| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:06:20 UTC |
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| Update date | 2025-11-18 22:57:03 UTC |
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| Primary ID | FDB004643 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Acetylcholine |
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| Description | Acetylcholine (ACh) is a neurotransmitter. 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. Its physiological and pharmacological effects, metabolism, release, and receptors have been well documented in several species. ACh has been considered an important excitatory neurotransmitter in the carotid body (CB). Various nicotinic and muscarinic ACh receptors are present in both afferent nerve endings and glomus cells. Therefore, ACh can depolarize or hyperpolarize the cell membrane depending on the available receptor type in the vicinity. Binding of ACh to its receptor can create a wide variety of cellular responses including opening cation channels (nicotinic ACh receptor activation), releasing Ca2+ from intracellular storage sites (via muscarinic ACh receptors), and modulating activities of K+ and Ca2+ channels. Interactions between ACh and other neurotransmitters (dopamine, adenosine, nitric oxide) have been known, and they may induce complicated responses. Cholinergic biology in the CB differs among species and even within the same species due to different genetic composition. Development and environment influence cholinergic biology. ; Pharmacological data clearly indicate that both muscarinic and nicotinic acetylcholine receptors have a role in the encoding of new memories. Localized lesions and antagonist infusions demonstrate the anatomical locus of these cholinergic effects, and computational modeling links the function of cholinergic modulation to specific cellular effects within these regions. Acetylcholine has been shown to increase the strength of afferent input relative to feedback, to contribute to theta rhythm oscillations, activate intrinsic mechanisms for persistent spiking, and increase the modification of synapses. These effects might enhance different types of encoding in different cortical structures. In particular, the effects in entorhinal and perirhinal cortex and hippocampus might be important for encoding new episodic memories.; The role of ACh in attention has been repeatedly demonstrated in several tasks. Acetylcholine is linked to response accuracy in voluntary and reflexive attention and also to response speed in reflexive attention. It is well known that those with Attention-deficit/hyperactivity disorders tend to be inaccurate and slow to respond. (PMID: 17284361, 17011181, 15556286); Acetylcholine is an ester of acetic acid and choline with chemical formula CH3COOCH2CH2N+(CH3)3. This structure is reflected in the systematic name, 2-acetoxy-N,N,N-trimethylethanaminium.; In the PNS, acetylcholine activates muscles, and is a major neurotransmitter in the autonomic nervous system.; In the peripheral nervous system, acetylcholine activates muscles, and is a major neurotransmitter in the autonomic nervous system. When acetylcholine binds to acetylcholine receptors on skeletal muscle fibers, it opens ligand gated sodium channels in the cell membrane. Sodium ions then enter the muscle cell, stimulating muscle contraction. Acetylcholine, while inducing contraction of skeletal muscles, instead inhibits contraction in cardiac muscle fibers. This distinction is attributed to differences in receptor structure between skeletal and cardiac fibers.; The chemical compound acetylcholine (often abbreviated ACh) is a neurotransmitter in both the peripheral nervous system (PNS) and central nervous system (CNS) in many organisms including humans. Acetylcholine is one of many neurotransmitters in the autonomic nervous system (ANS) and the only neurotransmitter used in the motor division of the somatic nervous system. (Sensory neurons use glutamate and various peptides at their synapses.) Acetylcholine is also the principal neurotransmitter in all autonomic ganglia. Acetylcholine is found in many foods, some of which are yellow bell pepper, coriander, anise, and cardamom. |
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| CAS Number | 51-84-3 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| ACh | ChEBI | | Azetylcholin | ChEBI | | Choline acetate | ChEBI | | O-Acetylcholine | ChEBI | | Choline acetic acid | Generator | | Acetylcholine iodide | HMDB | | Acetylcholine perchlorate | HMDB | | Acetylcholine sulfate (1:1) | HMDB | | Bromoacetylcholine | HMDB | | Cusi, acetilcolina | HMDB | | Iodide, acetylcholine | HMDB | | 2-(Acetyloxy)-N,N,N-trimethylethanaminium | HMDB | | Acetilcolina cusi | HMDB | | Acetylcholine fluoride | HMDB | | Acetylcholine L tartrate | HMDB | | Acetylcholine picrate | HMDB | | Chloroacetylcholine | HMDB | | Miochol | HMDB | | Perchlorate, acetylcholine | HMDB | | Acetylcholine L-tartrate | HMDB | | Acetylcholine picrate (1:1) | HMDB | | Hydroxide, acetylcholine | HMDB | | Acetylcholine bromide | HMDB | | Acetylcholine chloride | HMDB | | Acetylcholine hydroxide | HMDB | | Bromide, acetylcholine | HMDB | | Fluoride, acetylcholine | HMDB | | L-Tartrate, acetylcholine | HMDB | | Acetyl choline ion | HMDB | | Acetylcholine cation | HMDB | | Acetylcholinium: acetyl-choline | HMDB | | Choline acetate (ester) | HMDB | | Bournonville brand OF acetylcholine chloride | HMDB | | Iolab brand OF acetylcholine chloride | HMDB | | Alcon brand OF acetylcholine chloride | HMDB | | Ciba vision brand OF acetylcholine chloride | HMDB | | Acetylcholine | MeSH, HMDB | | 60-31-1 (chloride) | biospider | | 66-23-9 (bromide) | biospider | | 927-86-6 (perchlorate) | biospider |
