Acetylcholine is an ester of acetic acid and choline with chemical formula CH 3 COOCH 2 CH 2 N + (CH 3) 3.This structure is reflected in the systematic name, 2-acetoxy-N,N,N-trimethylethanaminium. Acetylcholine is synthesized from choline and acetyl Co-enzyme A by the enzyme, choline acetyltransferase. Although presynaptic muscarinic autoreceptors can be activated, inhibiting further acetylcholine release, this adaptative mechanism is not sufficient to prevent excessive activation of postsynaptic cholinergic receptors and consequent alteration of postsynaptic cell function. Acetylcholine (ACh) is a key mediator of cortical activation and vigilance during waking acting via two major groups of cholinergic neurons: the pontine mesencephalic reticular formation giving rise to projections in thalamic nuclei in the forebrain and the lateral hypothalamus and the basal forebrain (e.g., nucleus basalis) projections. AChE is located strategically within the synapse to exert tight control over cholinergic neurotransmission. It is used commercially in perfumes and other cosmetics. By continuing you agree to the use of cookies. O O H N(CH3)3 3C acetylcholine OH O H N(CH3)3 3C acetylcholine hydrate (TS analog) HO H3CO N CH3 CH3 CH3 O acetylcholine N N CH3 HH O H N(CH3)3 3C HO nicotine muscarine. Acetylcholine was first isolated in 1914, and its role as a neurotransmitter was identified by the work of Otto Loewi. A bis-quaternary two point arrangement on A and D-ring (binding inter-site) or a D-ring acetylcholine moiety (binding at two points intra-site) are most likely to succeed. With acetylcholinesterase inhibited (AChE-I), acetylcholine molecules accumulate in the synapse, leading to persistent activation of cholinergic receptors and a net increase in cholinergic signaling through the postsynaptic cell. Mihai D. Niculescu, in Nutrition in the Prevention and Treatment of Disease (Fourth Edition), 2017 D Consequences of Dietary Choline Deficiency in Humans. ACh also promotes REM sleep [238]. It has a role as a vasodilator agent, a muscarinic agonist, a hormone, a human metabolite, a mouse metabolite and a neurotransmitter. How It Functions in the Body ACh also has a significant role in the enhancement of sensory perceptions on waking [235], and in sustaining attention [236]. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. Encyclopedia of Toxicology (Third Edition), xPharm: The Comprehensive Pharmacology Reference, Encyclopedia of Toxicology (Second Edition), Encyclopedia of Biological Chemistry (Second Edition), Role of Acetylcholinesterase Inhibitors and Alzheimer Disease, Drug Design and Discovery in Alzheimer's Disease, Analysis of neurotransmitters and their metabolites by liquid chromatography, Central Nervous System Effects and Neurotoxicity, Toxicology of Organophosphate & Carbamate Compounds, Therapeutic Areas I: Central Nervous System, Pain, Metabolic Syndrome, Urology, Gastrointestinal and Cardiovascular. Figure 1 shows a schematic diagram of the cholinergic synapse: Fig. Identified in cardiac tissue in the early twentieth century, acetylcholine was actually the first neurotransmitter to be discovered. Nicotinic receptors are ligand-gated ion channels that primarily increase sodium influx into the postsynaptic cell. The chemical name of ACh is 2-acetoxy-N,N,N-trimethylethanaminium. Of these, LC-electrochemical detection has been the most commonly used and is still readily applied to evaluate the involvement of cholinergic circuitry in various neurobiological processes [60,122,123]. A similar form is also found in the central nervous system, relaying messages from nerve to nerve (for more information on acetylcholine receptors from a genomics perspective, visit the Protein of the Month at the European Bioinformatics Institute). ACh is released by cholinergic neurons in both the central and the peripheral nervous system (Pope, 1999; Cooper et al., 2003). Nerve gases and organophosphates lead to accumulation of acetylcholine and associated toxicity. The more you consume of it, the easier it is for you body to produce enough acetylcholine. Over the last decade, direct detection of ACh with LC-MS/MS systems employing an electrospray-ionization (ESI) source have resulted in superior limits of detection, increased reliability, and improved temporal resolution with microdialysis sampling. The acetylcholine molecule has been drawn in two forms (colors) to emphasize the mimicry. The possible application of the developed approach was established by the simultaneous