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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-10-09 21:01:02 UTC
HMDB IDHMDB0000895
Secondary Accession Numbers
  • HMDB00895
Metabolite Identification
Common NameAcetylcholine
DescriptionAcetylcholine (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 has been found to be a microbial product, urinary acetylcholine is produced by Lactobacillus (PMID: 24621061 ).
Structure
Data?1582752163
Synonyms
ValueSource
AChChEBI
AzetylcholinChEBI
Choline acetateChEBI
O-AcetylcholineChEBI
Choline acetic acidGenerator
Acetylcholine iodideHMDB
Acetylcholine perchlorateHMDB
Acetylcholine sulfate (1:1)HMDB
BromoacetylcholineHMDB
Cusi, acetilcolinaHMDB
Iodide, acetylcholineHMDB
2-(Acetyloxy)-N,N,N-trimethylethanaminiumHMDB
Acetilcolina cusiHMDB
Acetylcholine fluorideHMDB
Acetylcholine L tartrateHMDB
Acetylcholine picrateHMDB
ChloroacetylcholineHMDB
MiocholHMDB
Perchlorate, acetylcholineHMDB
AcetylcholineHMDB
Acetylcholine L-tartrateHMDB
Acetylcholine picrate (1:1)HMDB
Hydroxide, acetylcholineHMDB
Acetylcholine bromideHMDB
Acetylcholine chlorideHMDB
Acetylcholine hydroxideHMDB
Bromide, acetylcholineHMDB
Fluoride, acetylcholineHMDB
L-Tartrate, acetylcholineHMDB
Acetyl choline ionHMDB
Acetylcholine cationHMDB
Acetylcholinium: acetyl-cholineHMDB
Choline acetate (ester)HMDB
Bournonville brand OF acetylcholine chlorideHMDB
Iolab brand OF acetylcholine chlorideHMDB
Alcon brand OF acetylcholine chlorideHMDB
Ciba vision brand OF acetylcholine chlorideHMDB
Chemical FormulaC7H16NO2
Average Molecular Weight146.2074
Monoisotopic Molecular Weight146.118103761
IUPAC Name[2-(acetyloxy)ethyl]trimethylazanium
Traditional Nameacetylcholine
CAS Registry Number51-84-3
SMILES
CC(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1
InChI KeyOIPILFWXSMYKGL-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentAcyl cholines
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point148 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP-2.9ALOGPS
logP-4.2ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.35 m³·mol⁻¹ChemAxon
Polarizability16.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-9100000000-bf8d3f373f038db1a310Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000j-9600000000-ec60451904fda7dde556Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000l-9000000000-2ea4c086c3ab458a1d7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-98d5a70eed75a0945da4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-1900000000-2da10e016ac539b6e981Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9000000000-7efaaa08a6c43d816358Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-9000000000-eb7d66198d7674cbbd2aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000l-9000000000-41b87d773c58129802e9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-9e8e66250f2cf34a2046Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-f7fe18f2371596dc7333Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-000j-9800000000-b0f987ebcb0179a2c5abSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-9000000000-1be58612df9c1eef1282Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-1900000000-2da10e016ac539b6e981Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-7efaaa08a6c43d816358Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-eb7d66198d7674cbbd2aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000l-9000000000-41b87d773c58129802e9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-9ac44e29bdfbddf1b90dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-f7fe18f2371596dc7333Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000j-9800000000-b0f987ebcb0179a2c5abSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000j-9400000000-8a3a0b77e93715b85ed4Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Nucleus
Biospecimen Locations
  • Cerebrospinal Fluid (CSF)
  • Saliva
Tissue Locations
  • Adipose Tissue
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Lung
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.034 +/- 0.009 uMAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified8.56 +/- 5.19 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.01 +/- 0.005 uMAdult (>18 years old)Not SpecifiedAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.016 +/- 0.007 uMAdult (>18 years old)Not SpecifiedVascular dementia details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Jia JP, Jia JM, Zhou WD, Xu M, Chu CB, Yan X, Sun YX: Differential acetylcholine and choline concentrations in the cerebrospinal fluid of patients with Alzheimer's disease and vascular dementia. Chin Med J (Engl). 2004 Aug;117(8):1161-4. [PubMed:15361288 ]
Multi-infarct dementia
  1. Jia JP, Jia JM, Zhou WD, Xu M, Chu CB, Yan X, Sun YX: Differential acetylcholine and choline concentrations in the cerebrospinal fluid of patients with Alzheimer's disease and vascular dementia. Chin Med J (Engl). 2004 Aug;117(8):1161-4. [PubMed:15361288 ]
Associated OMIM IDs
DrugBank IDDB03128
Phenol Explorer Compound IDNot Available
FooDB IDFDB012191
KNApSAcK IDNot Available
Chemspider ID182
KEGG Compound IDC01996
BioCyc IDACETYLCHOLINE
BiGG ID38868
Wikipedia LinkAcetylcholine
METLIN ID57