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| Predicted Properties | |
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| Chemical Formula | C7H16NO2 |
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| IUPAC name | [2-(acetyloxy)ethyl]trimethylazanium |
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| InChI Identifier | InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1 |
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| InChI Key | OIPILFWXSMYKGL-UHFFFAOYSA-N |
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| Isomeric SMILES | CC(=O)OCC[N+](C)(C)C |
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| Average Molecular Weight | 146.2074 |
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| Monoisotopic Molecular Weight | 146.118103761 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH. |
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| Kingdom | Organic compounds |
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| Super Class | Organic nitrogen compounds |
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| Class | Organonitrogen compounds |
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| Sub Class | Quaternary ammonium salts |
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| Direct Parent | Acyl cholines |
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| Alternative Parents | |
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| Substituents | - Acyl choline
- Tetraalkylammonium salt
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic salt
- Organooxygen compound
- Carbonyl group
- Amine
- Organic cation
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Not Available | |
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| Physical Description | Not Available | |
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| Mass Composition | Not Available | |
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| Melting Point | 148 oC | |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | Not Available | |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | Acetylcholine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4r-9100000000-bf8d3f373f038db1a310 | Spectrum | | Predicted GC-MS | Acetylcholine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000j-9600000000-ec60451904fda7dde556 | 2012-07-24 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000l-9000000000-2ea4c086c3ab458a1d7c | 2012-07-24 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0006-9000000000-98d5a70eed75a0945da4 | 2012-07-24 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0002-1900000000-2da10e016ac539b6e981 | 2012-08-31 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-000i-9000000000-7efaaa08a6c43d816358 | 2012-08-31 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-000i-9000000000-eb7d66198d7674cbbd2a | 2012-08-31 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-000l-9000000000-41b87d773c58129802e9 | 2012-08-31 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-0006-9000000000-9e8e66250f2cf34a2046 | 2012-08-31 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0002-0900000000-f7fe18f2371596dc7333 | 2012-08-31 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-000j-9800000000-b0f987ebcb0179a2c5ab | 2012-08-31 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-9000000000-1be58612df9c1eef1282 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0002-1900000000-2da10e016ac539b6e981 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-9000000000-7efaaa08a6c43d816358 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-9000000000-eb7d66198d7674cbbd2a | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000l-9000000000-41b87d773c58129802e9 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-9ac44e29bdfbddf1b90d | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0002-0900000000-f7fe18f2371596dc7333 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000j-9800000000-b0f987ebcb0179a2c5ab | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - , positive | splash10-000j-9400000000-8a3a0b77e93715b85ed4 | 2017-09-14 | View Spectrum |
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| NMR | | Type | Description | | View |
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| 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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| External Links |
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| ChemSpider ID | 182 |
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| ChEMBL ID | CHEMBL667 |
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| KEGG Compound ID | C01996 |