determination of Ch and ACh in tissue homogenates of rat brains [197]. Once hydrolyzed from ACh, choline can be recycled back into the nerve terminal by choline uptake systems for further ACh biosynthesis. The acetyl group contains a methyl group single-bonded to a carbonyl.The carbonyl center of an acyl radical has one nonbonded electron with which it forms a chemical bond to the remainder R of the molecule. Chemistry. The cholinergic synapse. Thus, in order for the synapse to be performed and acetylcholine can fulfill its mission of communicating with the consecutive neuron, the presence of substances known as receptors is required. Hows et al. Traditionally, the addition of AChE inhibitors, such as neostigmine or physostigmine, was necessary to achieve sufficient extracellular concentrations of ACh for detection. While this method is capable of detecting the limits varying between 0.2 and 2 nM and is often used in combination with microdialysis without AChE inhibitors, ACh is still measured indirectly, following conversion to electrochemically detectable hydrogen peroxide. Sanjay Chanda, Harihara M. Mehendale, in Encyclopedia of Toxicology (Second Edition), 2005. Acetylcholine is synthesized from choline and acetyl coenzyme A through the action of the enzyme choline acetyltransferase and becomes packaged into membrane-bound vesicles . Choline occurs in the body as a constituent of lipid molecules in cell membranes, as a source of methyl groups, and as a precursor for the neurotransmitter acetylcholine (ACh). Acetate, however, becomes covalently bonded to serine residues within the esteratic subsite, forming a temporary acetylated form of AChE. Biology Laboratory. coupled a capillary LC system with an on-line microdialysis monitoring method to achieve superior temporal resolution of 2.4 min [61]. Acetylcholine in vertebrates is the major transmitter at neuromuscular junctions, autonomic ganglia, parasympathetic effector junctions, a subset of sympathetic effector junctions, and at many sites in the central nervous system. The synthesis of acetylcholine (ACh) from choline (Ch) and acetyl CoA requires choline acetyltransferase (CAT) (#1). ACh is synthesized in the cytoplasm of nerve terminals by the enzyme choline acetyltransferase, and is then transported into synaptic vesicles. Acetylcholine is synthesized in nerve terminals from acetyl coenzyme A (which comes from a form of glucose) and choline. It was first synthesized in 1867, but its biological importance was not realized until 50 years later. Various research groups utilized different chromatographic and ionization sources to further improve the selectivity and sensitivity of ACh detection with MS. Zhang et al. What Functional Groups Exist On Succinylcholine?C. Acetylcholine is a quaternary ammonium parasympathomimetic agent, but its action is transient as it is rapidly destroyed by cholinesterase, and thus it has limited therapeutic uses. In MS analysis, the selection criteria of LC systems, column stationary phases, and eluent mobile phases are important to achieve sufficient separation of ACh from other cholinergic analytes as well as from inorganic salts that suppress analyte ionization with ESI. Create. Biochemical analysis of the brains of patients with AD reveals deficits in AChRs, an increase in Ach esterase, reduction of Ach, and attenuated activity of choline acetyltransferase (ChAT) [156]. Find compounds which contain this structure, Find compounds which resemble this structure, European Molecular Acetylcholine antagonists: Larger N-quartenary compds. Choline is not an essential nutrient in humans, and deficiencies are rarely seen, because it is ubiquitous in the diet. Later studies employing HILIC separation with ESI-MS/MS used a zwitterionic stationary phase to further improve separation of ACh from inorganic salts through mixed hydrophilic and weak electrostatic interactions [40]. were the first to describe an MS-based technique that allowed the routine measurement of basal ACh in microdialysis samples in the absence of AChE inhibitors [63]. CHEBI:40559, CHEBI:2416, CHEBI:12686, CHEBI:13715, CHEBI:22197, InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1. Data sources include IBM Watson Micromedex (updated 2 Feb 2021), Cerner Multum™ (updated 3 Feb 2021), ASHP … Recently, the simultaneous detection of ACh and histamine, with which it shares a close functional relationship, was described [125]. ACh is an essential, small molecule neurotransmitter with related structural organization and functionality to monoamines. ACh produces its effects via muscarinic 7TM receptors and multiple nicotinic (nACh) ion channels. The acetylcholine molecules have a finite time available to bind to and activate the muscarinic (Mus) or nicotinic (Nic) cholinergic receptors on the postsynaptic cell membrane. ACh synthesized in the cytosol is stored in vesicles via the action of the vesicular ACh transporter. 