PubChem Compound187
PDB IDNot Available
ChEBI ID15355
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000277
References
Synthesis ReferenceSzutowicz, Andrzej. Acetylcholine synthesis in synaptosomes. Postepy Biochemii (1979), 25(1), 59-84.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nguyen VT, Ndoye A, Hall LL, Zia S, Arredondo J, Chernyavsky AI, Kist DA, Zelickson BD, Lawry MA, Grando SA: Programmed cell death of keratinocytes culminates in apoptotic secretion of a humectant upon secretagogue action of acetylcholine. J Cell Sci. 2001 Mar;114(Pt 6):1189-204. [PubMed:11228162 ]
  2. Chia S, Megson IL, Ludlam CA, Fox KA, Newby DE: Preserved endothelial vasomotion and fibrinolytic function in patients with acute stent thrombosis or in-stent restenosis. Thromb Res. 2003;111(6):343-9. [PubMed:14698651 ]
  3. Grando SA, Kist DA, Qi M, Dahl MV: Human keratinocytes synthesize, secrete, and degrade acetylcholine. J Invest Dermatol. 1993 Jul;101(1):32-6. [PubMed:8331294 ]
  4. Beilin B, Bessler H, Papismedov L, Weinstock M, Shavit Y: Continuous physostigmine combined with morphine-based patient-controlled analgesia in the postoperative period. Acta Anaesthesiol Scand. 2005 Jan;49(1):78-84. [PubMed:15675987 ]
  5. Tao J, Jin YF, Yang Z, Wang LC, Gao XR, Lui L, Ma H: Reduced arterial elasticity is associated with endothelial dysfunction in persons of advancing age: comparative study of noninvasive pulse wave analysis and laser Doppler blood flow measurement. Am J Hypertens. 2004 Aug;17(8):654-9. [PubMed:15288882 ]
  6. Jiang JL, Jiang DJ, Tang YH, Li NS, Deng HW, Li YJ: Effect of simvastatin on endothelium-dependent vaso-relaxation and endogenous nitric oxide synthase inhibitor. Acta Pharmacol Sin. 2004 Jul;25(7):893-901. [PubMed:15210062 ]
  7. Haug KH, Bogen IL, Osmundsen H, Walaas I, Fonnum F: Effects on cholinergic markers in rat brain and blood after short and prolonged administration of donepezil. Neurochem Res. 2005 Dec;30(12):1511-20. [PubMed:16362770 ]
  8. Katoh H, Shimada T, Inoue S, Takahashi N, Shimizu H, Ohta Y, Nakamura K, Murakami Y, Ishibashi Y, Matsumori A: Reduced high serum hepatocyte growth factor levels after successful cardioversion in patients with atrial fibrillation. Clin Exp Pharmacol Physiol. 2004 Mar;31(3):145-51. [PubMed:15008956 ]
  9. Main C, Blennerhassett P, Collins SM: Human recombinant interleukin 1 beta suppresses acetylcholine release from rat myenteric plexus. Gastroenterology. 1993 Jun;104(6):1648-54. [PubMed:8500722 ]
  10. Ikarashi Y, Harigaya Y, Tomidokoro Y, Kanai M, Ikeda M, Matsubara E, Kawarabayashi T, Kuribara H, Younkin SG, Maruyama Y, Shoji M: Decreased level of brain acetylcholine and memory disturbance in APPsw mice. Neurobiol Aging. 2004 Apr;25(4):483-90. [PubMed:15013569 ]
  11. Katz SD, Krum H: Acetylcholine-mediated vasodilation in the forearm circulation of patients with heart failure: indirect evidence for the role of endothelium-derived hyperpolarizing factor. Am J Cardiol. 2001 May 1;87(9):1089-92. [PubMed:11348607 ]
  12. Hanna ST, Cao K, Wang R: Interaction of acetylcholine with Kir6.1 channels heterologously expressed in human embryonic kidney cells. Eur J Pharmacol. 2005 May 16;515(1-3):34-42. [PubMed:15894309 ]
  13. Greig NH, Utsuki T, Ingram DK, Wang Y, Pepeu G, Scali C, Yu QS, Mamczarz J, Holloway HW, Giordano T, Chen D, Furukawa K, Sambamurti K, Brossi A, Lahiri DK: Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer beta-amyloid peptide in rodent. Proc Natl Acad Sci U S A. 2005 Nov 22;102(47):17213-8. Epub 2005 Nov 7. [PubMed:16275899 ]
  14. Shirahata M, Balbir A, Otsubo T, Fitzgerald RS: Role of acetylcholine in neurotransmission of the carotid body. Respir Physiol Neurobiol. 2007 Jul 1;157(1):93-105. Epub 2007 Jan 11. [PubMed:17284361 ]
  15. Hasselmo ME: The role of acetylcholine in learning and memory. Curr Opin Neurobiol. 2006 Dec;16(6):710-5. Epub 2006 Sep 29. [PubMed:17011181 ]
  16. Beane M, Marrocco RT: Norepinephrine and acetylcholine mediation of the components of reflexive attention: implications for attention deficit disorders. Prog Neurobiol. 2004 Oct;74(3):167-81. [PubMed:15556286 ]
  17. Mezzelani A, Landini M, Facchiano F, Raggi ME, Villa L, Molteni M, De Santis B, Brera C, Caroli AM, Milanesi L, Marabotti A: Environment, dysbiosis, immunity and sex-specific susceptibility: a translational hypothesis for regressive autism pathogenesis. Nutr Neurosci. 2015 May;18(4):145-61. doi: 10.1179/1476830513Y.0000000108. Epub 2014 Jan 21. [PubMed:24621061 ]
  18. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
  19. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in acyltransferase activity
Specific function:
Catalyzes the reversible synthesis of acetylcholine (ACh) from acetyl CoA and choline at cholinergic synapses.
Gene Name:
CHAT
Uniprot ID:
P28329
Molecular weight:
70425.285
Reactions
Acetyl-CoA + Choline → Coenzyme A + Acetylcholinedetails
General function:
Involved in carboxylesterase activity
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular weight:
67795.525
Reactions
Acetylcholine + Water → Choline + Acetic aciddetails
General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575