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| Pubchem Compound ID | 187 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB0000895 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | ACETYL-CHOLINE |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Acetylcholine |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| Allergenic | 50904 | A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions. | DUKE | | Anti-amblyopic | 52217 | An agent that improves vision by enhancing visual acuity and reducing amblyopia (lazy eye) symptoms. It promotes healthy visual development, commonly used in pediatric ophthalmology to treat amblyopia, especially during critical periods of visual development. | DUKE | | Anti diuretic | 52217 | An agent that reduces urine production, regulating water balance in the body. It plays a biological role in conserving water and electrolytes. Therapeutically, it is used to treat conditions like diabetes insipidus, nocturnal enuresis, and SIADH, helping to manage fluid balance and prevent dehydration. | DUKE | | Anti ileus | | An agent that treats intestinal obstruction, restoring bowel function and motility. It helps manage postoperative ileus, paralytic ileus, and other conditions causing intestinal blockage, promoting normal digestion and bowel movements. | DUKE | | Anti-tachycardic | 38070 | An agent that slows the heart rate, reducing tachycardia (rapid heartbeat). It plays a biological role in regulating cardiac function. Therapeutically, it is used to manage arrhythmias, hypertension, and cardiac conditions. Key medical uses include treating supraventricular tachycardia, atrial fibrillation, and ventricular tachycardia. | DUKE | | Cardiodepressant | 38070 | An agent that slows heart rate and reduces cardiac contractility, used to manage conditions like hypertension, angina, and arrhythmias, reducing the heart's workload and oxygen demand. | DUKE | | Cerebrostimulant | | An agent that increases central nervous system activity, providing temporary alertness, well-being, and relief from fatigue, commonly used to manage conditions like narcolepsy, attention deficit hyperactivity disorder (ADHD), and excessive daytime sleepiness. | DUKE | | Histaminic | | A physiologically active amine that stimulates gastric secretion, causes capillary dilation, constricts bronchial smooth muscle, and lowers blood pressure. It plays a key role in allergic reactions, and its therapeutic applications include treating allergies, gastric disorders, and respiratory issues, with medical uses in antihistamines and gastric acid regulators. | DUKE | | Hypotensive | | An agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications. | DUKE | | Miotic | 51068 | An agent that constricts the pupils, reducing intraocular pressure. It plays a biological role in regulating eye function and has therapeutic applications in treating glaucoma, uveitis, and other eye disorders, making it a key medical use in ophthalmology. | DUKE | | Myocontractant | | An agent that stimulates contractions of smooth muscle, playing a biological role in regulating muscle tone. Therapeutically, it has applications in treating conditions like uterine atony and gastrointestinal disorders. Key medical uses include inducing labor, managing postpartum hemorrhage, and treating gastrointestinal motility issues. | DUKE | | Myopic | | A condition of nearsightedness, where close objects are seen clearly but distant objects appear blurred. Biologically, it results from an elongated eyeball or steep cornea. Therapeutically, corrective lenses, refractive surgery, or orthokeratology are used to improve vision. Key medical uses include correcting myopia to reduce eye strain, improve visual acuity, and prevent complications like cataracts or retinal detachment. | DUKE | | Myotonic | | An agent that induces delayed relaxation of skeletal muscles after contraction, used to describe conditions like myotonia congenita, and having potential therapeutic applications in managing muscle tone and stiffness in muscular dystrophy and other neuromuscular disorders. | DUKE | | Neurotransmitter | 25512 | A chemical messenger that transmits signals between neurons, regulating various physiological and psychological processes. Therapeutically, neurotransmitter modulators are used to treat conditions such as depression, anxiety, and Parkinson's disease, by altering neurotransmitter levels or activity to restore balance and alleviate symptoms. | DUKE | | Parasympathomimetic | | A substance that stimulates the parasympathetic nervous system, mimicking acetylcholine by activating nicotinic or muscarinic receptors. Therapeutically, it's used to treat conditions like glaucoma, asthma, and gastrointestinal disorders, promoting smooth muscle contraction and glandular secretion, while also slowing heart rate. | DUKE | | Peristaltic | | An agent that stimulates peristalsis, promoting muscle contractions in the digestive tract to move food through the system, aiding digestion and bowel movements, with therapeutic applications in treating constipation, gastrointestinal disorders, and post-surgical bowel obstruction. | DUKE | | Sialogogue | | An agent that stimulates the flow of saliva, aiding digestion and oral health. Therapeutically, it helps manage dry mouth, protects teeth, and facilitates swallowing. Key medical uses include treating xerostomia, Sj�gren's syndrome, and radiation-induced salivary gland damage. | DUKE | | Spasmogenic | | An agent that induces spasms, causing sudden involuntary muscular contractions. It plays a biological role in stimulating muscle activity. Therapeutically, it has applications in diagnosing and treating muscle disorders. Key medical uses include assessing muscle function and treating conditions like muscle atrophy, with potential applications in physical therapy and rehabilitation. | DUKE | | Vasodilator | 35620 | An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload. | DUKE | | Hormone | 24621 | A chemical messenger produced by glands, regulating various bodily functions such as growth, metabolism, and reproductive processes. Therapeutically, hormones are used to treat hormonal imbalances, menopausal symptoms, and certain cancers, as well as to regulate fertility and manage endocrine disorders, including diabetes and thyroid conditions. | CHEBI |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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