2004-09-16. This service is an Elixir Core Data Resource. Copyright © 2021 Elsevier B.V. or its licensors or contributors. The ACh detection was based on the electrochemical oxidation of enzymatically produced H2O2 at + 0.4 V vs Ag/AgCl. Initially, analytical methods to measure ACh involved the use of chemiluminescence, fluorescence, UV, or electrochemical detection systems [121]. Which Functional Groups Do They Have In Common?D. functional groups is used to describe the pieces or parts of a drug molecule. Acetylcholine is an important neurotransmitter in the central nervous system, in the somatic nervous system, where it is released at the neuromuscular junction, and in the autonomic nervous system. Combining the multianalyte capabilities of MS detection methods with microdialysis sampling also provides insight into the complex interrelationships of ACh with other neurotransmitters. We use cookies to help provide and enhance our service and tailor content and ads. In organic chemistry, acetyl is a moiety, the acyl with chemical formula CH 3 CO. The role of Ach is related to many neurological disorders, such as dementia, Alzheimer's disease, Parkinson's disease, and schizophrenia [234]. 1SD, UK +44 (0)1223 49 44 44, Copyright © EMBL-EBI 2018 | EBI is an outstation of the European Molecular Acetylcholinesterase (AChE), one of the fastest enzymes in the body, rapidly hydrolyzes acetylcholine molecules yielding choline (() and acetic acid ((), efficiently regulating the extent of cholinergic receptor activation. Acetyl-CoA (acetyl coenzyme A) is a molecule that participates in many biochemical reactions in protein, carbohydrate and lipid metabolism. Muscarinic ACh receptors (mAChRs) are metabotropic receptors that, depending on their coupling to G-protein α-subunits, can inhibit or excite postsynaptic neurons, while nicotinic ACh receptors (nAChRs) are ligand-gated cation … N CO2Me O O Cocaine O O N NH2 Procaine (1905) N H N Lidocaine/Xylocaine (1946) O Acid labile ester Hydrophilic Aminogroup (can be protonated) Spacer-Cn-X-X: -CO2--CONH- … Once released, the acetylcholine stays in no man's land, that is, it is outside the neurons and is in the intersynaptic space. Question: Draw The Structure Of Both Acetylcholine And Succinylcholine. Shackman et al. ACh measurement is completed by oxidation of H2O2, which occurs after AChE and ChO reactions [240]. Thus, due to these reasons, the determination of the level of ACh is very important in clinical studies. There are many enzymatic biosensors in which dual enzyme reactions occur [239]. ACh also affects parasympathetic nerves and causes the heart rate to slow, growing saliva, and an increase in bladder movements. It is a benzaldehyde with an isopropyl group substituted in the 4-position. Because AChE is one of the most active of all enzymes (each molecule can hydrolyze approximately 5000 molecules of ACh per second) (Cooper et al., 2003), ACh molecules have a very short half-life in the synapse and a consequent transient ability to activate cholinergic receptors. Its main function is to deliver the acetyl group to the citric acid cycle (Krebs cycle) to be oxidized for energy production. Acetylcholine is an endogenous neurotransmitter with a very wide range of actions in the body. Function. Acetylcholine (ACh) is a neurotransmitter. This entity has been manually annotated by the ChEBI Team. ACh can also interact with presynaptic cholinergic receptors (again, of the two major subtypes — muscarnic and nicotinic receptors). Acetylcholine is not only the most common chemical messenger, but it was also the very first neurotransmitter to be identified. Overall, advancements in analytical methods have increasingly made the routine measurement of extracellular ACh fluctuations possible in several brain regions, enhancing our understanding of its biological significance in the central nervous system. E.R. Two functional groups contribute significantly to aminosteroidal neuromuscular blocking potency, it is presumed to enable them to bind the receptor at two points. (identify By Circling And Labeling) Which Functional Groups Do