012393.
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Fig. 1.
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Mercapturic acid or N-Acetyl-S-L-cysteine moiety, R in Table 4.
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Table 1
Example of creating the harmonized acronym for 4-Hydroxy-2-buten-1-yl mercapturic acid (current acronyms
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MHBMA or MHB3).
Example Step Action Acronym (s)
4-Hydroxy-2-buten-1-yl mercapturic acid N-Acetyl-S-(4-hydroxy-3- 1 4-Hydroxy-2-buten-1-yl mercapturic acid MA
buten-1-yl)-L-cysteine
2 4-Hydroxy, 2-buten-1-yl HBeMA
➝
H and Be
3 4-Hydroxy is first position in name 4HBeMA
4 Note whether the structure is E or Z (E)-4HBeMA
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Table 2
Example of creating the harmonized acronym for trichlorovinyl mercapturic acid (current acronyms TCVC,
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TCVMA or NAcTCVC).
Example Step Action Acronym (s)
Trichlorovinyl mercapturic acid N-Acetyl-S-(1,2,2-trichloroethenyl)-L- 1 Trichlorovinyl mercapturic acid MA
cysteine
2 Trichlorovinyl CVMA
➝
C and V
3 1,2,2-Trichlorovinyl is first position in name 122CVMA
4 Note whether the structure is E or Z No “E or Z”
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Table 3
Harmonized abbreviations for substituents.
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Substituent Abbreviation
Hydroxy H
Methyl M
Ethyl E
Propyl P
Propenyl Pe
Propynyl Py
Butyl B
Butenyl Be
Butynyl By
Carboxy Co
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Methoxy Mo
Ethoxy Eo
Propoxy Po
Cyano Cy
Fluoro F
Chloro C
Bromo Br
Iodo I
Phenyl Ph
Benzyl Bz
Thiazoline T
Thiazolidine Tl
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Thioxo To
Vinyl V
Nitro N
Amino A
Carbamoyl Ca
Naphthyl Np
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Table 4
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Harmonized VOCM acronyms with their parent VOCs, structures, and previously used acronyms.
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Int J Hyg Environ Health. Author manuscript; available in PMC 2022 June 01.Acronym refers to more than one metabolite.
Tevis et al. Page 20
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Non-unique acronym.
Consensus acronym.
b
a
c
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