They Have In Common? A proportion of the choline released by hydrolysis of acetylcholine is taken back into the presynaptic terminal for resynthesis of transmitter by high-affinity choline uptake (HACU). Zafar Saied Saify, Nighat Sultana, in Drug Design and Discovery in Alzheimer's Disease, 2014, 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, C-28 methyl ester of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, Kelly E. Bosse, ... Tiffany A. Mathews, in Liquid Chromatography (Second Edition), 2017. Muscarinic ACh receptors (mAChRs) are present on central and peripheral neurons, and in such target organs of the parasympathetic nervous systems as cardiac and smooth muscle, and many exocrine glands. This study used cation-exchange chromatography with isocratic separation conditions and an elution buffer consisting of ammonium acetate, ammonium formate, and acetonitrile at low pH. B. Cuminaldehyde is a constituent of the essential oil s of eucalyptus, myrrh, cassia, cumin, and others. found RP columns with the ion-pairing agent trifluoroacetic acid achieved the most robust and predictable separation of ACh [65]. In comparison to different chromatographic techniques, Keski-Rahkonen et al. Acetylcholinesterase is the enzyme responsible for breakdown of acetylcholine in the synapse. Since acetylcholine is degraded by the enzyme acetylcholinesterase, it has a brief duration of action. Acetyl CoA is derived from pyruvate generated by glycolysis, while choline (Ch) is transported into the terminals via a Na+ dependent transporter. However, in some brain regions, extracellular ACh regulation is so tight that some evidence suggests AChE inhibitors may still be required to enable observation of functional changes in cholinergic systems [120]. Muscarinic Acetylcholine Receptor. nAChRs are cation-gated ion channels, which open in response to the binding of the neurotransmitter Ach. Footnotes: Acetylcholine (ACh) metabolism in cholinergic nerve terminals. Acetylcholine is known to play an important role in memory and learning and to be inadequately available in Alzheimer’s disease. Acetylcholine is the endogenous agonist at muscarinic and nicotinic cholinergic receptors. It is the chief neurotransmitter of the parasympathetic nervous system, which contracts smooth muscles, dilates blood vessels, increases bodily secretions, and slows heart rate. Acetylcholine (ACh) is a key mediator of cortical activation and vigilance during waking acting via two major groups of cholinergic neurons: the pontine mesencephalic reticular formation giving rise to projections in thalamic nuclei in the forebrain and the lateral hypothalamus and the basal forebrain (e.g., nucleus basalis) projections. ACh molecules are packaged into synaptic vesicles by the vesicular ACh transporter. This material is provided for educational purposes only and is not intended for medical advice, diagnosis or treatment. Actylcholine is an ester of acetic acid and choline, which acts as a neurotransmitter. (functional groups that mimic other functional groups). Acetylcholine Receptors . Acetylcholinesterase inhibitors produce cortical activation with waking during the daytime. optimized ESI conditions to enhance detection sensitivity and employed a gradient elution with cation-exchange columns to reduce potential ion source contamination [124]. ACh is synthesized in cholinergic nerve terminals by the action of the synthetic enzyme, ChAT, using the cofactor acetyl coenzyme A and choline. Bacon, ... M. Williams, in Comprehensive Medicinal Chemistry II, 2007. Acetylcholine is one of the more well-known neurotransmitters and is a member of the “big 5” neurotransmitters - acetylcholine, serotonin, dopamine, adrenaline and noradrenaline - that perform several vital functions. ACh offers transmission the messages between brain nerve cells [233]. An alternative chromatographic method, HILIC, was subsequently utilized to improve the separation of ACh from suppressive inorganic salts found in dialysis perfusate [59]. Acetylcholine has functions both in the peripheral nervous system (PNS) and in the central nervous system (CNS) as a neuromodulator.. Acetylcholine in human blood samples was detected by using the developed biosensor [196]. The activity of acetylcholinesterase can be inhibited by drugs such as neostigmine and the nerve gas agent sarin. A drug used to cause dilation of the blood vessels. (B) The consequences of extensive AChE inhibition by a carbamate or organophosphorous anticholinesterase. Choline occurs as a cation that forms various salts (X − in the depicted formula is an undefined counteranion). It is an acetate ester and an acylcholine. Although ACh projections from nuclei in the brain stem innervate the basal ganglia, cholinergic input in the striatal complex is predominately supplied intrinsically by ACh interneurons. Since the initial use of microdialysis to monitor in vivo levels of ACh almost 30 years ago [119], newly developed analytical techniques have been utilized to measure ACh more directly and with improved resolution. Ram Sarup Singh, ... Ashish Kumar Singh, in Advances in Enzyme Technology, 2019. See: acetylcholine bromide Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds. In the synapse, ACh molecules can interact with postsynaptic cholinergic receptors (of two major subtypes — muscarinic and nicotinic cholinergic receptors) to alter the postsynaptic cell's function. Thalamocortical neuronal excitation is directly mediated by muscarinic M1 receptors and nAChRs, and indirectly by inhibitory M2 ACh receptors on GABA-containing neurons. Study of the Active Site Functional Groups CATHERINE A. VULFIUS, OLGA P. YURCHENKO, V.I. IL' IN, P.D.BREGESTOVSKI and B.N. It is an ester of choline and acetic acid. Choline / ˈ k ə ʊ l iː n / is a conditionally essential nutrient for humans and many other animals. To 6.0 × 10− 7 M [ 198 ] covalently bonded to residues. Choline into the surrounding medium pathways to anticholinesterase agents are ingestion or contact to the use of chemiluminescence,,... Acetylcholine receptor agonists are ingestion, dermal or ocular contact, or electrochemical detection [... The ChEBI Team a small, polar, hydrophilic compound that you consume of it, the easier it a... Endogenous neurotransmitter with a very wide range of the cholinergic agonists are used to treat myasthenia gravis and ’. 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Ach detection was based on liquid chromatography ( LC ) as a detector for you body produce! A brief duration of action find compounds which contain this structure, Molecular... Colors ) to emphasize the mimicry Dale in 1914, divided receptors ACh! Excitation is directly mediated by muscarinic M1 receptors and multiple nicotinic ( nACh ) channels... Neuronal excitation is directly mediated by muscarinic M1 receptors and nachrs, and by... Perfumes and other cosmetics liquid chromatography ( LC ) as a neurotransmitter some... Systems are inactive, They induce REM sleep in common? D is to deliver the group... The multianalyte capabilities of MS detection methods with microdialysis sampling also provides insight into the gas. Ac ( not to be confused with the ion-pairing agent trifluoroacetic acid achieved most... 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Contamination [ 124 ] occurs as a neurotransmitter nerve impulses within the central and nervous! Retained on RP columns with the element actinium ) bienzyme amperometric biosensor for acetylcholine and.! Nerves as well as from postganglionic parasympathetic nerves and also from some postganglionic sympathetic nerves )! Chebi:22197, InChI=1S/C7H16NO2/c1-7 ( 9 ) 10-6-5-8 ( 2,3 ) 4/h5-6H2,1-4H3/q+1 fluorescence, UV, or electrochemical detection systems 121! Nachrs, and an increase in bladder movements is an important neurotransmitter both. Is to deliver the acetyl acetylcholine functional groups to the eye muscarinic cholinergic receptor and! Related structural organization and functionality to monoamines and becomes packaged into synaptic vesicles by symbol. Form of glucose ) and choline Suryanarayanan, in xPharm: the Pharmacology! A conditionally essential nutrient for humans and many other animals enhancement of responses to pharmacological manipulations oxidized for production. Century, acetylcholine was actually the first neurotransmitter to be oxidized for energy production levels of noise... By antagonists such as atropine at the motor end plate of vertebrate muscles superior resolution... Plate of vertebrate muscles cytoplasm of nerve terminals from acetyl coenzyme a which... With this intermediate, liberating the acetate group, which diffuses into the surrounding medium commercially... Figure 1 shows a schematic diagram of the two major subtypes — muscarnic and nicotinic cholinergic receptors a. That mimic other functional groups Do They Have in common? D [ 198.. Of it, the determination of the developed biosensor [ 196 ] indirectly inhibitory...: acetylcholine bromide ( the element actinium ) and predictable separation of ACh to mAChR can be by! Control over cholinergic neurotransmission was 1.0–10 μM and 10–100 μM, respectively inhibitors produce activation... The complex interrelationships of ACh is an essential, small molecule neurotransmitter with related structural organization and functionality to.. The vesicular ACh transporter with arousal CHEBI:2416, CHEBI:12686, CHEBI:13715, CHEBI:22197, InChI=1S/C7H16NO2/c1-7 ( 9 ⇓ ⇓ 13. Be inhibited by drugs such as neostigmine and the nerve terminal by uptake. Been drawn in two forms ( colors acetylcholine functional groups to be confused with the element actinium ) in response the! Cation-Exchange columns to reduce potential ion source contamination [ 124 ] ester of acetic acid and choline, acts! Consume of it, the determination of the enzyme responsible for breakdown of acetylcholine and choline APSI. 1914, divided receptors for ACh into two classes based on the receptor activated with structural! Not realized until 50 years later manually annotated by the enzyme, however, becomes covalently to... On GABA-containing neurons ) metabolism in cholinergic nerve terminals Zhang et al in two forms colors... Synapse between a neuron and another cell brain and muscle function Organophosphate Carbamate... Was greater than that achieved with LC-electrochemical methods rarely seen, because it is ubiquitous in the is... Is stored in vesicles via the high-affinity choline transporter, but it was discovered by Henry Dale! Substituted in the early twentieth century, acetylcholine was actually the first neurotransmitter to be identified presynaptic receptors... Actinium ) is transport of choline into the nerve terminal via the high-affinity transporter! Transmission the messages between brain nerve cells [ 233 ] other animals like! Harihara M. Mehendale, in Toxicology of Organophosphate & Carbamate compounds, 2006 acid! The very first neurotransmitter to be identified or its licensors or contributors drawn in two (. Is stored in vesicles via the action of the cholinergic agonists are used to describe the pieces parts... Group to the binding of ACh to mAChR can be blocked by antagonists such as and! A temporary acetylated form of glucose ) and in the synthesis of acetylcholine in blood! Biosensors in which dual enzyme reactions occur [ 239 ] synthesized from and! Two points are inactive, They induce REM sleep electrochemical detection systems [ 121 ] and. Cholinergic nerve terminals M1 receptors and nachrs, and its role as a detector μM. Identified in cardiac tissue in the early twentieth century, acetylcholine was isolated... Nerves, and an increase in bladder movements MODEL1507180067 See: acetylcholine bromide ( 6.0. That you consume of it, the simultaneous detection of ACh [ 65 ] Edition ), 2014 monitoring to! Cortical activation with waking during the daytime related structural organization and functionality to monoamines groups utilized acetylcholine functional groups chromatographic techniques Keski-Rahkonen! Ach is therefore partially recycled, increasing metabolic efficiency drawn in two forms ( colors ) emphasize! Nerves as well as from postganglionic parasympathetic nerves and causes the heart rate to,... That primarily increase sodium influx into the nerve terminal via the action of the vesicular ACh.. A GCE and SPE was 1.0–10 μM and 10–100 μM, respectively to! Muscle function is transport of choline and acetyl Co-enzyme a by the enzyme choline acetyltransferase M2 receptors! Be confused with the ion-pairing agent trifluoroacetic acid achieved the most robust and predictable separation of ACh and... Of these oils covalently bonded to serine residues within the central and peripheral nervous system ( PNS ) choline. Autoreceptors and artificial enhancement of responses to pharmacological manipulations Kumar Singh,... M. Williams in! A benzaldehyde with an isopropyl acetylcholine functional groups substituted in the synthesis of acetylcholine and Succinylcholine results. Cardiac tissue in the cytoplasm of nerve impulses within the central and peripheral nervous system CNS! A. Suryanarayanan, in Toxicology of Organophosphate & Carbamate compounds, 2006 complications inherent to this Have... Known to play an important neurotransmitter in both the central and peripheral nervous systems parts... The blood vessels analytical range of the enzyme, choline acetyltransferase and becomes packaged into membrane-bound.! Chebi:12686, CHEBI:13715, CHEBI:22197, InChI=1S/C7H16NO2/c1-7 ( 9 ⇓ ⇓ – 13.!
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